메뉴 건너뛰기




Volumn 50, Issue 18, 2007, Pages 4340-4350

Lysosome and HER3 (ErbB3) selective anticancer agent Kahalalide F: Semisynthetic modifications and antifungal lead-exploration studies

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; AMINE; AMPHOTERICIN B; ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; AZOXYSTROBIN; CAPTAN; CIPROFLOXACIN; EPIDERMAL GROWTH FACTOR RECEPTOR 3; KAHALALIDE F; KAHALALIDE G; ORNITHINE; THREONINE; UNCLASSIFIED DRUG;

EID: 34548502668     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061288r     Document Type: Article
Times cited : (43)

References (44)
  • 1
    • 0027296890 scopus 로고    scopus 로고
    • Hamann, M. T.; Scheuer, P. J. Kahalalide F: a bioactive depsipeptide from the sacoglossan mollusk Elysia rufescens and the green alga Bryopsis sp. J. Am. Chem. Soc. 1993, 115, 5825-5826.
    • Hamann, M. T.; Scheuer, P. J. Kahalalide F: a bioactive depsipeptide from the sacoglossan mollusk Elysia rufescens and the green alga Bryopsis sp. J. Am. Chem. Soc. 1993, 115, 5825-5826.
  • 2
    • 0029842550 scopus 로고    scopus 로고
    • Kahalalides: Bioactive peptides from a marine mollusk Elysia rufescens and its algal diet Bryopsis sp
    • Hamann, M. T.; Otto, C. S.; Scheuer, P. J.; Dunbar, D. C. Kahalalides: bioactive peptides from a marine mollusk Elysia rufescens and its algal diet Bryopsis sp. J. Org. Chem. 1996, 61, 6594-6600.
    • (1996) J. Org. Chem , vol.61 , pp. 6594-6600
    • Hamann, M.T.1    Otto, C.S.2    Scheuer, P.J.3    Dunbar, D.C.4
  • 3
    • 0030982131 scopus 로고    scopus 로고
    • Two acyclic kahalalides from the sacoglossan mollusk Elysia rufescens
    • Goetz, G.; Nakao, Y.; Scheuer, P. J. Two acyclic kahalalides from the sacoglossan mollusk Elysia rufescens. J. Nat. Prod. 1997, 60, 562-567.
    • (1997) J. Nat. Prod , vol.60 , pp. 562-567
    • Goetz, G.1    Nakao, Y.2    Scheuer, P.J.3
  • 4
    • 0033974661 scopus 로고    scopus 로고
    • Horgen, F. D.; de los Santos, D. B.; Goetz, G.; Sakamoto, B.; Kan, Y.; Nagai, H.; Scheuer, P. J. A new depsipeptide from the sacoglossan mollusk Elysia ornata and the green alga Bryopsis species. J. Nat. Prod. 2000, 63, 152-154.
    • Horgen, F. D.; de los Santos, D. B.; Goetz, G.; Sakamoto, B.; Kan, Y.; Nagai, H.; Scheuer, P. J. A new depsipeptide from the sacoglossan mollusk Elysia ornata and the green alga Bryopsis species. J. Nat. Prod. 2000, 63, 152-154.
  • 5
    • 34548480022 scopus 로고    scopus 로고
    • Hill, R. T.; Hamann, M. T.; Enticknap, J.; Rao, K. V. Kahalalide-producing bacteria. PCT Int. Appl. WO 2005/042720, 2005.
    • Hill, R. T.; Hamann, M. T.; Enticknap, J.; Rao, K. V. Kahalalide-producing bacteria. PCT Int. Appl. WO 2005/042720, 2005.
  • 6
    • 29744462754 scopus 로고    scopus 로고
    • New cyclic depsipeptides from the green alga Bryopsis species; application of a carboxypeptidase hydrolysis reaction to the structure determination
    • Dmitrenok, A.; Iwashita, T.; Nakajima, T.; Sakamoto, B.; Namikoshi, M.; Nagai, H. New cyclic depsipeptides from the green alga Bryopsis species; application of a carboxypeptidase hydrolysis reaction to the structure determination. Tetrahedron 2006, 62, 1301-1308.
    • (2006) Tetrahedron , vol.62 , pp. 1301-1308
    • Dmitrenok, A.1    Iwashita, T.2    Nakajima, T.3    Sakamoto, B.4    Namikoshi, M.5    Nagai, H.6
  • 8
    • 33846583499 scopus 로고    scopus 로고
    • Tandem mass spectroscopy of kahalalides: Identification of two new cyclic depsipeptides, kahalalide R and S from Elysia grandifolia
    • Tilvi, S.; Naik C. G. Tandem mass spectroscopy of kahalalides: identification of two new cyclic depsipeptides, kahalalide R and S from Elysia grandifolia. J. Mass Spectrom. 2006, 42, 70-80.
    • (2006) J. Mass Spectrom , vol.42 , pp. 70-80
    • Tilvi, S.1    Naik, C.G.2
  • 11
    • 20144387163 scopus 로고    scopus 로고
    • Rademaker, J. M.; Horenblas, S.; Meinhardt, W.; Stokvis, E.; de Reijke, T. M.; Jimeno, J. M.; Lopez-Lazaro, S.; Lopez, Martin, J. A.; Beijnen, J. H.; Schellens, J. H. M. Phase I clinical and pharmacokinetic study of kahalalide F in patients with advanced androgen refractory prostate cancer. Clin. Cancer Res. 2005, 11, 1854-1862.
    • Rademaker, J. M.; Horenblas, S.; Meinhardt, W.; Stokvis, E.; de Reijke, T. M.; Jimeno, J. M.; Lopez-Lazaro, S.; Lopez, Martin, J. A.; Beijnen, J. H.; Schellens, J. H. M. Phase I clinical and pharmacokinetic study of kahalalide F in patients with advanced androgen refractory prostate cancer. Clin. Cancer Res. 2005, 11, 1854-1862.
  • 12
    • 11344287074 scopus 로고    scopus 로고
    • Technology evaluation: Kahalalide F (PharmaMar)
    • Hamann, M. T. Technology evaluation: kahalalide F (PharmaMar). Curr. Opin. Mol. Ther. 2004, 6, 657-665.
    • (2004) Curr. Opin. Mol. Ther , vol.6 , pp. 657-665
    • Hamann, M.T.1
  • 13
    • 34548472934 scopus 로고    scopus 로고
    • PharmaMar Biopharmaceutical Co. (www.pharmamar.com). Presented at the 31st European Society for Medical Oncology Congress (ESMO), Istanbul, Turkey, September 29 through October 3, 2006.
    • PharmaMar Biopharmaceutical Co. (www.pharmamar.com). Presented at the 31st European Society for Medical Oncology Congress (ESMO), Istanbul, Turkey, September 29 through October 3, 2006.
  • 14
    • 0030053875 scopus 로고    scopus 로고
    • The antitumoral compound kahalalide facts on cell lysosomes
    • Garcia-Rocha, M.; Bonay, P.; Avila, J. The antitumoral compound kahalalide facts on cell lysosomes. Cancer Lett. 1996, 99, 43-50.
    • (1996) Cancer Lett , vol.99 , pp. 43-50
    • Garcia-Rocha, M.1    Bonay, P.2    Avila, J.3
  • 15
    • 0642318239 scopus 로고    scopus 로고
    • Suarez, Y.; Gonzalez, L.; Cuadrado, A.; Berciano, M.; Lafarga, M.; Munoz, A. Kahalalide F, a new marine-derived compound, induces oncosis in human prostate and breast cancer cells. Mol. Cancer Ther. 2003, 2, 863-872.
    • Suarez, Y.; Gonzalez, L.; Cuadrado, A.; Berciano, M.; Lafarga, M.; Munoz, A. Kahalalide F, a new marine-derived compound, induces oncosis in human prostate and breast cancer cells. Mol. Cancer Ther. 2003, 2, 863-872.
  • 17
    • 23044479629 scopus 로고    scopus 로고
    • Kahalalide F induces necrosis-like cell death that involves depletion of ErbB3 and inhibition of Akt signaling
    • Janmaat, M.; Rodriguez, J.; Jimeno, J.; Kruyt, F.; Giaccone, G. Kahalalide F induces necrosis-like cell death that involves depletion of ErbB3 and inhibition of Akt signaling. Mol. Pharmacol. 2005, 68, 502-510.
    • (2005) Mol. Pharmacol , vol.68 , pp. 502-510
    • Janmaat, M.1    Rodriguez, J.2    Jimeno, J.3    Kruyt, F.4    Giaccone, G.5
  • 18
    • 30844456008 scopus 로고    scopus 로고
    • Adding pharmacogenomics to the development of new marine-derived anticancer agents
    • Jimeno, J.; Aracil, M.; Tercero, J. Adding pharmacogenomics to the development of new marine-derived anticancer agents. J. Transl. Med. 2006, 4, 1-9.
    • (2006) J. Transl. Med , vol.4 , pp. 1-9
    • Jimeno, J.1    Aracil, M.2    Tercero, J.3
  • 19
    • 33747584372 scopus 로고    scopus 로고
    • Battling breast cancer by targeting multiple HER-family receptors, small-molecule drugs could fill the therapeutic gaps left by Herceptin
    • (a) Jarvis, L. M. Battling breast cancer by targeting multiple HER-family receptors, small-molecule drugs could fill the therapeutic gaps left by Herceptin. Chem. Eng. News 2006, 84 (32), 21-27.
    • (2006) Chem. Eng. News , vol.84 , Issue.32 , pp. 21-27
    • Jarvis, L.M.1
  • 20
    • 0042307325 scopus 로고    scopus 로고
    • The ErbB2/ErbB3 heterodimer functions as an oncogenic unit: ErbB2 requires ErbB3 to drive breast tumor cell proliferation
    • (b) Holbro, T.; Beerli, R. R.; Maurer, F.; Koziczak, M.; Barbas, C. F.; Hynes, N. E. The ErbB2/ErbB3 heterodimer functions as an oncogenic unit: ErbB2 requires ErbB3 to drive breast tumor cell proliferation. Proc. Natl. Acad. Sci. U.S.A. 2003, 100 (15), 8933-8938.
    • (2003) Proc. Natl. Acad. Sci. U.S.A , vol.100 , Issue.15 , pp. 8933-8938
    • Holbro, T.1    Beerli, R.R.2    Maurer, F.3    Koziczak, M.4    Barbas, C.F.5    Hynes, N.E.6
  • 22
    • 34548484209 scopus 로고    scopus 로고
    • Albericio, P. F.; Fernandez, D. A.; Giralt, L. E.; Gracia, C. C.; Lopez, R. P.; Varon, C. S.; Cuevas, M. C.; Lopez, M. A.; Francesca, S. A.; Jiménez, G. J.-C.; Royo, E. M. New antitumoral compounds. PCT Int. Appl. WO 2005/023846, 2005.
    • Albericio, P. F.; Fernandez, D. A.; Giralt, L. E.; Gracia, C. C.; Lopez, R. P.; Varon, C. S.; Cuevas, M. C.; Lopez, M. A.; Francesca, S. A.; Jiménez, G. J.-C.; Royo, E. M. New antitumoral compounds. PCT Int. Appl. WO 2005/023846, 2005.
  • 23
    • 33749003452 scopus 로고    scopus 로고
    • Convergent approaches for the synthesis of the antitumoral peptide, kahalalide F. Study of orthogonal protecting groups
    • Gracia, C.; Isidro-Llobet, A.; Cruz, L. J.; Acosta, G. A.; Alvarez, M.; Cuevas, C.; Giralt, E.; Albericio, F. Convergent approaches for the synthesis of the antitumoral peptide, kahalalide F. Study of orthogonal protecting groups. J. Org. Chem. 2006, 71, 7196-7204.
    • (2006) J. Org. Chem , vol.71 , pp. 7196-7204
    • Gracia, C.1    Isidro-Llobet, A.2    Cruz, L.J.3    Acosta, G.A.4    Alvarez, M.5    Cuevas, C.6    Giralt, E.7    Albericio, F.8
  • 24
    • 34548477507 scopus 로고    scopus 로고
    • Faircloth, G. T.; Elices, M.; Sasak, H.; Aviles Marin, P. M.; Cuevas Marchante, M. D. C. Preparation of kahalalide antitumoral compounds. PCT Int. Appl. WO 2004/035613, 2004.
    • Faircloth, G. T.; Elices, M.; Sasak, H.; Aviles Marin, P. M.; Cuevas Marchante, M. D. C. Preparation of kahalalide antitumoral compounds. PCT Int. Appl. WO 2004/035613, 2004.
  • 26
    • 34548475864 scopus 로고    scopus 로고
    • Scheuer, P. J, Hamann, M. T, Gravalos, D. G. Cytotoxic and antimicrobial activities of kahalalide F from Elysia rufescens. U.S. Patent 6274551, 2001
    • Scheuer, P. J.; Hamann, M. T.; Gravalos, D. G. Cytotoxic and antimicrobial activities of kahalalide F from Elysia rufescens. U.S. Patent 6274551, 2001.
  • 28
  • 29
    • 0033029445 scopus 로고    scopus 로고
    • Facile non-racemizing route for the N-alkylation of hindered secondary amines
    • (c) Insaf, S. S.; Witiak, D. T. Facile non-racemizing route for the N-alkylation of hindered secondary amines. Synthesis 1999, 3, 435.
    • (1999) Synthesis , vol.3 , pp. 435
    • Insaf, S.S.1    Witiak, D.T.2
  • 30
    • 0036077640 scopus 로고    scopus 로고
    • New agents for the treatment of systemic fungal infections - current status
    • Arikan, S.; Rex, J. H. New agents for the treatment of systemic fungal infections - current status. Expert Opin. Emerging Drugs 2002, 7, 3-32.
    • (2002) Expert Opin. Emerging Drugs , vol.7 , pp. 3-32
    • Arikan, S.1    Rex, J.H.2
  • 31
    • 0033971949 scopus 로고    scopus 로고
    • Antifungal peptides: Potential candidates for the treatment of fungal infections
    • De Lucca, A. J. Antifungal peptides: potential candidates for the treatment of fungal infections. Expert Opin. Invest. Drugs 2000, 9, 273-299.
    • (2000) Expert Opin. Invest. Drugs , vol.9 , pp. 273-299
    • De Lucca, A.J.1
  • 35
    • 33751158088 scopus 로고
    • Acceleration of the Dess-Martin oxidation by water
    • Meyer, S. D.; Schreiber, S. L. Acceleration of the Dess-Martin oxidation by water. J. Org. Chem. 1994, 59, 7549-7552.
    • (1994) J. Org. Chem , vol.59 , pp. 7549-7552
    • Meyer, S.D.1    Schreiber, S.L.2
  • 36
    • 4043071644 scopus 로고
    • Cyanohydridoborate anion as a selective reducing agent
    • (a) Borch, R. F.; Bernstein, M. D.; Durst, H. D. Cyanohydridoborate anion as a selective reducing agent. J. Am. Chem. Soc. 1971, 93, 2897-2904.
    • (1971) J. Am. Chem. Soc , vol.93 , pp. 2897-2904
    • Borch, R.F.1    Bernstein, M.D.2    Durst, H.D.3
  • 37
    • 0000160435 scopus 로고    scopus 로고
    • A mild, pyridine-borane-based reductive amination protocol
    • (b) Bomann, M. D.; Guch, I. C.; DiMare, M. A mild, pyridine-borane-based reductive amination protocol. J. Org. Chem. 1996, 60, 5995-5996.
    • (1996) J. Org. Chem , vol.60 , pp. 5995-5996
    • Bomann, M.D.1    Guch, I.C.2    DiMare, M.3
  • 38
    • 0342993927 scopus 로고    scopus 로고
    • Szardenings, A. K.; Burkoth, T. S.; Look, G. C.; Campbell, D. A. A reductive alkylation procedure applicable to both solution- and solid-phase syntheses of secondary amines. J. Org. Chem. 1996, 61, 6720-6722.
    • (c) Szardenings, A. K.; Burkoth, T. S.; Look, G. C.; Campbell, D. A. A reductive alkylation procedure applicable to both solution- and solid-phase syntheses of secondary amines. J. Org. Chem. 1996, 61, 6720-6722.
  • 39
    • 37049138917 scopus 로고
    • Reactions of sodium borohydride in acidic media. Selective reduction of aldehydes with sodium triacetoxyborohydride
    • (a) Gribble, G. W.; Ferguson, D. C. Reactions of sodium borohydride in acidic media. Selective reduction of aldehydes with sodium triacetoxyborohydride. J. Chem. Soc., Chem. Commun. 1975, 535-536.
    • (1975) J. Chem. Soc., Chem. Commun , pp. 535-536
    • Gribble, G.W.1    Ferguson, D.C.2
  • 40
    • 0013548653 scopus 로고
    • Chemoselective reduction of aldehydes with tetra-n-butylammonium triacetoxyborohydride
    • (b) Nutaitis, C. F.; Gribble, G. W. Chemoselective reduction of aldehydes with tetra-n-butylammonium triacetoxyborohydride. Tetrahedron Lett. 1983, 24, 4287.
    • (1983) Tetrahedron Lett , vol.24 , pp. 4287
    • Nutaitis, C.F.1    Gribble, G.W.2
  • 44
    • 0030903133 scopus 로고    scopus 로고
    • Microplate Alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium
    • Collins, L.; Franzblau, S. G. Microplate Alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob. Agents Chemother. 1997, 41, 1004-1009.
    • (1997) Antimicrob. Agents Chemother , vol.41 , pp. 1004-1009
    • Collins, L.1    Franzblau, S.G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.