Design,synthesis and photoinduced DNA cleavage studies of [1,2,4]-triazolo[4,3-a]quinoxalin-4(5H)-ones |
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| Affiliation: | 1. Department of Chemistry, D. A. V. College (Lahore), Ambala City 134 002, Haryana, India;2. Department of Chemistry, Kurukshetra University, Kurukshetra 136 119, India;3. Biochemistry Department, University College, Kurukshetra University, Kurukshetra 136 119, India;4. Birla Institute of Technology and Science, Pilani-K. K. Birla Goa Campus, Goa 403 726, India;5. Department of Chemistry, Dronacharya Government College, Gurgaon 122 001, India;1. Department of Chemistry, Kurukshetra University, Kurukshetra 136119, India;2. Università degli Studi di Firenze, Laboratorio di Chimica Bioinorganica, Rm 188, and Neurofarba Department, Sezione di Scienze Farmaceutiche, Via U. Schiff 6, I-50019 Sesto Fiorentino, Firenze, Italy;1. Department of Chemistry and Pharmacy, University of Sassari, Via Muroni 23, 07100 Sassari, Italy;2. Department of Biomedical Sciences, University of Cagliari, Cittadella Universitaria, 09042 Monserrato, Cagliari, Italy;3. Molecular Simulation Engineering (MOSE) Laboratory, University of Trieste, Piazzale Europa 1, 34127 Trieste, Italy;1. Department of Chemistry, Kurukshetra University, Kurukshetra, 136119, Haryana, India;2. Departamento de Química Orgánica y Bio-orgánica, Facultad de Ciencias, UNED, Senda del Rey 9, E-28040, Madrid, Spain;3. School of Chemistry, Trinity College, Dublin, Dublin 2, Ireland;4. School of Chemistry, Trinity Biomedical Sciences Institute, Trinity College, Dublin, Dublin 2, Ireland;1. Department of Pharmaceutical Chemistry, R.C. Patel Institute of Pharmaceutical Education and Research, Shirpur (Dhule), 425405, Maharashtra, India;2. Department of Biotechnology, Bioinformatics and Pharmacy, Jaypee University of Information Technology, Waknaghat, Solan, 173234, Himachal Pradesh, India;3. Department of Pharmaceutical Chemistry, Shree Dhanvantary Pharmacy College, Kim, Surat, 394110, Gujarat, India;4. School of Public Health, Postgraduate Institute of Medical Education & Research (PGIMER), Chandigarh, 160012, India;1. Fox Chase Chemical Diversity Center, Inc, 3805 Old Easton Road, Doylestown, PA 18902, United States;2. Department of Pathobiology, School of Veterinary Medicine, University of Pennsylvania, Philadelphia, PA 19104, United States |
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| Abstract: | An expedient and eco-friendly synthesis of 1-aryl/heteroaryl-[1,2,4]-triazolo[4,3-a]quinoxalin-4(5H)-ones (4) has been accomplished via iodobenzene diacetate mediated oxidative intramolecular cyclization of 3-(2-(aryl/heteroarylidene)hydrazinyl)-quinoxalin-2(1H)-ones (3). Ten synthesized compounds 3 and 4 (10–40 μg) on irradiation with UV light at λmax 312 nm could lead to cleavage of supercoiled pMaxGFP DNA (Form I) into the relaxed DNA (Form II) without any additive. Further, DNA cleaving ability of triazoles was quantitatively evaluated and was found to be dependent on its structure, concentration, and strictly on photoirradiation time. Mechanistic investigations using several additives as potential inhibitors/activator revealed that the DNA photocleavage reaction involves Type-I pathway leading to formation of superoxide anion radicals (O2− ) as the major reactive oxygen species responsible for photocleavage process. |
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| Keywords: | Iodobenzene diacetate Supercoiled plasmid Superoxide anion radical Photocleavage AM1 calculations |
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