Synthesis, Characterization, and Bioactivity of the Photoisomerizable Tubulin Polymerization Inhibitor azo-Combretastatin A4.
Combretastatin A4 is a stilbenoid tubulin binding mitotic inhibitor whose conformation greatly influences its potency, making it an excellent candidate for adaptation as a photoactivatable tool. Herein we report a novel synthesis, the facile isomerization with commercial grade equipment, and biological activity of azo-combretastatin A4 in vitro and in human cancer cells. Photoisomerized azo-combretestatin A4 is at least 200-fold more potent in cellular culture, making it a promising phototherapeutic and biomedical research tool.
Department of Chemistry & Biochemistry, St. Mary's College of Maryland , 18952 East Fisher Road, St. Mary's City, Maryland 20686, United States.
Ashton J
AJ
Engdahl
Department of Chemistry & Biochemistry, St. Mary's College of Maryland , 18952 East Fisher Road, St. Mary's City, Maryland 20686, United States.
Edith A
EA
Torres
Department of Chemistry & Biochemistry, St. Mary's College of Maryland , 18952 East Fisher Road, St. Mary's City, Maryland 20686, United States.
Sarah E
SE
Lock
Department of Chemistry & Biochemistry, St. Mary's College of Maryland , 18952 East Fisher Road, St. Mary's City, Maryland 20686, United States.
Taylor B
TB
Engdahl
Department of Chemistry & Biochemistry, St. Mary's College of Maryland , 18952 East Fisher Road, St. Mary's City, Maryland 20686, United States.
Pamela S
PS
Mertz
Department of Chemistry & Biochemistry, St. Mary's College of Maryland , 18952 East Fisher Road, St. Mary's City, Maryland 20686, United States.
Craig N
CN
Streu
D006801:Humans; D015394:Molecular Structure; D055668:Photochemical Processes; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D014404:Tubulin / Q000378:metabolism; D050257:Tubulin Modulators
D013267:Stilbenes; D014404:Tubulin; D050257:Tubulin Modulators; C058728:fosbretabulin