Photo-induced cytotoxicity of prodigiosin analogues

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

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Prodigiosin (1) is the parent member of a class of polypyrrole natural products that exhibit promising anticancer activities. They can facilitate copper-promoted oxidative DNA damage by binding to copper ions, and this activity is thought to represent their mechanism of cytotoxicity in the dark. They also possess photoinduced cytotoxicity, although 1 is too toxic in the dark to be used effectively for the treatment of cancer by photodynamic therapies. To circumvent dark toxicity by prodigiosins, the semi-synthetic analogue 2, in which the N-pyrrolic atoms of 1 are methylated to block copper coordination, and the synthetic phenyl analogues 3 and 4, which lack the copper-coordinating A-pyrrole ring of 1, were tested for their ability to inhibit colony formation of HL-60 cancer cells in the absence and presence of visible light (λ > 495 nm). Our results show that 2-4 lack cytotoxicity in the dark, but are able to inhibit colony formation of HL-60 cells following irradiation for 30 min. The synthetic derivative 4 exhibits photo-induced cytotoxicity similar to that of the natural product 1, demonstrating the potential use of prodigiosin-based compounds for treatment of cancers following irradiation with visible light.

Original languageEnglish (US)
Pages (from-to)49-52
Number of pages4
JournalBulletin of the Korean Chemical Society
Volume28
Issue number1
DOIs
StatePublished - Jan 1 2007
Externally publishedYes

Fingerprint

Prodigiosin
Cytotoxicity
Copper
Biological Products
Irradiation
Photodynamic therapy
Pyrroles
Poisons
Toxicity
Cells
Ions
Derivatives
Atoms
DNA

Keywords

  • Cancer treatment
  • Cytotoxicity
  • Photophysical property
  • Prodigiosin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Park, G., Tomlinson, J. T., Misenheimer, J. A., Kucera, G. L., & Manderville, R. A. (2007). Photo-induced cytotoxicity of prodigiosin analogues. Bulletin of the Korean Chemical Society, 28(1), 49-52. https://doi.org/10.5012/bkcs.2007.28.1.049

Photo-induced cytotoxicity of prodigiosin analogues. / Park, Gyungse; Tomlinson, John T.; Misenheimer, Jacob A; Kucera, Gregory L.; Manderville, Richard A.

In: Bulletin of the Korean Chemical Society, Vol. 28, No. 1, 01.01.2007, p. 49-52.

Research output: Contribution to journalArticle

Park, G, Tomlinson, JT, Misenheimer, JA, Kucera, GL & Manderville, RA 2007, 'Photo-induced cytotoxicity of prodigiosin analogues', Bulletin of the Korean Chemical Society, vol. 28, no. 1, pp. 49-52. https://doi.org/10.5012/bkcs.2007.28.1.049
Park G, Tomlinson JT, Misenheimer JA, Kucera GL, Manderville RA. Photo-induced cytotoxicity of prodigiosin analogues. Bulletin of the Korean Chemical Society. 2007 Jan 1;28(1):49-52. https://doi.org/10.5012/bkcs.2007.28.1.049
Park, Gyungse ; Tomlinson, John T. ; Misenheimer, Jacob A ; Kucera, Gregory L. ; Manderville, Richard A. / Photo-induced cytotoxicity of prodigiosin analogues. In: Bulletin of the Korean Chemical Society. 2007 ; Vol. 28, No. 1. pp. 49-52.
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