Design, synthesis, and biological evaluation of a series of lavendustin A analogues that inhibit EGFR and Syk tyrosine kinases, as well as tubulin polymerization

Journal of Medicinal Chemistry

Volumn 44, Issue 3, 2001, Pages 441-452

  Mu, F ^a   Coffing, S L ^a   Riese II, D J ^a   Geahlen, R L ^a   Verdier Pinard, P ^b   Hamel, E ^b   Johnson, J ^c   Cushman, M ^a  

^a PURDUE UNIVERSITY   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

^c NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 [N [(2,5 DIHYDROXYPHENYL)METHYL]AMINO] N (4 FLUOROPHENETHYL)SALICYLAMIDE; ANTINEOPLASTIC AGENT; DRUG ANALOG; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE; LAVENDUSTIN A; PROTEIN KINASE SYK; PROTEIN TYROSINE KINASE; PROTEIN TYROSINE KINASE INHIBITOR; TUBULIN; UNCLASSIFIED DRUG;

ALGORITHM; ARTICLE; BREAST CANCER; COLON CANCER; DNA SYNTHESIS INHIBITION; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; KIDNEY CANCER; LEUKEMIA CELL; LUNG CANCER; MELANOMA; MICROTUBULE ASSEMBLY; OVARY CANCER; PROSTATE CANCER;

ANIMALS; ANTINEOPLASTIC AGENTS; BIOPOLYMERS; CELL-FREE SYSTEM; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; ENZYME PRECURSORS; HUMANS; INHIBITORY CONCENTRATION 50; INTRACELLULAR SIGNALING PEPTIDES AND PROTEINS; MICE; PHENOLS; PHOSPHORYLATION; PROTEIN-TYROSINE KINASES; RECEPTOR, EPIDERMAL GROWTH FACTOR; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN; TUMOR CELLS, CULTURED;

EID: 0035254244     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000387g     Document Type: Article

References (44)

1. Protein tyrosine kinase inhibitors as novel therapeutic agents
2. Strategies toward the design of novel and selective protein tyrosine kinase inhibitors
3. Small molecule inhibitors of tumor-promoted angiogenesis, including protein tyrosine kinase inhibitors
4. Isolation of a novel tyrosine kinase inhibitor, lavendustin A, from Streptomyces griseolavendus
5. Kinetic analysis of the inhibition of the epidermal growth factor receptor tyrosine kinase by lavendustin A and its analogue
6. Involvement of tyrosine kinase in growth factor-induced phospholipase C activation in NIH3T3 Cells
7. Non-amine based analogues of lavendustin A as protein-tyrosine kinase inhibitors
8. Hydroxylated 2-(5′-Salicyl)napthalenes as protein-tyrosine kinase inhibitors
9. Synthesis and structure-activity studies of a series of [(hydroxybenzyl)arnino]salicylates as inhibitors of EGF receptor-associated tyrosine kinase activity
10. Structure-Activity relationships in a series of 5-[(2 5-Dihydroxybenzyl)-amino]salicylate inhibitors of EGF-receptor-associated tyrosine kinase: Importance of additional hydrophobic aromatic interactions
11. F527 in vitro and in intact cells
12. Novel antiproliferative agents derived from lavendustin A
13. Synthesis and biological activity of 5-[2 5-dihydroxybenzyl)-amino]salicylic acid analogues as inhibitors of EGF receptor-associated protein tyrosine kinase
14. Solid-phase synthesis of lavendustin A and analogues
15. A versatile solid phase synthesis of lavendustin A and certain biologically active analogues
16. Display and analysis of patterns of differential activity of drugs against human tumor cell lines: Development of mean graph and COMPARE Algorithm
17. Some practical considerations and applications of the National Cancer Institute In Vitro Anticancer Drug Discovery Screen
18. Identification of novel antimitotic agents acting at the tubulin level by computer-assisted evaluation of differential cytotoxicity data
19. Protein-linked DNA strand breaks induced by NSC 314622, a novel noncamptothecin topoisomerase I poison
20. Topoisomerase II inhibition and cytotoxicity of the anthrapyrazoles DuP 937 and DuP 941 (Losaxantrone) in the National Cancer Institute Preclinical Antitumor Drug Discovery Screen
21. Site of action of two pyrimidine biosynthesis inhibitors accurately predicted by the COMPARE program
22. Cucurbitacin E-induced disruption of the actin and vimentin cytoskeleton in prostate carcinoma cells
23. Jasplakinolide, a cytotoxic natural product, induces actin polymerization and competitively inhibits the binding of phalloidin to F-Actin
24. 2-(4-Aminophenyl)benzothiazoles: Novel agents with selective profiles of in vitro antitumor activity
25. Identification of epidermal growth factor receptor and C-erb-b2 pathway inhibitors by correlation with gene expression patterns
26. The cellular response to neuregulins is governed by complex interactions of the ErbB receptor family
27. Amphiregulin as an autocrine growth factor for C-Ha-ras- and c-erbB-2-transformed human mammary epithelial cells
28. Isolation and characterization of a spontaneously immortalized human breast epithelial cell line, MCF-10
29. Increased epidermal growth factor receptor in an estrogen-responsive, adriamycin-resistant MCF-7 cell line
30. Cell cycle phase dependence of estrogen and epidermal growth factor EGF receptor expression in MCF-7 cells
31. Piceatannol 3,4,3′,5′-tetrahydroxy-trans-stilbene) is a naturally occurring protein tyrosine kinase inhibitor
32. Synthesis and protein-tyrosine kinase inhibitory activity of polyhydroxylated stilbene analogues of piceatannol
33. Interactions of tubulin with potent natural and synthetic analogues of the antimitotic agent combretastatin: A Structure-Activity Study
34. Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization
35. Synthesis and evaluation of analogues of (Z)-1-4-Methoxyphenyl-2-(3,4,5-trimethoxyphenyl)ethene as potential cytotoxic and antimitotic agents
36. Synthesis and evaluation of a series of benzylanillne hydrochlorides as potential cytotoxlc and antimitotic agents acting by inhibition of tubulin polymerization
37. SDZ 281-977: A modified partial structure of lavendustin A that exerts potent and selective antiproliferative activities in vitro and in vivo
38. Separation of active tubulin and microtubule-associated proteins by ultracentrifugation and isolation of a component causing the formation of microtubule bundles
39. Structure-activity analysis of the interaction of curacin A, the potent colchicine site antimitotic agent with tubulin and effects of analogues of the growth of MCF-7 breast cancer cells
40. Syk, activated by cross-linking the B-cell antigen receptor localizes to the cytosol where it interacts with and phosphorylates α-tubulin on tyrosine
41. Heregulin induces tyrosine phosphorylation of HER4/p180erbB4
42. Activation of ErbB4 by the bifunctional EGF family hormone epiregulin is regulated by ErbB2
43. Inhibition of cervival carcinoma cell line proliferation by the introduction of a bovine papillomavirus regulatory gene