Cell protein cross-linking by erbstatin and related compounds

Biochemical Pharmacology

Volumn 52, Issue 3, 1996, Pages 475-480

  Stanwell, Caroline ^a   Ye, Bin ^a   Yuspa, Stuart H ^a   Burke Jr , Terrence R ^a,b  

^a NATIONAL CANCER INSTITUTE   (United States)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

cross link; erbstatin; herbimycin A; lavendustin A; oxidation; protein tyrosine kinase

Indexed keywords

CELL PROTEIN; ERBSTATIN; ERBSTATIN DERIVATIVE; HERBIMYCIN A; LAVENDUSTIN A; PROTEIN TYROSINE KINASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL STRAIN 3T3; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG MECHANISM; DRUG SYNTHESIS; FIBROBLAST; KERATINOCYTE; MOUSE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; PROTEIN CROSS LINKING; STRUCTURE ACTIVITY RELATION; TEMPERATURE;

EID: 0030576651     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/0006-2952(96)00250-X     Document Type: Article

References (21)

1. 1. Burke TR Jr, Protein-tyrosine kinase inhibitors. Drugs Future 17: 119-131, 1992.
2. 2. Levitzki A and Gazit A, Tyrosine kinase inhibition: An approach to drug development. Science 267: 1782-1788, 1995.
3. 3. Umezawa H, Imoto M, Sawa T, Isshiki K, Matsuda N, Uchida T, Iinuma H, Hamada M and Takeuchi T, Studies on a new epidermal growth factor-receptor kinase inhibitor, erbstatin produced by MH435-hF3. J Antibiot (Tokyo) 39: 170-173, 1986.
4. 4. Imoto M, Umezawa K, Sawa T, Takeuchi T and Umezawa H, In situ inhibition of tyrosine protein kinase by erbstatin. Biochem Int 15: 989-995, 1987.
5. 5. Onoda T, Inuma H, Sasaki Y, Hamada M, Isshiki K, Naganawa H and Takeguchi T, Isolation of a novel tyrosine kinase inhibitor, lavendustin A, from Streptomyces griseolavendus. J Nat Prod 52: 1252-1257, 1989.
6. src in rat kidney cells infected with Rous sarcoma virus. Mol Cell Biol 6: 2198-2206, 1986.
7. 7. Isshiki K, Imoto M, Sawa T, Umezawa K, Takeuchi T, Umezawa H, Tsuchida T, Yoshioka T and Tatsuta K, Inhibition of tyrosine protein kinase by synthetic erbstatin analogs. J Antibiot (Tokyo) 40: 1209-1210, 1987.
8. 8. Gazit A, Yaish P, Gilon C and Levitzki A, Tyrphostins I: Synthesis and biological activity of protein tyrosine kinase inhibitors. J Med Chem 32: 2344-2352, 1989.
9. 9. Bishop WR, Petrin J, Wang L, Ramesh U and Doll RJ, Inhibition of protein kinase C by the tyrosine kinase inhibitor erbstatin. Biochem Pharmacol 40: 2129-2135, 1990.
10. 10. Young SW, Poole RC, Hudson AT, Halestrap AP, Denton RM and Tavare JM, Effects of tyrosine kinase inhibitors on protein kinase-independent systems. FEBS Lett 316: 278-282, 1993.
11. 11. Burke TR Jr, Fesen M, Mazumder A, Yung J, Wang J, Carothers AM, Grunberger D, Driscoll J, Kohn K and Pommier Y, Hydroxylated aromatic inhibitors of HIV-1 integrase. J Med Chem 38: 4171-4178, 1995.
12. 12. Umezawa K, Hori T, Tajima H, Imoto M, Isshiki K and Takeuchi T, Inhibition of epidermal growth factor-induced DNA synthesis by tyrosine kinase inhibitors. FEBS Lett 260:198-200, 1990.
13. 13. Stanwell C, Burke TR Jr and Yuspa SH, The erbstatin analog methyl 2,5-dihydroxycinnamate cross-links proteins and is cytotoxic to normal and neoplastic epithelial cells by a mechanism independent of tyrosine kinase inhibition. Cancer Res 55: 4950-4956, 1995.
14. 14. Burke TR Jr, A direct approach toward the synthesis of analogs of erbstatin. Org Prep Proc Int 23: 127-130, 1991.
15. 15. Grunberger D, Banerjee R, Eisinger K, Oltz EM, Efros L, Caldwell M, Estevez V and Nakanishi K, Preferential cytotoxicity on tumor cells by caffeic acid phenethyl ester isolated from propolis. Experientia 44: 230-232, 1988.
16. lck. J Med Chem 36: 425-432, 1993.
17. 17. Bankova V, Synthesis of natural esters of substituted cinnamic acids. J Nat Prod 53: 821-824, 1990.
18. 18. Hough-Monroe L and Milstone LM, Quantitation of cross-linked protein: An alternative to counting cornified envelopes as an index of keratinocyte differentiation. Anal Biochem 65: 25-28, 1991.
19. 19. Dlugosz AA and Yuspa SH, Staurosporine induces protein kinase C agonist effects and maturation of normal and neoplastic mouse keratinocytes in vitro. Cancer Res 51: 4677-4684, 1991.
20. 20. Stanwell C, Denning MF, Rutberg SE, Cheng C, Yuspa SH and Dlugosz AA, Staurosporine induces a sequential program of mouse keratinocyte terminal differentiation through activation of PKC isoenzymes. J Invest Dermatol 106: 482-489, 1996.
21. 21. Okabe M and Uehara M, New insight into oncoprotein-targeted antitumor effect - Herbimycin-A as an antagonist of protein tyrosine kinase against pH(1)-positive leukemia cells. Leuk Lymphoma 12: 41-49, 1993.