Photoinduced cytotoxicity and thioadduct formation by a prodigiosin analogue.
[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.
Tomlinson
John T
JT
Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109-7486, USA.
Park
Gyungse
G
Misenheimer
Jacob A
JA
Kucera
Gregory L
GL
Hesp
Kevin
K
Manderville
Richard A
RA
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
D000470:Alkaloids; D000970:Antineoplastic Agents; D013457:Sulfur Compounds; D011353:Prodigiosin