Discovery of S-phase arresting agents derived from noscapine

Journal of Medicinal Chemistry

Volumn 48, Issue 8, 2005, Pages 2756-2758

  Anderson, James T ^a   Ting, Anthony E ^a   Boozer, Sherry ^a   Brunden, Kurt R ^a   Danzig, Joel ^a   Dent, Tom ^a   Harrington, John J ^a   Murphy, Steven M ^a   Perry, Rob ^a   Raber, Amy ^a   Rundlett, Stephen E ^a   Wang, Jianmin ^a   Wang, Nancy ^a   Bennani, Youssef L ^a  

^a ATHERSYS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMITOTIC AGENT; ANTINEOPLASTIC AGENT; COLCHICINE; DIMETHYL SULFOXIDE; NATURAL PRODUCT; NOSCAPINE;

ALKYLATION; APOPTOSIS; ARTICLE; CELL CYCLE S PHASE; CELL PROLIFERATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DEMETHYLATION; DIASTEREOISOMER; DNA CONTENT; DRUG POTENCY; DRUG SYNTHESIS; EPIMERIZATION; FLOW CYTOMETRY; FLUORESCENCE ACTIVATED CELL SORTING; HUMAN; HUMAN CELL; MAMMAL CELL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; NOSCAPINE; S PHASE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 20944431721     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0494220     Document Type: Article

References (18)

1. Simon, S. M.; Schindler, M. Cell biological mechanisms of multidrug resistance in tumors. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3497-3504.
2. Dahlstrom, B.; Mellstrand, T.; Lofdahl, C.-G.; Johansson, M. Pharmakokinetic properties of noscapine. Eur. J. Clin. Pharmacol. 1982, 22, 535-539.
3. (a) Lettre, H. Synergists and antagonists of mitotic poisons. Afin. N.Y. Acad. Sci. 1954, 58, 1264-1275.
4. (b) Lettre, H.; Albrecht, M. Narcotin, ein mitosegift (Narcotine, a mitotic poison). Naturwissenschaften 1942, 30, 184-185.
5. (a) Ye, K.; Ke, Y.; Keshava, N.; Shanks, J.; Kapp, J. A.; Tekmal, R. R.; Petros, J.; Joshi, H. C. Opium alkaloid noscapine is an antitumor agent that arrests metaphase and induces apoptosis in dividing cells. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 1601-1606.
6. (b) Joshi, H. C.; Zhou, J. Noscapine and analogues as potential chemotherapeutic agents. Drug News Perspect. 2000, 13 (9), 543-546.
7. (c) Ke, Y.; Ye, K.; Grossniklaus, H. E.; Archer, D. R.; Joshi, H. C.; Kapp, J. A. Noscapine inhibits tumor growth with little toxicity to normal tissues or inhibition of immune responses. Cancer Immunol. Immunother. 2000, 49, 217-225.
8. (d) Landen, J. W.; Lang, R.; McMahon, S. J.; Rusan, N. M.; Yvon, A.-M.; Adams, A. W.; Sorcinelli, M. D.; Campbell, R.; Bonaccorsi, P.; Ansel, J. C.; Archer, D. R.; Wadsworth, P.; Armstrong, C. A.; Joshi, H. C. Noscapine alters microtubule dynamics in living cells and inhibits the progression of melanoma. Cancer Res. 2002, 62, 4109-4114.
9. Schmidhammer, H.; Klotzer, W. Neue Reaktionen an Phthalid-isochinolin- alkaloiden. Alkoxytauschreaktionen und Isomerisierungen an α- und β-Narcotin (New reactions of phthalidoisoquinoline alkaloids. Alkoxy exchange reactions and isomerisations of α- and β-narcotine). Arch. Pharm. (Weinheim, Ger.) 1978, 311, 664-671.
10. Compound 3 was shown to arrest cells in the G2/M phase (unpublished results).
11. See Supporting Information for the crystal structure of 3.
12. Some epimerization (∼10-15%) was seen at longer reaction times and higher temperatures.
13. Davis, A.; Jiang, J.-D.; Middleton, K. M.; Wang, Y.; Weisz, I.; Ling, Y.-H.;. Bekesi, J. G. Novel suicide ligands of tubulin arrest cancer cells in S-phase. Neoplasia 1998, 1, 498-507.
14. Lawrence, N. J.; McGown, A. T.; Ducki, S.; Hadfield, J. A. The interaction of chalcones with tubulin. Anti-Cancer Drug Des. 2000, 15, 135-141.
15. Shi, Z.; Azuma, A.; Sampath, D.; Li, Y.-X.; Huang, P.; Plunkett, W. S-phase arrest by nucleoside analogues and abrogation of survival without cell cycle progression by 7-hydroxystaurosporine. Cancer Res. 2001, 61, 1065-1072.
16. Joe, A. K.; Liu, H.; Suzui, M.; Vural, M. E.; Xiao, D.; Weinstein, I. B. Resveratrol induces growth inhibition, S-phase arrest, apoptosis, and changes in biomarker expression in several human cancer cell lines. Clin. Cancer Res. 2002, 8, 893-903.
17. Li, Y.; Sun, X.; LaMont, J. T.; Pardee, A. B.; Li, C. J. Selective killing of cancer cells by β-lapachone: Direct checkpoint activation as a strategy against cancer. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 2674-2678.
18. Holden, J. A. DNA topoisomerases as anticancer drug targets: From the laboratory to the clinic. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1, 1-25.