title: Photoinduced cytotoxicity and thioadduct formation by a prodigiosin analogue.
abstract: [reaction: see text] 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.
authors.affiliation: Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109-7486, USA.
authors.forename: John T
authors.initials: JT
authors.lastname: Tomlinson
authors.forename: Gyungse
authors.initials: G
authors.lastname: Park
authors.forename: Jacob A
authors.initials: JA
authors.lastname: Misenheimer
authors.forename: Gregory L
authors.initials: GL
authors.lastname: Kucera
authors.forename: Kevin
authors.initials: K
authors.lastname: Hesp
authors.forename: Richard A
authors.initials: RA
authors.lastname: Manderville
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D008958:Models, Molecular; D010084:Oxidation-Reduction; D010777:Photochemistry; D011353:Prodigiosin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013457:Sulfur Compounds / Q000737:chemistry
chemical_list: D000470:Alkaloids; D000970:Antineoplastic Agents; D013457:Sulfur Compounds; D011353:Prodigiosin