{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,22]],"date-time":"2025-10-22T10:49:10Z","timestamp":1761130150230,"version":"build-2065373602"},"reference-count":50,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2024,4,10]],"date-time":"2024-04-10T00:00:00Z","timestamp":1712707200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Coimbra Chemistry Centre","award":["UID\/QUI\/UI0313\/2013"],"award-info":[{"award-number":["UID\/QUI\/UI0313\/2013"]}]},{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia (FCT)","award":["UID\/QUI\/UI0313\/2013"],"award-info":[{"award-number":["UID\/QUI\/UI0313\/2013"]}]},{"name":"Portuguese Agency for Scientific Research","award":["UID\/QUI\/UI0313\/2013"],"award-info":[{"award-number":["UID\/QUI\/UI0313\/2013"]}]},{"name":"COMPETE Programme","award":["UID\/QUI\/UI0313\/2013"],"award-info":[{"award-number":["UID\/QUI\/UI0313\/2013"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biomolecules"],"abstract":"<jats:p>This scientific study employs the Taylor dispersion technique for diffusion measurements to investigate the interaction between sulfamerazine (NaSMR) and macromolecular cyclodextrins (\u03b2-CD and HP-\u03b2-CD). The results reveal that the presence of \u03b2-CD influences the diffusion of the solution component, NaSMR, indicating a counterflow of this drug due to solute interaction. However, diffusion data indicate no inclusion of NaSMR within the sterically hindered HP-\u03b2-CD cavity. Additionally, toxicity tests were conducted, including pollen germination (Actinidia deliciosa) and growth curve assays in BY-2 cells. The pollen germination tests demonstrate a reduction in sulfamerazine toxicity, suggesting potential applications for this antimicrobial agent with diminished adverse effects. This comprehensive investigation contributes to a deeper understanding of sulfamerazine\u2013cyclodextrin interactions and their implications for pharmaceutical and biological systems.<\/jats:p>","DOI":"10.3390\/biom14040462","type":"journal-article","created":{"date-parts":[[2024,4,10]],"date-time":"2024-04-10T03:07:48Z","timestamp":1712718468000},"page":"462","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["On Interactions of Sulfamerazine with Cyclodextrins from Coupled Diffusometry and Toxicity Tests"],"prefix":"10.3390","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2005-8990","authenticated-orcid":false,"given":"Sara P. C.","family":"Sofio","sequence":"first","affiliation":[{"name":"CQC-IMS, Department of Chemistry, University of Coimbra, Rua Larga, 3004-535 Coimbra, Portugal"},{"name":"Faculty of Health Sciences, Catholic University of \u00c1vila, Calle Los Canteros s\/n, 05005 \u00c1vila, Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6197-7761","authenticated-orcid":false,"given":"Andr\u00e9","family":"Caeiro","sequence":"additional","affiliation":[{"name":"Laboratory Associate TERRA, Centre for Functional Ecology, Department of Life Sciences, University of Coimbra, 3000-456 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3005-1963","authenticated-orcid":false,"given":"Ana C. F.","family":"Ribeiro","sequence":"additional","affiliation":[{"name":"CQC-IMS, Department of Chemistry, University of Coimbra, Rua Larga, 3004-535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2912-0028","authenticated-orcid":false,"given":"Ana M. T. D. P. V.","family":"Cabral","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, University of Coimbra, 3000-548 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4612-7686","authenticated-orcid":false,"given":"Artur J. M.","family":"Valente","sequence":"additional","affiliation":[{"name":"CQC-IMS, Department of Chemistry, University of Coimbra, Rua Larga, 3004-535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2299-298X","authenticated-orcid":false,"given":"Jorge","family":"Canhoto","sequence":"additional","affiliation":[{"name":"Laboratory Associate TERRA, Centre for Functional Ecology, Department of Life Sciences, University of Coimbra, 3000-456 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9736-3999","authenticated-orcid":false,"given":"Miguel A.","family":"Esteso","sequence":"additional","affiliation":[{"name":"Faculty of Health Sciences, Catholic University of \u00c1vila, Calle Los Canteros s\/n, 05005 \u00c1vila, Spain"}]}],"member":"1968","published-online":{"date-parts":[[2024,4,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"951","DOI":"10.1038\/s41551-021-00698-w","article-title":"The evolution of commercial drug delivery technologies","volume":"5","author":"Vargason","year":"2021","journal-title":"Nat. Biomed. Eng."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Trucillo, P. (2021). Drug Carriers: Classification, Administration, Release Profiles, and Industrial Approach. Processes, 9.","DOI":"10.3390\/pr9030470"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"441","DOI":"10.1016\/j.saa.2014.01.057","article-title":"Investigation of inclusion complexes of sulfamerazine with \u03b1-and \u03b2-cyclodextrins: An experimental and theoretical study","volume":"124","author":"Rajendiran","year":"2014","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Saokham, P., Muankaew, C., Jansook, P., and Loftsson, T. (2018). Solubility of Cyclodextrins and Drug\/Cyclodextrin Complexes. Molecules, 23.","DOI":"10.3390\/molecules23051161"},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Mu, K., Jiang, K., Wang, Y., Zhao, Z., Cang, S., Bi, K., Li, Q., and Liu, R. (2022). The biological fate of pharmaceutical excipient \u03b2-cyclodextrin: Pharmacokinetics, tissue distribution, excretion, and metabolism of \u03b2-cyclodextrin in rats. Molecules, 27.","DOI":"10.3390\/molecules27031138"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1451","DOI":"10.1016\/j.fct.2005.03.007","article-title":"2-Hydroxypropyl-\u03b2-cyclodextrin (HP-\u03b2-CD): A toxicology review","volume":"43","author":"Gould","year":"2005","journal-title":"Food Chem. Toxicol."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Liu, H., Wang, L., and Yao, C. (2023). Optimization of Antibacterial Activity and Biosafety through Ultrashort Peptide\/Cyclodextrin Inclusion Complexes. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms241914801"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"252","DOI":"10.1016\/j.ijpharm.2011.05.056","article-title":"Enhanced anti-tumor effect of 9-nitro-camptothecin complexed by hydroxypropyl-\u03b2-cyclodextrin and safety evaluation","volume":"415","author":"Jiang","year":"2011","journal-title":"Int. J. Pharm."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Gidwani, B., and Vyas, A. (2015). A comprehensive review on cyclodextrin-based carriers for delivery of chemotherapeutic cytotoxic anticancer drugs. BioMed Res. Int., 2015.","DOI":"10.1155\/2015\/198268"},{"key":"ref_10","first-page":"31","article-title":"Use of cyclodextrins as excipients in pharmaceutical products: Why not in extemporaneous preparations?","volume":"46","year":"2022","journal-title":"Farm. Hosp."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"121500","DOI":"10.1016\/j.carbpol.2023.121500","article-title":"Cyclodextrins and derivatives in drug delivery: New developments, relevant clinical trials, and advanced products","volume":"324","author":"Kali","year":"2024","journal-title":"Carbohydr. Polym."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"121763","DOI":"10.1016\/j.carbpol.2023.121763","article-title":"Pharmacokinetics and pharmacodynamics of cyclodextrin-based oral drug delivery formulations for disease therapy","volume":"329","author":"Liu","year":"2024","journal-title":"Carbohydr. Polym."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"102156","DOI":"10.1016\/j.jddst.2020.102156","article-title":"Technological evolution of cyclodextrins in the pharmaceutical field","volume":"61","author":"Riascos","year":"2021","journal-title":"J. Drug Deliv. Sci. Technol."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"609","DOI":"10.1007\/s00253-002-1057-x","article-title":"Enzymatic production of cyclodextrins","volume":"59","author":"Biwer","year":"2002","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/j.ijpharm.2012.06.055","article-title":"Cyclodextrins","volume":"453","author":"Kurkov","year":"2013","journal-title":"Int. J. Pharm."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"272","DOI":"10.1016\/j.ijpharm.2017.11.018","article-title":"Cyclodextrins: Structure, physicochemical properties and pharmaceutical applications","volume":"535","author":"Jansook","year":"2018","journal-title":"Int. J. Pharm."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Aiassa, V., Garnero, C., Zoppi, A., and Longhi, M.R. (2023). Cyclodextrins and Their Derivatives as Drug Stability Modifiers. Pharmaceuticals, 16.","DOI":"10.3390\/ph16081074"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"859406","DOI":"10.3389\/fchem.2022.859406","article-title":"Cyclodextrin-Based Nanosponges: Overview and Opportunities","volume":"10","author":"Utzeri","year":"2022","journal-title":"Front. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"25655","DOI":"10.1021\/acsomega.0c02760","article-title":"Molecular View into the Cyclodextrin Cavity: Structure and Hydration","volume":"5","author":"Sandilya","year":"2020","journal-title":"ACS Omega"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1005","DOI":"10.3109\/14756366.2015.1079183","article-title":"Synthesis of novel sulfonamide analogs containing sulfamerazine\/sulfaguanidine and their biological activities","volume":"31","author":"Aday","year":"2016","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3166","DOI":"10.1002\/jps.22062","article-title":"Complexation of sulfonamides with \u03b2-cyclodextrin studied by experimental and theoretical methods","volume":"99","author":"Zoppi","year":"2010","journal-title":"J. Pharm. Sci."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Mohamed Ameen, H., Kuns\u00e1gi-M\u00e1t\u00e9, S., Bogn\u00e1r, B., Szente, L., Po\u00f3r, M., and Lemli, B. (2019). Thermodynamic characterization of the interaction between the antimicrobial drug sulfamethazine and two selected cyclodextrins. Molecules, 24.","DOI":"10.3390\/molecules24244565"},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Nagata, T., Nemoto, Y., and Hasezawa, S. (1992). Tobacco BY-2 Cell Line as the \u201cHeLa\u201d Cell in the Cell Biology of Higher Plants, Academic Press.","DOI":"10.1016\/S0074-7696(08)62452-3"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"473","DOI":"10.1111\/j.1399-3054.1962.tb08052.x","article-title":"A Revised Medium for Rapid Growth and Bio Assays with Tobacco Tissue Cultures","volume":"15","author":"Murashige","year":"1962","journal-title":"Physiol. Plant."},{"key":"ref_25","unstructured":"Tyrrell, H.J.V., and Harris, K.R. (1984). Diffusion in Liquids: A Theoretical and Experimental Study, Butterworth."},{"key":"ref_26","unstructured":"Erdey-Gruz, T. (1974). Transport Phenomena in Aqueous Solutions, Adam Hilger. [2nd ed.]."},{"key":"ref_27","unstructured":"Robinson, R., and Stokes, R. (2002). Electrolyte Solutions, Dover. [2nd ed.]."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"541","DOI":"10.1590\/S0100-40421997000500015","article-title":"A t\u00e9cnica de dispers\u00e3o de taylor para estudos de difus\u00e3o em l\u00edquidos e suas aplica\u00e7\u00f5es","volume":"20","author":"Loh","year":"1997","journal-title":"Quim. Nova"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"353","DOI":"10.1007\/s10953-005-9000-2","article-title":"Diffusion Coefficients for Binary, Ternary, and Polydisperse Solutions from Peak-Width Analysis of Taylor Dispersion Profiles","volume":"35","author":"Callendar","year":"2006","journal-title":"J. Solut. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"921","DOI":"10.1007\/BF00972589","article-title":"Taylor dispersion measurements at low electrolyte concentrations. I. Tetraalkylammonium perchlorate aqueous solutions","volume":"25","author":"Barthel","year":"1996","journal-title":"J. Solut. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"58","DOI":"10.1016\/j.molliq.2010.04.020","article-title":"Differential mutual diffusion coefficients of binary and ternary aqueous systems measured by the open ended conductometric capillary cell and by the Taylor technique","volume":"156","author":"Ribeiro","year":"2010","journal-title":"J. Mol. Liq."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"282","DOI":"10.1016\/j.jct.2019.06.022","article-title":"Coupled mutual diffusion in aqueous sodium (salicylate + sodium chloride) solutions at 25 \u00b0C","volume":"138","author":"Ribeiro","year":"2019","journal-title":"J. Chem. Thermodyn."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2949","DOI":"10.1021\/j100709a019","article-title":"Diffusion in ternary systems","volume":"74","author":"Vitagliano","year":"1970","journal-title":"J. Phys. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"2610","DOI":"10.1021\/je900853f","article-title":"Quaternary Diffusion Coefficients of \u03b2-Cyclodextrin + KCl + Caffeine + Water at 298.15 K Using a Taylor Dispersion Method","volume":"55","author":"Ribeiro","year":"2010","journal-title":"J. Chem. Eng. Data"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1368","DOI":"10.1021\/je060092t","article-title":"Binary Mutual Diffusion Coefficients of Aqueous Solutions of \u03b2-Cyclodextrin at Temperatures from 298.15 to 312.15 K","volume":"51","author":"Ribeiro","year":"2006","journal-title":"J. Chem. Eng. Data"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"pls010","DOI":"10.1093\/aobpla\/pls010","article-title":"The evolution of pollen germination timing in flowering plants: Austrobaileya scandens (Austrobaileyaceae)","volume":"2012","author":"Williams","year":"2012","journal-title":"AoB Plants"},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Breygina, M., Klimenko, E., and Schekaleva, O. (2021). Pollen Germination and Pollen Tube Growth in Gymnosperms. Plants, 10.","DOI":"10.3390\/plants10071301"},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Fragallah, S., Lin, S., Li, N., Ligate, E., and Chen, Y. (2019). Effects of Sucrose, Boric Acid, pH, and Incubation Time on in Vitro Germination of Pollen and Tube Growth of Chinese fir (Cunnighamial lanceolata L.). Forests, 10.","DOI":"10.3390\/f10020102"},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Zheng, R., Su, S., Xiao, H., and Tian, H. (2019). Calcium: A Critical Factor in Pollen Germination and Tube Elongation. Int. J. Mol. Sci., 20.","DOI":"10.3390\/ijms20020420"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"13461","DOI":"10.1021\/acs.chemrev.7b00231","article-title":"Interactions of Native Cyclodextrins with Metal Ions and Inorganic Nanoparticles: Fertile Landscape for Chemistry and Materials Science","volume":"117","author":"Prochowicz","year":"2017","journal-title":"Chem. Rev."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"107987","DOI":"10.1016\/j.carres.2020.107987","article-title":"The non-covalent complexes of \u03b1-or \u03b3-cyclodextrin with divalent metal cations determined by mass spectrometry","volume":"492","author":"Chen","year":"2020","journal-title":"Carbohydr. Res."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"939","DOI":"10.1007\/s00214-011-1014-9","article-title":"DFT studies of cation binding by \u03b2-cyclodextrin","volume":"130","author":"Stachowicz","year":"2011","journal-title":"Theor. Chem. Acc."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"21","DOI":"10.3389\/fchem.2017.00021","article-title":"Folates in Plants: Research Advances and Progress in Crop Biofortification","volume":"5","author":"Gorelova","year":"2017","journal-title":"Front. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Sabater-Jara, A.B., Mar\u00edn-Mar\u00edn, M.J., Almagro, L., and Pedre\u00f1o, M.A. (2022). Cyclodextrins Increase Triterpene Production in Solanum lycopersicum Cell Cultures by Activating Biosynthetic Genes. Plants, 11.","DOI":"10.3390\/plants11202782"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"34972","DOI":"10.1021\/acsomega.3c04428","article-title":"Characterization, Preparation, and Promotion of Plant Growth of 1,3-Diphenylurea\/\u03b2-Cyclodextrin Derivatives Inclusion Complexes","volume":"8","author":"Yamamoto","year":"2023","journal-title":"ACS Omega"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"139","DOI":"10.1016\/S0167-7322(98)00088-9","article-title":"Diffusion coefficients in aqueous solutions of potassium chloride at high and low concentrations","volume":"78","author":"Lobo","year":"1998","journal-title":"J. Mol. Liq."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1460","DOI":"10.1021\/ja01172a090","article-title":"The differential diffusion coefficient of potassium chloride in aqueous solutions","volume":"71","author":"Harned","year":"1949","journal-title":"J. Am. Chem. Soc."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1009","DOI":"10.1007\/s10953-005-6987-3","article-title":"Binary diffusion coefficients for aqueous solutions of lactic acid","volume":"34","author":"Ribeiro","year":"2005","journal-title":"J. Solut. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"4506","DOI":"10.1021\/ja01166a047","article-title":"Diffusion Studies on Dilute Aqueous Glycine Solutions at 1 and 25 with the Gouy Interference Method","volume":"72","author":"Lyons","year":"1950","journal-title":"J. Am. Chem. Soc."},{"key":"ref_50","first-page":"285","article-title":"Measurement of Liquid Diffusion Coefficients of Aqueous Solutions of Glycine, L-Alanine, L-Valine and L-Isoleucine by Holographic Interferometry","volume":"13","author":"Changwei","year":"2005","journal-title":"Chin. J. Chem. Eng."}],"container-title":["Biomolecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2218-273X\/14\/4\/462\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T14:25:26Z","timestamp":1760106326000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2218-273X\/14\/4\/462"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,4,10]]},"references-count":50,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2024,4]]}},"alternative-id":["biom14040462"],"URL":"https:\/\/doi.org\/10.3390\/biom14040462","relation":{},"ISSN":["2218-273X"],"issn-type":[{"type":"electronic","value":"2218-273X"}],"subject":[],"published":{"date-parts":[[2024,4,10]]}}}