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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Vesna Vucić et al.
Investigational new drugs, 26(4), 309-317 (2007-12-07)
The antiproliferative and cytotoxic potential of the nucleotide analog 8-Cl-cAMP was tested in PC-3 and DU145 metastatic human prostate cancer cells. The drug was examined as the only therapeutic agent and in combination with ionizing irradiation (IR). Highly synergistic effects
Judith A Enyeart et al.
American journal of physiology. Endocrinology and metabolism, 301(5), E941-E954 (2011-08-04)
The regulation of cortisol synthesis and the expression of genes coding for steroidogenic proteins by 8-substituted cAMP and 8-substituted adenine derivatives were studied in bovine adrenal zona fasciculata (AZF) cells. At concentrations of 10-50 μM, 8-(4-chlorophenylthio)-cAMP (8CPT-cAMP), but not the
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
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
Audrey J Robinson-White et al.
The Journal of clinical endocrinology and metabolism, 94(10), 4061-4069 (2009-09-24)
Carney complex, a multiple neoplasia syndrome, characterized primarily by spotty skin pigmentation and a variety of endocrine and other tumors, is caused by mutations in PRKAR1A, the gene that codes for the RIalpha subunit of protein kinase A (PKA). PKA
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