Carbocyclic 3′-deoxyadenosine-based highly potent bisubstrate-analog inhibitor of basophilic protein kinases

Conjugation of a nucleoside analog and a transport peptide led to a highly potent inhibitor of basophilic protein kinases. Carbocyclic analogs of 3′-deoxyadenosine were synthesized as racemates and the resulting stereoisomers were separated by chromatography on a chiral column. The conjugation of ob...

Full description

Saved in:
Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2007-10, Vol.17 (19), p.5336-5339
Main Authors: Enkvist, Erki, Raidaru, Gerda, Vaasa, Angela, Pehk, Tõnis, Lavogina, Darja, Uri, Asko
Format: Article
Language:English
Subjects:
Adenine - analogs & derivatives
Adenine - chemical synthesis
Adenine - pharmacology
Adenosine Triphosphate - metabolism
Aminocaproic Acid - chemistry
Analytical, structural and metabolic biochemistry
Arginine - chemistry
Biological and medical sciences
Bisubstrate inhibitors
Carbocyclic nucleoside
Cyclic AMP-Dependent Protein Kinases - antagonists & inhibitors
Cyclopentanes - chemical synthesis
Cyclopentanes - pharmacology
Enzymes and enzyme inhibitors
Fluorometry
Fundamental and applied biological sciences. Psychology
Kinetics
Medical sciences
Miscellaneous
Oligoarginine
Pharmacology. Drug treatments
Protein Kinase Inhibitors - chemical synthesis
Protein Kinase Inhibitors - pharmacology
Protein kinases
Stereoisomerism
Structure-Activity Relationship
Substrate Specificity
Transferases
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Conjugation of a nucleoside analog and a transport peptide led to a highly potent inhibitor of basophilic protein kinases. Carbocyclic analogs of 3′-deoxyadenosine were synthesized as racemates and the resulting stereoisomers were separated by chromatography on a chiral column. The conjugation of obtained compounds with hexa-( d-arginine) via 6-aminohexanoic acid linker led to a highly potent inhibitor of several basophilic protein kinases with some selectivity towards cAMP-dependent protein kinase.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2007.08.016