Dehalogenation of Halogenated Nucleobases and Nucleosides by Organoselenium Compounds

Mondal, S and Mugesh, G (2019) Dehalogenation of Halogenated Nucleobases and Nucleosides by Organoselenium Compounds. In: Chemistry - A European Journal, 25 (7). pp. 1773-1780.

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Abstract

Halogenated nucleosides, such as 5-iodo-2′-deoxyuridine and 5-iodo-2′-deoxycytidine, are incorporated into the DNA of replicating cells to facilitate DNA single-strand breaks and intra- or interstrand crosslinks upon UV irradiation. In this work, it is shown that the naphthyl-based organoselenium compounds can mediate the dehalogenation of halogenated pyrimidine-based nucleosides, such as 5-X-2′-deoxyuridine and 5-X-2′-deoxycytidine (X=Br or I). The rate of deiodination was found to be significantly higher than that of the debromination for both nucleosides. Furthermore, the deiodination of iodo-cytidines was found to be faster than that of iodo-uridines. The initial rates of the deiodinations of 5-iodocytosine and 5-iodouracil indicated that the nature of the sugar moiety influences the kinetics of the deiodination. For both the nucleobases and nucleosides, the deiodination and debromination reactions follow a halogen-bond-mediated and addition/elimination pathway, respectively.

Item Type:	Journal Article
Publication:	Chemistry - A European Journal
Publisher:	Wiley-VCH Verlag
Additional Information:	The copyright for this article belongs to Wiley-VCH Verlag. .
Keywords:	Dehalogenation; DNA; Halogenation; Irradiation; Selenium; Selenium compounds, Debromination; Halogen bonds; Initial rate; Interstrand cross-links; nucleosides; Organoselenium compounds; Single-strand breaks; UV irradiation, Biomolecules, 5'-deoxy-5'-iodouridine; idoxuridine; nucleoside; organoselenium derivative, analogs and derivatives; chemistry; conformation; halogenation; nuclear magnetic resonance spectroscopy; X ray crystallography, Crystallography, X-Ray; Halogenation; Idoxuridine; Magnetic Resonance Spectroscopy; Molecular Conformation; Nucleosides; Organoselenium Compounds
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	29 Nov 2022 06:03
Last Modified:	29 Nov 2022 06:03
URI:	https://eprints.iisc.ac.in/id/eprint/78073

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