{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,14]],"date-time":"2026-05-14T01:14:44Z","timestamp":1778721284446,"version":"3.51.4"},"reference-count":44,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2019,5,20]],"date-time":"2019-05-20T00:00:00Z","timestamp":1558310400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100011665","name":"Deanship of Scientific Research, King Saud University","doi-asserted-by":"publisher","award":["RG-1439-65"],"award-info":[{"award-number":["RG-1439-65"]}],"id":[{"id":"10.13039\/501100011665","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>In this work, we present the synthesis and biological evaluation of novel series of diamide-based benzenesulfonamides 5a\u2013h as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I, II, IX and XII. The target tumor-associated isoforms hCA IX and XII were undeniably the most affected ones (KIs: 8.3\u2013123.3 and 9.8\u2013134.5 nM, respectively). Notably, diamides 5a and 5h stood out as a single-digit nanomolar hCA IX inhibitors (KIs = 8.8 and 8.3 nM). The SAR outcomes highlighted that bioisosteric replacement of the benzylidene moiety, compounds 5a\u2013g, with the hetero 2-furylidene moiety, compound 5h, achieved the best IX\/I and IX\/II selectivity herein reported with SIs of 985 and 13.8, respectively. Molecular docking simulations of the prepared diamides within CA IX active site revealed the ability of 5h to establish an additional H-bond between the heterocyclic oxygen and HE\/Gln67. Moreover, benzenesulfonamides 5a, 5b and 5h were evaluated for their antitumor activity against renal cancer UO-31 cell line. Compound 5h was the most potent derivative with about 1.5-fold more enhanced activity (IC50 = 4.89 \u00b1 0.22 \u03bcM) than the reference drug Staurosporine (IC50 = 7.25 \u00b1 0.43 \u03bcM). Moreover, 5a and 5h were able to induce apoptosis in UO-31 cells as evidenced by the significant increase in the percent of annexinV-FITC positive apoptotic cells by 22.5- and 26.5-folds, respectively.<\/jats:p>","DOI":"10.3390\/ijms20102484","type":"journal-article","created":{"date-parts":[[2019,5,20]],"date-time":"2019-05-20T11:05:07Z","timestamp":1558350307000},"page":"2484","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["Novel Diamide-Based Benzenesulfonamides as Selective Carbonic Anhydrase IX Inhibitors Endowed with Antitumor Activity: Synthesis, Biological Evaluation and In Silico Insights"],"prefix":"10.3390","volume":"20","author":[{"given":"Mohamed A.","family":"Abdelrahman","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Egyptian Russian University, Badr City, Cairo 11829, Egypt"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6996-4017","authenticated-orcid":false,"given":"Wagdy M.","family":"Eldehna","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Kafrelsheikh University, Kafrelsheikh 33516, Egypt"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3342-702X","authenticated-orcid":false,"given":"Alessio","family":"Nocentini","sequence":"additional","affiliation":[{"name":"Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, University of Florence, Polo Scientifico, Via U. Schiff 6, Sesto Fiorentino, 50019 Firenze, Italy"},{"name":"Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, Laboratory of Molecular Modeling Cheminformatics &amp; QSAR, University of Florence, Polo Scientifico, Via U. Schiff 6, Sesto Fiorentino, 50019 Firenze, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0107-2682","authenticated-orcid":false,"given":"Silvia","family":"Bua","sequence":"additional","affiliation":[{"name":"Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, University of Florence, Polo Scientifico, Via U. Schiff 6, Sesto Fiorentino, 50019 Firenze, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sara T.","family":"Al-Rashood","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3347-1047","authenticated-orcid":false,"given":"Ghada S.","family":"Hassan","sequence":"additional","affiliation":[{"name":"Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alessandro","family":"Bonardi","sequence":"additional","affiliation":[{"name":"Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, University of Florence, Polo Scientifico, Via U. Schiff 6, Sesto Fiorentino, 50019 Firenze, Italy"},{"name":"Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, Laboratory of Molecular Modeling Cheminformatics &amp; QSAR, University of Florence, Polo Scientifico, Via U. Schiff 6, Sesto Fiorentino, 50019 Firenze, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8711-3873","authenticated-orcid":false,"given":"Abdulrahman A.","family":"Almehizia","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hamad M.","family":"Alkahtani","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Amal","family":"Alharbi","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9137-2509","authenticated-orcid":false,"given":"Paola","family":"Gratteri","sequence":"additional","affiliation":[{"name":"Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, Laboratory of Molecular Modeling Cheminformatics &amp; QSAR, University of Florence, Polo Scientifico, Via U. Schiff 6, Sesto Fiorentino, 50019 Firenze, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4262-0323","authenticated-orcid":false,"given":"Claudiu T.","family":"Supuran","sequence":"additional","affiliation":[{"name":"Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, University of Florence, Polo Scientifico, Via U. Schiff 6, Sesto Fiorentino, 50019 Firenze, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2019,5,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"4421","DOI":"10.1021\/cr200176r","article-title":"Multiple Binding Modes of Inhibitors to Carbonic Anhydrases: How to Design Specific Drugs Targeting 15 Different Isoforms?","volume":"112","author":"Alterio","year":"2012","journal-title":"Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"689","DOI":"10.3109\/14756366.2015.1059333","article-title":"A magnificent enzyme superfamily: Carbonic anhydrases, their purification and characterization","volume":"31","author":"Capasso","year":"2016","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"5857","DOI":"10.1021\/acs.jmedchem.6b00462","article-title":"Monothiocarbamates Strongly Inhibit Carbonic Anhydrases in Vitro and Possess Intraocular Pressure Lowering Activity in an Animal Model of Glaucoma","volume":"59","author":"Vullo","year":"2016","journal-title":"J. Med. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Supuran, C.T. (2017). Carbonic Anhydrase Inhibition and the Management of Hypoxic Tumors. Metabolites, 7.","DOI":"10.3390\/metabo7030048"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"5591","DOI":"10.1021\/jm300529u","article-title":"Antimetastatic Effect of Sulfamate Carbonic Anhydrase IX Inhibitors in Breast Carcinoma Xenografts","volume":"55","author":"Gieling","year":"2012","journal-title":"J. Med. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1896","DOI":"10.1021\/jm101541x","article-title":"Ureido-Substituted Benzenesulfonamides Potently Inhibit Carbonic Anhydrase IX and Show Antimetastatic Activity in a Model of Breast Cancer Metastasis","volume":"54","author":"Pacchiano","year":"2011","journal-title":"J. Med. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"794","DOI":"10.1016\/j.bioorg.2019.04.002","article-title":"Novel synthesized SLC-0111 thiazole and thiadiazole analogues: Determination of their carbonic anhydrase inhibitory activity and molecular modeling studies","volume":"87","author":"Eldehna","year":"2019","journal-title":"Bioorg. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"549","DOI":"10.1016\/j.bioorg.2018.11.014","article-title":"SLC-0111 enaminone analogs, 3\/4-(3-aryl-3-oxopropenyl) aminobenzenesulfonamides, as novel selective subnanomolar inhibitors of the tumor-associated carbonic anhydrase isoform IX","volume":"83","author":"Eldehna","year":"2019","journal-title":"Bioorganic Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.ejmech.2018.04.016","article-title":"Dual-tail arylsulfone-based benzenesulfonamides differently match the hydrophobic and hydrophilic halves of human carbonic anhydrases active sites: Selective inhibitors for the tumor-associated hCA IX isoform","volume":"152","author":"Ibrahim","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1016\/j.ejmech.2016.01.030","article-title":"Amido\/ureidosubstituted benzenesulfonamides-isatin conjugates as low nanomolar\/subnanomolar inhibitors of the tumor-associated carbonic anhydrase isoform XII","volume":"110","author":"Eldehna","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1016\/j.ejmech.2018.10.068","article-title":"Enhancement of the tail hydrophobic interactions within the carbonic anhydrase IX active site via structural extension: Design and synthesis of novel N-substituted isatins-SLC-0111 hybrids as carbonic anhydrase inhibitors and antitumor agents","volume":"162","author":"Eldehna","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_12","first-page":"425","article-title":"Tumor-associated carbonic anhydrase isoform IX and XII inhibitory properties of certain isatin-bearing sulfonamides endowed with in vitro anticancer activity towards colon cancer, Bioorg","volume":"81","author":"Eldehna","year":"2018","journal-title":"Med. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"250","DOI":"10.1016\/j.ejmech.2017.07.073","article-title":"Novel 4\/3-((4-oxo-5-(2-oxoindolin-3-ylidene)thiazolidin-2-ylidene)amino) benzenesulfonamides: Synthesis, carbonic anhydrase inhibitory activity, anticancer activity and molecular modelling studies","volume":"139","author":"Eldehna","year":"2017","journal-title":"Eur. J. Med. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/jlac.18932750102","article-title":"Ueber die Condensation der Hippurs\u00e4ure mit Phtals\u00e4ureanhydrid und mit Benzaldehyd","volume":"275","author":"Jun","year":"1893","journal-title":"Justus Liebigs Ann. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Acheson, R.M., Booth, D.A., Brettle, R., and Harris, A.M. (1960). 694. The synthesis of some acylglycines and related oxazolones. J. Chem. Soc., 3457.","DOI":"10.1039\/jr9600003457"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1533","DOI":"10.1016\/j.tetlet.2009.11.125","article-title":"Catalyzing the Erlenmeyer Pl\u00f6chl reaction: Organic bases versus sodium acetate","volume":"51","author":"Cleary","year":"2010","journal-title":"Tetrahedron Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2561","DOI":"10.1016\/S0021-9258(18)62326-9","article-title":"The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C","volume":"246","author":"Khalifah","year":"1971","journal-title":"J. Boil. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1107","DOI":"10.1093\/jnci\/82.13.1107","article-title":"New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening","volume":"82","author":"Skehan","year":"1990","journal-title":"J. Natl. Cancer Inst."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1016\/j.ejmech.2018.11.061","article-title":"Type IIA-Type IIB protein tyrosine kinase inhibitors hybridization as an efficient approach for potent multikinase inhibitor development: Design, synthesis, anti-proliferative activity, multikinase inhibitory activity and molecular modeling of novel indolinone-based ureides and amides","volume":"163","author":"Eldehna","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Eldehna, W.M., Fares, M., Ibrahim, H.S., Alsherbiny, M.A., Aly, M.H., Ghabbour, H.A., Abdel-Aziz, H.A., Eynde, J.J.V., and Mayence, A. (2016). Synthesis and Cytotoxic Activity of Biphenylurea Derivatives Containing Indolin-2-one Moieties. Molecules, 21.","DOI":"10.3390\/molecules21060762"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/0022-1759(83)90303-4","article-title":"Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays","volume":"65","author":"Mosmann","year":"1983","journal-title":"J. Immunol. Methods"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"10692","DOI":"10.1021\/acs.jmedchem.6b01389","article-title":"Benzenesulfonamides Incorporating Flexible Triazole Moieties Are Highly Effective Carbonic Anhydrase Inhibitors: Synthesis and Kinetic, Crystallographic, Computational, and Intraocular Pressure Lowering Investigations","volume":"59","author":"Nocentini","year":"2016","journal-title":"J. Med. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"9004","DOI":"10.1021\/acs.jmedchem.5b01343","article-title":"Efficient Expression and Crystallization System of Cancer-Associated Carbonic Anhydrase Isoform IX","volume":"58","author":"Leitans","year":"2015","journal-title":"J. Med. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"538","DOI":"10.1016\/j.saa.2012.11.054","article-title":"Synthesis, bioassay, crystal structure and ab initio studies of Erlenmeyer azlactones, Spectrochim","volume":"104","author":"Parveen","year":"2013","journal-title":"Acta A Mol. Biomol. Spectrosc."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2935","DOI":"10.1016\/j.tet.2009.02.011","article-title":"A simple and efficient method for the synthesis of Erlenmeyer azlactones","volume":"65","author":"Conway","year":"2009","journal-title":"Tetrahedron"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1016\/j.ejmech.2016.01.001","article-title":"Development of certain new 2-substituted-quinazolin-4-yl-aminobenzenesulfonamide as potential antitumor agents","volume":"109","author":"Alafeefy","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2210","DOI":"10.1016\/j.bmc.2017.02.037","article-title":"Synthesis of bulky-tailed sulfonamides incorporating pyrido [2, 3-d][1,2,4] triazolo [4, 3-a] pyrimidin-1 (5H)-yl) moieties and evaluation of their carbonic anhydrases I, II, IV and IX inhibitory effects","volume":"25","author":"Fares","year":"2017","journal-title":"Bioorg. Med. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1016\/j.ejmech.2018.07.054","article-title":"Novel hydrazido benzenesulfonamides-isatin conjugates: Synthesis, carbonic anhydrase inhibitory activity and molecular modeling studies","volume":"157","author":"Eldehna","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1080\/14756366.2016.1235042","article-title":"Isatin: A privileged scaffold for the design of carbonic anhydrase inhibitors","volume":"32","author":"Melis","year":"2017","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"757","DOI":"10.1093\/jnci\/83.11.757","article-title":"Feasibility of a High-Flux Anticancer Drug Screen Using a Diverse Panel of Cultured Human Tumor Cell Lines","volume":"83","author":"Monks","year":"1991","journal-title":"J. Natl. Cancer Inst."},{"key":"ref_31","unstructured":"Beverly, A.T. (2014). Cancer Drug Discovery and Development. Anticancer Drug Development Guide: Preclinical Screening, Clinical Trials and Approval, Humana Press. [2nd ed.]. (Chapter 1)."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1002\/ddr.430340203","article-title":"Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen","volume":"34","author":"Boyd","year":"1995","journal-title":"Drug Dev. Res."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"322","DOI":"10.1080\/14756366.2018.1547286","article-title":"Synthesis and in vitro anticancer activity of certain novel 1-(2-methyl-6-arylpyridin-3-yl)-3-phenylureas as apoptosis-inducing agents","volume":"34","author":"Eldehna","year":"2019","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1016\/j.ejmech.2018.10.008","article-title":"Novel indole-thiazolidinone conjugates: Design, synthesis and whole-cell phenotypic evaluation as a novel class of antimicrobial agents","volume":"160","author":"Eldehna","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"443","DOI":"10.1016\/j.bioorg.2018.01.034","article-title":"Development of novel synthesized phthalazinone-based PARP-1 inhibitors with apoptosis inducing mechanism in lung cancer","volume":"77","author":"Almahli","year":"2018","journal-title":"Bioorg. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"782","DOI":"10.1016\/j.ejmech.2018.06.024","article-title":"Novel series of 6-(2-substitutedacetamido)-4-anilinoquinazolines as EGFR-ERK signal transduction inhibitors in MCF-7 breast cancer cells","volume":"155","author":"Ismail","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1095","DOI":"10.1080\/14756366.2018.1477137","article-title":"Novel coumarin-6-sulfonamides as apoptotic anti-proliferative agents: Synthesis, in vitro biological evaluation, and QSAR studies","volume":"33","author":"Sabt","year":"2018","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"309","DOI":"10.1080\/14756366.2017.1417276","article-title":"Abdel-Aziz One-pot three-component synthesis of novel spirooxindoles with potential cytotoxic activity against triple-negative breast cancer MDAMB-231 cells","volume":"33","author":"Eldehna","year":"2018","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"600","DOI":"10.1080\/14756366.2017.1279155","article-title":"Synthesis and in vitro anti-proliferative activity of some novel isatins conjugated with quinazoline\/phthalazine hydrazines against triple-negative breast cancer MDA-MB-231 cells as apoptosis-inducing agents","volume":"32","author":"Eldehna","year":"2017","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"686","DOI":"10.1080\/14756366.2017.1421181","article-title":"Novel [(3-indolylmethylene)hydrazono]indolin-2-ones as apoptotic anti-proliferative agents: Design, synthesis and in vitro biological evaluation","volume":"33","author":"Eldehna","year":"2018","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_41","unstructured":"(2018). Schr\u00f6dinger Suite Release 2018-2: (a) Maestrov.11.6; (b) Epik, v.4.4; (c) Impact, v.7.9; (d) Prime, v.5.2; (e) Macromodel v.12.0. (f) Glide, v.7.9, Schr\u00f6dinger, L.L.C."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"7840","DOI":"10.1002\/chem.201800941","article-title":"Deciphering the Mechanism of Human Carbonic Anhydrases Inhibition with Sulfocoumarins: Computational and Experimental Studies","volume":"24","author":"Nocentini","year":"2018","journal-title":"Chemistry"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1188","DOI":"10.1002\/chem.201805039","article-title":"Phosphorus versus Sulfur: Discovery of Benzenephosphonamidates as Versatile Sulfonamide-Mimic Chemotypes Acting as Carbonic Anhydrase Inhibitors","volume":"25","author":"Nocentini","year":"2019","journal-title":"Chemistry"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1453","DOI":"10.1080\/14756366.2018.1512597","article-title":"Steroids interfere with human carbonic anhydrase activity by using alternative binding mechanisms","volume":"33","author":"Nocentini","year":"2018","journal-title":"J. Enzym. Inhib. Med. Chem."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/20\/10\/2484\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T12:53:36Z","timestamp":1760187216000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/20\/10\/2484"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,5,20]]},"references-count":44,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2019,5]]}},"alternative-id":["ijms20102484"],"URL":"https:\/\/doi.org\/10.3390\/ijms20102484","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,5,20]]}}}