title: Differential apoptotic and redox regulatory activities of curcumin and its derivatives.
abstract: We have synthesized different bioconjugates of curcumin, which were tested for their pro- and antioxidant properties. In the present study five representative derivatives of curcumin, i.e., 4,4'-di-(O-acetyl) curcumin, 4,4'-di-(O-glycinoyl) curcumin, 4,4'-di-(O-glycinoyl-di-N-piperoyl) curcumin, 4,4'-di-(O-piperoyl) curcumin, and 4,4'-(O,O-cystinoyl)-3,3'-dimethoxydiphenyl-1,6-heptadiene-3,5-dione, were used for testing their apoptotic potential on tumor cells. Dipiperoyl and diglycinoyl derivatives showed higher apoptotic activity at lower concentrations, whereas diacetyl curcumin had slightly lower apoptotic activity on tumor cells. On the other hand, diglycinoyl-dipiperoyl and cystinoyl heptadiene derivatives had lost their apoptotic potential significantly. The apoptotic activity of these derivatives correlated very well with the generation of ROS by the tumor cells, whereas GSH levels remained unaltered. Our studies also indicate downregulation of Bcl-2 and participation of caspase-3 in the apoptotic death of tumor cells.
authors.affiliation: Nucleic Acids Research Laboratory, Department of Chemistry, University of Allahabad, Allahabad 211002, India.
authors.forename: Satyendra
authors.initials: S
authors.lastname: Mishra
authors.forename: Neha
authors.initials: N
authors.lastname: Kapoor
authors.forename: A
authors.initials: A
authors.lastname: Mubarak Ali
authors.forename: B V V
authors.initials: BV
authors.lastname: Pardhasaradhi
authors.forename: A Leela
authors.initials: AL
authors.lastname: Kumari
authors.forename: Ashok
authors.initials: A
authors.lastname: Khar
authors.forename: Krishna
authors.initials: K
authors.lastname: Misra
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects*; D053148:Caspase 3; D020169:Caspases / Q000378:metabolism; D003474:Curcumin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology*; D015536:Down-Regulation; D005978:Glutathione / Q000378:metabolism; D018219:Histiocytoma, Benign Fibrous / Q000378:metabolism / Q000473:pathology*; D010084:Oxidation-Reduction; D019253:Proto-Oncogene Proteins c-bcl-2 / Q000378:metabolism; D051381:Rats; D017382:Reactive Oxygen Species / Q000378:metabolism; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D019253:Proto-Oncogene Proteins c-bcl-2; D017382:Reactive Oxygen Species; C505410:Casp3 protein, rat; D053148:Caspase 3; D020169:Caspases; D005978:Glutathione; D003474:Curcumin