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Volumn 57, Issue 20, 2014, Pages 8635-8645

Structural insights into carbonic anhydrase IX isoform specificity of carbohydrate-based sulfamates

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CARBOHYDRATE DERIVATIVE; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IX; CARBONIC ANHYDRASE IX INHIBITOR; ISOENZYME; SULFAMATE DERIVATIVE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG; ZINC; CA9 PROTEIN, HUMAN; CARBONATE DEHYDRATASE; MOLECULAR LIBRARY; SULFAMIC ACID; SULFONIC ACID DERIVATIVE; TUMOR ANTIGEN; TUMOR MARKER;

EID: 84908383763     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm5012935     Document Type: Article
Times cited : (46)

References (50)
  • 3
    • 78650750585 scopus 로고    scopus 로고
    • Role of hypoxia and EGF on expression, activity, localization and phosphorylation of carbonic anhydrase IX in MDA-MB-231 breast cancer cells
    • Li, Y.; Wang, H.; Tu, C.; Shiverick, K. T.; Silverman, D. N.; Frost, S. C. Role of hypoxia and EGF on expression, activity, localization and phosphorylation of carbonic anhydrase IX in MDA-MB-231 breast cancer cells Biochim. Biophys. Acta 2011, 1813, 159-167
    • (2011) Biochim. Biophys. Acta , vol.1813 , pp. 159-167
    • Li, Y.1    Wang, H.2    Tu, C.3    Shiverick, K.T.4    Silverman, D.N.5    Frost, S.C.6
  • 4
    • 84908377710 scopus 로고    scopus 로고
    • Regulation and role of carbonic anhydrase IX and use as a biomarker and therapeutic target in cancer
    • Mahon, B. P.; McKenna, R. Regulation and role of carbonic anhydrase IX and use as a biomarker and therapeutic target in cancer Res. Trends Curr. Top. Biochem. Res. 2013, 15, 1
    • (2013) Res. Trends Curr. Top. Biochem. Res. , vol.15 , pp. 1
    • Mahon, B.P.1    McKenna, R.2
  • 5
    • 80053563164 scopus 로고    scopus 로고
    • Interfering with pH regulation in tumours as a therapeutic strategy
    • Neri, D.; Supuran, C. T. Interfering with pH regulation in tumours as a therapeutic strategy Nature Rev. Drug Discovery 2011, 10, 767-777
    • (2011) Nature Rev. Drug Discovery , vol.10 , pp. 767-777
    • Neri, D.1    Supuran, C.T.2
  • 6
    • 38849143765 scopus 로고    scopus 로고
    • Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators
    • Supuran, C. T. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators Nature Rev. Drug Discovery 2008, 7, 168-181
    • (2008) Nature Rev. Drug Discovery , vol.7 , pp. 168-181
    • Supuran, C.T.1
  • 7
    • 0035925098 scopus 로고    scopus 로고
    • Tumor hypoxia: Definitions and current clinical, biologic, and molecular aspects
    • Höckel, M.; Vaupel, P. Tumor hypoxia: Definitions and current clinical, biologic, and molecular aspects J. Natl. Cancer Inst. 2001, 93, 266-276
    • (2001) J. Natl. Cancer Inst. , vol.93 , pp. 266-276
    • Höckel, M.1    Vaupel, P.2
  • 9
    • 84859870939 scopus 로고    scopus 로고
    • Recent developments in targeting carbonic anhydrase IX for cancer therapeutics
    • McDonald, P. C.; Winum, J.-Y.; Supuran, C. T.; Dedhar, S. Recent developments in targeting carbonic anhydrase IX for cancer therapeutics Oncotarget 2012, 3, 84-97
    • (2012) Oncotarget , vol.3 , pp. 84-97
    • McDonald, P.C.1    Winum, J.-Y.2    Supuran, C.T.3    Dedhar, S.4
  • 12
    • 33750471952 scopus 로고    scopus 로고
    • A novel class of carbonic anhydrase inhibitors: Glycoconjugate benzene sulfonamides prepared by "click-tailing"
    • Wilkinson, B. L.; Bornaghi, L. F.; Houston, T. A.; Innocenti, A.; Supuran, C. T.; Poulsen, S.-A. A novel class of carbonic anhydrase inhibitors: glycoconjugate benzene sulfonamides prepared by "click-tailing" J. Med. Chem. 2006, 49, 6539-6548
    • (2006) J. Med. Chem. , vol.49 , pp. 6539-6548
    • Wilkinson, B.L.1    Bornaghi, L.F.2    Houston, T.A.3    Innocenti, A.4    Supuran, C.T.5    Poulsen, S.-A.6
  • 13
    • 34147144592 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Inhibition of isozymes I, II, and IX with triazole-linked O -glycosides of benzene sulfonamides
    • Wilkinson, B. L.; Bornaghi, L. F.; Houston, T. A.; Innocenti, A.; Vullo, D.; Supuran, C. T.; Poulsen, S.-A. Carbonic anhydrase inhibitors: inhibition of isozymes I, II, and IX with triazole-linked O -glycosides of benzene sulfonamides J. Med. Chem. 2007, 50, 1651-1657
    • (2007) J. Med. Chem. , vol.50 , pp. 1651-1657
    • Wilkinson, B.L.1    Bornaghi, L.F.2    Houston, T.A.3    Innocenti, A.4    Vullo, D.5    Supuran, C.T.6    Poulsen, S.-A.7
  • 14
    • 33846575753 scopus 로고    scopus 로고
    • Inhibition of membrane-associated carbonic anhydrase isozymes IX, XII and XIV with a library of glycoconjugate benzenesulfonamides
    • Wilkinson, B. L.; Bornaghi, L. F.; Houston, T. A.; Innocenti, A.; Vullo, D.; Supuran, C. T.; Poulsen, S.-A. Inhibition of membrane-associated carbonic anhydrase isozymes IX, XII and XIV with a library of glycoconjugate benzenesulfonamides Bioorg. Med. Chem. Lett. 2007, 17, 987-992
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 987-992
    • Wilkinson, B.L.1    Bornaghi, L.F.2    Houston, T.A.3    Innocenti, A.4    Vullo, D.5    Supuran, C.T.6    Poulsen, S.-A.7
  • 15
    • 41149177054 scopus 로고    scopus 로고
    • Inhibition of carbonic anhydrases with glycosyltriazole benzene sulfonamides
    • Wilkinson, B. L.; Innocenti, A.; Vullo, D.; Supuran, C. T.; Poulsen, S.-A. Inhibition of carbonic anhydrases with glycosyltriazole benzene sulfonamides J. Med. Chem. 2008, 51, 1945-1953
    • (2008) J. Med. Chem. , vol.51 , pp. 1945-1953
    • Wilkinson, B.L.1    Innocenti, A.2    Vullo, D.3    Supuran, C.T.4    Poulsen, S.-A.5
  • 16
    • 77950563961 scopus 로고    scopus 로고
    • Sulfonamide linked neoglycoconjugates - A new class of inhibitors for cancer-associated carbonic anhydrases
    • Lopez, M.; Bornaghi, L. F.; Innocenti, A.; Vullo, D.; Charman, S. A.; Supuran, C. T.; Poulsen, S.-A. Sulfonamide linked neoglycoconjugates-a new class of inhibitors for cancer-associated carbonic anhydrases J. Med. Chem. 2010, 53, 2913-2926
    • (2010) J. Med. Chem. , vol.53 , pp. 2913-2926
    • Lopez, M.1    Bornaghi, L.F.2    Innocenti, A.3    Vullo, D.4    Charman, S.A.5    Supuran, C.T.6    Poulsen, S.-A.7
  • 17
    • 63149151675 scopus 로고    scopus 로고
    • Inhibition of carbonic anhydrase isozymes with benzene sulfonamides incorporating thio, sulfinyl and sulfonyl glycoside moieties
    • Singer, M.; Lopez, M.; Bornaghi, L. F.; Innocenti, A.; Vullo, D.; Supuran, C. T.; Poulsen, S.-A. Inhibition of carbonic anhydrase isozymes with benzene sulfonamides incorporating thio, sulfinyl and sulfonyl glycoside moieties Bioorg. Med. Chem. Lett. 2009, 19, 2273-2276
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 2273-2276
    • Singer, M.1    Lopez, M.2    Bornaghi, L.F.3    Innocenti, A.4    Vullo, D.5    Supuran, C.T.6    Poulsen, S.-A.7
  • 18
    • 66149131065 scopus 로고    scopus 로고
    • Therapeutic applications of glycosidic carbonic anhydrase inhibitors
    • Winum, J.-Y.; Poulsen, S.-A.; Supuran, C. T. Therapeutic applications of glycosidic carbonic anhydrase inhibitors Med. Res. Rev. 2009, 29, 419-435
    • (2009) Med. Res. Rev. , vol.29 , pp. 419-435
    • Winum, J.-Y.1    Poulsen, S.-A.2    Supuran, C.T.3
  • 19
    • 84874513802 scopus 로고    scopus 로고
    • Glycosidic carbonic anhydrase IX inhibitors: A sweet approach against cancer
    • Winum, J.-Y.; Colinas, P.; Supuran, C. T. Glycosidic carbonic anhydrase IX inhibitors: a sweet approach against cancer Bioorg. Med. Chem. 2013, 21, 1419-1426
    • (2013) Bioorg. Med. Chem. , vol.21 , pp. 1419-1426
    • Winum, J.-Y.1    Colinas, P.2    Supuran, C.T.3
  • 20
    • 84885838420 scopus 로고    scopus 로고
    • Structural study of interaction between brinzolamide and dorzolamide inhibition of human carbonic anhydrases
    • Pinard, M. A.; Boone, C. D.; Rife, B. D.; Supuran, C. T.; McKenna, R. Structural study of interaction between brinzolamide and dorzolamide inhibition of human carbonic anhydrases Bioorg. Med. Chem. 2013, 21, 7210
    • (2013) Bioorg. Med. Chem. , vol.21 , pp. 7210
    • Pinard, M.A.1    Boone, C.D.2    Rife, B.D.3    Supuran, C.T.4    McKenna, R.5
  • 21
    • 84863501358 scopus 로고    scopus 로고
    • Multiple binding modes of inhibitors to carbonic anhydrases: How to design specific drugs targeting 15 different isoforms?
    • Alterio, V.; Di Fiore, A.; D'Ambrosio, K.; Supuran, C. T.; De Simone, G. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? Chem. Rev. 2012, 112, 4421-4468
    • (2012) Chem. Rev. , vol.112 , pp. 4421-4468
    • Alterio, V.1    Di Fiore, A.2    D'Ambrosio, K.3    Supuran, C.T.4    De Simone, G.5
  • 22
    • 84865850354 scopus 로고    scopus 로고
    • Structure-based drug discovery of carbonic anhydrase inhibitors
    • Supuran, C. T. Structure-based drug discovery of carbonic anhydrase inhibitors J. Enzyme Inhib. Med. Chem. 2012, 27, 759-772
    • (2012) J. Enzyme Inhib. Med. Chem. , vol.27 , pp. 759-772
    • Supuran, C.T.1
  • 24
    • 79952268421 scopus 로고    scopus 로고
    • Design, synthesis, and biological evaluation of novel carbohydrate-based sulfamates as carbonic anhydrase inhibitors
    • Lopez, M.; Trajkovic, J.; Bornaghi, L.; Innocenti, A.; Vullo, D.; Supuran, C.; Poulsen, S. Design, synthesis, and biological evaluation of novel carbohydrate-based sulfamates as carbonic anhydrase inhibitors J. Med. Chem. 2011, 54, 1481-1489
    • (2011) J. Med. Chem. , vol.54 , pp. 1481-1489
    • Lopez, M.1    Trajkovic, J.2    Bornaghi, L.3    Innocenti, A.4    Vullo, D.5    Supuran, C.6    Poulsen, S.7
  • 25
    • 80755129209 scopus 로고    scopus 로고
    • Promiscuity of carbonic anhydrase II. Unexpected ester hydrolysis of carbohydrate-based sulfamate inhibitors
    • Lopez, M.; Vu, H.; Wang, C. K.; Wolf, M. G.; Groenhof, G.; Innocenti, A.; Supuran, C. T.; Poulsen, S.-A. Promiscuity of carbonic anhydrase II. Unexpected ester hydrolysis of carbohydrate-based sulfamate inhibitors J. Am. Chem. Soc. 2011, 133, 18452-18462
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 18452-18462
    • Lopez, M.1    Vu, H.2    Wang, C.K.3    Wolf, M.G.4    Groenhof, G.5    Innocenti, A.6    Supuran, C.T.7    Poulsen, S.-A.8
  • 26
    • 84897611549 scopus 로고    scopus 로고
    • Sulfamic acid and its N - And O - ituted derivatives
    • Spillane, W.; Malaubier Sulfamic acid and its N-and O-substituted derivatives Chem. Rev. 2014, 114, 2507-2598
    • (2014) Chem. Rev. , vol.114 , pp. 2507-2598
    • Spillane, W.1    Malaubier2
  • 28
    • 85178467634 scopus 로고
    • Degradation of the reducing bioses. I. Direct determination of the constitution of cellobiose
    • Zemplén, G. Degradation of the reducing bioses. I. Direct determination of the constitution of cellobiose Ber. Dtsch. Chem. Ges. 1926, 59, 1254-1266
    • (1926) Ber. Dtsch. Chem. Ges. , vol.59 , pp. 1254-1266
    • Zemplén, G.1
  • 29
    • 21844474059 scopus 로고    scopus 로고
    • Colorimetric calcium-response of b-lactosylated m -oxo-bis-[5,15-meso-diphenylporphyrinatoiron(III)]
    • Hasegawa, T.; Numata, M.; Asai, M.; M, T.; Shinkai, S. Colorimetric calcium-response of b-lactosylated m -oxo-bis-[5,15-meso-diphenylporphyrinatoiron(III)] Tetrahedron 2005, 7783-7788
    • (2005) Tetrahedron , pp. 7783-7788
    • Hasegawa, T.1    Numata, M.2    Asai, M.M.T.3    Shinkai, S.4
  • 30
    • 21544460203 scopus 로고    scopus 로고
    • Mild and chemoselcective deacetylation method using a catalytic amount of acetyl chloride in methanol
    • Yeom, C.-E.; Lee, S. Y.; Kim, Y. J.; Kim, B. M. Mild and chemoselcective deacetylation method using a catalytic amount of acetyl chloride in methanol Synlett 2005, 10, 1527-1530
    • (2005) Synlett , vol.10 , pp. 1527-1530
    • Yeom, C.-E.1    Lee, S.Y.2    Kim, Y.J.3    Kim, B.M.4
  • 31
    • 0035971953 scopus 로고    scopus 로고
    • A facile chemoselective deacetylation in presence of benzoyl and p -bromobenzoyl groups using p -toluenesulfonic acid
    • González, A. G.; Brouard, I.; León, F.; Padrón, J. I.; Bermejo, J. A facile chemoselective deacetylation in presence of benzoyl and p -bromobenzoyl groups using p -toluenesulfonic acid Tetrahedron Lett. 2001, 42, 3187-3188
    • (2001) Tetrahedron Lett. , vol.42 , pp. 3187-3188
    • González, A.G.1    Brouard, I.2    León, F.3    Padrón, J.I.4    Bermejo, J.5
  • 34
    • 58249094845 scopus 로고    scopus 로고
    • Hypoxia-inducible carbonic anhydrase IX and XII promote tumor cell growth by counteracting acidosis through the regulation of the intracellular pH
    • Chiche, J.; Ilc, K.; Laferriere, J.; Trottier, E.; Dayan, F.; Mazure, N. M.; Brahimi-Horn, M. C.; Pouyssegur, J. Hypoxia-inducible carbonic anhydrase IX and XII promote tumor cell growth by counteracting acidosis through the regulation of the intracellular pH Cancer Res. 2009, 69, 358-368
    • (2009) Cancer Res. , vol.69 , pp. 358-368
    • Chiche, J.1    Ilc, K.2    Laferriere, J.3    Trottier, E.4    Dayan, F.5    Mazure, N.M.6    Brahimi-Horn, M.C.7    Pouyssegur, J.8
  • 35
    • 84874526048 scopus 로고    scopus 로고
    • Insights towards sulfonamide drug specificity in alpha carbonic anhydrases
    • Aggarwal, M.; Kondeti, B.; McKenna, R. Insights towards sulfonamide drug specificity in alpha carbonic anhydrases Bioorg. Med. Chem. 2013, 21, 1526-1533
    • (2013) Bioorg. Med. Chem. , vol.21 , pp. 1526-1533
    • Aggarwal, M.1    Kondeti, B.2    McKenna, R.3
  • 36
    • 0141485298 scopus 로고    scopus 로고
    • Reaction of 1,2- trans -glycosyl acetates with thiourea: A new entry to 1-thiosugars
    • Ibatullin, F. M.; Shabalin, K. A.; Jänis, J. V.; Shavvac, A. G. Reaction of 1,2- trans -glycosyl acetates with thiourea: a new entry to 1-thiosugars Tetrahedron Lett. 2003, 44, 7961-7964
    • (2003) Tetrahedron Lett. , vol.44 , pp. 7961-7964
    • Ibatullin, F.M.1    Shabalin, K.A.2    Jänis, J.V.3    Shavvac, A.G.4
  • 37
    • 0034596449 scopus 로고    scopus 로고
    • Efficient general method for sulfamoylation of a hydroxyl group
    • Okada, M.; Iwashita, S.; Koizumi, N. Efficient general method for sulfamoylation of a hydroxyl group Tetrahedron Lett. 2000, 41, 7047-7051
    • (2000) Tetrahedron Lett. , vol.41 , pp. 7047-7051
    • Okada, M.1    Iwashita, S.2    Koizumi, N.3
  • 38
    • 51849155973 scopus 로고    scopus 로고
    • Inhibition of siderophore biosynthesis in Mycobacterium tuberculosis with nucleoside bisubstrate analogues: Structure-activity relationships of the nucleobase domain of 5′- O -[ N -(salicyl)sulfamoyl]adenosine
    • Neres, J.; Labello, N. P.; Somu, R. V.; Boshoff, H. I.; Wilson, D. J.; Vannada, J.; Chen, L.; Barry, C. E.; Bennett, E. M.; Aldrich, C. C. Inhibition of siderophore biosynthesis in Mycobacterium tuberculosis with nucleoside bisubstrate analogues: structure-activity relationships of the nucleobase domain of 5′- O -[ N -(salicyl)sulfamoyl]adenosine J. Med. Chem. 2008, 51, 5349-5370
    • (2008) J. Med. Chem. , vol.51 , pp. 5349-5370
    • Neres, J.1    Labello, N.P.2    Somu, R.V.3    Boshoff, H.I.4    Wilson, D.J.5    Vannada, J.6    Chen, L.7    Barry, C.E.8    Bennett, E.M.9    Aldrich, C.C.10
  • 39
    • 84893314621 scopus 로고    scopus 로고
    • Synthesis of sulfonamide-conjugated glycosyl-amino acid building blocks
    • Lopez, M. L.; Bornaghi, L. F.; Poulsen, S.-A. Synthesis of sulfonamide-conjugated glycosyl-amino acid building blocks Carbohydr. Res. 2014, 386, 78-85
    • (2014) Carbohydr. Res. , vol.386 , pp. 78-85
    • Lopez, M.L.1    Bornaghi, L.F.2    Poulsen, S.-A.3
  • 43
    • 3242798849 scopus 로고    scopus 로고
    • A simple method for improving protein solubility and long-term stability
    • Golovanov, A. P.; Hautbergue, G. M.; Wilson, S. A.; Lian, L.-Y. A simple method for improving protein solubility and long-term stability J. Am. Chem. Soc. 2004, 126, 8933
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 8933
    • Golovanov, A.P.1    Hautbergue, G.M.2    Wilson, S.A.3    Lian, L.-Y.4
  • 47
    • 0015239422 scopus 로고
    • The carbon dioxide hydration activity of carbonic anhydrase
    • Khalifah, R. G. The carbon dioxide hydration activity of carbonic anhydrase J. Biol. Chem. 1971, 246, 2561-2573
    • (1971) J. Biol. Chem. , vol.246 , pp. 2561-2573
    • Khalifah, R.G.1
  • 49
    • 0038587356 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Inhibition of cytosolic isozymes i and II and the membrane-bound, tumor associated isozyme IX with sulfamates also acting as steroid sulfatase inhibitors
    • Winum, J.-Y.; Vullo, D.; Casini, A.; Montero, J.-L.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: inhibition of cytosolic isozymes I and II and the membrane-bound, tumor associated isozyme IX with sulfamates also acting as steroid sulfatase inhibitors J. Med. Chem. 2003, 46, 2197-2204
    • (2003) J. Med. Chem. , vol.46 , pp. 2197-2204
    • Winum, J.-Y.1    Vullo, D.2    Casini, A.3    Montero, J.-L.4    Scozzafava, A.5    Supuran, C.T.6
  • 50
    • 16244377468 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides - A new target for the design of antitumor and antiglaucoma drugs?
    • Vullo, D.; Innocenti, A.; Nishimori, I.; Pastorek, J.; Scozzafava, A.; Pastoreková, S.; Supuran, C. T. Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs? Bioorg. Med. Chem. Lett. 2005, 15, 963-969
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 963-969
    • Vullo, D.1    Innocenti, A.2    Nishimori, I.3    Pastorek, J.4    Scozzafava, A.5    Pastoreková, S.6    Supuran, C.T.7


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