{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,18]],"date-time":"2026-10-18T14:52:57Z","timestamp":1792335177749,"version":"4.4.0"},"reference-count":120,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2022,11,10]],"date-time":"2022-11-10T00:00:00Z","timestamp":1668038400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Russian Science Foundation","award":["20-63-47070"],"award-info":[{"award-number":["20-63-47070"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The occurrence and distribution of antibiotics in the environment has received increasing attention due to their potential adverse effects on human health and ecosystems. Humic substances (HS) influence the mobility, reactivity, and bioavailability of antibiotics in the environment significantly due to their interaction. As a result, HS can affect the dissemination of antibiotic-resistance genes, which is one of the main problems arising from contamination with antibiotics. The review provides quantitative data on the binding of HS with fluoroquinolones, macrolides, sulfonamides, and tetracyclines and reports the proposed mechanisms of their interaction. The main issues of the quantification of antibiotic\u2013HS interaction are discussed, which are a development of standard approaches and the accumulation of a dataset using a standard methodology. This would allow the implementation of a meta-analysis of data to reveal the patterns of the binding of antibiotics to HS. Examples of successful development of humic-based sorbents for fluoroquinolone and tetracycline removal from environmental water systems or polluted wastewaters were given. Data on the various effects of HS on the dissemination of antibiotic-resistance genes (ARGs) were summarized. The detailed characterization of HS properties as a key point of assessing the environmental consequences of the formation of antibiotic\u2013HS complexes, such as the dissemination of antibiotic resistance, was proposed.<\/jats:p>","DOI":"10.3390\/molecules27227754","type":"journal-article","created":{"date-parts":[[2022,11,10]],"date-time":"2022-11-10T21:33:02Z","timestamp":1668115982000},"page":"7754","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":50,"title":["Interaction of Antibiotics and Humic Substances: Environmental Consequences and Remediation Prospects"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0143-2908","authenticated-orcid":false,"given":"Natalia A.","family":"Kulikova","sequence":"first","affiliation":[{"name":"Department of Soil Science, Lomonosov Moscow State University, Leninskiye Gory 1-12, 119991 Moscow, Russia"},{"name":"Bach Institute of Biochemistry, Fundamentals of Biotechnology Federal Research Center, Russian Academy of Sciences, pr. Leninskiy 33, 119071 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexandra A.","family":"Solovyova","sequence":"additional","affiliation":[{"name":"Department of Soil Science, Lomonosov Moscow State University, Leninskiye Gory 1-12, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9084-7851","authenticated-orcid":false,"given":"Irina V.","family":"Perminova","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Lomonosov Moscow State University, Leninskiye Gory 1-3, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,11,10]]},"reference":[{"key":"ref_1","unstructured":"(2022, October 10). Merriam-Webster Dictionary, s.v. \u201cAntibiotic\u201d. Available online: https:\/\/www.merriam-webster.com\/dictionary\/antibiotic."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1385","DOI":"10.1016\/j.scitotenv.2018.07.415","article-title":"The occurrence, distribution and degradation of antibiotics by ionizing radiation: An overview","volume":"646","author":"Wang","year":"2019","journal-title":"Sci. Total Environ."},{"key":"ref_3","unstructured":"(2022, October 10). Drugs.com. Antibiotics Guide. Available online: https:\/\/www.drugs.com\/article\/antibiotics.html."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1477","DOI":"10.1007\/s10311-020-01152-0","article-title":"Occurrence and removal of antibiotics from industrial wastewater","volume":"19","author":"Akhil","year":"2021","journal-title":"Environ. Chem. Lett."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1016\/j.chemosphere.2018.04.163","article-title":"Antibiotic resistance in urban and hospital wastewaters and their impact on a receiving freshwater ecosystem","volume":"206","author":"Lorenzo","year":"2018","journal-title":"Chemosphere"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"7234","DOI":"10.1021\/acs.est.9b01131","article-title":"Insights into fate and removal of antibiotics in engineered biological 2 treatment systems: A critical review","volume":"53","author":"Jia","year":"2019","journal-title":"Environ. Sci. Technol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"742","DOI":"10.1016\/S1473-3099(14)70780-7","article-title":"Global antibiotic consumption 2000 to 2010: An analysis of national pharmaceutical sales data","volume":"14","author":"Gandra","year":"2014","journal-title":"Lancet Infect. Dis."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"585","DOI":"10.1093\/jac\/49.4.585","article-title":"Antimicrobial resistance: Priorities for action","volume":"49","author":"Wise","year":"2002","journal-title":"J. Antimicrob. Chemother."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"520","DOI":"10.1016\/j.cmi.2020.12.018","article-title":"Antibiotic prescribing in patients with COVID-19: Rapid review and meta-analysis","volume":"27","author":"Langford","year":"2021","journal-title":"Clin. Microbiol. Infect."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Grau, S., Echeverria-Esnal, D., G\u00f3mez-Zorrilla, S., Navarrete-Rouco, M.E., Masclans, J.R., Espona, M., Gracia-Arnillas, M.P., Duran, X., Comas, M., and Horcajada, J.P. (2021). Evolution of antimicrobial consumption during the first wave of COVID-19 pandemic. Antibiotics, 10.","DOI":"10.3390\/antibiotics10020132"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"260","DOI":"10.1016\/j.eti.2015.09.004","article-title":"Study of molecular interactions between humic acid from Brazilian soil and the antibiotic oxytetracycline","volume":"4","author":"Vaz","year":"2015","journal-title":"Environ. Technol. Innov."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"704","DOI":"10.2134\/jeq2007.0030","article-title":"Sorption of the antibiotic tetracycline to humic-mineral complexes","volume":"37","author":"Gu","year":"2008","journal-title":"J. Environ. Qual."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"5185","DOI":"10.1021\/es400624w","article-title":"Modeling manure colloid-facilitated transport of the weakly hydrophobic antibiotic florfenicol in saturated soil columns","volume":"47","author":"Zou","year":"2013","journal-title":"Environ. Sci. Technol."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1467","DOI":"10.1002\/etc.2214","article-title":"Complexes of the antimicrobial ciprofloxacin with soil, peat, and aquatic humic substances","volume":"32","author":"Aristilde","year":"2013","journal-title":"Environ. Toxicol. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"10903","DOI":"10.1021\/acs.est.5b02158","article-title":"Influence of dissolved organic matter on tetracycline bioavailability to an antibiotic-resistant bacterium","volume":"49","author":"Chen","year":"2015","journal-title":"Environ. Sci. Technol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"314","DOI":"10.1016\/j.chemosphere.2012.11.039","article-title":"Measurement of associations of pharmaceuticals with dissolved humic substances using solid phase extraction","volume":"91","author":"Ding","year":"2013","journal-title":"Chemosphere"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2512","DOI":"10.1177\/0003702817715655","article-title":"A fluorescence quenching analysis of the binding of fluoroquinolones to humic acid","volume":"71","author":"Ferrie","year":"2017","journal-title":"Appl. Spectrosc."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1494","DOI":"10.1016\/j.chemosphere.2006.08.028","article-title":"Complexation of the antibiotic tetracycline with humic acid","volume":"66","author":"Gu","year":"2007","journal-title":"Chemosphere"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"58865","DOI":"10.1039\/C5RA08684A","article-title":"Sorption behavior of tylosin and sulfamethazine on humic acid: Kinetic and thermodynamic studies","volume":"5","author":"Guo","year":"2015","journal-title":"RSC Adv."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"208","DOI":"10.1016\/j.jes.2015.10.020","article-title":"Sorption of tylosin and sulfamethazine on solid humic acid","volume":"43","author":"Guo","year":"2016","journal-title":"J. Environ. Sci."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"8857","DOI":"10.1007\/s10661-014-4049-2","article-title":"Mechanism of ofloxacin fluorescence quenching and its interaction with sequentially extracted dissolved organic matter from lake sediment of Dianchi, China","volume":"186","author":"Lei","year":"2014","journal-title":"Environ. Monit. Assess."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"50449","DOI":"10.1039\/C7RA06231A","article-title":"Adsorption of sulfamethoxazole (SMZ) and ciprofloxacin (CIP) by humic acid (HA): Characteristics and mechanism","volume":"7","author":"Liu","year":"2017","journal-title":"RSC Adv."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"6632","DOI":"10.1021\/es900946u","article-title":"Cation binding of antimicrobial sulfathiazole to leonardite humic acid","volume":"43","author":"Richter","year":"2009","journal-title":"Environ. Sci. Technol."},{"key":"ref_24","first-page":"159189","article-title":"Sorption of sulfonamide antibiotics to soil organic sorbents: Batch experiments with model compounds and computational chemistry","volume":"2012","author":"Schwarz","year":"2012","journal-title":"Int. Sch. Res. Not."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1934","DOI":"10.1002\/etc.248","article-title":"Tetracycline sorption to coal and soil humic acids: An examination of humic structural heterogeneity","volume":"29","author":"Sun","year":"2010","journal-title":"Environ. Toxicol. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"23834","DOI":"10.1007\/s11356-017-0038-7","article-title":"Co-contaminant effects on ofloxacin adsorption onto activated carbon, graphite, and humic acid. Environ","volume":"24","author":"Wang","year":"2017","journal-title":"Sci. Pollut. Res."},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Wang, R., Yang, S., Fang, J., Wang, Z., Chen, Y., Zhang, D., and Yang, C. (2018). Characterizing the interaction between antibiotics and humic acid by fluorescence quenching method. Int. J. Environ. Res. Public Health, 15.","DOI":"10.3390\/ijerph15071458"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1016\/j.jenvman.2011.12.036","article-title":"Sorption of norfloxacin onto humic acid extracted from weathered coal","volume":"102","author":"Zhang","year":"2012","journal-title":"J. Environ. Manag."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1205","DOI":"10.1016\/j.scitotenv.2019.06.287","article-title":"Coating magnetic biochar with humic acid for high efficient removal of fluoroquinolone antibiotics in water","volume":"688","author":"Zhao","year":"2019","journal-title":"Sci. Total Environ."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"160","DOI":"10.1007\/s11270-018-3821-2","article-title":"The influence of humification degree of humic acid on its sorption of norfloxacin during sewage sludge composting","volume":"229","author":"Zhu","year":"2018","journal-title":"Water Air Soil Pollut."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"6832","DOI":"10.1021\/es049509a","article-title":"Antibiotics in the environment:\u2009 occurrence in Italian STPs, fate, and preliminary assessment on algal toxicity of amoxicillin","volume":"38","author":"Andreozzi","year":"2004","journal-title":"Environ. Sci. Technol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1016\/j.watres.2015.11.036","article-title":"Correlating the chemical and spectroscopic characteristics of natural organic matter with the photodegradation of sulfamerazine","volume":"93","author":"Batista","year":"2016","journal-title":"Water Res."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"4463","DOI":"10.1021\/es0500916","article-title":"Cross-coupling of sulfonamide antimicrobial agents with model humic constituents","volume":"39","author":"Bialk","year":"2005","journal-title":"Environ. Sci. Technol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"106","DOI":"10.1021\/es070779d","article-title":"NMR investigation of enzymatic coupling of sulfonamide antimicrobials with humic substances","volume":"42","author":"Bialk","year":"2008","journal-title":"Environ. Sci. Technol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"11783","DOI":"10.1021\/acs.est.9b04105","article-title":"Inhibitory effect of dissolved organic matter on the transformation of selected anilines and sulfonamide antibiotics induced by the sulfate radical","volume":"53","author":"Canonica","year":"2019","journal-title":"Environ. Sci. Technol."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"9801","DOI":"10.1021\/jf302564d","article-title":"Photodegradation of ormetoprim in aquaculture and stream-derived dissolved organic matter","volume":"60","author":"Guerard","year":"2012","journal-title":"J. Agric. Food Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"8587","DOI":"10.1021\/es9020537","article-title":"Photochemical fate of sulfadimethoxine in aquaculture waters","volume":"43","author":"Guerard","year":"2009","journal-title":"Environ. Sci. Technol."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"2102","DOI":"10.1021\/es202272w","article-title":"Reactions of a sulfonamide antimicrobial with model humic constituents: Assessing pathways and stability of covalent bonding","volume":"46","author":"Gulkowska","year":"2012","journal-title":"Environ. Sci. Technol."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1231","DOI":"10.1016\/j.scitotenv.2016.08.041","article-title":"The effect of natural organic matter polarity and molecular weight on NDMA formation from two antibiotics containing dimethylamine functional groups","volume":"572","author":"Krasner","year":"2016","journal-title":"Sci. Total Environ."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"134","DOI":"10.1016\/j.jhazmat.2016.05.100","article-title":"Photolytic and photocatalytic degradation of tetracycline: Effect of humic acid on degradation kinetics and mechanisms","volume":"318","author":"Li","year":"2016","journal-title":"J. Hazard. Mater."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"12310","DOI":"10.1021\/acs.est.7b03482","article-title":"Elucidating the stimulatory and inhibitory effects of dissolved organic matter from poultry litter on photodegradation of antibiotics","volume":"51","author":"Mangalgiri","year":"2017","journal-title":"Environ. Sci. Technol."},{"key":"ref_42","first-page":"346","article-title":"Erythromycin oxidation and ERY-resistant Escherichia coli inactivation in urban wastewater by sulfate radical-based oxidation process under UV-C irradiation","volume":"85","author":"Iacovou","year":"2012","journal-title":"Water Res."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.watres.2016.02.024","article-title":"Role of humic substances in the degradation pathways and residual antibacterial activity during the photodecomposition of the antibiotic ciprofloxacin in water","volume":"94","author":"Porras","year":"2016","journal-title":"Water Res."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"182","DOI":"10.1016\/j.jhazmat.2017.02.058","article-title":"Transformation and toxicity evaluation of tetracycline in humic acid solution by laccase coupled with 1-hydroxybenzotriazole","volume":"331","author":"Sun","year":"2017","journal-title":"J. Hazard. Mater."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1465","DOI":"10.1016\/j.scitotenv.2018.07.206","article-title":"Modelled phototransformation kinetics of the antibiotic sulfadiazine in organic matter-rich lakes","volume":"645","author":"Vione","year":"2018","journal-title":"Sci. Total Environ."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"125642","DOI":"10.1016\/j.chemosphere.2019.125642","article-title":"Molecular characteristics of leonardite humic acid and the effect of its fractionations on sulfamethoxazole photodegradation","volume":"246","author":"Zhang","year":"2019","journal-title":"Chemosphere"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"135023","DOI":"10.1016\/j.scitotenv.2019.135023","article-title":"Degradation of antibiotics by advanced oxidation processes: An overview","volume":"701","author":"Wang","year":"2020","journal-title":"Sci. Total Environ."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"549","DOI":"10.1016\/j.chemosphere.2018.03.117","article-title":"Ciprofloxacin-metal complexes -stability and toxicity tests in the presence of humic substances","volume":"202","author":"Cuprys","year":"2018","journal-title":"Chemosphere"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"122013","DOI":"10.1016\/j.cej.2019.122013","article-title":"Effects of struvite-humic acid loaded biochar\/bentonite composite amendment on Zn(II) and antibiotic resistance genes in manure-soil","volume":"375","author":"Li","year":"2019","journal-title":"Chem. Eng. J."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"109463","DOI":"10.1016\/j.jenvman.2019.109463","article-title":"Application of humic acid changes the microbial communities and inhibits the expression of tetracycline resistance genes in 4-chlorophenol wastewater treatment","volume":"250","author":"Zhao","year":"2019","journal-title":"J. Environ. Manage."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"583","DOI":"10.1016\/j.watres.2016.10.042","article-title":"Co-occurrence of mobile genetic elements and antibiotic resistance genes in municipal solid waste landfill leachates: A preliminary insight into the role of landfill age","volume":"106","author":"Yu","year":"2016","journal-title":"Water Res."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"60","DOI":"10.1016\/j.envint.2018.04.011","article-title":"Antibiotics and antibiotic resistance genes in global lakes: A review and meta-analysis","volume":"116","author":"Yang","year":"2018","journal-title":"Environ. Int."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"76","DOI":"10.1016\/j.jcis.2019.01.083","article-title":"Enhanced removal of ciprofloxacin using humic acid modified hydrogel beads","volume":"543","author":"Afzal","year":"2019","journal-title":"J. Colloid Interface Sci."},{"key":"ref_54","first-page":"1231","article-title":"Photocatalytic degradation of metronidazole using BIOI-MWCNT composites: Synthesis, characterization, and operational parameters","volume":"37","author":"Balarak","year":"2019","journal-title":"Sigma J. Eng. Nat. Sci."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"444","DOI":"10.1016\/j.chemosphere.2016.04.008","article-title":"Effect of humic monomers on the adsorption of sulfamethoxazole sulfonamide antibiotic into a high silica zeolite Y: An interdisciplinary study","volume":"155","author":"Braschi","year":"2016","journal-title":"Chemosphere"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"228","DOI":"10.2134\/jeq2008.0274","article-title":"Sorption of sulfonamide antimicrobial agents to humic acid-clay complexes","volume":"39","author":"Gao","year":"2010","journal-title":"J. Environ. Qual."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"519","DOI":"10.2134\/jeq2015.06.0320","article-title":"Sorption of lincomycin by manure-derived biochars from water","volume":"45","author":"Liu","year":"2016","journal-title":"J. Environ. Qual."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"121520","DOI":"10.1016\/j.jhazmat.2019.121520","article-title":"Variable surface charge of humic acid-ferrihydrite composite: Influence of electrolytes on ciprofloxacin adsorption","volume":"385","author":"Urdiales","year":"2020","journal-title":"J. Hazard. Mater."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"122812","DOI":"10.1016\/j.biortech.2020.122812","article-title":"An easy and unique design strategy for insoluble humic acid\/cellulose nanocomposite beads with highly enhanced adsorption performance of low concentration ciprofloxacin in water","volume":"302","author":"Wang","year":"2020","journal-title":"Bioresour. Technol."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1016\/j.watres.2019.01.011","article-title":"Enhanced transformation of sulfonamide antibiotics by manganese(IV) oxide in the presence of model humic constituents","volume":"153","author":"Song","year":"2019","journal-title":"Water Res."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"125135","DOI":"10.1016\/j.colsurfa.2020.125135","article-title":"Effective adsorption of oxytetracycline from aqueous solution by lanthanum modified magnetic humic acid","volume":"602","author":"Yang","year":"2020","journal-title":"Colloids Surf. A"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"2689","DOI":"10.1016\/j.cjche.2020.06.039","article-title":"Adsorptive removal of tetracycline from water using Fe (III)-functionalized carbonized humic acid","volume":"28","author":"Xie","year":"2020","journal-title":"Chin. J. Chem. Eng."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"9","DOI":"10.2478\/pjct-2020-0022","article-title":"Calcium alginate\/activated carbon\/humic acid tri-system porous fibers for removing tetracycline from aqueous solution","volume":"22","author":"Sun","year":"2020","journal-title":"Pol. J. Chem. Technol."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1016\/j.seppur.2019.04.010","article-title":"Adsorption of levofloxacin onto mechanochemistry treated zeolite: Modeling and site energy distribution analysis","volume":"22","author":"Chen","year":"2019","journal-title":"Sep. Purif. Technol."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"298","DOI":"10.1016\/j.chemosphere.2019.03.098","article-title":"Removal of chloramphenicol in aqueous solutions by modified humic acid loaded with nanoscale zero-valent iron particles","volume":"226","author":"Yao","year":"2019","journal-title":"Chemosphere"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"793","DOI":"10.1016\/j.scitotenv.2019.01.406","article-title":"Antibiotic pollution in surface fresh waters: Occurrence and effects","volume":"664","author":"Danner","year":"2019","journal-title":"Sci. Total Environ."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"736","DOI":"10.1016\/j.envint.2016.06.025","article-title":"Antibiotics in the aquatic environments: A review of the European scenario","volume":"94","author":"Carvalho","year":"2016","journal-title":"Environ. Int."},{"key":"ref_68","doi-asserted-by":"crossref","unstructured":"Kraemer, S.A., Ramachandran, A., and Perron, G.G. (2019). Antibiotic pollution in the environment: From microbial ecology to public policy. Microorganisms, 7.","DOI":"10.3390\/microorganisms7060180"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"104796","DOI":"10.1016\/j.jece.2020.104796","article-title":"A comprehensive update on antibiotics as an emerging water pollutant and their removal using nano-structured photocatalysts","volume":"9","author":"Roy","year":"2021","journal-title":"J. Environ. Chem. Eng."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"479","DOI":"10.1002\/clen.201300989","article-title":"Antibiotic pollution in the environment: A review","volume":"43","author":"Gothwal","year":"2015","journal-title":"Clean Soil Air Water"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"461","DOI":"10.1016\/j.watres.2016.08.040","article-title":"Occurrence and removal of multiple classes of antibiotics and antimicrobial agents in biological wastewater treatment processes","volume":"104","author":"Tran","year":"2016","journal-title":"Water Res."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"1873","DOI":"10.1007\/s10311-020-01117-3","article-title":"Synergetic effect of antibiotic mixtures on soil bacterial N2O-reducing communities","volume":"19","author":"David","year":"2021","journal-title":"Environ. Chem. Lett."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"142865","DOI":"10.1016\/j.scitotenv.2020.142865","article-title":"Antibiotics in surface water of East and Southeast Asian countries: A focused review on contamination status, pollution sources, potential risks, and future perspectives","volume":"764","author":"Anh","year":"2021","journal-title":"Sci. Total Environ."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"309","DOI":"10.1007\/s13593-011-0062-9","article-title":"Occurrence, fate, and ecotoxicity of antibiotics in agro-ecosystems. A review","volume":"32","author":"Du","year":"2012","journal-title":"Agron. Sustain. Develop."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"114554","DOI":"10.1016\/j.envpol.2020.114554","article-title":"Ecotoxicological effects of sulfonamides and fluoroquinolones and their removal by a green alga (Chlorella vulgaris) and a cyanobacterium (Chrysosporum ovalisporum)","volume":"63","author":"Chen","year":"2020","journal-title":"Environ. Poll."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"461","DOI":"10.1080\/03601230902935139","article-title":"The effects of residual tetracycline on soil enzymatic activities and plant growth","volume":"44","author":"Wei","year":"2009","journal-title":"J. Environ. Sci. Health Part B"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"1636","DOI":"10.1016\/j.envpol.2008.12.021","article-title":"Effects of six selected antibiotics on plant growth and soil microbial and enzymatic activities","volume":"157","author":"Liu","year":"2009","journal-title":"Environ. Pollut."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"2992","DOI":"10.1016\/j.envpol.2010.05.023","article-title":"Occurrence and source analysis of typical veterinary antibiotics in manure, soil, vegetables and groundwater from organic vegetable bases, northern China","volume":"158","author":"Hu","year":"2010","journal-title":"Environ. Pollut."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"114752","DOI":"10.1016\/j.envpol.2020.114752","article-title":"Antibiotic-contaminated wastewater irrigated vegetables pose resistance selection risks to the gut microbiome","volume":"264","author":"Gudda","year":"2020","journal-title":"Environ. Pollut."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"10975","DOI":"10.1021\/acs.est.8b02204","article-title":"Global survey of antibiotic resistance genes in air","volume":"52","author":"Li","year":"2018","journal-title":"Environ. Sci. Technol."},{"key":"ref_81","unstructured":"(2021, February 21). AMR Alliance Science-Based PNEC Targets for Risk Assessments. Available online: https:\/\/www.amrindustryalliance.org\/wp-content\/uploads\/2020\/01\/AMR-Table-1-Update-February-2021.pdf."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"1387","DOI":"10.1016\/j.scitotenv.2017.09.012","article-title":"Towards the understanding of antibiotic occurrence and transport in groundwater: Findings from the Baix Fluvi\u00e0 alluvial aquifer (NE Catalonia, Spain)","volume":"612","author":"Petrovic","year":"2018","journal-title":"Sci. Total Environ."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"101681","DOI":"10.1016\/j.jwpe.2020.101681","article-title":"A critical review of antibiotic removal strategies: Performance and mechanisms","volume":"38","author":"Lu","year":"2020","journal-title":"J. Water Process Eng."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"140","DOI":"10.1016\/j.envint.2015.10.015","article-title":"Concentrations of antibiotics predicted to select for resistant bacteria: Proposed limits for environmental regulation","volume":"86","author":"Larsson","year":"2016","journal-title":"Environ. Int."},{"key":"ref_85","unstructured":"National Library of Medicine (2021, March 30). National Center for Biotechnology Information, Available online: https:\/\/pubchem.ncbi.nlm.nih.gov\/compound."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"2874","DOI":"10.1016\/j.watres.2004.03.017","article-title":"Potentiometric determination of acid dissociation constants (pKa) for human and veterinary antibiotics","volume":"38","author":"Qiang","year":"2004","journal-title":"Water Res."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"1325","DOI":"10.1016\/0731-7085(94)00081-6","article-title":"Dissociation and complexation of the fluoroquinolone antimicrobials\u2014An update","volume":"12","author":"Ross","year":"1994","journal-title":"J. Pharmac. Biomed. Anal."},{"key":"ref_88","unstructured":"Enna, S.J., and Bylund, D.B. (2007). Enoxacin. xPharm: The Comprehensive Pharmacology Reference, Elsevier."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"715","DOI":"10.2147\/DDDT.S239307","article-title":"Synthesis, characterization, and pharmacodynamics study of enrofloxacin mesylate","volume":"14","author":"Pei","year":"2020","journal-title":"Drug Des. Dev. Ther."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"631","DOI":"10.1016\/S0039-9140(01)00471-4","article-title":"High-performance liquid chromatographic assay of fleroxacin in human serum using fluorescence detection","volume":"55","author":"Djurdjevic","year":"2011","journal-title":"Talanta"},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"918","DOI":"10.1002\/jps.2600771103","article-title":"Isoelectric points of some sulfonamides: Determination by microelectrophoresis and by calculations involving acid\u2013base strength","volume":"77","author":"Schott","year":"1988","journal-title":"J. Pharmac. Sci."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1016\/S0021-9673(97)01181-3","article-title":"Migration behavior and separation of tetracycline antibiotics by micellar electrokinetic chromatography","volume":"802","author":"Chen","year":"1998","journal-title":"J. Chromatogr. A"},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/bs.pmch.2014.11.001","article-title":"Fluorine in medicinal chemistry","volume":"54","author":"Swallow","year":"2015","journal-title":"Prog. Med. Chem."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1071\/CH9900301","article-title":"The acidity of norfloxacin","volume":"43","author":"Buckingham","year":"1990","journal-title":"Aust. J. Chem."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"538","DOI":"10.1016\/j.cplett.2006.10.078","article-title":"A DFT study of hydration in neutral and zwitterionic norfloxacin","volume":"432","author":"Vitorino","year":"2006","journal-title":"Chem. Phys. Lett."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"462","DOI":"10.1016\/j.cej.2017.10.049","article-title":"Quaternary magnetic BiOCl\/g-C3N4\/Cu2O\/Fe3O4 nano-junction for visible light and solar powered degradation of sulfamethoxazole from aqueous environment","volume":"334","author":"Kumar","year":"2018","journal-title":"Chem. Eng. J."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1016\/S0003-2670(00)84425-6","article-title":"Micro-ionization acidity constants for tetracyclines from fluorescence measurements","volume":"167","author":"Bhatt","year":"1985","journal-title":"Anal. Chim. Acta"},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"6726","DOI":"10.1021\/jf070905x","article-title":"Interaction of different polyphenols with bovine serum albumin (BSA) and human salivary a-amylase (HSA) by fluorescence quenching","volume":"55","author":"Soares","year":"2007","journal-title":"J. Agric. Food Chem."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"421","DOI":"10.1016\/j.chemosphere.2017.08.112","article-title":"Multi-spectroscopic investigation on the complexation of tetracycline with dissolved organic matter derived from algae and macrophyte","volume":"187","author":"Bai","year":"2017","journal-title":"Chemosphere"},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"955","DOI":"10.1021\/es001996g","article-title":"Evidence for Nonlinear Binding of PAHs to Dissolved Humic Acids","volume":"36","author":"Laor","year":"2002","journal-title":"Environ. Sci. Technol."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"815","DOI":"10.1016\/j.envpol.2019.02.077","article-title":"Noncovalent interactions between fluoroquinolone antibiotics with dissolved organic matter: A 1H NMR binding site study and multi-spectroscopic methods","volume":"248","author":"Zhao","year":"2019","journal-title":"Environ. Pollut."},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1016\/S0380-1330(92)71277-5","article-title":"Distribution of hydrophobic organic compounds between dissolved and particulate organic matter in Green Bay waters","volume":"18","author":"Eadie","year":"1992","journal-title":"J. Great Lakes Res."},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/S0003-2670(00)01258-7","article-title":"Partition coefficients of pyrene to lake aquatic humic matter determined by fluorescence quenching and solubility enhancement","volume":"429","author":"Peuravuori","year":"2001","journal-title":"Anal. Chim. Acta"},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"1928","DOI":"10.1021\/es062316y","article-title":"Sorption of tetracycline and chlortetracycline on K- and Ca-saturated soil clays, humic substances, and clay-humic complexes","volume":"41","author":"Plis","year":"2007","journal-title":"Environ. Sci. Technol."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"9933","DOI":"10.1021\/acs.est.5b04693","article-title":"Clarithromycin and tetracycline binding to soil humic acid in the absence and presence of calcium","volume":"50","author":"Christl","year":"2016","journal-title":"Environ. Sci. Technol."},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"262","DOI":"10.1016\/j.jhazmat.2015.09.058","article-title":"Kinetics and thermodynamics of interaction between sulfonamide antibiotics and humic acids: Surface plasmon resonance and isothermal titration microcalorimetry analysis","volume":"302","author":"Xu","year":"2016","journal-title":"J. Hazard. Mater."},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"752","DOI":"10.1016\/j.envpol.2018.09.002","article-title":"Rapidly probing the interaction between sulfamethazine antibiotics and fulvic acids","volume":"243","author":"Xu","year":"2018","journal-title":"Environ. Pollut."},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"3748","DOI":"10.1021\/acs.est.7b06164","article-title":"Interactions of 15N-sulfadiazine and soil components as evidenced by 15N-CPMAS NMR","volume":"52","author":"Berns","year":"2018","journal-title":"Environ. Sci. Technol."},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"3096","DOI":"10.1021\/bi00514a017","article-title":"Thermodynamics of protein association reactions: Forces contributing to stability","volume":"20","author":"Ross","year":"1981","journal-title":"Biochemistry"},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"7452","DOI":"10.1021\/es0480217","article-title":"Sorption of three tetracyclines by several soils: Assessing the role of pH and cation exchange","volume":"39","author":"Sassman","year":"2005","journal-title":"Environ. Sci. Technol."},{"key":"ref_111","doi-asserted-by":"crossref","first-page":"2788","DOI":"10.1021\/es9802394","article-title":"Modeling short-term soil-water phase distribution of aromatic amines","volume":"32","author":"Fabrega","year":"1998","journal-title":"Environ. Sci. Technol."},{"key":"ref_112","first-page":"997","article-title":"Research progress on mechanisms about the effect of ionic strength on adsorption","volume":"29","author":"Wu","year":"2010","journal-title":"Environ. Chem."},{"key":"ref_113","doi-asserted-by":"crossref","first-page":"1964","DOI":"10.2134\/jeq2005.0014","article-title":"Oxytetracycline sorption to organic matter by metal-bridging","volume":"34","author":"MacKay","year":"2005","journal-title":"J. Environ. Qual."},{"key":"ref_114","doi-asserted-by":"crossref","first-page":"3593","DOI":"10.1021\/es0617338","article-title":"Laccase-mediated Michael addition of N-15-sulfapyridine to a model humic constituent","volume":"41","author":"Bialk","year":"2007","journal-title":"Environ. Sci. Technol."},{"key":"ref_115","doi-asserted-by":"crossref","first-page":"829708","DOI":"10.1155\/2015\/829708","article-title":"Enzymatic transformation and bonding of sulfonamide antibiotics to model humic substances","volume":"2015","author":"Schwarz","year":"2015","journal-title":"J. Chem."},{"key":"ref_116","doi-asserted-by":"crossref","unstructured":"Kulikova, N.A., and Perminova, I.V. (2021). Interactions between humic substances and microorganisms and their implications for nature-like bioremediation technologies. Molecules, 29.","DOI":"10.3390\/molecules26092706"},{"key":"ref_117","doi-asserted-by":"crossref","first-page":"910","DOI":"10.2166\/wh.2019.160","article-title":"Antibiotic resistance genes removal and membrane fouling in secondary effluents by combined processes of PAC\/BPAC\u2013UF","volume":"17","author":"Sun","year":"2019","journal-title":"J. Water Health"},{"key":"ref_118","doi-asserted-by":"crossref","first-page":"10732","DOI":"10.1021\/acs.est.9b03096","article-title":"Enhanced photodegradation of extracellular antibiotic resistance genes by dissolved organic matter photosensitization","volume":"53","author":"Zhang","year":"2019","journal-title":"Environ. Sci. Technol."},{"key":"ref_119","doi-asserted-by":"crossref","first-page":"110461","DOI":"10.1016\/j.ecoenv.2020.110461","article-title":"Putative environmental levels of levofloxacin facilitate the dissemination of antibiotic-resistant Escherichia coli via plasmid-mediated transformability","volume":"195","author":"Wu","year":"2020","journal-title":"Ecotoxicol. Environ. Saf."},{"key":"ref_120","doi-asserted-by":"crossref","first-page":"771510","DOI":"10.3389\/fcimb.2021.771510","article-title":"Antibiotic resistance: One health one world outlook","volume":"11","author":"Aslam","year":"2021","journal-title":"Front. Cell Infect. Microbiol."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/22\/7754\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:14:12Z","timestamp":1760145252000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/22\/7754"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,11,10]]},"references-count":120,"journal-issue":{"issue":"22","published-online":{"date-parts":[[2022,11]]}},"alternative-id":["molecules27227754"],"URL":"https:\/\/doi.org\/10.3390\/molecules27227754","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,11,10]]}}}