Evaluation of O-alkyl and aryl sulfonyl aromatic and heteroaromatic amidoximes as novel potent DNA photo-cleavers
- 22 January 2016
- journal article
- research article
- Published by Springer Science and Business Media LLC in Photochemical & Photobiological Sciences
- Vol. 15 (3), 351-360
- https://doi.org/10.1039/c5pp00439j
Abstract
Several stable O-alkyl and aryl sulfonyl conjugated p-nitro-Ph and o-, m-, p-pyridine N′-hydroxy imidamides, were subjected to UV irradiation at 312 nm with supercoiled circular plasmid DNA pBluescript KS II. The generated amidinyl and sulfonyloxyl radicals led to effective DNA photo-cleavage. Both alkyl and aryl sulfonyl derivatives were active and the order p-pyridine > p-nitro-Ph > o-pyridine > m-pyridine was schematized for the N′-hydroxy imidamides moiety. Calf thymus-DNA affinity studies which comprised UV interactions, viscosity experiments and competitive studies with ethidium bromide showed good to excellent affinity of the compounds. These properties revealed sulfonyl amidoximes as novel effective DNA-photo-cleavers and may serve in the discovery of new leads for “on demand” biotechnological and medical applications.Keywords
This publication has 58 references indexed in Scilit:
- Photodynamic therapy of malignant brain tumours: A complementary approach to conventional therapiesCancer Treatment Reviews, 2014
- Oxime Esters of 2,6-Diazaanthracene-9,10-dione and 4,5-Diazafluoren-9-one as Photo-induced DNA-Cleaving AgentsMolecules, 2012
- Synthesis and DNA cleavage studies of novel quinoline oxime estersBioorganic & Medicinal Chemistry Letters, 2012
- Convenient synthesis and biological profile of 5-amino-substituted 1,2,4-oxadiazole derivativesEuropean Journal of Medicinal Chemistry, 2010
- A Convenient Synthesis of 5-Amino-Substituted 1,2,4-Oxadiazole Derivatives via Reactions of Amidoximes with CarbodiimidesHETEROCYCLES, 2008
- Synthesis of oxadiazoloquinoxaline, oxathiadiazoloquinoxaline and oxadiazolobenzothiazine derivativesJournal of Heterocyclic Chemistry, 2006
- Synthesis and Cytotoxicity of Silicon and Germanium Containing Pyridine Oxime O-EthersBioinorganic Chemistry and Applications, 2003
- Synthesis and biological evaluation of several coumarin-4-carboxamidoxime and 3-(coumarin-4-yl)-1,2,4-oxadiazole derivativesEuropean Journal of Medicinal Chemistry, 1998
- A procedure for the isolation of deoxyribonucleic acid from micro-organismsJournal of Molecular Biology, 1961
- A Further Examination of the Molecular Weight and Size of Desoxypentose Nucleic AcidJournal of the American Chemical Society, 1954