C1081
8-Chloroadenosine 3′,5′-cyclic-monophosphate
≥85%
Synonym(s):
8-Chloro-cAMP, 8-Chloroadenosine 3′,5′-monophosphate, 8-Cl-cAMP
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About This Item
Empirical Formula (Hill Notation):
C10H11ClN5O6P
CAS Number:
Molecular Weight:
363.65
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.77
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Assay
≥85%
form
powder
solubility
aqueous base: soluble
storage temp.
−20°C
SMILES string
Nc1ncnc2n(C3OC4COP(O)(=O)OC4C3O)c(Cl)nc12
InChI
1S/C10H11ClN5O6P/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)
InChI key
CLLFEJLEDNXZNR-UHFFFAOYSA-N
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Related Categories
Biochem/physiol Actions
Membrane-permeable cAMP analog; resistant to hydrolysis by phosphodiesterases.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Young-Ho Ahn et al.
Cancer research, 65(11), 4896-4901 (2005-06-03)
8-Chloro-cyclic AMP (8-Cl-cAMP), which is known to induce growth inhibition, apoptosis, and differentiation in various cancer cell lines, has been studied as a putative anticancer drug. However, the mechanism of anticancer activities of 8-Cl-cAMP has not been fully understood. Previously
Jee Hae Han et al.
Journal of cellular physiology, 218(1), 104-112 (2008-08-30)
8-Cl-cAMP (8-chloro-cyclic AMP), which induces differentiation, growth inhibition and apoptosis in various cancer cells, has been investigated as a putative anti-cancer drug. Although we reported that 8-Cl-cAMP induces growth inhibition via p38 mitogen-activated protein kinase (MAPK) and a metabolite of
R G Halgren et al.
Blood, 92(8), 2893-2898 (1998-10-09)
We have examined the cytotoxic effects of cyclic adenosine-3', 5'-monophosphate (cAMP) derivatives on multiple myeloma cells lines and determined that the 8-Chloro substituted derivative (8Cl-cAMP) is one of the most potent. We report here that 8Cl-cAMP is cytotoxic to both
Young-Ho Ahn et al.
Journal of cellular physiology, 209(3), 1039-1045 (2006-09-15)
8-Cl-cAMP, which is known to induce differentiation, growth inhibition, and apoptosis in various cancer cells, has been investigated as a putative anti-cancer drug. Previously, we reported that 8-Cl-cAMP and its metabolite 8-Cl-adenosine induce growth inhibition and apoptosis through p38 mitogen-activated
Dragana Janković et al.
Investigational new drugs, 24(1), 15-25 (2005-12-28)
To identify purine analogs that could be effective in treating neuroblastomas, we tested the anticancer properties of sulfinosine, 8-Cl-cAMP and 8-Cl-adenosine in the SK-N-SH cell line. First we examined the effects of these three agents on cell growth inhibition and
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