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Medicinal Chemistry of the Noncanonical Cyclic Nucleotides cCMP and cUMP

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Non-canonical Cyclic Nucleotides

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 238))

Abstract

After decades of intensive research on adenosine-3′,5′-cyclic monophosphate (cAMP)- and guanosine-3′,5′-cyclic monophosphate (cGMP)-related second messenger systems, also the noncanonical congeners cyclic cytidine-3′,5′-monophosphate (cCMP) and cyclic uridine-3′,5′-monophosphate (cUMP) gained more and more interest. Until the late 1980s, only a small number of cCMP and cUMP analogs with sometimes undefined purities had been described. Moreover, most of these compounds had been rather synthesized as precursors of antitumor and antiviral nucleoside-5′-monophosphates and hence had not been tested for any second messenger activity. Along with the recurring interest in cCMP- and cUMP-related signaling in the early 2000s, it became evident that well-characterized small molecule analogs with reliable purities would serve as highly valuable tools for the evaluation of a putative second messenger role of cyclic pyrimidine nucleotides. Meanwhile, for this purpose new cCMP and cUMP derivatives have been developed, and already known analogs have been resynthesized and highly purified. This chapter summarizes early medicinal chemistry work on cCMP and cUMP and analogs thereof, followed by a description of recent synthetic developments and an outlook on potential future directions.

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Authors and Affiliations

  1. BIOLOG Life Science Institute, Forschungslabor und Biochemica-Vertrieb GmbH, Flughafendamm 9a, 28199, Bremen, Germany

    Frank Schwede, Andreas Rentsch & Hans-Gottfried Genieser

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  1. Frank Schwede
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  2. Andreas Rentsch
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  3. Hans-Gottfried Genieser
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Correspondence to Frank Schwede .

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  1. Medical School of Hannover Insitute of Pharmakology, Hannover, Niedersachsen, Germany

    Roland Seifert

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Schwede, F., Rentsch, A., Genieser, HG. (2015). Medicinal Chemistry of the Noncanonical Cyclic Nucleotides cCMP and cUMP. In: Seifert, R. (eds) Non-canonical Cyclic Nucleotides. Handbook of Experimental Pharmacology, vol 238. Springer, Cham. https://doi.org/10.1007/164_2015_41

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