1,816
Views
6
CrossRef citations to date
0
Altmetric
Research Paper

Synthesis and biological evaluation of new 3-substituted coumarin derivatives as selective inhibitors of human carbonic anhydrase IX and XII

, , ORCID Icon, , , , , ORCID Icon & show all
Article: 2185760 | Received 16 Jan 2023, Accepted 24 Feb 2023, Published online: 06 Mar 2023

References

  • Zengin Kurt B, Sonmez F, Ozturk D, Akdemir A, Angeli A, Supuran CT. Synthesis of coumarin-sulfonamide derivatives and determination of their cytotoxicity, carbonic anhydrase inhibitory and molecular docking studies. Eur J Med Chem. 2019;183:111702.
  • Thacker PS, Sridhar Goud N, Argulwar OS, Soman J, Angeli A, Alvala M, Arifuddin M, Supuran CT. Synthesis and biological evaluation of some coumarin hybrids as selective carbonic anhydrase IX and XII inhibitors. Bioorg Chem. 2020;104:104272.
  • Aimene Y, Eychenne R, Rodriguez F, Mallet-Ladeira S, Saffon-Merceron N, Winum J-Y, Nocentini A, Supuran CT, Benoist E, Seridi A. Synthesis, crystal structure, inhibitory activity and molecular docking of coumarins/sulfonamides containing triazolyl pyridine moiety as potent selective carbonic anhydrase IX and XII inhibitors. Crystals. 2021;11(9):1076.
  • McDonald PC, Chafe SC, Supuran CT, Dedhar S. Cancer therapeutic targeting of hypoxia induced carbonic anhydrase IX: from bench to bedside. Cancers. 2022;14(14):3297.
  • Mahon BP, Pinard MA, McKenna R. Targeting carbonic anhydrase IX activity and expression. Molecules. 2015;20(2):2323–2348.
  • Bonardi A, Bua S, Combs J, Lomelino C, Andring J, Osman SM, Toti A, Di Cesare Mannelli L, Gratteri P, Ghelardini C, et al. The three-tails approach as a new strategy to improve selectivity of action of sulphonamide inhibitors against tumour-associated carbonic anhydrase IX and XII. J Enzyme Inhib Med Chem. 2022;37(1):930–939.
  • Neri D, Supuran CT. Interfering with PH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov. 2011;10(10):767–777.
  • Alterio V, Di Fiore A, D'Ambrosio K, Supuran CT, De Simone G. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? Chem Rev. 2012;112(8):4421–4468.
  • Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem. 2016;31(3):345–360.
  • Maresca A, Temperini C, Vu H, Pham NB, Poulsen S-A, Scozzafava A, Quinn RJ, Supuran CT. Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors. J Am Chem Soc. 2009;131(8):3057–3062.
  • Abdel-Aziz AA-M, El-Azab AS, Ceruso M, Supuran CT. Carbonic anhydrase inhibitory activity of sulfonamides and carboxylic acids incorporating cyclic imide scaffolds. Bioorg Med Chem Lett. 2014;24(22):5185–5189.
  • Nocentini A, Lucidi A, Perut F, Massa A, Tomaselli D, Gratteri P, Baldini N, Rotili D, Mai A, Supuran CT. α,γ-Diketocarboxylic acids and their esters act as carbonic anhydrase IX and XII selective inhibitors. ACS Med Chem Lett. 2019;10(4):661–665.
  • Giovannuzzi S, Hewitt CS, Nocentini A, Capasso C, Flaherty DP, Supuran CT. Coumarins effectively inhibit bacterial α-carbonic anhydrases. J Enzyme Inhib Med Chem. 2022;37(1):333–338.
  • Lipeeva AV, Zakharov DO, Burova LG, Frolova TS, Baev DS, Shirokikh IV, Evstropov AN, Sinitsyna OI, Tolsikova TG, Shults EE. Design, synthesis and antibacterial activity of coumarin-1,2,3-triazole hybrids obtained from natural furocoumarin peucedanin. Molecules. 2019;24(11):2126.
  • Chougala BM, Samundeeswari S, Holiyachi M, Shastri LA, Dodamani S, Jalalpure S, Dixit SR, Joshi SD, Sunagar VA. Synthesis, characterization and molecular docking studies of substituted 4-coumarinylpyrano[2,3-c]pyrazole derivatives as potent antibacterial and anti-inflammatory agents. Eur J Med Chem. 2017;125:101–116.
  • Fayed EA, Sabour R, Harras MF, Mehany ABM. Design, synthesis, biological evaluation and molecular modeling of new coumarin derivatives as potent anticancer agents. Med Chem Res. 2019;28(8):1284–1297.
  • Thacker PS, Srikanth D, Angeli A, Singh P, Chinchilli KK, Arifuddin M, Supuran CT. Coumarin‐thiourea hybrids show potent carbonic anhydrase IX and XIII inhibitory action. ChemMedChem. 2021;16(8):1252–1256.
  • Abdelrahman MA, Ibrahim HS, Nocentini A, Eldehna WM, Bonardi A, Abdel-Aziz HA, Gratteri P, Abou-Seri SM, Supuran CT. Novel 3-substituted coumarins as selective human carbonic anhydrase IX and XII inhibitors: synthesis, biological and molecular dynamics analysis. Eur J Med Chem. 2021;209:112897.
  • Tawfik HO, Shaldam MA, Nocentini A, Salem R, Almahli H, Al-Rashood ST, Supuran CT, Eldehna WM. Novel 3-(6-methylpyridin-2-yl)coumarin-based chalcones as selective inhibitors of cancer-related carbonic anhydrases IX and XII endowed with anti-proliferative activity. J Enzyme Inhib Med Chem. 2022;37(1):1043–1052.
  • Chandra KM, Goud NS, Arifuddin M, Alvala M, Alvala R, Angeli A, Supuran CT. Synthesis and biological evaluation of novel 4,7-disubstituted coumarins as selective tumor-associated carbonic anhydrase IX and XII inhibitors. Bioorg Med Chem Lett. 2021;39:127877.
  • Thacker PS, Alvala M, Arifuddin M, Angeli A, Supuran CT. Design, synthesis and biological evaluation of coumarin-3-carboxamides as selective carbonic anhydrase IX and XII inhibitors. Bioorg Chem. 2019;86:386–392.
  • Bozdag M, Ferraroni M, Carta F, Vullo D, Lucarini L, Orlandini E, Rossello A, Nuti E, Scozzafava A, Masini E, et al. Structural insights on carbonic anhydrase inhibitory action, isoform selectivity, and potency of sulfonamides and coumarins incorporating arylsulfonylureido groups. J Med Chem. 2014;57(21):9152–9167.
  • Eldehna WM, Taghour MS, Al-Warhi T, Nocentini A, Elbadawi MM, Mahdy HA, Abdelrahman MA, Alotaibi OJ, Aljaeed N, Elimam DM, et al. Discovery of 2,4-thiazolidinedione-tethered coumarins as novel selective inhibitors for carbonic anhydrase IX and XII isoforms. J Enzyme Inhib Med Chem. 2022;37(1):531–541.
  • Ibrahim HS, Abdelrahman MA, Nocentini A, Bua S, Abdel-Aziz HA, Supuran CT, Abou-Seri SM, Eldehna WM. Insights into the effect of elaborating coumarin-based aryl enaminones with sulfonamide or carboxylic acid functionality on carbonic anhydrase inhibitory potency and selectivity. Bioorg Chem. 2022;126:105888.
  • Mesiti F, Gaspar A, Chavarria D, Maruca A, Rocca R, Gil Martins E, Barreiro S, Silva R, Fernandes C, Gul S, et al. Mapping chromone-3-phenylcarboxamide pharmacophore: Quid Est Veritas? J Med Chem. 2021; 64 (15):11169–11182.
  • Zhang J, Jiang C-S. Synthesis and evaluation of coumarin/piperazine hybrids as acetylcholinesterase inhibitors. Med Chem Res. 2018;27(6):1717–1727.
  • Woods LL, Johnson D. Coumarins from 2-hydroxyaryl acids and malonic acid. J Org Chem. 1965;30(12):4343–4344.
  • Akunuri R, Veerareddy V, Kaul G, Akhir A, Unnissa T, Parupalli R, Madhavi YV, Chopra S, Nanduri S. Synthesis and antibacterial evaluation of (E)-1-(1H-indol-3-yl) ethanone O-benzyl oxime derivatives against MRSA and VRSA strains. Bioorg Chem. 2021;116:105288.
  • Khalifah RG. The carbon dioxide hydration activity of carbonic anhydrase: I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem. 1971;246(8):2561–2573.
  • Maresca A, Temperini C, Pochet L, Masereel B, Scozzafava A, Supuran CT. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem. 2010;53(1):335–344.
  • Carta F, Temperini C, Innocenti A, Scozzafava A, Kaila K, Supuran CT. Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule. J Med Chem. 2010;53(15):5511–5522.
  • Hilvo M, Baranauskiene L, Salzano AM, Scaloni A, Matulis D, Innocenti A, Scozzafava A, Monti SM, Fiore AD, Simone GD, et al. Biochemical characterization of CA IX, one of the most active carbonic anhydrase isozymes. J Biol Chem. 2008;283(41):27799–27809.
  • Di Fiore A, Truppo E, Supuran CT, Alterio V, Dathan N, Bootorabi F, Parkkila S, Monti SM, Simone GD. Crystal structure of the C183S/C217S mutant of human CA VII in complex with acetazolamide. Bioorg Med Chem Lett. 2010;20(17):5023–5026.
  • Mahon BP, Bhatt A, Socorro L, Driscoll JM, Okoh C, Lomelino CL, Mboge MY, Kurian JJ, Tu C, Agbandje-McKenna M, et al. The structure of carbonic anhydrase IX Is adapted for low-pH catalysis. Biochemistry. 2016;55(33):4642–4653.
  • Whittington DA, Waheed A, Ulmasov B, Shah GN, Grubb JH, Sly WS, Christianson DW. Crystal structure of the dimeric extracellular domain of human carbonic anhydrase XII, a bitopic membrane protein overexpressed in certain cancer tumor cells. Proc Natl Acad Sci USA. 2001;98(17):9545–9550.
  • Protein Preparation Wizard. New York (NY): Schrödinger, LLC; 2021.
  • LigPrep. New York (NY): Schrödinger, LLC; 2021.
  • Glide. New York (NY): Schrödinger, LLC; 2021.
  • Prime. New York (NY): Schrödinger, LLC; 2021.
  • Schrödinger Release 2021-2: Desmond Molecular Dynamics System. New York (NY): D. E. Shaw Research; 2021.
  • Pustenko A, Nocentini A, Gratteri P, Bonardi A, Vozny I, Žalubovskis R, Supuran CT. The antibiotic furagin and its derivatives are isoform-selective human carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem. 2020;35(1):1011–1020.