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Photohydrate-Mediated Reactions of Uridine, 2′-Deoxyuridine and 2′-Deoxycytidine with Amines at Near Neutral pH

Authors

  • Martin D. Shetlar,

    Corresponding author
    • Department of Pharmaceutical Chemistry, School of Pharmacy, University of California, San Francisco, CA
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  • Kellie Hom,

    1. Department of Pharmaceutical Chemistry, School of Pharmacy, University of California, San Francisco, CA
    2. Department of Pharmaceutical Sciences, School of Pharmacy, University of Maryland, Baltimore, MD
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  • Vincent J. Venditto

    1. Department of Bioengineering and Therapeutic Sciences, School of Pharmacy, University of California, San Francisco, CA
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Corresponding author email: shetlar@cgl.ucsf.edu (Martin D. Shetlar)

Abstract

Photohydrates are formed in high yield when uridine (Urd), 2′-deoxyuridine (dUrd), cytidine (Cyd) and 2′-deoxycytidine (dCyd) are irradiated with UVC in aqueous solution. The thermal reactions of the photohydrates of Urd with amines at pH values near pH 7.5 have been studied using UV spectroscopy, HPLC, mass spectrometry and, in some cases, NMR. It has been found that a number of amines (i.e. ethylenediamine, N,N′-dimethylethylenediamine, glycine, glycinamide, glycylglycine, glycylgylcylglycine, putrescine, spermidine and spermine) react thermally with such hydrates to form products with UV spectra characteristic of opened ring uridine-amine adducts. In general, these products display a strong absorption peak with λmax in the range between 288 and 310 nm. Mass spectral studies of a number of the products indicate that they contain one molecule of parent nucleoside and one molecule of reactant amine. Upon standing in water these products revert to parent hydrate, while heating produces parent nucleoside. Less comprehensive studies indicate that photohydrates of dUrd and dCyd undergo analogous thermal reactions. Preliminary results suggest that UV-irradiated polyuridylic acid and polycytidylic acid undergo similar reactions. These results may have relevance for obtaining a complete understanding of the biological effects of producing Urd and dCyd photohydrates in a cellular environment.

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