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Volumn 56, Issue 1, 2013, Pages 293-300

Sulfocoumarins (1,2-benzoxathiine-2,2-dioxides): A class of potent and isoform-selective inhibitors of tumor-associated carbonic anhydrases

Author keywords

[No Author keywords available]

Indexed keywords

1 (2,2 DIOXIDO 1,2 BENZOXATHIIN 6 YL) 4 PHENYL 1H 1,2,3 TRITRIAZOLE; 1,2 BENZOXATHIINE 2,2 DIOXIDE DERIVATIVE; 6 AZIDO 1,2 BENZOXATHIINE 2,2 DIOXIDE; ACETAZOLAMIDE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE XII; COUMARIN DERIVATIVE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84872343989     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301625s     Document Type: Article
Times cited : (198)

References (49)
  • 1
    • 41149115712 scopus 로고    scopus 로고
    • Direct screening of natural product extracts using mass spectrometry
    • Vu, H.; Pham, N. B.; Quinn, R. J. Direct screening of natural product extracts using mass spectrometry J. Biomol. Screening 2008, 13, 265-275
    • (2008) J. Biomol. Screening , vol.13 , pp. 265-275
    • Vu, H.1    Pham, N.B.2    Quinn, R.J.3
  • 3
    • 74849118851 scopus 로고    scopus 로고
    • Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins
    • Maresca, A.; Temperini, C.; Pochet, L.; Masereel, B.; Scozzafava, A.; Supuran, C. T. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins J. Med. Chem. 2010, 53, 335-344
    • (2010) J. Med. Chem. , vol.53 , pp. 335-344
    • Maresca, A.1    Temperini, C.2    Pochet, L.3    Masereel, B.4    Scozzafava, A.5    Supuran, C.T.6
  • 4
    • 77955424195 scopus 로고    scopus 로고
    • Coumarins incorporating hydroxy- and chloro- moieties selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones i and II
    • Maresca, A.; Supuran, C. T. Coumarins incorporating hydroxy- and chloro- moieties selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II Bioorg. Med. Chem. Lett. 2010, 20, 4511-4514
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 4511-4514
    • Maresca, A.1    Supuran, C.T.2
  • 5
    • 78449303755 scopus 로고    scopus 로고
    • 7,8-Disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones i and II in the low nanomolar/subnanomolar range
    • Maresca, A.; Scozzafava, A.; Supuran, C. T. 7,8-Disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II in the low nanomolar/subnanomolar range Bioorg. Med. Chem. Lett. 2010, 20, 7255-7258
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 7255-7258
    • Maresca, A.1    Scozzafava, A.2    Supuran, C.T.3
  • 7
    • 84055176334 scopus 로고    scopus 로고
    • Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors
    • Touisni, N.; Maresca, A.; McDonald, P. C.; Lou, Y.; Scozzafava, A.; Dedhar, S.; Winum, J.-Y.; Supuran, C. T. Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors J. Med. Chem. 2011, 54, 8271-8277
    • (2011) J. Med. Chem. , vol.54 , pp. 8271-8277
    • Touisni, N.1    Maresca, A.2    McDonald, P.C.3    Lou, Y.4    Scozzafava, A.5    Dedhar, S.6    Winum, J.-Y.7    Supuran, C.T.8
  • 8
    • 84874530114 scopus 로고    scopus 로고
    • Natural product coumarins that inhibit human carbonic anhydrases
    • in press (DOI: 10.1016/j.bmc.2012.07.021)
    • Davis, R. A.; Vullo, D.; Maresca, A.; Supuran, C. T.; Poulsen, S. A. Natural product coumarins that inhibit human carbonic anhydrases. Bioorg. Med. Chem. 2012, in press (DOI: 10.1016/j.bmc.2012.07.021).
    • (2012) Bioorg. Med. Chem.
    • Davis, R.A.1    Vullo, D.2    Maresca, A.3    Supuran, C.T.4    Poulsen, S.A.5
  • 9
    • 84859843439 scopus 로고    scopus 로고
    • Flavones and structurally related 4-chromenones inhibit carbonic anhydrases by a different mechanism of action compared to coumarins
    • Balboni, G.; Congiu, C.; Onnis, V.; Maresca, A.; Scozzafava, A.; Winum, J. Y.; Supuran, C. T. Flavones and structurally related 4-chromenones inhibit carbonic anhydrases by a different mechanism of action compared to coumarins Bioorg. Med. Chem. Lett. 2012, 22, 3063-3066
    • (2012) Bioorg. Med. Chem. Lett. , vol.22 , pp. 3063-3066
    • Balboni, G.1    Congiu, C.2    Onnis, V.3    Maresca, A.4    Scozzafava, A.5    Winum, J.Y.6    Supuran, C.T.7
  • 10
    • 84864247302 scopus 로고    scopus 로고
    • Update on carbonic anhydrase inhibitors: A patent review (2008-2011)
    • Aggarwal, M.; McKenna, R. Update on carbonic anhydrase inhibitors: a patent review (2008-2011) Expert Opin. Ther. Pat. 2012, 22, 903-915
    • (2012) Expert Opin. Ther. Pat. , vol.22 , pp. 903-915
    • Aggarwal, M.1    McKenna, R.2
  • 11
    • 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
  • 12
    • 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
  • 13
    • 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
  • 15
    • 42549148009 scopus 로고    scopus 로고
    • Carbonic Anhydrase IX: A new druggable target for the design of antitumor agents
    • Winum, J. Y.; Rami, M.; Scozzafava, A.; Montero, J. L.; Supuran, C. Carbonic Anhydrase IX: a new druggable target for the design of antitumor agents Med. Res. Rev. 2008, 28, 445-463
    • (2008) Med. Res. Rev. , vol.28 , pp. 445-463
    • Winum, J.Y.1    Rami, M.2    Scozzafava, A.3    Montero, J.L.4    Supuran, C.5
  • 17
    • 84866414247 scopus 로고    scopus 로고
    • Neutron Diffraction of Acetazolamide-Bound Human Carbonic Anhydrase II Reveals Atomic Details of Drug Binding
    • Fisher, S. Z.; Aggarwal, M.; Kovalevsky, A. Y.; Silverman, D. N.; McKenna, R. Neutron Diffraction of Acetazolamide-Bound Human Carbonic Anhydrase II Reveals Atomic Details of Drug Binding J. Am. Chem. Soc. 2012, 134, 14726-14729
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 14726-14729
    • Fisher, S.Z.1    Aggarwal, M.2    Kovalevsky, A.Y.3    Silverman, D.N.4    McKenna, R.5
  • 18
    • 33745644458 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX
    • Alterio, V.; Vitale, R. M.; Monti, S. M.; Pedone, C.; Scozzafava, A.; Cecchi, A.; De Simone, G.; Supuran, C. T. Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX J. Am. Chem. Soc. 2006, 128, 8329-8335
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 8329-8335
    • Alterio, V.1    Vitale, R.M.2    Monti, S.M.3    Pedone, C.4    Scozzafava, A.5    Cecchi, A.6    De Simone, G.7    Supuran, C.T.8
  • 20
    • 0027949918 scopus 로고
    • Two-site binding of phenol in the active site of human carbonic anhydrase II: Structural implications for substrate association
    • Nair, S. K.; Ludwig, P. A.; Christianson, D. W. Two-site binding of phenol in the active site of human carbonic anhydrase II: structural implications for substrate association J. Am. Chem. Soc. 1994, 116, 3659-60
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 3659-60
    • Nair, S.K.1    Ludwig, P.A.2    Christianson, D.W.3
  • 21
    • 40049101317 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV)
    • Innocenti, A.; Vullo, D.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV) Bioorg. Med. Chem. Lett. 2008, 18, 1583-1587
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 1583-1587
    • Innocenti, A.1    Vullo, D.2    Scozzafava, A.3    Supuran, C.T.4
  • 22
    • 44849119872 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols
    • Innocenti, A.; Hilvo, M.; Scozzafava, A.; Parkkila, S.; Supuran, C. T. Carbonic anhydrase inhibitors: inhibition of the new membrane-associated isoform XV with phenols Bioorg. Med. Chem. Lett. 2008, 18, 3593-3596
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 3593-3596
    • Innocenti, A.1    Hilvo, M.2    Scozzafava, A.3    Parkkila, S.4    Supuran, C.T.5
  • 23
    • 7044228995 scopus 로고    scopus 로고
    • Carbonic anhydrase activators
    • Supuran, C.T. Scozzafava, A. Conway, J. CRC Press: Boca Raton, FL
    • Ilies, M.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase activators. In Carbonic Anhydrase-Its Inhibitors and Activators; Supuran, C.T.; Scozzafava, A.; Conway, J. Eds.; CRC Press: Boca Raton, FL, 2004; pp 317-352
    • (2004) Carbonic Anhydrase - Its Inhibitors and Activators , pp. 317-352
    • Ilies, M.1    Scozzafava, A.2    Supuran, C.T.3
  • 24
    • 0030772018 scopus 로고    scopus 로고
    • Carbonic anhydrase activators: X-ray crystallographic and spectroscopic investigations for the interaction of isozymes i and II with histamine
    • Briganti, F.; Mangani, S.; Orioli, P.; Scozzafava, A.; Vernaglione, G.; Supuran, C. T. Carbonic anhydrase activators: X-ray crystallographic and spectroscopic investigations for the interaction of isozymes I and II with histamine Biochemistry 1997, 36, 10384-10392
    • (1997) Biochemistry , vol.36 , pp. 10384-10392
    • Briganti, F.1    Mangani, S.2    Orioli, P.3    Scozzafava, A.4    Vernaglione, G.5    Supuran, C.T.6
  • 25
    • 0037122754 scopus 로고    scopus 로고
    • Carbonic anhydrase activators: High affinity isozymes I, II and IV activators, incorporating a β-alanyl-histidine scaffold
    • Scozzafava, A.; Supuran, C. T. Carbonic anhydrase activators: high affinity isozymes I, II and IV activators, incorporating a β-alanyl- histidine scaffold J. Med. Chem. 2002, 45, 284-291
    • (2002) J. Med. Chem. , vol.45 , pp. 284-291
    • Scozzafava, A.1    Supuran, C.T.2
  • 27
    • 84855702121 scopus 로고    scopus 로고
    • Dithiocarbamates: A new class of carbonic anhydrase inhibitors. Crystallographic and kinetic investigations
    • Carta, F.; Aggarwal, M.; Maresca, A.; Scozzafava, A.; McKenna, R.; Supuran, C. T. Dithiocarbamates: a new class of carbonic anhydrase inhibitors. Crystallographic and kinetic investigations Chem. Commun. 2012, 48, 1868-1870
    • (2012) Chem. Commun. , vol.48 , pp. 1868-1870
    • Carta, F.1    Aggarwal, M.2    Maresca, A.3    Scozzafava, A.4    McKenna, R.5    Supuran, C.T.6
  • 28
    • 84855658697 scopus 로고    scopus 로고
    • Dithiocarbamates strongly inhibit the beta-class fungal carbonic anhydrases from Cryptococcus neoformans, Candida albicans, and Candida glabrata
    • Monti, S. M.; Maresca, A.; Carta, F.; De Simone, G.; Mühlschlegel, F. A.; Scozzafava, A.; Supuran, C. T. Dithiocarbamates strongly inhibit the beta-class fungal carbonic anhydrases from Cryptococcus neoformans, Candida albicans, and Candida glabrata Bioorg. Med. Chem. Lett. 2012, 22, 859-862
    • (2012) Bioorg. Med. Chem. Lett. , vol.22 , pp. 859-862
    • Monti, S.M.1    Maresca, A.2    Carta, F.3    De Simone, G.4    Mühlschlegel, F.A.5    Scozzafava, A.6    Supuran, C.T.7
  • 30
    • 84858288806 scopus 로고    scopus 로고
    • Novel coumarins and 2-thioxo-coumarins as inhibitors of the tumor-associated carbonic anhydrases IX and XII
    • Carta, F.; Maresca, A.; Scozzafava, A.; Supuran, C. T. Novel coumarins and 2-thioxo-coumarins as inhibitors of the tumor-associated carbonic anhydrases IX and XII Bioorg. Med. Chem. 2012, 20, 2266-2273
    • (2012) Bioorg. Med. Chem. , vol.20 , pp. 2266-2273
    • Carta, F.1    Maresca, A.2    Scozzafava, A.3    Supuran, C.T.4
  • 31
    • 84857918967 scopus 로고    scopus 로고
    • New chemotypes acting as isozyme-selective carbonic anhydrase inhibitors with low affinity for the offtarget cytosolic isoform II
    • Carta, F.; Vullo, D.; Maresca, A.; Scozzafava, A.; Supuran, C. T. New chemotypes acting as isozyme-selective carbonic anhydrase inhibitors with low affinity for the offtarget cytosolic isoform II Bioorg. Med. Chem. Lett. 2012, 22, 2182-2185
    • (2012) Bioorg. Med. Chem. Lett. , vol.22 , pp. 2182-2185
    • Carta, F.1    Vullo, D.2    Maresca, A.3    Scozzafava, A.4    Supuran, C.T.5
  • 32
    • 84862004700 scopus 로고    scopus 로고
    • Facile synthesis of coumarin bioisosteres - 1,2-benzoxathiine 2,2-dioxides
    • Grandane, A.; Belyakov, S.; Trapencieris, P.; Zalubovskis, R. Facile synthesis of coumarin bioisosteres-1,2-benzoxathiine 2,2-dioxides Tetrahedron 2012, 68, 5541-5546
    • (2012) Tetrahedron , vol.68 , pp. 5541-5546
    • Grandane, A.1    Belyakov, S.2    Trapencieris, P.3    Zalubovskis, R.4
  • 33
    • 67651091693 scopus 로고    scopus 로고
    • In vivo targeting of tumor-associated carbonic anhydrases using acetazolamide derivatives
    • Ahlskog, J. K. J.; Dumelin, C. E.; Trüssel, S.; Marlind, J.; Neri, D. In vivo targeting of tumor-associated carbonic anhydrases using acetazolamide derivatives Bioorg. Med. Chem. Lett. 2009, 19, 4851-4855
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 4851-4855
    • Ahlskog, J.K.J.1    Dumelin, C.E.2    Trüssel, S.3    Marlind, J.4    Neri, D.5
  • 36
    • 33748925555 scopus 로고    scopus 로고
    • One-pot synthesis of macrocycles by a tandem three-component reaction and intramolecular [3 + 2] cycloaddition
    • Pirali, T.; Tron, G. C.; Zhu, J. One-pot synthesis of macrocycles by a tandem three-component reaction and intramolecular [3 + 2] cycloaddition Org. Lett. 2006, 8, 4145-4148
    • (2006) Org. Lett. , vol.8 , pp. 4145-4148
    • Pirali, T.1    Tron, G.C.2    Zhu, J.3
  • 39
    • 0015239422 scopus 로고
    • The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C
    • Khalifah, R. G. 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, 2561-2573
    • (1971) J. Biol. Chem. , vol.246 , pp. 2561-2573
    • Khalifah, R.G.1
  • 40
    • 77955391402 scopus 로고    scopus 로고
    • Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule
    • Carta, F.; Temperini, C.; Innocenti, A.; Scozzafava, A.; Kaila, K.; Supuran, C. T. Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule J. Med. Chem. 2010, 53, 5511-5522
    • (2010) J. Med. Chem. , vol.53 , pp. 5511-5522
    • Carta, F.1    Temperini, C.2    Innocenti, A.3    Scozzafava, A.4    Kaila, K.5    Supuran, C.T.6
  • 42
    • 84860795258 scopus 로고    scopus 로고
    • Nucleophile recognition as an alternative inhibition mode for benzoic acid based carbonic anhydrase inhibitors
    • Martin, D. P.; Cohen, S. M. Nucleophile recognition as an alternative inhibition mode for benzoic acid based carbonic anhydrase inhibitors Chem. Commun. 2012, 48, 5259-5261
    • (2012) Chem. Commun. , vol.48 , pp. 5259-5261
    • Martin, D.P.1    Cohen, S.M.2
  • 49
    • 0030589514 scopus 로고    scopus 로고
    • Phi/psi-chology: Ramachandran revisited
    • Kleywegt, G. J.; Jones, T. A. Phi/psi-chology: Ramachandran revisited Structure 1996, 4, 1395-1400
    • (1996) Structure , vol.4 , pp. 1395-1400
    • Kleywegt, G.J.1    Jones, T.A.2


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