3v5g › Citations

Development of potent carbonic anhydrase inhibitors incorporating both sulfonamide and sulfamide groups.

D'Ambrosio K, Smaine FZ, Carta F, De Simone G, Winum JY, Supuran CT
J Med Chem 55 6776-83 (2012)
Cited: 32 times
EuropePMC logo PMID: 22775345

Abstract

A series of compounds incorporating both sulfonamide and sulfamide as zinc-binding groups (ZBGs) are reported as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). Crystallographic studies on the complex of hCA II with the lead compound of this series, namely, 4-sulfamido-benzenesulfonamide, revealed the binding of two molecules in the enzyme active site cavity, the first one canonically coordinated to the zinc ion by means of the sulfonamide group and the second one located at the entrance of the cavity. This observation led to the design of elongated molecules incorporating these two ZBGs, separated by a linker of proper length, to allow the simultaneous binding to these different sites. The "long" inhibitors indeed showed around 10 times better enzyme inhibitory properties as compared to the shorter molecules against four physiologically relevant human (h) isoforms, hCA I, II, IX, and XII.

Reviews citing this publication (6)

  1. Inhibition of carbonic anhydrase IX targets primary tumors, metastases, and cancer stem cells: Three for the price of one. Supuran CT, Alterio V, Di Fiore A, D' Ambrosio K, Carta F, Monti SM, De Simone G. Med Res Rev 38 1799-1836 (2018)
  2. Emerging trends in enzyme inhibition by multivalent nanoconstructs. Kanfar N, Bartolami E, Zelli R, Marra A, Winum JY, Ulrich S, Dumy P. Org Biomol Chem 13 9894-9906 (2015)
  3. Thermodynamic, kinetic, and structural parameterization of human carbonic anhydrase interactions toward enhanced inhibitor design. Linkuvienė V, Zubrienė A, Manakova E, Petrauskas V, Baranauskienė L, Zakšauskas A, Smirnov A, Gražulis S, Ladbury JE, Matulis D. Q Rev Biophys 51 e10 (2018)
  4. Novel approaches for designing drugs that interfere with pH regulation. Berrino E, Supuran CT. Expert Opin Drug Discov 14 231-248 (2019)
  5. Multivalent Carbonic Anhydrases Inhibitors. Carta F, Dumy P, Supuran CT, Winum JY. Int J Mol Sci 20 E5352 (2019)
  6. α-CAs from Photosynthetic Organisms. Langella E, Di Fiore A, Alterio V, Monti SM, De Simone G, D'Ambrosio K. Int J Mol Sci 23 12045 (2022)

Articles citing this publication (26)

  1. Design, synthesis and evaluation of N-substituted saccharin derivatives as selective inhibitors of tumor-associated carbonic anhydrase XII. D'Ascenzio M, Carradori S, De Monte C, Secci D, Ceruso M, Supuran CT. Bioorg Med Chem 22 1821-1831 (2014)
  2. Novel Sulfamide-Containing Compounds as Selective Carbonic Anhydrase I Inhibitors. Berrino E, Bua S, Mori M, Botta M, Murthy VS, Vijayakumar V, Tamboli Y, Bartolucci G, Mugelli A, Cerbai E, Supuran CT, Carta F. Molecules 22 E1049 (2017)
  3. Synthesis and bioactivities of halogen bearing phenolic chalcones and their corresponding bis Mannich bases. Yamali C, Gul HI, Sakagami H, Supuran CT. J Enzyme Inhib Med Chem 31 125-131 (2016)
  4. 5-Substituted-(1,2,3-triazol-4-yl)thiophene-2-sulfonamides strongly inhibit human carbonic anhydrases I, II, IX and XII: solution and X-ray crystallographic studies. Leitans J, Sprudza A, Tanc M, Vozny I, Zalubovskis R, Tars K, Supuran CT. Bioorg Med Chem 21 5130-5138 (2013)
  5. The inhibitory effects of phenolic Mannich bases on carbonic anhydrase I and II isoenzymes. Yamali C, Tugrak M, Gul HI, Tanc M, Supuran CT. J Enzyme Inhib Med Chem 31 1678-1681 (2016)
  6. Carbonic anhydrase inhibition and cytotoxicity studies of Mannich base derivatives of thymol. Inci Gul H, Yamali C, Tugce Yasa A, Unluer E, Sakagami H, Tanc M, Supuran CT. J Enzyme Inhib Med Chem 31 1375-1380 (2016)
  7. Effect of incorporating a thiophene tail in the scaffold of acetazolamide on the inhibition of human carbonic anhydrase isoforms I, II, IX and XII. Biswas S, McKenna R, Supuran CT. Bioorg Med Chem Lett 23 5646-5649 (2013)
  8. Discovery of dehydroabietic acid sulfonamide based derivatives as selective matrix metalloproteinases inactivators that inhibit cell migration and proliferation. Huang RZ, Liang GB, Huang XC, Zhang B, Zhou MM, Liao ZX, Wang HS. Eur J Med Chem 138 979-992 (2017)
  9. Designing, synthesis and bioactivities of 4-[3-(4-hydroxyphenyl)-5-aryl-4,5-dihydro-pyrazol-1-yl]benzenesulfonamides. Gul HI, Mete E, Eren SE, Sakagami H, Yamali C, Supuran CT. J Enzyme Inhib Med Chem 32 169-175 (2017)
  10. In Vivo Evaluation of Selective Carbonic Anhydrase Inhibitors as Potential Anticonvulsant Agents. Bruno E, Buemi MR, De Luca L, Ferro S, Monforte AM, Supuran CT, Vullo D, De Sarro G, Russo E, Gitto R. ChemMedChem 11 1812-1818 (2016)
  11. Azobenzene-based inhibitors of human carbonic anhydrase II. Runtsch LS, Barber DM, Mayer P, Groll M, Trauner D, Broichhagen J. Beilstein J Org Chem 11 1129-1135 (2015)
  12. Synthesis of novel acridine and bis acridine sulfonamides with effective inhibitory activity against the cytosolic carbonic anhydrase isoforms II and VII. Ulus R, Yeşildağ I, Tanç M, Bülbül M, Kaya M, Supuran CT. Bioorg Med Chem 21 5799-5805 (2013)
  13. Synthesis of novel benzenesulfamide derivatives with inhibitory activity against human cytosolic carbonic anhydrase I and II and Vibrio cholerae α- and β-class enzymes. Bua S, Berrino E, Del Prete S, Murthy VS, Vijayakumar V, Tamboli Y, Capasso C, Cerbai E, Mugelli A, Carta F, Supuran CT. J Enzyme Inhib Med Chem 33 1125-1136 (2018)
  14. Ferrier sulfamidoglycosylation of glycals catalyzed by nitrosonium tetrafluoroborate: towards new carbonic anhydrase glycoinhibitors. Ombouma J, Vullo D, Supuran CT, Winum JY. Bioorg Med Chem 22 6353-6359 (2014)
  15. Nitroimidazole-based inhibitors DTP338 and DTP348 are safe for zebrafish embryos and efficiently inhibit the activity of human CA IX in Xenopus oocytes. Aspatwar A, Becker HM, Parvathaneni NK, Hammaren M, Svorjova A, Barker H, Supuran CT, Dubois L, Lambin P, Parikka M, Parkkila S, Winum JY. J Enzyme Inhib Med Chem 33 1064-1073 (2018)
  16. Synthesis, antioxidant and carbonic anhydrase I and II inhibitory activities of novel sulphonamide-substituted coumarylthiazole derivatives. Kurt BZ, Sönmez F, Bilen Ç, Ergun A, Gençer N, Arslan O, Kucukislamoglu M. J Enzyme Inhib Med Chem 31 991-998 (2016)
  17. Structural study of the location of the phenyl tail of benzene sulfonamides and the effect on human carbonic anhydrase inhibition. Güzel-Akdemir O, Biswas S, Lastra K, McKenna R, Supuran CT. Bioorg Med Chem 21 6674-6680 (2013)
  18. Discovery of a series of small molecules as potent histone deacetylase inhibitors. Zhang L, Wang X, Li X, Xu W. J Enzyme Inhib Med Chem 29 333-337 (2014)
  19. Toxicity evaluation of sulfamides and coumarins that efficiently inhibit human carbonic anhydrases. Aspatwar A, Berrino E, Bua S, Carta F, Capasso C, Parkkila S, Supuran CT. J Enzyme Inhib Med Chem 35 1765-1772 (2020)
  20. Biochemical, structural, and computational studies of a γ-carbonic anhydrase from the pathogenic bacterium Burkholderia pseudomallei. Di Fiore A, De Luca V, Langella E, Nocentini A, Buonanno M, Monti SM, Supuran CT, Capasso C, De Simone G. Comput Struct Biotechnol J 20 4185-4194 (2022)
  21. Design of 4-Substituted Sulfonamidobenzoic Acid Derivatives Targeting Coxsackievirus B3. Shetnev AA, Volobueva AS, Panova VA, Zarubaev VV, Baykov SV. Life (Basel) 12 1832 (2022)
  22. Inhibitory effects of benzimidazole containing new phenolic Mannich bases on human carbonic anhydrase isoforms hCA I and II. Gul HI, Yazici Z, Tanc M, Supuran CT. J Enzyme Inhib Med Chem 31 1540-1544 (2016)
  23. Synthesis, Carbonic Anhydrase II/IX/XII Inhibition, DFT, and Molecular Docking Studies of Hydrazide-Sulfonamide Hybrids of 4-Methylsalicyl- and Acyl-Substituted Hydrazide. Khushal A, Mumtaz A, Shadoul WA, Zaidi SHM, Rafique H, Munir A, Maalik A, Shah SJA, Baig A, Khawaja W, Al-Rashida M, Hashmi MA, Iqbal J. Biomed Res Int 2022 5293349 (2022)
  24. 4-(3-Phenyl-4-(3,4,5-trimethoxybenzoyl)-1H-pyrrol-1-yl)benzenesulfonamide, a Novel Carbonic Anhydrase and Wnt/β-Catenin Signaling Pathway Dual-Targeting Inhibitor with Potent Activity against Multidrug Resistant Cancer Cells. Masci D, Puxeddu M, Di Magno L, D'Ambrosio M, Parisi A, Nalli M, Bai R, Coluccia A, Sciò P, Orlando V, D'Angelo S, Biagioni S, Urbani A, Hamel E, Nocentini A, Filiberti S, Turati M, Ronca R, Kopecka J, Riganti C, Fionda C, Bordone R, Della Rocca G, Canettieri G, Supuran CT, Silvestri R, La Regina G. J Med Chem 66 14824-14842 (2023)
  25. Evaluation of carbonic anhydrase and paraoxonase inhibition activities and molecular docking studies of highly water-soluble sulfonated phthalocyanines. GÜzel E, SÖnmez F, Erkan S, ÇikrikÇi K, ErgÜn A, GenÇer N, Arslan O, KoÇak MB. Turk J Chem 44 1565-1573 (2020)
  26. Synthesis and Evaluation of Amide and Thiourea Derivatives as Carbonic Anhydrase (CA) Inhibitors. Hussain Z, Mahmood A, Shah Q, Imran A, Mughal EU, Khan W, Baig A, Iqbal J, Mumtaz A. ACS Omega 7 47251-47264 (2022)


Quick links