Structure activity relationships and mechanism of action of antitumor benzo[b]acronycine antitumor agents;Relations structure, activité et mécanisme d'action des antitumoraux de série benzo[b]acronycine

Annales Pharmaceutiques Francaises

Volumn 63, Issue 1, 2005, Pages 44-52

  Seguin, E ^a   Tillequin, Fr ^b  

^a UNIVERSITÉ DE ROUEN   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Acronycine; Alkylating agent; Antitumor activity; S23906

Indexed keywords

1,2 DIACETOXY 1,2 DIHYDROBENZ[B]ACRONYCINE; 1,2 DIHYDROXY 1,2 DIHYDROBENZ[B]ACRONYCINE; ACRONINE; ANTINEOPLASTIC AGENT; BENZ[B]ACRONYCINE; GENOMIC DNA; S 23906; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; COLON CANCER; CYTOTOXICITY; DNA ADDUCT; DNA HELIX; DRUG ISOLATION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; LUNG CANCER; MOUSE; NONHUMAN; NUDE MOUSE; OVARY CANCER; RUTACEAE; SARCOMELICOPE; SOLID TUMOR; STRUCTURE ACTIVITY RELATION; TUMOR XENOGRAFT;

EID: 14244263940     PISSN: 00034509     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0003-4509(05)82250-3     Document Type: Article

References (32)

1. Hughes GK, Lahey FN, Price JR. Alkaloids of the Australian Rutaceae. Nature 1948; 162: 223-4.
2. Hartley TG. A revision of the genus Sarcomelicope (Rutaceae). Aust J Bot 1982; 30: 359-72.
3. Macdonald PL, Robertson AV. The structure of acronycine. Aust J Chem 1966; 19: 275-81.
4. Svoboda GH. Alkaloids of Acronichia baueri - Extraction of the alkaloids and structure - activity relationships. Lloydia 1966; 29: 206-24.
5. Svoboda GH, Poore GA, Simpson PJ, Boder GB. Alkaloids of Acronychia baueri - Isolation of the alkaloids and study of the antitumor and other biological properties of acronycine. J Pharm Sci 1966; 55: 758-68.
6. Scarffe JH, Beaumont AR, Crowther D. Phase I-II evaluation of acronycine in patients with multiple myeloma. Cancer Treat Rep 1983; 67: 93-4.
7. Michel S, Tillequin F, Seguin E. Structure-activity relationships in the acronycine series. Curr Med Chem 2002; 9: 1241-53.
8. Brum-Bousquet M, Mitaku S, Skaltsounis A-L, Tillequin F, Koch, M. Acronycine epoxide: a new acridone alkaloid from several Sarcomelicope species. Planta Med 1988; 54: 470-1.
9. Elomri A, Mitaku S, Michel S, Skaltsounis A-L, Tillequin F, Koch M et al. Synthesis and cytotoxic and antitumor activity of esters in the 1,2-dihydroxy-1,2-dihydroacronycine series. J Med Chem 1996; 39: 4762-66.
10. Magiatis P, Mitaku S, Skaltsounis A-L, Tillequin F, Koch M, Pierré A. Synthesis and biological activity of esters in the trans-1,2-dihydroxy-1,2- dihydroacronycine series. J Nat Prod 1998; 61: 198-201.
11. Tillequin F. Conception de nouveaux agents antitumoraux en série acronycine. An Pharm Fr 2002; 60: 246-52.
12. Dorr RT, Liddil JD. Development of a parenteral formulation of the antitumour agent acronycine. J Drug Dev 1988; 1: 31-9.
13. Costes N, Le Deit H, Michel S, Tillequin F, Koch M, Pfeiffer B et al. Synthesis and cytotoxic and antitumor activity of benzo[b]pyrano[3,2-h]acridine- 7-one analogues of acronycine. J Med Chem 2000; 43: 2395-402.
14. Doan Thi Mai H, Gaslonde T, Michel S, Tillequin F, Koch M, Bongui J-B et al. Structure-Activity relationships and mechanism of action of antitumor benzo[b] pyrano[3,2-h]acridine-7-one acronycine analogues. J Med Chem 2003; 46: 3072-82.
15. Doan Thi Mai H, Gaslonde T, Michel S, Koch M, Tillequin F, Pfeiffer B et al. Synthesis and cytotoxic and antitumor activity of 1,2-dihydroxy-1,2- dihydrobenzo[b]acronycine diacid hemiesters and carbamates. Chem Pharm Bull 2004; 52: 293-7.
16. Guilbaud N, Kraus-Berthier L, Meyer F, Tillequin F, Koch M, Pfeiffer B et al. Preclinical antitumor activity of S 23906-1, a new acronycine derivative in human orthotopic models. Proc Amer Assoc Cancer Res 2000; 41: 600.
17. Guilbaud N, Kraus-Berthier L, Meyer-Loisic F, Malivet V, Chacun C, Jan M et al. Marked antitumor activity of a new potent acronycine derivative in orthotopic models of human solid tumors. Clin Cancer Res 2001; 7: 2573-80.
18. Guilbaud N, Léonce S, Tillequin F, Koch M, Hickman JA, Pierré A. Acronycine derivatives as promising antitumor agents. Anti-Cancer Drugs 2002; 13: 445-9.
19. Gout PW, Dunn BP, Beer CT. Effects of acronycine on nucleic acid synthesis and population growth in mammalian tumor cell cultures. J Cell Physiol 1971; 78: 127-38.
20. Dunn BP, Gout PW, Beer CT. Effects of the antineoplastic alkaloid acronycine on nucleoside uptake and incorporation into nucleic acids by cultured L5178Y cells. Cancer Res 1973; 33: 2310-9.
21. Tan P, Auersperg N. Effects of the antineoplastic alkaloid acronycine on the ultrastructure and growth patterns of cultured cells. Cancer Res 1973; 33: 2320-9.
22. Kessel D. Effects of acronycine on cell-surface properties of murine leukemia cells. Biochem Pharmacol 1977; 26: 1077-81.
23. Plagemann PGW, Marz R, Wohlhuetter RM. Uridine transport in Novikoff rat hepatoma cells and other cell lines and its relationship to uridine phosphorylation and phosphorolysis. J Cell Physiol 1978; 97: 49-72.
24. Kennedy B. Nucleoside uptake, acronycine action and membrane fluidity during lymphocyte activation. Biochem Soc Trans 1979; 7: 1002-3.
25. Low RS, Auersperg N. Effects of acronycine and cytochalasin B on the division of rat leukemia cells. Exp Cell Res 1981; 131: 15-24.
26. Shieh H-L, Pezzuto JM, Cordell GA. Evaluation of the cytotoxic mechanisms mediated by the broad-spectrum antitumor alkaloid acronycine and selected semisynthetic derivatives. Chem-Biol Interactions 1992; 81: 35-55.
27. Léonce S, Perez V, Lambel S, Burbridge F, Tillequin F, Koch M et al. Cytotoxicity and cell cycle effect of S 23906-1, a new acronycine derivative. Proc Amer Assoc Cancer Res 2000; 41: 601.
28. Léonce S, Perez V, Lambel S, Peyroulan D, Tillequin F, Michel S et al. Induction of cyclin E and inhibition of DNA synthesis by the novel acronycine derivative S23906-1 precede the irreversible arrest of the tumor cells in S phase leading to apoptosis. Mol Pharmacol 2001; 60: 1383-91.
29. Kluza J, Lansiaux A, Wattez N, Hildebrand M-P, Léonce S, Pierré A et al. Induction of apoptosis in HL-60 leukemia and B16 melanoma cells by the acronycine derivative S23906-1. Biochem Pharmacol 2002; 63: 1443-52.
30. David-Cordonnier M-H, Laine W, Lansiaux A, Kouach M, Briand G, Pierré A et al. Alkylation of guanine in DNA by S23906-1, a novel potent antitumor compound derived from the plant alkaloid acronycine. Biochemistry 2002; 41: 9911-20.
31. David-Cordonnier M-H, Laine W, Joubert A, Tardy C, Goosens J-F, Kouach M et al. Covalent binding to glutathione of the DNA-alkylating antitumor agent, S23906-1. Eur J Biochem 2003; 270: 2848-59.
32. David-Cordonnier M-H, Laine W, Kouach M, Briand G, Vézin H, Gaslonde T et al. A transesterification reaction is implicated in the covalent binding of benzo[b]acronycine anticancer agents with DNA and glutathione. Bioorg Med Chem 2004; 12: 23-9.