Synthesis of 5''-branched derivatives of cyclic ADP-carbocyclic-ribose, a potent Ca2+-mobilizing agent: The first antagonists modified at the N1-ribose moiety

Natsumi Sakaguchi; Takashi Kudoh; Takayoshi Tsuzuki; Takashi Murayama; Takashi Sakurai; Akira Matsuda; Mitsuhiro Arisawa; Satoshi Shuto

doi:10.1016/j.bmcl.2008.04.083

Synthesis of 5''-branched derivatives of cyclic ADP-carbocyclic-ribose, a potent Ca2+-mobilizing agent: The first antagonists modified at the N1-ribose moiety

Bioorg Med Chem Lett. 2008 Jul 1;18(13):3814-8. doi: 10.1016/j.bmcl.2008.04.083. Epub 2008 May 20.

Authors

Natsumi Sakaguchi¹, Takashi Kudoh, Takayoshi Tsuzuki, Takashi Murayama, Takashi Sakurai, Akira Matsuda, Mitsuhiro Arisawa, Satoshi Shuto

Affiliation

¹ Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.

PMID: 18534848
DOI: 10.1016/j.bmcl.2008.04.083

Abstract

The 5''-branched cyclic ADP-carbocyclic-ribose derivatives were designed and synthesized. These target compounds were identified as the first antagonists of cADPR without a substituent at the adenine 8-position, and were shown to be stable due to the N1-carbocyclic-ribosyl structure.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adenine / chemistry
Adenosine Diphosphate Ribose / chemistry
Calcium / chemistry
Calcium Signaling
Chemistry, Pharmaceutical / methods
Cyclic ADP-Ribose / analogs & derivatives*
Cyclic ADP-Ribose / antagonists & inhibitors
Cyclic ADP-Ribose / chemistry
Drug Design
Hydrogen-Ion Concentration
Models, Chemical
Phosphates / chemistry
Ribose / chemistry*
Signal Transduction
Stereoisomerism

Substances

Phosphates
cyclic ADP-carbocyclic-ribose
Cyclic ADP-Ribose
Adenosine Diphosphate Ribose
Ribose
Adenine
Calcium