title: Synthesis, photochemistry, DNA cleavage/binding and cytotoxic properties of fluorescent quinoxaline and quinoline hydroperoxides.
abstract: Novel fluorescent quinoxaline and quinoline hydroperoxides were shown to perform dual role as both fluorophores for cell imaging and photoinduced DNA cleaving agents. Photophysical studies of newly synthesized quinoxaline and quinoline hydroperoxides showed that they all exhibited moderate to good fluorescence. Photolysis of quinoxaline and quinoline hydroperoxides in acetonitrile using UV light above 350nm resulted in the formation of corresponding ester compounds via γ-hydrogen abstraction by excited carbonyl chromophore. Single strand DNA cleavage was achieved on irradiation of newly synthesized hydroperoxides by UV light (⩾350nm). Both hydroxyl radicals and singlet oxygen were identified as reactive oxygen species (ROS) responsible for the DNA cleavage. Further, we showed quinoline hydroperoxide binds to ct-DNA via intercalative mode. In vitro biological studies revealed that quinoline hydroperoxide has good biocompatibility, cellular uptake property and cell imaging ability. Finally, we showed that quinoline hydroperoxide can permeate into cells efficiently and may cause cytotoxicity upon irradiation by UV light.
authors: Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India.
authors: Nilanjana
authors: N
authors: Chowdhury
authors: Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India.
authors: Moumita
authors: M
authors: Gangopadhyay
authors: Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India.
authors: S
authors: S
authors: Karthik
authors: Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India. Electronic address: ndpradeep@chem.iitkgp.ernet.in.
authors: N D
authors: ND
authors: Pradeep Singh
authors: Department of Biotechnology, Indian Institute of Technology Kharagpur, Kharagpur 721302, India.
authors: Mithu
authors: M
authors: Baidya
authors: Department of Biotechnology, Indian Institute of Technology Kharagpur, Kharagpur 721302, India.
authors: S K
authors: SK
authors: Ghosh
mesh_terms: D002470:Cell Survival / Q000187:drug effects; D004247:DNA / Q000737:chemistry / Q000378:metabolism; D053837:DNA Cleavage; D004277:DNA, Single-Stranded / Q000737:chemistry / Q000378:metabolism; D005456:Fluorescent Dyes / Q000737:chemistry / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D017665:Hydroxyl Radical / Q000737:chemistry; D062105:Molecular Docking Simulation; D010545:Peroxides / Q000737:chemistry / Q000494:pharmacology / Q000528:radiation effects; D010782:Photolysis; D011804:Quinolines / Q000737:chemistry / Q000494:pharmacology / Q000528:radiation effects; D011810:Quinoxalines / Q000737:chemistry / Q000494:pharmacology / Q000528:radiation effects; D026082:Singlet Oxygen / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D014466:Ultraviolet Rays
chemical_list: D004277:DNA, Single-Stranded; D005456:Fluorescent Dyes; D010545:Peroxides; D011804:Quinolines; D011810:Quinoxalines; D026082:Singlet Oxygen; D017665:Hydroxyl Radical; D004247:DNA; C427203:calf thymus DNA
keywords: Cytotoxicity; Hydroperoxides; Intercalation; Photoinduced DNA cleavage; Quinoline; Quinoxaline