Adenophostins A and B: Potent agonists of inositol-1,4,5-trisphosphate receptor produced by Penicillium brevicompactum. Structure elucidation.

The Journal of Antibiotics
1994.0

Abstract

Adenophostins A (1, C16H26N5O18P3) and B (2, C18H28N5O19P3), potent agonists of inositol-1,4,5-triphosphate (InsP3) receptor, were isolated from the culture broths of Penicillium brevicompactum SANK 11991 and SANK 12177. Hydrolysis of 2 with aq NaOH gave 1. Oxidation of 2 with NaNO2 gave the hypoxanthine derivative (3). Treatment of 1 or 2 with alkaline phosphatase gave 4 and 5. Treatment of 4 with alpha-glucosidase gave adenosine. Thus, their structures were deduced to be adenosine nucleotides by NMR, MS and the enzymatic degradation. The inhibitory constants (Ki value) of 1, 2, 3 and InsP3 itself for binding to the InsP3 receptor were 0.18 nM, 0.18 nM, 0.29 nM and 15 nM, respectively.

Knowledge Graph

Similar Paper

Adenophostins A and B: Potent agonists of inositol-1,4,5-trisphosphate receptor produced by Penicillium brevicompactum. Structure elucidation.
The Journal of Antibiotics 1994.0
Adenophostins A and B: Potent agonists of inositol-1,4,5-trisphosphate receptor produced by Penicillium brevicompactum. Taxonomy, fermentation, isolation, physico-chemical and biological properties.
The Journal of Antibiotics 1993.0
Bicyclic Analogues of <scp>d</scp>-myo-Inositol 1,4,5-Trisphosphate Related to Adenophostin A:  Synthesis and Biological Activity
Journal of Medicinal Chemistry 2001.0
Contribution of Phosphates and Adenine to the Potency of Adenophostins at the IP<sub>3</sub>Receptor: Synthesis of All Possible Bisphosphates of Adenophostin A
Journal of Medicinal Chemistry 2012.0
<scp>d</scp>-chiro-Inositol Ribophostin: A Highly Potent Agonist of <scp>d</scp>-myo-Inositol 1,4,5-Trisphosphate Receptors: Synthesis and Biological Activities
Journal of Medicinal Chemistry 2020.0
Synthesis of Adenophostin A Analogues Conjugating an Aromatic Group at the 5‘-Position as Potent IP<sub>3</sub> Receptor Ligands
Journal of Medicinal Chemistry 2006.0
A Systematic Study of C-Glucoside Trisphosphates as myo-Inositol Trisphosphate Receptor Ligands. Synthesis of β-C-Glucoside Trisphosphates Based on the Conformational Restriction Strategy
Journal of Medicinal Chemistry 2006.0
Both <scp>d</scp>- and <scp>l</scp>-Glucose Polyphosphates Mimic <scp>d</scp>-myo-Inositol 1,4,5-Trisphosphate: New Synthetic Agonists and Partial Agonists at the Ins(1,4,5)P<sub>3</sub> Receptor
Journal of Medicinal Chemistry 2020.0
Benzomalvins, new suhstance P inhibitors from a Penicillium sp.
The Journal of Antibiotics 1994.0
Isolation and Structure Determination of Novel Phosphatidylinositol Kinase Inhibitors, Echiguanines A and B, from Streptomyces sp.
Journal of Natural Products 1991.0