- Nicotinic acid adenine dinucleotide phosphate analogues containing substituted nicotinic acid: Effect of modification on Ca2+ release
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Analogues of nicotinic acid adenine dinucleotide phosphate (NAADP) with substitution at either the 4- or the 5-position position of the nicotinic acid moiety have been synthesized from NADP enzymatically using Aplysia californica ADP-ribosyl cyclase or mammalian NAD glycohydrolase. Substitution at the 4-position of the nicotinic acid resulted in the loss of agonist potency for release of Ca2+-ions from sea urchin egg homogenates and in potency for competition ligand binding assays using [32P]NAADP. In contrast, several 5-substituted NAADP derivatives showed high potency for binding and full agonist activity for Ca2+ release. 5-Azido-NAADP was shown to release calcium from sea urchin egg homogenates at low concentration and to compete with [32P]NAADP in a competition ligand binding assay with an IC50 of 18 nM, indicating that this compound might be a potential photoprobe useful for specific labeling and identification of the NAADP receptor.
- Jain, Pooja,Slama, James T.,Perez-Haddock, Leroy A.,Walseth, Timothy F.
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experimental part
p. 7599 - 7612
(2011/02/22)
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- STEREOSPECIFIC SYNTHESIS OF A NOVEL SERIES OF PYRIDINE NUCLEOSIDES
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Condensation of 3,5-di-O-benzoyl-β-D-ribofuranosyl chloride severally with 3-acetyl-5-alkylpyridines, 5-alkyl-3-methoxycarbonylpyridines (alkyl= Me, Et, Pr, and iPr), 5-isopropylnicotinamide, and 3,5-diacetylpyridine bis(ethylene acetal) in acetonitrile at -5 deg C gave the corresponding 1-(3,5-di-O-benzoyl-β-D-ribofuranosyl)-3,5-disubstituted pyridinium chlorides in excellent yield (90percent).From the reaction of a series of 2,3-O-isopropylidene-β-D-ribofuranosyl halides with 3-acetyl-5-methyl-pyridine at room temperature, the α-nucleosides were obtained.
- Freyne, Eddy J.,Esmans, Eddy L.,Lepoivre, Josef A.,Alderweireldt, Frank C.
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p. 235 - 242
(2007/10/02)
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