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

Research output: Contribution to journalArticle

17 Citations (Scopus)

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
Externally publishedYes

Fingerprint

Prodigiosin
alkaloids
photooxidation
Cytotoxicity
activity (biology)
thiols
cancer
analogs
Photooxidation
causes
HL-60 Cells
Bioactivity
Alkaloids
Sulfhydryl Compounds
water
Oxidation-Reduction
Cells
Water
Neoplasms

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

Photoinduced cytotoxicity and thioadduct formation by a prodigiosin analogue. / Tomlinson, John T.; Park, Gyungse; Misenheimer, Jacob A; Kucera, Gregory L.; Hesp, Kevin; Manderville, Richard A.

In: Organic Letters, Vol. 8, No. 21, 12.10.2006, p. 4951-4954.

Research output: Contribution to journalArticle

Tomlinson, JT, Park, G, Misenheimer, JA, Kucera, GL, Hesp, K & Manderville, RA 2006, 'Photoinduced cytotoxicity and thioadduct formation by a prodigiosin analogue', Organic Letters, vol. 8, no. 21, pp. 4951-4954. https://doi.org/10.1021/ol061998r
Tomlinson JT, Park G, Misenheimer JA, Kucera GL, Hesp K, Manderville RA. Photoinduced cytotoxicity and thioadduct formation by a prodigiosin analogue. Organic Letters. 2006 Oct 12;8(21):4951-4954. https://doi.org/10.1021/ol061998r
Tomlinson, John T. ; Park, Gyungse ; Misenheimer, Jacob A ; Kucera, Gregory L. ; Hesp, Kevin ; Manderville, Richard A. / Photoinduced cytotoxicity and thioadduct formation by a prodigiosin analogue. In: Organic Letters. 2006 ; Vol. 8, No. 21. pp. 4951-4954.
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