Small molecules that mimic the thiol-triggered alkylating properties seen in the natural product leinamycin

Journal of the American Chemical Society

Volumn 125, Issue 17, 2003, Pages 4996-4997

  Chatterji, Tonika ^a   Kizil, Murat ^b   Keerthi, Kripa ^a   Chowdhury, Goutam ^a   Pospísil, Tomás ^a   Gates, Kent S ^a  

^a UNIVERSITY OF MISSOURI   (United States)

^b DICLE UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; DNA; LEINAMYCIN; LEINAMYCIN DERIVATIVE; NATURAL PRODUCT; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DNA ALKYLATION; DNA BINDING; DRUG TARGETING;

EID: 0242584837     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029169y     Document Type: Article

References (24)

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7. Reaction of leinamycin with thiols also results in the generation of reactive oxygen species. See: (a) Mitra, K.; Kim, W.; Daniels, J. S.; Gates, K. S. J. Am. Chem. Soc. 1997, 119, 11691-11692. (b) Behroozi, S. B.; Kim, W.; Dannaldson, J.; Gates, K. S. Biochemistry 1996, 35, 1768-1774.
8. Reaction of leinamycin with thiols also results in the generation of reactive oxygen species. See: (a) Mitra, K.; Kim, W.; Daniels, J. S.; Gates, K. S. J. Am. Chem. Soc. 1997, 119, 11691-11692. (b) Behroozi, S. B.; Kim, W.; Dannaldson, J.; Gates, K. S. Biochemistry 1996, 35, 1768-1774.
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20. Sibi, M. P.; Jalil Miah, M. A.; Snieckus, V. J. Org. Chem. 1984, 49, 737-747.
21. Markovnikov addition of nucleophiles to episulfonium ions is common. See, for example: Smit, W. A.; Zefirov, N. S.; Bodrikov, I. V.; Krimer, M. Z. Acc. Chem. Res. 1979, 12, 282-288. Toshimitsu, A.; Hirosawa, C.; Tanimoto, S. Tetrahedron Lett. 1991, 32, 4317-4320.
22. Markovnikov addition of nucleophiles to episulfonium ions is common. See, for example: Smit, W. A.; Zefirov, N. S.; Bodrikov, I. V.; Krimer, M. Z. Acc. Chem. Res. 1979, 12, 282-288. Toshimitsu, A.; Hirosawa, C.; Tanimoto, S. Tetrahedron Lett. 1991, 32, 4317-4320.
23. Alkyl substituents are known to increase the rate at which alkenes react with electrophilic sulfur compounds. Schmid, G. H.; Garratt, D. G. Can. J. Chem. 1973, 51, 2463-2468.
24. Breydo, L.; Zang, H.; Dutta, S.; Gates, K. S., unpublished data.