메뉴 건너뛰기




Volumn 52, Issue 8, 2009, Pages 2181-2184

Pyranonaphthoquinone lactones: A new class of AKT selective kinase inhibitors alkylate a regulatory loop cysteine

Author keywords

[No Author keywords available]

Indexed keywords

CELL MARKER; CYSTEINE; DEOXYFRENOLICIN; FRENOLICIN B; KALAFUNGIN; LACTONE DERIVATIVE; LACTOQUINOMYCIN; PROTEIN KINASE B INHIBITOR; PYRANONAPHTHOQUINONE LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 65249178820     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900075g     Document Type: Article
Times cited : (68)

References (31)
  • 2
    • 0036632368 scopus 로고    scopus 로고
    • The phosphatidylinositol 3-kinase-AKT pathway in human cancer
    • (a) Vivanco, I.; Sawyers, C. L. The phosphatidylinositol 3-kinase-AKT pathway in human cancer. Nat. Rev. Cancer 2002, 2, 489-501.
    • (2002) Nat. Rev. Cancer , vol.2 , pp. 489-501
    • Vivanco, I.1    Sawyers, C.L.2
  • 3
    • 23944526062 scopus 로고    scopus 로고
    • Activation of AKT kinases in cancer: Implications for therapeutic targeting
    • (b) Bellacosa, A.; Kumar, C. C.; DiCristofano, A.; Testa, J. R. Activation of AKT kinases in cancer: implications for therapeutic targeting. Adv. Cancer Res. 2005, 94, 29-86.
    • (2005) Adv. Cancer Res , vol.94 , pp. 29-86
    • Bellacosa, A.1    Kumar, C.C.2    DiCristofano, A.3    Testa, J.R.4
  • 5
    • 0017173899 scopus 로고    scopus 로고
    • Takano, S.; Hasuda, K.; Ito, A; Koide, Y.; Ishii, F.; Haneda, I.; Chihara, S.; Koyama, Y. A new antibiotic, medermycin. J. Antibiot. 1976, 29, 765-768.
    • (a) Takano, S.; Hasuda, K.; Ito, A; Koide, Y.; Ishii, F.; Haneda, I.; Chihara, S.; Koyama, Y. A new antibiotic, medermycin. J. Antibiot. 1976, 29, 765-768.
  • 6
    • 0022361389 scopus 로고    scopus 로고
    • Tanaka, N.; Okabe, T.; Isono, F.; Kashiwagi, M.; Nomoto, K.; Takahashi, M.; Shimazu, A.; Nishimura, T. Lacto-quinomycin, a novel anticancer antibiotic. I. Taxonomy, isolation and biological activity. J. Antibiot. 1985, 38, 1327-1332.
    • (b) Tanaka, N.; Okabe, T.; Isono, F.; Kashiwagi, M.; Nomoto, K.; Takahashi, M.; Shimazu, A.; Nishimura, T. Lacto-quinomycin, a novel anticancer antibiotic. I. Taxonomy, isolation and biological activity. J. Antibiot. 1985, 38, 1327-1332.
  • 7
    • 0022357264 scopus 로고    scopus 로고
    • Okabe, T.; Nomoto, K.; Funabashi, H.; Okuda, S.; Suzuki, H.; Tanaka, N. Lactoquinomycin, a novel anticancer antibiotic. II. Physicochemical properties and structure assignment. J. Antibiot. 1985, 38, 1333-1336.
    • (c) Okabe, T.; Nomoto, K.; Funabashi, H.; Okuda, S.; Suzuki, H.; Tanaka, N. Lactoquinomycin, a novel anticancer antibiotic. II. Physicochemical properties and structure assignment. J. Antibiot. 1985, 38, 1333-1336.
  • 8
    • 0014308357 scopus 로고
    • a new broad spectrum antibiotic: Isolation and characterization
    • (a) Bergy, M. E. Kalafungin, a new broad spectrum antibiotic: Isolation and characterization. J. Antibiot. 1968, 21, 454-457.
    • (1968) J. Antibiot , vol.21 , pp. 454-457
    • Bergy, M.E.K.1
  • 9
    • 0017177238 scopus 로고    scopus 로고
    • Hoeksema, H.; Krueger, W. C. Kalafungin. II. Chemical transformations and the absolute configuration. J. Antibiot. 1976, 29, 704-709.
    • (b) Hoeksema, H.; Krueger, W. C. Kalafungin. II. Chemical transformations and the absolute configuration. J. Antibiot. 1976, 29, 704-709.
  • 10
    • 0018115773 scopus 로고
    • Production of deoxyfrenolicin and a new antibiotic, frenolicin B by Streptomyces roseofulvus strain AM-3867
    • Iwai, Y.; Kora, A.; Takahashi, Y.; Ayashi, T.; Awaya, J.; Masuma, R.; Oiwa, R.; Omura, S. Production of deoxyfrenolicin and a new antibiotic, frenolicin B by Streptomyces roseofulvus strain AM-3867. J. Antibiot. 1978, 31, 959-965.
    • (1978) J. Antibiot , vol.31 , pp. 959-965
    • Iwai, Y.1    Kora, A.2    Takahashi, Y.3    Ayashi, T.4    Awaya, J.5    Masuma, R.6    Oiwa, R.7    Omura, S.8
  • 12
    • 2742567582 scopus 로고    scopus 로고
    • Amer, R. E.; Dutton, C. J.; Fenner, B. R.; Greenwood, S. D. W.; Hall, K. T.; Rudge, A. J. Anticoccidial activity of novel semisynthetic analogs of frenolicin B. Part I. Heterocycl. Commun. 1998, 4, 309-315.
    • Amer, R. E.; Dutton, C. J.; Fenner, B. R.; Greenwood, S. D. W.; Hall, K. T.; Rudge, A. J. Anticoccidial activity of novel semisynthetic analogs of frenolicin B. Part I. Heterocycl. Commun. 1998, 4, 309-315.
  • 14
    • 0034737427 scopus 로고    scopus 로고
    • Synthetic strategies towards pyranonaphthoquinone antibiotics
    • Brimble, M. A.; Nairn, M. R.; Prabaharan, H. Synthetic strategies towards pyranonaphthoquinone antibiotics. Tetrahedron 2000, 56, 1937-1992.
    • (2000) Tetrahedron , vol.56 , pp. 1937-1992
    • Brimble, M.A.1    Nairn, M.R.2    Prabaharan, H.3
  • 15
    • 0031040493 scopus 로고    scopus 로고
    • Naphthopyranoquinone antibiotics. Novel enentioselective syntheses of frenolicin B and some of its stereoisomers
    • Masquelin, T.; Hengartner, U.; Streith, J. Naphthopyranoquinone antibiotics. Novel enentioselective syntheses of frenolicin B and some of its stereoisomers. Helv. Chim. Acta 1997, 80, 43-58.
    • (1997) Helv. Chim. Acta , vol.80 , pp. 43-58
    • Masquelin, T.1    Hengartner, U.2    Streith, J.3
  • 16
    • 84981404991 scopus 로고
    • Alkylation of quinones with radicals: Generation of radicals in redox reactions
    • (a) Jacobsen, N.; Torssell, K. Alkylation of quinones with radicals: Generation of radicals in redox reactions. Justus Liebigs Ann. Chem. 1972, 763, 135-147.
    • (1972) Justus Liebigs Ann. Chem , vol.763 , pp. 135-147
    • Jacobsen, N.1    Torssell, K.2
  • 17
    • 0000726532 scopus 로고
    • Synthesis of naturally occurring quinones
    • (b) Jacobsen, N.; Torssell, K. Synthesis of naturally occurring quinones. Acta Chem. Scand. 1973, 27, 3211-3216.
    • (1973) Acta Chem. Scand , vol.27 , pp. 3211-3216
    • Jacobsen, N.1    Torssell, K.2
  • 18
    • 0032943266 scopus 로고    scopus 로고
    • Synthesis of racemic frenolicin B and 5-epi-frenolicin B via intramolecular palladium-catalyzed aryloxycarbonylation
    • Contant, P.; Haess, M.; Riegl, J.; Scalone, M.; Visnick, M. Synthesis of racemic frenolicin B and 5-epi-frenolicin B via intramolecular palladium-catalyzed aryloxycarbonylation. Synthesis 1999, 821-828.
    • (1999) Synthesis , pp. 821-828
    • Contant, P.1    Haess, M.2    Riegl, J.3    Scalone, M.4    Visnick, M.5
  • 20
    • 0029123454 scopus 로고
    • Coccidiostatic agents: Synthesis of some analogs of (±) -frenolicin B
    • (b) Masquelin, T.; Hengartner, U.; Streith, J. Coccidiostatic agents: Synthesis of some analogs of (±) -frenolicin B. Synthesis 1995, 780-786.
    • (1995) Synthesis , pp. 780-786
    • Masquelin, T.1    Hengartner, U.2    Streith, J.3
  • 21
    • 0027258034 scopus 로고
    • Enantioselective synthesis of (-) -5-deoxyjuglomycin A
    • Mohan, H. R.; Rao, A. S. Enantioselective synthesis of (-) -5-deoxyjuglomycin A. Synth. Commun. 1993, 23, 2579-2585.
    • (1993) Synth. Commun , vol.23 , pp. 2579-2585
    • Mohan, H.R.1    Rao, A.S.2
  • 22
    • 58149305978 scopus 로고    scopus 로고
    • A detailed study of the stereochemical aspects of this transformation is reported in: Eid, C. N.; Shim, J.; Bikker, J.; Lin, M. Direct oxa-Pictet-Spengler cyclization to the natural (3a, 5) -trans stereochemistry in the synthesis of (+) -7-deoxyfrenolicin B and (+) -7-deoxykalafun-gin. J. Org. Chem. 2009, 74, 423-426.
    • A detailed study of the stereochemical aspects of this transformation is reported in: Eid, C. N.; Shim, J.; Bikker, J.; Lin, M. Direct oxa-Pictet-Spengler cyclization to the natural (3a, 5) -trans stereochemistry in the synthesis of (+) -7-deoxyfrenolicin B and (+) -7-deoxykalafun-gin. J. Org. Chem. 2009, 74, 423-426.
  • 23
    • 0021927869 scopus 로고
    • Enantiodivergent total syntheses of nanaomycins and their enantiomers, kalafungins
    • (a) Tatsuta, K.; Akimoto, K.; Annaka, M.; Ohno, Y.; Kinoshita, M. Enantiodivergent total syntheses of nanaomycins and their enantiomers, kalafungins. Bull. Chem. Soc. Jpn. 1985, 58, 1699-1706.
    • (1985) Bull. Chem. Soc. Jpn , vol.58 , pp. 1699-1706
    • Tatsuta, K.1    Akimoto, K.2    Annaka, M.3    Ohno, Y.4    Kinoshita, M.5
  • 24
    • 0025848141 scopus 로고
    • Total synthesis and biological evaluation of unnatural (-) -medermycin [(-) -lactoquinomycin]
    • (b) Tatsuta, K; Ozeki, H.; Yamaguchi, M.; Tanaka, M.; Okui, T.; Nakata, M. Total synthesis and biological evaluation of unnatural (-) -medermycin [(-) -lactoquinomycin]. J. Antibiot. 1991, 44, 901-902.
    • (1991) J. Antibiot , vol.44 , pp. 901-902
    • Tatsuta, K.1    Ozeki, H.2    Yamaguchi, M.3    Tanaka, M.4    Okui, T.5    Nakata, M.6
  • 25
    • 0017397793 scopus 로고
    • Bioactivation as a model for drug design bioreductive alkylation
    • (a) Moore, H. W. Bioactivation as a model for drug design bioreductive alkylation. Science 1977, 197, 527-532.
    • (1977) Science , vol.197 , pp. 527-532
    • Moore, H.W.1
  • 26
    • 0019724691 scopus 로고
    • Naturally occurring quinones as potential bioreductive alkylating agents
    • (b) Moore, H. W.; Czerniak, R. Naturally occurring quinones as potential bioreductive alkylating agents. Med. Res. Rev. 1981, 1, 249-280.
    • (1981) Med. Res. Rev , vol.1 , pp. 249-280
    • Moore, H.W.1    Czerniak, R.2
  • 28
    • 0141868865 scopus 로고    scopus 로고
    • Covalent modification of cysteine 193 impairs ATPase function of nucleotide-binding domain of a Candida drug efflux pump
    • (a) Jha, S.; Karnani, N.; Lynn, A. M.; Prasada, R. Covalent modification of cysteine 193 impairs ATPase function of nucleotide-binding domain of a Candida drug efflux pump. Biochem. Biophys. Res. Commun. 2003, 310, 869-875.
    • (2003) Biochem. Biophys. Res. Commun , vol.310 , pp. 869-875
    • Jha, S.1    Karnani, N.2    Lynn, A.M.3    Prasada, R.4
  • 29
    • 0021112583 scopus 로고
    • Selective protection of sulfhydryl groups in cAMP-dependent protein kinase II
    • (b) Nelson, N. C.; Taylor, S. S. Selective protection of sulfhydryl groups in cAMP-dependent protein kinase II. J. Biol. Chem. 1983, 258, 10981-10987.
    • (1983) J. Biol. Chem , vol.258 , pp. 10981-10987
    • Nelson, N.C.1    Taylor, S.S.2
  • 31
    • 0032793485 scopus 로고    scopus 로고
    • Alkylation of human serum albumin by sulfur mustard in vitro and in vivo: Mass spectrometric analysis of a cysteine adduct as a sensitive biomarker of exposure
    • Noort, D.; Hulst, A. G.; de Jong, L. P. A.; Benschop, H. P. Alkylation of human serum albumin by sulfur mustard in vitro and in vivo: mass spectrometric analysis of a cysteine adduct as a sensitive biomarker of exposure. Chem. Res. Toxicol. 1999, 12, 715-721.
    • (1999) Chem. Res. Toxicol , vol.12 , pp. 715-721
    • Noort, D.1    Hulst, A.G.2    de Jong, L.P.A.3    Benschop, H.P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.