Design and synthesis of new mitomycin dimers containing a seven-membered cyclic disulfide and a diol linkers

Archives of Pharmacal Research

Volumn 35, Issue 8, 2012, Pages 1413-1420

  Kim, Jae Jin ^a   Kim, Hyoung Rae ^a   Arai, Hitoshi ^b   Lee, Sang Hyup ^a  

^a Duksung Women's University   (South Korea)

^b KYOWA HAKKO KOGYO CO LTD   (Japan)

Author keywords

1,2 Dithiepane; Antitumor agent; Diol mitomycin; Disulfide formation; Disulfide mitomycin; Mitomycin dimers

Indexed keywords

7 N,7' N' (1'',2'' DITHIEPANYL 3'',7'' DIMETHYLENYL)BISMITOMYCIN C; 7 N,7' N' (2'',6'' DIHYDROXY 1'',7'' HEPTANEDIYL)BIS MITOMYCIN C; DIAMINE DERIVATIVE; DISULFIDE; MITOMYCIN A; MITOMYCIN C; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; DNA ADDUCT; DNA ALKYLATION; DNA CROSS LINKING; DRUG DESIGN; DRUG SYNTHESIS; PROTEIN CLEAVAGE;

ANTIBIOTICS, ANTINEOPLASTIC; DIMERIZATION; MITOMYCINS;

EID: 84866388567     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-012-0811-6     Document Type: Article

References (22)

1. Carter, S. C. and Crooke, S. T., Mitomycin C. Current status and new developments. Academic Press, New York, (1979).
2. Hata, T., Sano, Y., Sugawara, R., Matumae, A., Kanamorei, K., Shima, T., and Hoshi, T., Mitomycin, a new antibiotic from Streptomyces. J. Antibiot. Ser. A, 9, 141-146 (1956).
3. He, Q.-Y., Maruenda, H., and Tomasz, M., Novel bioreductive activation mechanism of mitomycin C derivatives bearing a disulfide substituent in their quinone. J. Am. Chem. Soc., 116, 9349-9350 (1994). (Pubitemid 24336962)
4. Hornemann, U., Keller, P. J., and Kozlowski, J. F., Formation of 1-ethylxanthyl-2,7-diaminomitosene and 1,10-diethylxanthyl-2,7- diaminodecarbamoylmitosene in aqueous solution upon reduction-reoxidation of mitomycin C in the presence of potassium ethylxanthate. J. Am. Chem. Soc., 101, 7121-7124 (1979). (Pubitemid 10169555)
5. Iyer, V. N. and Szybalski, W., Mitomycins and porfiromycin: chemical mechanism of activation and cross-linking of DNA. Science, 145, 55-58 (1964).
6. Keyes, S. R., Loomis, R., DiGiovanna, M. P., Pritsos, C. A., Rockwee, S., and Sartorelli, A. C., Cytotoxicity and DNA crosslinks produced by mitomycin analogs in aerobic and hypoxic EMT6 cells. Cancer Commun., 3, 351-356 (1991).
7. Kobayashi, E., Okabe, M., Kono, M., Arai, H., Kasai, M., Gomi, K., Lee, J.-H., Inaba, M., and Tsuruo, T., Comparison of uptake of mitomycin C and KW-2149 by murine P388 leukemia cells sensitive or resistant to mitomycin C. Cancer Chemother. Pharmacol., 32, 20-24 (1993). (Pubitemid 23105002)
8. Kohn, H. and Wang, S., Studies on the mechanism of activation of C(7) ethylenediamine substituted mitomycins. Relevance to the proposed mode of action of BMY-25067 and KW-2149. Tetrahedron Lett., 37, 2337-2340 (1996). (Pubitemid 26116162)
9. Kono, M., Saitoh, Y., Kasai, M., Sato, A., Shirahata, K., Morimoto, M., and Ashizawa, T., Synthesis and antitumor activity of a novel water soluble mitomycin analog; 7-N-[2-[[2-(γ-L-glutamylamino)ethyl]dithio]ethyl] mitomycin C. Chem. Pharm. Bull., 37, 1128-1130 (1989). (Pubitemid 19144154)
10. Lee, S. H. and Kohn, H., Efficient synthesis of medium-sized cyclic ether diamines. J. Org. Chem., 67, 1692-1695 (2002). (Pubitemid 34213255)
11. Lee, S. H., Synthesis and Mechanistic Studies of Novel Mitomycins. Ph.D. Thesis, University of North Carolina, North Carolina, (2003).
12. Lee, S. H. and Kohn, H., Cyclic disulfide C(8) iminoporfiromycin: nucleophilic activation of a porfiromycin. J. Am. Chem. Soc., 126, 4281-4292 (2004). (Pubitemid 38453887)
13. Lee, S. H. and Kohn, H., 7-N,7′-N′-(1″,2″- Dithianyl-3″,6″-dimethylenyl) bismitomycin C: synthesis and nucleophilic activation of a dimeric mitomycin. Org. Biomol. Chem., 3, 471-482 (2005). (Pubitemid 40285713)
14. Lee, S. H., Brodnick, R. L., Glish, G. L., and Kohn, H., 3,8,11, 16-Tetrakis(aminomethyl)-1,2,9,10-tetrathia-cyclohexadecane tetra- trifluoroacetic acid: synthetic precursor to a novel thio-substituted diamine. Tetrahedron, 61, 1749-1754 (2005). (Pubitemid 40174943)
15. Moore, H. W. and Czerniack, R., Naturally occurring quinones as potential bioreductive alkylating agents. Med. Res. Rev., 1, 249-280 (1981). (Pubitemid 12039203)
16. Na, Y., Wang, S., and Kohn, H., 7-N-(Mercaptoalkyl)mitomycins: Implications of cyclization for drug function. J. Am. Chem. Soc., 124, 4666-4677 (2002). (Pubitemid 34465004)
17. Park, H. J., Kim, J. J., Kim, H. R., Lee, E. K., Kim, E. S., Jeong, C. S., Moon, A., and Lee, S. H., Synthesis and mechanistic studies of a mitomycin dimer containing an eight-membered cyclic disulfide. Bioorg. Med. Chem., 19, 4004-4013 (2011).
18. Ramos, L. A., Lipman, R., Tomasz, M., and Basu, A. K., Effect of a site-specifically located mitomycin C adduct in Escherichia coli. Proc. Am. Assoc. Cancer Res., 38, 182 (1997).
19. Szybalski, W. and Iyer, V. N., Antibiotics. Mechanism of action. vol. 1, Gottlieb, D. and Shaw, P. D. (Eds.), Springer-Verlag, New York, pp. 211-245, (1967).
20. Tomasz, M. and Palom, Y., The mitomycin bioreductive antitumor agents: Cross-linking and alkylation of DNA as the molecular basis of their activity. Pharmacol. Ther., 76, 73-87 (1997). (Pubitemid 28078561)
21. Vyas, D. M., Chiang, Y., Benigni, D., Rose, W. C., and Brander, W. T., Recent advances in chemotherapy. Anticancer section. Tshigami, J. (Ed.), University of Tokyo Press, Tokyo, pp. 485-486, (1985).
22. Wang, S. and Kohn, H., Studies on the mode of action of mitomycin C(7) aminoethylene disulfides (BMS-181174 and KW-2149):reactivity of 7-N-(mercaptoethyl)mitomycin C. J. Med. Chem., 42, 788-790 (1999). (Pubitemid 29136169)