Relationship between cytotoxicity and conversion of thiosangivamycin analogs to toyocamycin analogs in cell culture medium
dc.contributor.author | Renau, Thomas E. | en_US |
dc.contributor.author | Lee, James S. | en_US |
dc.contributor.author | Kim, Hanna | en_US |
dc.contributor.author | Young, Christopher G. | en_US |
dc.contributor.author | Wotring, Linda L. | en_US |
dc.contributor.author | Townsend, Leroy B. | en_US |
dc.contributor.author | Drach, John C. | en_US |
dc.date.accessioned | 2006-04-10T17:57:23Z | |
dc.date.available | 2006-04-10T17:57:23Z | |
dc.date.issued | 1994-08-17 | en_US |
dc.identifier.citation | Renau, Thomas E., Lee, James S., Kim, Hanna, Young, Christopher G., Wotring, Linda L., Townsend, Leroy B., Drach, John C. (1994/08/17)."Relationship between cytotoxicity and conversion of thiosangivamycin analogs to toyocamycin analogs in cell culture medium." Biochemical Pharmacology 48(4): 801-807. <http://hdl.handle.net/2027.42/31387> | en_US |
dc.identifier.uri | http://www.sciencedirect.com/science/article/B6T4P-478BR2P-2M/2/cd165bbb4df3a8c83772401fb46d3898 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/31387 | |
dc.identifier.uri | http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=retrieve&db=pubmed&list_uids=8080454&dopt=citation | en_US |
dc.description.abstract | Non-nucleoside analogs of the pyrrolopyrimidine nucleosides toyocamycin, sangivamycin and thiosangivamycin have been synthesized and their cytotoxicity in mammalian cells determined. While studying the effects of 5-thioamide-substituted analogs on cell growth, we observed an interesting phenomenon in which cells recovered spontaneously from growth inhibition during extended incubations. HPLC studies demonstrated that the 5-thioamide moiety of several structurally dissimilar 7-substituted 4-aminopyrrolo[2,3-d]pyrimidines, including thiosangivamycin, is unstable in cell culture medium and is converted to the corresponding 5-nitrile with a half-life of approximately 48 hr. In contrast, different substituents at the 4-position of the heterocycle significantly affected the stability of the 5-thioamide moiety. Conversion of the thioamide to the nitrile was caused by components in the cell culture medium, not components of serum. The above observations demonstrate that caution should be exercised in interpreting biological data obtained in vitro for 5-thioamide pyrrolo(2,3-d]pyrimidines. | en_US |
dc.format.extent | 815001 bytes | |
dc.format.extent | 3118 bytes | |
dc.format.mimetype | application/pdf | |
dc.format.mimetype | text/plain | |
dc.language.iso | en_US | |
dc.publisher | Elsevier | en_US |
dc.title | Relationship between cytotoxicity and conversion of thiosangivamycin analogs to toyocamycin analogs in cell culture medium | en_US |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | en_US |
dc.subject.hlbsecondlevel | Biological Chemistry | en_US |
dc.subject.hlbtoplevel | Science | en_US |
dc.subject.hlbtoplevel | Health Sciences | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | Interdepartmental Graduate Program in Medicinal Chemistry, College of Pharmacy, U.S.A.;Department of Biologic and Materials Sciences, School of Dentistry, University of Michigan, Ann Arbor, MI 48109-1078, U.S.A. | en_US |
dc.contributor.affiliationum | Interdepartmental Graduate Program in Medicinal Chemistry, College of Pharmacy, U.S.A.;Department of Biologic and Materials Sciences, School of Dentistry, University of Michigan, Ann Arbor, MI 48109-1078, U.S.A. | en_US |
dc.contributor.affiliationum | Interdepartmental Graduate Program in Medicinal Chemistry, College of Pharmacy, U.S.A.;Department of Biologic and Materials Sciences, School of Dentistry, University of Michigan, Ann Arbor, MI 48109-1078, U.S.A. | en_US |
dc.contributor.affiliationum | Interdepartmental Graduate Program in Medicinal Chemistry, College of Pharmacy, U.S.A.;Department of Biologic and Materials Sciences, School of Dentistry, University of Michigan, Ann Arbor, MI 48109-1078, U.S.A. | en_US |
dc.contributor.affiliationum | Interdepartmental Graduate Program in Medicinal Chemistry, College of Pharmacy, U.S.A.;Department of Biologic and Materials Sciences, School of Dentistry, University of Michigan, Ann Arbor, MI 48109-1078, U.S.A. | en_US |
dc.contributor.affiliationum | Interdepartmental Graduate Program in Medicinal Chemistry, College of Pharmacy, U.S.A.;Department of Biologic and Materials Sciences, School of Dentistry, University of Michigan, Ann Arbor, MI 48109-1078, U.S.A. | en_US |
dc.contributor.affiliationum | Interdepartmental Graduate Program in Medicinal Chemistry, College of Pharmacy, U.S.A.;Department of Biologic and Materials Sciences, School of Dentistry, University of Michigan, Ann Arbor, MI 48109-1078, U.S.A. | en_US |
dc.identifier.pmid | 8080454 | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/31387/1/0000300.pdf | en_US |
dc.identifier.doi | http://dx.doi.org/10.1016/0006-2952(94)90059-0 | en_US |
dc.identifier.source | Biochemical Pharmacology | en_US |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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