1514901-11-1

Basic information

• Product Name: 3-(2′,3′-O-isopropylidene-5′-amino-5′-deoxyadenosine)-4-(cyclopentylamino)-cyclobut-3-ene-1,2-dione
• Synonyms: 3-(2′,3′-O-isopropylidene-5′-amino-5′-deoxyadenosine)-4-(cyclopentylamino)-cyclobut-3-ene-1,2-dione
• CAS NO: 1514901-11-1
• Molecular Weight: 469.5
• Mol File: 1514901-11-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-(2′,3′-O-isopropylidene-5′-amino-5′-deoxyadenosine)-4-(cyclopentylamino)-cyclobut-3-ene-1,2-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2′,3′-O-isopropylidene-5′-amino-5′-deoxyadenosine)-4-(cyclopentylamino)-cyclobut-3-ene-1,2-dione(1514901-11-1)
• EPA Substance Registry System: 3-(2′,3′-O-isopropylidene-5′-amino-5′-deoxyadenosine)-4-(cyclopentylamino)-cyclobut-3-ene-1,2-dione(1514901-11-1)

Safety Data

• Hazardous Substances Data: 1514901-11-1(Hazardous Substances Data)

Upstream product

• 21950-36-7 5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine 

Relevant articles and documents

Structure-activity relationship of adenosine 5′-diphosphoribose at the transient receptor potential melastatin 2 (TRPM2) channel: Rational design of antagonists

Adenosine 5′-diphosphoribose (ADPR) activates TRPM2, a Ca 2+, Na+, and K+ permeable cation channel. Activation is induced by ADPR binding to the cytosolic C-terminal NudT9-homology domain. To generate the first structure-activity relationship, systematically modified ADPR analogues were designed, synthesized, and evaluated as antagonists using patch-clamp experiments in HEK293 cells overexpressing human TRPM2. Compounds with a purine C8 substituent show antagonist activity, and an 8-phenyl substitution (8-Ph-ADPR, 5) is very effective. Modification of the terminal ribose results in a weak antagonist, whereas its removal abolishes activity. An antagonist based upon a hybrid structure, 8-phenyl-2′-deoxy-ADPR (86, IC50 = 3 μM), is more potent than 8-Ph-ADPR (5). Initial bioisosteric replacement of the pyrophosphate linkage abolishes activity, but replacement of the pyrophosphate and the terminal ribose by a sulfamate-based group leads to a weak antagonist, a lead to more drug-like analogues. 8-Ph-ADPR (5) inhibits Ca2+ signalling and chemotaxis in human neutrophils, illustrating the potential for pharmacological intervention at TRPM2.