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C1081

Sigma-Aldrich

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:
41941-56-4
Molecular Weight:
363.65
MDL number:
MFCD00153938
UNSPSC Code:
41106305
PubChem Substance ID:
24892338
NACRES:
NA.77

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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
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
Lela B Korićanac et al.
Annals of the New York Academy of Sciences, 1030, 384-392 (2005-01-22)
Novel antineoplastic agents, 8-chloroadenosine 3',5'-monophosphate (8-Cl-cAMP) and tiazofurin (TR), have been shown to be effective against different malignant cells. Through specific mechanisms of action they modulate the cellular signal transduction pathway, thereby causing growth inhibition, cell differentiation, and apoptosis. The
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