{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,14]],"date-time":"2026-05-14T15:31:46Z","timestamp":1778772706799,"version":"3.51.4"},"reference-count":59,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2020,5,22]],"date-time":"2020-05-22T00:00:00Z","timestamp":1590105600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006109","name":"Vedeck\u00e1 Grantov\u00e1 Agent\u00fara M\u0160VVa\u0160 SR a SAV","doi-asserted-by":"publisher","award":["VEGA 1\/0463\/18"],"award-info":[{"award-number":["VEGA 1\/0463\/18"]}],"id":[{"id":"10.13039\/501100006109","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Various sulfonamide derivatives are intensively studied as anticancer agents owing to their inhibitory activity against human tumor-associated carbonic anhydrase isoforms. In this work, different synthetic procedures for the series of 1,3,5-triazinyl-aminobenzenesulfonamide conjugates with amino acids, possessing polar uncharged, negatively charged, and hydrophobic side chain, were studied and optimized with respect to the yield\/purity of the synthesis\/product as well as the time of synthetic reaction. These procedures were compared to each other via characteristic HPLC-ESI-DAD\/QTOF\/MS analytical product profiles, and their benefits as well as limitations were discussed. For new sulfonamide derivatives, incorporating s-triazine with a symmetric pair of polar and some less-polar proteinogenic amino acids, inhibition constants (KIs) against four human carboanhydrases (hCAs), namely cytosolic hCA I, II, transmembrane hCA IV, and the tumor-associated, membrane-bound hCA IX isoforms, were computationally predicted applying various methods of the advanced statistical analysis. Quantitative structure-activity relationship (QSAR) analysis indicated an impressive KI ratio (hCA II\/hCA IX) 139.1 and hCA IX inhibition constant very similar to acetazolamide (KI = 29.6 nM) for the sulfonamide derivative disubstituted with Gln. The derivatives disubstituted with Ser, Thr, and Ala showed even lower KIs (8.7, 13.1, and 8.4 nM, respectively).<\/jats:p>","DOI":"10.3390\/ijms21103661","type":"journal-article","created":{"date-parts":[[2020,5,25]],"date-time":"2020-05-25T06:43:40Z","timestamp":1590389020000},"page":"3661","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthetic Strategies and Computational Inhibition Activity Study for Triazinyl-Substituted Benzenesulfonamide Conjugates with Polar and Hydrophobic Amino Acids as Inhibitors of Carbonic Anhydrases"],"prefix":"10.3390","volume":"21","author":[{"given":"M\u00e1ria Bodn\u00e1r","family":"Mikulov\u00e1","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical Analysis and Nuclear Pharmacy, Faculty of Pharmacy, Comenius University in Bratislava, Odboj\u00e1rov 10, SK-832 32 Bratislava, Slovakia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"D\u00e1\u0161a","family":"Kru\u017elicov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Analysis and Nuclear Pharmacy, Faculty of Pharmacy, Comenius University in Bratislava, Odboj\u00e1rov 10, SK-832 32 Bratislava, Slovakia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9284-1493","authenticated-orcid":false,"given":"Daniel","family":"Pecher","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Analysis and Nuclear Pharmacy, Faculty of Pharmacy, Comenius University in Bratislava, Odboj\u00e1rov 10, SK-832 32 Bratislava, Slovakia"},{"name":"Toxicological and Antidoping Center, Faculty of Pharmacy, Comenius University in Bratislava, Odboj\u00e1rov 10, SK-832 32 Bratislava, Slovakia"}],"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":"Neurofarba Department, Section of Pharmaceutical and Nutriceutical Sciences, University of Florence, 50139 Florence, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5755-9970","authenticated-orcid":false,"given":"Peter","family":"Miku\u0161","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Analysis and Nuclear Pharmacy, Faculty of Pharmacy, Comenius University in Bratislava, Odboj\u00e1rov 10, SK-832 32 Bratislava, Slovakia"},{"name":"Toxicological and Antidoping Center, Faculty of Pharmacy, Comenius University in Bratislava, Odboj\u00e1rov 10, SK-832 32 Bratislava, Slovakia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2020,5,22]]},"reference":[{"key":"ref_1","unstructured":"Penttinen, J. 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