8-Bromoadenosine 3′,5′-cyclic monophosphate - ≥98% , CAS No.23583-48-4

CAS: 23583-48-4 Cat. No.: B693917 Molecular Weight: 408.10

GRADE & PURITY ≥98%

Synonyms

8-Br-A-3:5-MP | 8-Br-cAMP | Cyclic 8-bromoadenosine 3',5'-monophosphate | 8-Bromoadenosine 3',5'-monophosphate | 8-bromo-cAMP

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Application：
8-Bromoadenosine 3′,5′-cyclic monophosphate has been used:
to treat H295R cells as positive controls for CYP19 induction
as a membrane permeable cAMP analog to study its effect on short-circuit current (Isc)
to investigate its potential as an inducer of differentiation in Wharton′s jelly-derived mesenchymal stem cells (WJ-MSCs).
Biochemical/physiological effects:
8-Bromoadenosine 3′,5′-cyclic monophosphate is a cell-permeable cAMP analog having greater resistance to hydrolysis by phosphodiesterases than cAMP. 8-Bromoadenosine 3′,5′-cyclic monophosphate activates protein kinase A, inhibits growth, decreases proliferation, increases differentiation, and induces apoptosis of cultured cells. 8-bromo-adenosine 3′,5′-cyclic monophosphate (8-bromo-cAMP), added to hepatocytes during plating helps to increase the acquisition of beta-adrenoceptors. Cell-permeable cAMP analog having greater resistance to hydrolysis by phosphodiesterases than cAMP.

Specifications

Synonyms

8-Br-A-3:5-MP | 8-Br-cAMP | Cyclic 8-bromoadenosine 3', 5'-monophosphate | 8-Bromoadenosine 3', 5'-monophosphate | 8-bromo-cAMP

Specifications & Purity

≥98%

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

ACTIVATOR

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1C2C(C(C(O2)N3C4=NC=NC(=C4N=C3Br)N)O)OP(=O)(O1)O
• IUPAC Name: (4aR,6R,7R,7aS)-6-(6-amino-8-bromopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
• InChIKey: DVKQVRZMKBDMDH-UUOKFMHZSA-N
• INCHI: 1S/C10H11BrN5O6P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,17H,1H2,(H,18,19)(H2,12,13,14)/t3-,5-,6-,9-/m1/s1
• Isomeric SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C4=NC=NC(=C4N=C3Br)N)O)OP(=O)(O1)O
• Molecular Weight: 408.10

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Purine nucleotides
      • Subclass Cyclic purine nucleotides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Purine nucleotides
• Subclass: Cyclic purine nucleotides
• Intermediate Tree Nodes: Not available
• Direct Parent: 3',5'-cyclic purine nucleotides
• Alternative Parents: Pentose phosphates Glycosylamines 6-aminopurines Monosaccharide phosphates Aminopyrimidines and derivatives Aryl bromides Imidolactams N-substituted imidazoles Organic phosphoric acids and derivatives Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Azacyclic compounds Hydrocarbon derivatives Primary amines Organic oxides Organobromides Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 3',5'-cyclic purine ribonucleotide - Pentose phosphate - Glycosyl compound - N-glycosyl compound - 6-aminopurine - Monosaccharide phosphate - Imidazopyrimidine - Purine - Aminopyrimidine - Aryl bromide - Aryl halide - Monosaccharide - N-substituted imidazole - Organic phosphoric acid derivative - Pyrimidine - Imidolactam - Tetrahydrofuran - Azole - Imidazole - Heteroaromatic compound - Secondary alcohol - Organoheterocyclic compound - Azacycle - Oxacycle - Organic nitrogen compound - Alcohol - Amine - Hydrocarbon derivative - Organic oxide - Organohalogen compound - Organic oxygen compound - Organopnictogen compound - Primary amine - Organobromide - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group.
• External Descriptors: organobromine compound - 3',5'-cyclic purine nucleotide - adenyl ribonucleotide

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

PDE4A Tclin Phosphodiesterase 4 (3344 Activities)

Discover Target: PDE4A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Moisture sensitive;light sensitive
• Melt Point(°C): 254℃
• Molecular Weight: 408.100 g/mol
• XLogP3: -1.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 1
• Exact Mass: 406.963 Da
• Monoisotopic Mass: 406.963 Da
• Topological Polar Surface Area: 155.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 532.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1