ePrints@IIScePrints@IISc Home | About | Browse | Latest Additions | Advanced Search | Contact | Help

Copper(ii) curcumin complexes for endoplasmic reticulum targeted photocytotoxicity

Banaspati, A and Ramu, V and Raza, MK and Goswami, TK (2022) Copper(ii) curcumin complexes for endoplasmic reticulum targeted photocytotoxicity. In: RSC Advances, 12 (47). pp. 30722-30733.

RSC_adv_ 12-47_30722 - 30733_2022.pdf - Published Version

Download (824kB) | Preview
Official URL: https://doi.org/10.1039/d2ra04813b


Three copper(ii) complexes viz. [Cu(cur)(L)(ClO4)] (1-3), where Hcur is curcumin and L is 1,10-phenanthroline (phen, 1), dipyrido[3,2-d:2′,3′-f]quinoxaline (dpq, 2), or dipyrido[3,2-a:2′,3′-c]phenazine (dppz, 3) were synthesized, fully characterized by various physicochemical methods and evaluated for their light-assisted chemotherapeutic potential. The complexes [Cu(acac)(L)(ClO4)] (4-6), where Hacac is acetylacetone and L is phen (in 4), dpq (in 5) and dppz (in 6), were synthesized and used as controls. The solid state structures of complexes 4 and 5 were determined by single crystal X-ray diffraction. The curcumin complexes (1-3) were redox inactive at the copper centre, whereas the acetylacetonato complexes (4-6) displayed a Cu(ii)/Cu(i) couple at ∼0.1 V vs. Ag/AgCl reference electrode in DMF. Complexes 1-3 showed an intense curcumin-based band at ∼440 nm in DMF-Tris-HCl buffer (pH = 7.2) (1 : 9 v/v) which masks the copper based d-d band. The complexes bind to human serum albumin (HSA) with moderate efficacy. They also displayed significant binding affinity for calf-thymus (CT) DNA. The lipophilic curcumin complexes show remarkable visible light induced cytotoxicity (IC50 = ∼4 μM) with high phototoxic indices (PI) with low dark toxicity in human cervical carcinoma (HeLa) and human lung carcinoma (A549) cells. The corresponding acetylacetonato controls (4-6) did not show significant cytotoxicity in the dark or light. DCFDA and annexin V-FITC/PI assays using flow cytometry confirm the induction of significant apoptosis in cancer cells via generation of cytotoxic reactive oxygen species upon photoactivation. Confocal microscopic images using complex 3 demonstrate localization of the complexes predominantly in the endoplasmic reticulum of HeLa cells. © 2022 The Royal Society of Chemistry.

Item Type: Journal Article
Publication: RSC Advances
Publisher: Royal Society of Chemistry
Additional Information: The copyright for this article belongs to the Authors.
Keywords: Acetone; Binding energy; Cancer cells; Chlorine compounds; Computerized tomography; Copper compounds; Cytotoxicity; Lanthanum compounds; Light; Single crystals; Synthesis (chemical), Acetylacetone; Complex 1; Copper complexes; Curcumin; Endoplasmic reticulum; Phenanthrolines; Photocytotoxicity; Physicochemical methods; Quinoxalines; Synthesised, Cell death
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 03 Jan 2023 05:07
Last Modified: 03 Jan 2023 05:07
URI: https://eprints.iisc.ac.in/id/eprint/78668

Actions (login required)

View Item View Item