Adenosine plays important roles in various biological processes. There is also a range of adenosine derivatives used in in clinical practice as cardioprotective, anticancer or antiviral drugs. In spite of advantages there are also limitations of adenosine drugs such as low stability in vivo, low selectivity or low affinity towards protein target. [1] Introduction of cycloalkyl, phenyl, boron cluster or other highly lipophilic substituent can improve stability, selectivity and bioavailability of drug molecule. [2,3] Although UV spectroscopy is not sufficient to determine compound structure it is useful for molecule characterisation due to spectrum-structure relationships. Using reference nucleosides enables obtaining valuable information on the structural characterisation of nucleosides. [4] In the present communication we describe an effect of boron cluster modification on UV spectra of series of adenosine and deoxyadenosine derivatives substituted at position 2 or 8 through rigid ethynyl linker. Spectra of unmodified nucleosides and ethynyl- or phenylethynyl-modified molecules were studied for comparison. An electronic properties of the boron cluster modification relevant for the observed phenomenon are discussed. Acknowledgment This work was supported by National Science Center (grant 2015/16/W/ST5/00413) and statutory fund of IBM PAS. References [1] F. Issa, M. Kassiou, L. M. Rendina, Chem. Rev., 2011, 111, 5701-5722. [2] V. Ralevic, G. Burnstock, Pharmacol. Rev., 1998, 50 (3), 413-492. [3] Z. J. Leśnikowski, J. Med. Chem. 2016, 59, 7738. [4] C. W. Gehrke, K. C. T. Kuo, Analytical Methods for Major and Modified Nucleosides - HPLC, GC, MS, NMR, UV and FT-IR, Elsevier, 1989

Unusual effect of boron luster substitution on electromagnetic spectra of purine nucleosides

Carla Sardo;
2018-01-01

Abstract

Adenosine plays important roles in various biological processes. There is also a range of adenosine derivatives used in in clinical practice as cardioprotective, anticancer or antiviral drugs. In spite of advantages there are also limitations of adenosine drugs such as low stability in vivo, low selectivity or low affinity towards protein target. [1] Introduction of cycloalkyl, phenyl, boron cluster or other highly lipophilic substituent can improve stability, selectivity and bioavailability of drug molecule. [2,3] Although UV spectroscopy is not sufficient to determine compound structure it is useful for molecule characterisation due to spectrum-structure relationships. Using reference nucleosides enables obtaining valuable information on the structural characterisation of nucleosides. [4] In the present communication we describe an effect of boron cluster modification on UV spectra of series of adenosine and deoxyadenosine derivatives substituted at position 2 or 8 through rigid ethynyl linker. Spectra of unmodified nucleosides and ethynyl- or phenylethynyl-modified molecules were studied for comparison. An electronic properties of the boron cluster modification relevant for the observed phenomenon are discussed. Acknowledgment This work was supported by National Science Center (grant 2015/16/W/ST5/00413) and statutory fund of IBM PAS. References [1] F. Issa, M. Kassiou, L. M. Rendina, Chem. Rev., 2011, 111, 5701-5722. [2] V. Ralevic, G. Burnstock, Pharmacol. Rev., 1998, 50 (3), 413-492. [3] Z. J. Leśnikowski, J. Med. Chem. 2016, 59, 7738. [4] C. W. Gehrke, K. C. T. Kuo, Analytical Methods for Major and Modified Nucleosides - HPLC, GC, MS, NMR, UV and FT-IR, Elsevier, 1989
2018
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11386/4728447
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