In vitro photodynamic therapy and quantitative structure-activity relationship studies with stable synthetic near-infrared-absorbing bacteriochlorin photosensitizers

Ying Ying Huang, Pawel Mroz, Timur Zhiyentayev, Sulbha K. Sharma, Thiagarajan Balasubramanian, Christian Ruzié, Michael Krayer, Dazhong Fan, K. Eszter Borbas, Eunkyung Yang, Hooi Ling Kee, Christine Kirmaier, James R. Diers, David F. Bocian, Dewey Holten, Jonathan S. Lindsey, Michael R. Hamblin

Research output: Contribution to journalArticlepeer-review

80 Scopus citations

Abstract

Photodynamic therapy (PDT) is a rapidly developing approach to treating cancer that combines harmless visible and near-infrared light with a nontoxic photoactivatable dye, which upon encounter with molecular oxygen generates the reactive oxygen species that are toxic to cancer cells. Bacteriochlorins are tetrapyrrole compounds with two reduced pyrrole rings in the macrocycle. These molecules are characterized by strong absorption features from 700 to >800 nm, which enable deep penetration into tissue. This report describes testing of 12 new stable synthetic bacteriochlorins for PDT activity. The 12 compounds possess a variety of peripheral substituents and are very potent in killing cancer cells in vitro after illumination. Quantitative structure-activity relationships were derived, and subcellular localization was determined. The most active compounds have both low dark toxicity and high phototoxicity. This combination together with near-infrared absorption gives these bacteriochlorins great potential as photosensitizers for treatment of cancer.

Original languageEnglish (US)
Pages (from-to)4018-4027
Number of pages10
JournalJournal of medicinal chemistry
Volume53
Issue number10
DOIs
StatePublished - May 27 2010

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