Glucose-Appended Platinum(II)-BODIPY Conjugates for Targeted Photodynamic Therapy in Red Light

Ramu, Vanitha and Gautam, Srishti and Garai, Aditya and Kondaiah, Paturu and Chakravarty, Akhil R (2018) Glucose-Appended Platinum(II)-BODIPY Conjugates for Targeted Photodynamic Therapy in Red Light. In: INORGANIC CHEMISTRY, 57 (4). pp. 1717-1726.

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Abstract

Platinum(II) complexes Pt(L-1)(R-BODIPY)]Cl (1) and Pt(L-2)(R-BODIPY)]Cl (2), where R-BODIPY is 8-(4-ethynylphenyl)-distyryl-4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diaz a-s-indacene-3, L-1 is 4'-phenyl-2,2':6',2 `'-terpyridine, and L-2 is (2,2':6',2 `'-terpyridin-4'-oxy)ethyl-beta-D-glucopyranoside, were synthesized and characterized, and their photocytotoxicity was studied. The phenylacetylide complex Pt(L-1)(C CPh)]Cl (3) was prepared and used as a control. Complexes 1 and 2 showed near-IR absorption bands at 713 nm (epsilon = 3.47 X 10(4) M-1 cm(-1)) and 715 nm (3.2 X 10(4) cm(-1)) in 10% dimethyl sulfoxide (DMSO)-Dulbecco's Modified Eagle's Medium (DMEM) (pH 7.2). The BODIPY complexes are emissive in 10% DMSO-DMEM at pH 7.2 with lambda(em) (lambda(ex), Phi(f)) = 822 nm (710 nm, 0.022) for complex 1 and lambda(ex) (lambda(ex), Phi(f)) = 825 nm (710 nm, 0.026) for complex 2. They generated singlet oxygen (O-1(2)) in red light as evidenced from 1,3-diphenylisobenzofuran (DPBF) titration experiments. The singlet oxygen quantum yield (Phi(Delta)) values for 1 and 2 were similar to 0.6 signifying their photosensitizing ability. They were remarkably photodynamic therapy (PDT) active in red light showing significant red light-induced cytotoxicity in cervical HeLa, lung cancer A549, and breast cancer MCF-7 cells (IC50: 2.3-24.7 mu M in light) with negligible dark toxicity (IC50 > 100 mu M). A significant enhancement in cellular uptake was observed for 2 having glucose-appended terpyridine ligand compared to 1. The confocal microscopy showed significant mitochondrial localization of the complexes as evidenced from the JC-1 assay. The complexes released the photoactive R-BODIPY ligand upon red light-irradiation as evidenced from the mass and H-1 NMR spectral studies. Complex 2 is remarkable in satisfying the essential requirements of targeted PDT in red light.

Item Type:	Journal Article
Publication:	INORGANIC CHEMISTRY
Publisher:	AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Additional Information:	Copy right for the article belong to AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Department/Centre:	Division of Biological Sciences > Molecular Reproduction, Development & Genetics Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	19 Mar 2018 18:28
Last Modified:	19 Mar 2018 18:28
URI:	http://eprints.iisc.ac.in/id/eprint/59246

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