Photoinduced cytotoxicity and thioadduct formation by a prodigiosin analogue

John T. Tomlinson, Gyungse Park, Jacob A Misenheimer, Gregory L. Kucera, Kevin Hesp, Richard A. Manderville

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17 Scopus citations

Abstract

(Chemical Equation Presented) The prodigiosin alkaloid 1 and the synthetic analogue 2 show photoinduced cytotoxicity against HL-60 cancer cells. Photoirradiation of 1 and 2 causes photofading, photooxidation, and thioadduct formation. These results provide a model for the redox properties of prodigiosins that play a role in their biological activity and provide a new way to functionalize their pyrromethene entity with water-soluble thiol groups.

Original languageEnglish (US)
Pages (from-to)4951-4954
Number of pages4
JournalOrganic Letters
Volume8
Issue number21
DOIs
StatePublished - Oct 12 2006

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Tomlinson, J. T., Park, G., Misenheimer, J. A., Kucera, G. L., Hesp, K., & Manderville, R. A. (2006). Photoinduced cytotoxicity and thioadduct formation by a prodigiosin analogue. Organic Letters, 8(21), 4951-4954. https://doi.org/10.1021/ol061998r