Alteration of the bis-tetrahydrofuran core stereochemistries in asimicin can affect the cytotoxicity

Journal of Medicinal Chemistry

Volumn 51, Issue 22, 2008, Pages 7045-7048

  Sinha, Subhash C ^a   Chen, Zhiyong ^a   Huang, Zheng Zheng ^a   Nakamaru Ogiso, Eiko ^a   Pietraszkiewicz, Halina ^b   Edelstein, Matthew ^b   Valeriote, Frederick ^b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b HENRY FORD HEALTH SYSTEM   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASIMICIN; BULLATACIN; TETRAHYDROFURAN DERIVATIVE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONCENTRATION RESPONSE; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; MOUSE; NONHUMAN; STEREOCHEMISTRY;

ANIMALS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; FURANS; HUMANS; MICE; MOLECULAR CONFORMATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 56749106139     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801028c     Document Type: Article

References (36)

1. (a) McLaughlin, J. L. Paw paw and cancer: Annonaceous acetogenins from discovery to commercial products. J. Nat. Prod. 2008, 71, 1311-1321.
2. (b) Bermejo, A.; Figadere, B.; Zafra-Polo, M.-C.; Barrachina, I.; Estornell, E.; Cortes, D. Acetogenins from annonaceae. Recent progress in isolation, synthesis, and mechanisms of action. Nat. Prod. Rep. 2005, 22, 269-303.
3. (c) Alali, Q.; Liu, X.-X.; McLaughlin, J. L. Annonaceous acetogenins: recent progress. J. Nat. Prod. 1999, 62, 504-540, and references cited therein.
4. (a) Yuan, S.-S. F.; Chang, H.-L.; Chen, H.-W.; Kuo, F.-C.; Liaw, C.-C.; Su, J.-H.; Wu, Y.-C. Selective cytotoxicity of squamocin on T24 bladder cancer cells at the S-phase via a Bax-, Bad-, and caspase-3-related pathways. Life Sci. 2006, 78, 869-874.
5. (b) Lu, M.-C.; Yang, S.-H.; Hwang, S.-L.; Lu, Y.-J.; Lin, Y.-H.; Wang, S.-R.; Wu, Y.-C.; Lin, S.-R. Induction of G2/M phase arrest by squamocin in chronic myeloid leukemia (K562) cells. Life Sci. 2006, 78, 2378-2383.
6. (a) Derbre, S.; Roue, G.; Poupon, E.; Susin, S. A.; Hocquemiller, R. The hydroxyl groups and THF rings are crucial structural elements for targeting the mitochondria, demonstration with the synthesis of fluorescent squamocin analogues. ChemBioChem 2005, 6, 979-982.
7. (b) Abe, M.; Kenmochi, A.; Ichimaru, N.; Hamada, T.; Nishioka, T.; Miyoshi, H. Essential structural features of acetogenins: role of hydroxy groups adjacent to the bis-THF rings. Bioorg. Med. Chem. Lett. 2004, 14, 779-782.
8. He, K.; Shi, G.; Zhao, G.-X.; Zeng, L.; Ye, Q.; Schwedler, J. T.; Wood, K. V.; McLaughlin, J. L. Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba. J. Nat. Prod. 1996, 59, 1029-1034.
9. (a) Oberlies, N. H.; Croy, V. L.; Harrison, M. L.; McLaughlin, J. L. The Annonaceous acetogenin bullatacin is cytotoxic against multidrug-resistant human mammary adenocarcinoma cells. Cancer Lett. 1997, 115, 73-79.
10. (b) Oberlies, N. H.; Chang, C.-J.; McLaughlin, J. L. Structure-activity relationships of diverse Annonaceous acetogenins against multidrug resistant human mammary adenocarcinoma (MCF-7/Adr) cells. J. Med. Chem. 1997, 40, 2102-2106.
11. Das, S.; Li, L.-S.; Abraham, S.; Chen, Z.; Sinha, S. C. A bidirectional approach to the synthesis of a complete library of adjacent-bis-THF Annonaceous acetogenins. J. Org. Chem. 2005, 70, 5922-5931.
12. (a) Chen, Z.; Sinha, S. C. Total synthesis of 27-hydroxy-bullatacin and its C-15 epimer, and studies on their inhibitory effect on bovine heart mitochondrial complex I functions. Tetrahedron 2008, 64, 1603-1611,
13. Also see: (b) Tian, S. K.; Wang, Z. M.; Jiang, J. K.; Shi, M. Stereocontrolled construction of the trans-tetrahydrofuran units in Annonaceous acetogenins. Tetrahedron: Asymmetry 1999, 10, 2551-2562.
14. (c) Zhao, H.; Gorman, J. S. T.; Pagenkopf, B. L. Advances in lewis acid controlled carbon-carbon bond-forming reactions enable a concise and convergent total synthesis of bullatacin. Org. Lett. 2006, 8, 4379-4382.
15. For the recent synthesis of the adjacent bis-THF acetogenins from this laboratory, see: (a) refs 6 and 7a.
16. (b) Avedissian, H.; Sinha, S. C.; Yazbak, A.; Sinha, A.; Neogi, P.; Sinha, S. C.; Keinan, E. Total synthesis of asimicin and bullatacin. J. Org. Chem. 2000, 65, 6035-6051.
17. (c) Han, H.; Sinha, M. K.; D'Souza, L. J.; Keinan, E.; Sinha, S. C. Total synthesis of 34-hydroxyasimicin and its photoactive derivative for affinity labeling of the mitochondrial Complex I. Chem. - Eur. J. 2004, 10, 2149-2158, and references cited therein.
18. For the recent synthesis of the adjacent bisTHF acetogenins from other laboratories, see: (a) Huh, C. W.; Roush, W. R. Highly stereoselective and modular syntheses of 10-hydroxytrilobacin and three diastereomers via stereodivergent [3 + 2]-annulation reactions. Org. Lett. 2008, 10, 3371-3374.
19. (b) Marshall, J. A.; Sabatini, J. J.; Valeriote, F. ABC synthesis and antitumor activity of a series of Annonaceous acetogenin analogs with a threo, trans, threo, trans, threo-bis-tetrahydrofuran core unit. Bioorg. Med. Chem. Lett. 2007, 17, 2434-2437.
20. (c) Nattrass, G. L.; Diez, E.; McLachlan, M. M.; Dixon, D. J.; Ley, S. V. The total synthesis of the Annonaceous acetogenin 10-hydroxyasimicin. Angew. Chem., Int. Ed. 2005, 44, 580-584.
21. (d) Hu, Y.; Brown, R. C. D. A metal-oxo mediated approach to the synthesis of 21,22-diepi-membrarollin. Chem. Commun. 2005, 45, 5636-5637.
22. (e) Keum, G.; Hwang, C. H.; Kang, S. B.; Kim, Y.; Lee, E. Stereoselective syntheses of rolliniastatin 1, rollimembrin, and membranacin. J. Am. Chem. Soc. 2005, 127, 10396-10399.
23. (a) Frantz, D. E.; Fässler, R.; Carreira, E. M. Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes. J. Am. Chem. Soc. 2000, 122, 1806-1807.
24. (b) Kojima, N.; Maezaki, N.; Tominaga, H.; Asai, M.; Yanai, M.; Tanaka, T. Systematic construction of a monotetrahydrofuran-ring library in annonaceous acetogenins by asymmetric alkynylation and stereodivergent tetrahydrofuran-ring formation. Chem. - Eur. J. 2003, 9, 4980-4990.
25. Brown, H. C.; Jadhav, P. K. Asymmetric carbon-carbon bond formation via β-allyldiisopinocampheylborane. Simple synthesis of secondary homoallylic alcohols with excellent enantiomeric purities. J. Am. Chem. Soc. 1983, 105, 2092-2093.
26. Metathesis approach has become a highly versatile route for the synthesis of acetogenins. For the representative reports, see: (a) refs 6 and 7a.
27. (b) Marshall, J. A.; Sabatini, J. J. An outside-in approach to adjacent bis-tetrahydrofuran Annonaceous acetogenins with C2 core symmetry. Total synthesis of asimicin and a C32 analogue. Org. Lett. 2006, 8, 3557-3560.
28. (c) Hoye, T. R.; Eklov, B. M.; Jeon, J.; Khoroosi, M. Sequencing of three-component olefin metatheses: total synthesis of either (+)-gigantecin or (+)-14-deoxy-9-oxygigantecin. Org. Lett. 2006, 8, 3383-3386.
29. (d) Mootoo, D. R.; Zhu, L. Total synthesis of the nonadjacently linked bis-tetrahydrofuran acetogenin bullatanocin (squamostatin C). J. Org. Chem. 2004, 69, 3154-3157, and references cited therein.
30. Grubbs, R. H. Olefin metathesis. Tetrahedron 2004, 60, 7117-7140.
31. References 5 and 12b. (b) Ye, Q.; He, K.; Oberlies, N. H.; Zeng, L.; Shi, G.; Evert, D.; McLaughlin, J. L. Longimicins A-D: Novel bioactive acetogenins from Asimina longifolia (Annonaceae) and structure-activity relationships of asimicin type of Annonaceous acetogenins. J. Med. Chem. 1996, 39, 1790-1796.
32. (c) Tormo, J. R.; DePedro, N.; Royo, I.; Barrachina, I.; Zafra-Polo, M. C.; Cuadrillero, C.; Hernandez, P.; Cortes, D.; Pelaez, F. In vitro antitumor structure-activity relationships of threo/trans/threo/trans/erythro bis-tetrahydrofuranic acetogenins: Correlations with their inhibition of mitochondrial complex I. Oncol. Res. 2005, 15, 129-138, and references cited therein.
33. For the analogous stereoisomeric mono-THF acetogenin library, see: Curran, D. P.; Zhang, Q.; Richard, C.; Lu, H.; Gudipati, V.; Wilcox, C. S. Total synthesis of a 28-member stereoisomer library of murisolins. J. Am. Chem. Soc. 2006, 128, 9561-9573.
34. SMPs are prepared as described earlier, see: Matsuno-Yagi, A.; Hatefi, Y. Studies on the mechanism of oxidative phosphorylation. J. Biol. Chem. 1985, 260, 14424-14427.
35. (a) Valeriote, F.; Grieshaber, C. K.; Media, J.; Pietraszkewicz, H.; Hoffmann, J.; Pan, M.; McLaughlin, S. J. Discovery and development of anticancer agents from plants. Exp. Ther. Oncol. 2002, 2, 228-236.
36. (b) Marshall, J. A.; Piettre, A.; Paige, M. A.; Valeriote, F. A modular synthesis of Annonaceous acetogenins. J. Org. Chem. 2003, 68, 1771-1779.