Anticancer carbonic anhydrase inhibitors: a patent and literature update 2018-2022

References

• Aspatwar A, Tolvanen MEE, Barker H, et al. Carbonic anhydrases in metazoan model organisms: molecules, mechanisms, and physiology. Physiol Rev. 2022;102:1327–1383.
   PubMed Web of Science ®Google Scholar
• Tashian RE. The carbonic anhydrases: widening perspectives on their evolution, expression and function. Bioassays. 1989;10:186–192.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases and metabolism. Metabolites. 2018;8:25.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Structure and function of carbonic anhydrases. Biochem J. 2016;473:2023–2032.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem. 2007;15(13):4336–4350.
   PubMed Web of Science ®Google Scholar
• Pastorekova S, Parkkila S, Pastorek J, et al. Carbonic anhydrases: current state of the art, therapeutic applications and future prospects. J Enzyme Inhib Med Chem. 2004;19(3):199–229.
   PubMed Web of Science ®Google Scholar
• Nocentini A, Supuran CT, Capasso C. An overview on the recently discovered iota-carbonic anhydrases. J Enzyme Inhib Med Chem. 2021;36(1):1988–1995.
   PubMed Web of Science ®Google Scholar
• Amedei A, Capasso C, Nannini G, et al. Microbiota, bacterial carbonic anhydrases, and modulators of their activity: links to human diseases? Mediators Inflamm. 2021;2021:6926082.
   PubMedGoogle Scholar
• Potter CPS, Harris AL. Diagnostic, prognostic and therapeutic implications of carbonic anhydrases in Cancer. Br J Cancer. 2003;89(1):2–7.
   PubMed Web of Science ®Google Scholar
• Pastorekova S, Gillies RJ. The role of carbonic anhydrase ix in cancer development: links to hypoxia, acidosis, and beyond. Cancer Metastasis Rev. 2019;38(1–2):65–77.
   PubMed Web of Science ®Google Scholar
• Waheed A, Sly WS. Carbonic anhydrase XII functions in health and disease. Gene. 2017;623:33–40.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Emerging role of carbonic anhydrase inhibitors. Clin Sci. 2021;135(10):1233–1249.
   PubMed Web of Science ®Google Scholar
• Alterio V, Hilvo M, Di Fiore A, et al. Crystal structure of the catalytic domain of the tumor-associated human carbonic anhydrase IX. Proc Natl Acad Sci USA. 2009;106(38):16233–16238.
   PubMed Web of Science ®Google Scholar
• Kannan KK, Ramanadham M, Jones TA. Structure, refinement, and function of carbonic anhydrase isozymes: refinement of human carbonic anhydrase I. Ann NY Acad Sci. 1984;429(1 Biology and C):49–60.
   PubMedGoogle Scholar
• Whittington DA, Waheed A, Ulmasov B, et al. 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.
   PubMed Web of Science ®Google Scholar
• Stams T, Nair SK, Okuyama T, et al. Crystal structure of the secretory form of membrane-associated human carbonic anhydrase IV at 2.8-A Resolution. Proc Natl Acad Sci USA. 1996;93(24):13589–13594.
   PubMed Web of Science ®Google Scholar
• Heck RW, Boriack-Sjodin PA, Qian M, et al. Structure-based design of an intramolecular proton transfer site in murine carbonic anhydrase V. Biochemistry. 1996;35(36):11605–11611.
   PubMedGoogle Scholar
• Alterio V, Pan P, Parkkila S, et al. The structural comparison between membrane-associated human carbonic anhydrases provides insights into drug design of selective inhibitors. Biopolymers. 2014;101(7):769–778.
   PubMedGoogle Scholar
• Di Fiore A, Monti SM, Hilvo M, et al. Crystal structure of human carbonic anhydrase XIII and its complex with the inhibitor Acetazolamide. Proteins. 2009;74(1):164–175.
   PubMed Web of Science ®Google Scholar
• Lindskog S, Coleman JE. The catalytic mechanism of carbonic anhydrase. Proc Natl Acad Sci U S A. 1973;70(9):2505–2508.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov. 2008;7(2):168–181.
   PubMed Web of Science ®Google Scholar
• Mishra CB, Tiwari M, Supuran CT. Progress in the development of human carbonic anhydrase inhibitors and their pharmacological applications: where are we today? Med Res Rev. 2020;40(6):2485–2565.
   PubMed Web of Science ®Google Scholar
• Nocentini A, Angeli A, Carta F, et al. Reconsidering anion inhibitors in the general context of drug design studies of modulators of activity of the classical enzyme carbonic anhydrase. J Enzyme Inhib Med Chem. 2021;36(1):561–580.
   PubMed Web of Science ®Google Scholar
• Pastorek J, Pastoreková S, Callebaut I, et al. Cloning and characterization of MN, a human tumor-associated protein with a domain homologous to carbonic anhydrase and a putative helix-Loop-Helix DNA binding segment. Oncogene. 1994;9(10):2877–2888.
   PubMed Web of Science ®Google Scholar
• Potter C, Harris AL. Hypoxia inducible carbonic anhydrase IX, marker of tumour hypoxia, survival pathway and therapy target. Cell Cycle. 2004;3(2):164–167.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibitors: an update on experimental agents for the treatment and imaging of hypoxic tumors. Expert Opin Investig Drugs. 2021;30(12):1197–1208.
   PubMed Web of Science ®Google Scholar
• McDonald PC, Swayampakula M, Dedhar S. Coordinated regulation of metabolic transporters and migration/invasion by carbonic anhydrase IX. Metabolites. 2018;8(1):E20.
   PubMed Web of Science ®Google Scholar
• Chafe SC, Vizeacoumar FS, Venkateswaran G, et al. Genome-wide synthetic lethal screen unveils novel CAIX-NFS1/xCT axis as a targetable vulnerability in hypoxic solid tumors. Sci Adv. 2021;7(35):eabj0364.
   PubMed Web of Science ®Google Scholar
• Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov. 2011;10(10):767–777.
   PubMed Web of Science ®Google Scholar
• Angeli A, Carta F, Nocentini A, et al. Carbonic anhydrase inhibitors targeting metabolism and tumor microenvironment. Metabolites. 2020;10(10):412.
   PubMed Web of Science ®Google Scholar
• Cianchi F, Vinci MC, Supuran CT, et al. Selective inhibition of carbonic anhydrase IX decreases cell proliferation and induces ceramide-mediated apoptosis in human cancer cells. J Pharmacol Exp Ther. 2010;334(3):710–719.
   PubMed Web of Science ®Google Scholar
• Lou Y, McDonald PC, Oloumi A, et al. Targeting tumor hypoxia: suppression of breast tumor growth and metastasis by novel carbonic anhydrase IX inhibitors. Cancer Res.2011;71(9):3364–3376.
   PubMed Web of Science ®Google Scholar
• Lock FE, McDonald PC, Lou Y, et al. Targeting carbonic anhydrase IX depletes breast cancer stem cells within the hypoxic niche. Oncogene. 2013;32(44):5210–5219.
   PubMed Web of Science ®Google Scholar
• Winum JY, Rami M, Scozzafava A, et al. Carbonic anhydrase IX: a new druggable target for the design of antitumor agents. Med Res Rev. 2008;28(3):445–463.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Experimental carbonic anhydrase inhibitors for the treatment of hypoxic tumors. J Exp Pharmacol. 2020;12:603–617.
   PubMedGoogle Scholar
• Benej M, Pastorekova S, Pastorek J. Carbonic anhydrase IX: regulation and role in cancer. In: Frost SC, McKenna R, editors. Carbonic anhydrase: mechanism, regulation, links to disease, and industrial applications. Springer verlag, Heidelberg: Subcellular Biochemistry; Vol. 75. 2014. p. 199–219.
   Google Scholar
• Robertson N, Potter C, Harris AL. Role of carbonic anhydrase IX in human tumor cell growth, survival, and invasion. Cancer Res. 2004;64(17):6160–6165.
   PubMed Web of Science ®Google Scholar
• Thacker PS, Sridhar Goud N, Argulwar OS, et al. Synthesis and biological evaluation of some coumarin hybrids as selective carbonic anhydrase IX and XII inhibitors. Bioorg Chem. 2020;104:104272.
   PubMed Web of Science ®Google Scholar
• Gros SJ, Holland-Cunz SG, Supuran CT, et al. Personalized treatment response assessment for rare childhood tumors using microcalorimetry-Exemplified by use of carbonic anhydrase IX and aquaporin 1 inhibitors. Int J Mol Sci. 2019;20(20):4984.
   Web of Science ®Google Scholar
• Riemann A, Güttler A, Haupt V, et al. Inhibition of carbonic anhydrase IX by ureidosulfonamide inhibitor U104 reduces prostate cancer cell growth, but does not modulate daunorubicin or cisplatin cytotoxicity. Oncol Res. 2018;26(2):191–200.
   PubMed Web of Science ®Google Scholar
• McDonald PC, Chia S, Bedard PL, et al., A phase 1 study of SLC-0111, a novel inhibitor of carbonic anhydrase IX, in patients with advanced solid tumors. Am J Clin Oncol. 2020;43(7):484–490.
   PubMed Web of Science ®Google Scholar
• Tureci O, Sahin U, Vollmar E, et al. Human carbonic anhydrase XII: CDNA cloning, expression, and chromosomal localization of a carbonic anhydrase gene that is overexpressed in some renal cell cancers. Proc Natl Acad Sci USA. 1998;95(13):7608–7613.
   PubMed Web of Science ®Google Scholar
• Gu XF, Shi CB, Zhao W. Prognostic value of carbonic anhydrase XII (CA XII) overexpression in hepatocellular carcinoma. Int J Clin Exp Pathol. 2019;12(6):2173–2183.
   PubMedGoogle Scholar
• Singh P, Sigalapalli DK, Sridhar Goud N, et al. Ureidosulfocoumarin derivatives as selective and potent carbonic anhydrase IX and XII Inhibitors. ChemMedChem. 2022;17(5):e202100725.
   PubMedGoogle Scholar
• Ivanov S, Liao SY, Ivanova A, et al. Expression of hypoxia-Inducible cell-surface transmembrane carbonic anhydrases in human cancer. Am J Pathol. 2001;158(3):905–919.
   PubMed Web of Science ®Google Scholar
• Ilie MI, Hofman V, Ortholan C, et al. Overexpression of carbonic anhydrase XII in tissues from resectable non-small cell lung cancers is a biomarker of Good Prognosis. Int J Cancer. 2011;128(7):1614–1623.
   PubMed Web of Science ®Google Scholar
• Hsieh MJ, Chen KS, Chiou HL, et al. Carbonic anhydrase XII promotes invasion and migration ability of MDA-MB-231 breast cancer cells through the p38 MAPK signaling pathway. Eur J Cell Biol. 2010;89(8):598–606.
   PubMed Web of Science ®Google Scholar
• Alterio V, Kellner M, Esposito D, et al. Biochemical and structural insights into carbonic anhydrase XII/Fab6A10 complex. J Mol Biol. 2019;431(24):4910–4921.
   PubMed Web of Science ®Google Scholar
• Krasavin M, Kalinin S, Sharonova T, et al. Inhibitory activity against carbonic anhydrase IX and XII as a candidate selection criterion in the development of new anticancer agents. J Enzyme Inhib Med Chem. 2020;35(1):1555–1561.
   PubMed Web of Science ®Google Scholar
• Nocentini A, Supuran CT. Carbonic anhydrase inhibitors as antitumor/antimetastatic agents: a patent review (2008–2018). Expert Opin Ther Pat. 2018;28(10):729–740.
   PubMed Web of Science ®Google Scholar
• Testa C, Papini AM, Zeidler R, et al. First studies on tumor associated carbonic anhydrases IX and XII monoclonal antibodies conjugated to small molecule inhibitors. J Enzyme Inhib Med Chem. 2022;37(1):592–596.
   PubMed Web of Science ®Google Scholar
• Eldehna WM, Taghour MS, Al-Warhi T, 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.
   PubMed Web of Science ®Google Scholar
• Fuentes-Aguilar A, Merino-Montiel P, Montiel-Smith S, et al. 2-Aminobenzoxazole-Appended coumarins as potent and selective inhibitors of tumour-associated carbonic anhydrases. J Enzyme Inhib Med Chem. 2022;37(1):168–177.
   PubMed Web of Science ®Google Scholar
• Havránková E, Garaj V, Mascaretti Š, et al. Novel 1,3,5-triazinyl aminobenzenesulfonamides incorporating aminoalcohol, aminochalcone and aminostilbene structural motifs as potent anti-VRE agents, and carbonic anhydrases I, II, VII, IX, and XII Inhibitors. Int J Mol Sci. 2021;23(1):231.
   PubMedGoogle Scholar
• Chandra KM, Goud NS, Arifuddin M, et al. 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.
   PubMed Web of Science ®Google Scholar
• Ghorab MM, Soliman AM, Bua S, et al. Biological evaluation, radiosensitizing activity and structural insights of novel halogenated quinazoline-sulfonamide conjugates as selective human carbonic anhydrases IX/XII inhibitors. Bioorg Chem. 2021;107:104618.
   PubMed Web of Science ®Google Scholar
• Grandāne A, Nocentini A, Domračeva I, et al. Development of oxathiino[6,5-b]Pyridine 2,2-Dioxide derivatives as selective inhibitors of tumor-related carbonic anhydrases IX and XII. Eur J Med Chem. 2020;200:112300.
   PubMed Web of Science ®Google Scholar
• Akocak S, Güzel-Akdemir Ö, Kishore Kumar SR, et al. Pyridinium derivatives of 3-Aminobenzenesulfonamide are nanomolar-potent inhibitors of tumor-expressed carbonic anhydrase isozymes CA IX and CA XII. Bioorg Chem. 2020;103:104204.
   PubMed Web of Science ®Google Scholar
• Alhameed RA, Berrino E, Almarhoon Z, et al. A class of carbonic anhydrase IX/XII - selective carboxylate inhibitors. J Enzyme Inhib Med Chem. 2020;35:549–554.
   PubMed Web of Science ®Google Scholar
• Lambin P, Winum JY, Supuran C. Cancer targeting using carbonic anhydrase isoform IX inhibitors. 2015.
   Google Scholar
• Zaihui Z. Aryl sulfonamide compounds as carbonic anhydrase inhibitors and their therapeutic use. 2017.
   Google Scholar
• Brynda J, Cigler P, Gruner B, et al. Carbonic anhydrase inhibitors and method of their production. 2016.
   Google Scholar
• Matulis D, Capkauskaite E, Zaksauskas A, et al. Selective inhibitors of carbonic anhydrase. 2017.
   Google Scholar
• Matulis D, Virginija D, Asta Z. Fluorinated benzene sulfonamides as inhibitors of carbonic anhydrase. US20150266900A1. 2015.
   Google Scholar
• Riganti C, Salaroglio IC, Mujumdar P, et al. Carbonic anhydrase inhibitors. 2018.
   Google Scholar
• Lenferink AEG, Oconnor MD, Marcil A, et al. Carbonic anhydrase IX-specific antibodies and uses thereof. WO 2016/199097 A1. 2016.
   Google Scholar
• Krall N, Decurtins W, Scheuermann J, et al. Small molecule drug conjugates. 2015.
   Google Scholar
• Low PS, Pengcheng LU. Carbonic anhydrase IX targeting agents and methods. 2017.
   Google Scholar
• Baldassarre L, Chen L, Lani R, et al. Bicyclic peptide ligands specific for CA IX. 2020.
   Google Scholar
• Sahin F, Mohammed E, Celik M. 2-(3-(2-methyl-6-(p-tolyl) pyridine-3-yl) ureido) benzenesulfonamide and derivatives as inhibitor of carbonic anhydrase ix for the treatment of cancer. 2021.
   Google Scholar
• Mao Z, Zhou D, Yang G, et al. Carbonic anhydrase (CA)-targeting tetravalent platinum coordination compound, preparation method and application thereof as or to preparing antineoplastic. 2019.
   Google Scholar
• Moon YR, Ji GY. Antibody binding to carbonic anhydrase and use thereof. 2017.
   Google Scholar
• Zhang Z. Arylsulfonamide compounds as carbonic anhydrase inhibitors and their therapeutic use. 2015.
   Google Scholar
• Xinhua H, Zhou T, Yang C. Oxadiazole substituted benzene sulfonamide compound, preparation method thereof and application of oxadiazole substituted benzene sulfonamide compound as carbonic anhydrase inhibitor. 2019.
   Google Scholar
• Lambin P, Winum JY. Dual action carbonic anhydrase inhibitors. WO2015/025283 A2. 2015.
   Google Scholar
• Lambin P, Winum JY. sulfonamide, sulfamate and sulfamide derivatives of anti-cancer agents. 2016.
   Google Scholar
• Sau S, Iyer AK, Alsaab H. Method of treatment for solid tumors containing hypoxia and or stroma features. 2020.
   Google Scholar
• Lenferink EG, Oconnor MD. High affinity monoclonal antibodies (mabs) against cell surface expressed human carbonic anhydrase IX (hCA IX) and uses thereof. US2021/0238302A1. 2021.
   Google Scholar
• Lenferink AEG, Connor MD, Marcil A, et al. carbonic anhydrase ix - specific antibodies and uses thereof. US010487153B2. 2019.
   Google Scholar
• Haaga J, Haaga R. Targeted treatment of anerobic cancer. US2017056350. 2017.
   Google Scholar
• Haaga J, Haaga R. Targeted treatment of anerobic cancer. US20160279084. 2017.
   Google Scholar
• Krall N, Decurtins W, Neri D, et al. Small molecule drug conjugates. 2017.
   Google Scholar
• Bonardi A, Nocentini A, Bua S, et al. Sulfonamide inhibitors of human carbonic anhydrases designed through a three-tails approach: improving ligand/isoform matching and selectivity of action. J Med Chem.2020;63(13):7422–7444.
   PubMed Web of Science ®Google Scholar
• Bonardi A, Bua S, Combs J, et al. The three-tails approach as a new strategy to improve selectivity of action of sulfonamide inhibitors against tumor-associated carbonic anhydrase IX and XII. J Enzyme Inhib Med Chem. 2022;37(1):930–939.
   PubMed Web of Science ®Google Scholar
• Said MF, George RF, Petreni A, et al. Synthesis, molecular modelling and QSAR study of new N- phenylacetamide-2-oxoindole benzensulfonamide conjugates as carbonic anhydrase inhibitors with antiproliferative activity. J Enzyme Inhib Med Chem. 2022;37(1):701–717.
   PubMed Web of Science ®Google Scholar
• Giovannuzzi S, D’Ambrosio M, Luceri C, et al. Aromatic sulfonamides including a sulfonic acid tail: new membrane impermeant carbonic anhydrase inhibitors for targeting selectively the cancer-associated isoforms. Int J Mol Sci. 2021;23(1):461.
   PubMedGoogle Scholar
• Onyılmaz M, Koca M, Bonardi A, et al. Isocoumarins: a new class of selective carbonic anhydrase IX and XII inhibitors. J Enzyme Inhib Med Chem. 2022;37(1):743–748.
   PubMed Web of Science ®Google Scholar
• Petreni A, Osman SM, Alasmary FA, et al. Binding site comparison for coumarin inhibitors and amine/amino acid activators of human carbonic anhydrases. Eur J Med Chem. 2021;226:113875.
   PubMed Web of Science ®Google Scholar
• Biagiotti G, Angeli A, Giacomini A, et al. Glyco-Coated CdSe/ZnS quantum dots as nanoprobes for carbonic anhydrase IX imaging in cancer cells. ACS Appl Nano Mater.2021;4(12):14153–14160.
   PubMed Web of Science ®Google Scholar
• Dixon SJ, Lemberg KM, Lamprecht MR, et al. Ferroptosis: an iron-dependent form of nonapoptotic cell death. Cell. 2012;149(5):1060–1072.
   PubMed Web of Science ®Google Scholar
• Mussi S, Rezzola S, Chiodelli P, et al. Antiproliferative effects of sulphonamide carbonic anhydrase inhibitors C18, SLC-0111 and Acetazolamide on bladder, glioblastoma and pancreatic cancer cell lines. J Enzyme Inhib Med Chem. 2022;37(1):280–286.
   PubMed Web of Science ®Google Scholar
• Huo Z, Bilang R, Supuran CT, et al. Perfusion-based bioreactor culture and isothermal microcalorimetry for preclinical drug testing with the carbonic anhydrase inhibitor SLC-0111 in patient-derived neuroblastoma. Int J Mol Sci. 2022;23(6):3128.
   PubMedGoogle Scholar
• Yusuf ZS, Uysal TK, Simsek E, et al. The inhibitory effect of boric acid on hypoxia-regulated tumour-associated carbonic anhydrase IX. J Enzyme Inhib Med Chem. 2022;37(1):1340–1345.
   PubMed Web of Science ®Google Scholar