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
Audrey J Robinson-White et al.
The Journal of clinical endocrinology and metabolism, 93(3), 1020-1029 (2007-12-13)
Protein kinase A (PKA) affects cell proliferation in many cell types and is a potential target for cancer treatment. PKA activity is stimulated by cAMP and cAMP analogs. One such substance, 8-Cl-cAMP, and its metabolite 8-Cl-adenosine (8-Cl-ADO) are known inhibitors
Young-Ho Ahn et al.
Journal of cellular physiology, 201(2), 277-285 (2004-08-31)
8-Chloro-cyclic AMP (8-Cl-cAMP) is known to be most effective in inducing growth inhibition and differentiation of a number of cancer cells. Also, its cellular metabolite, 8-Cl-adenosine was shown to induce growth inhibition in a variety of cell lines. However, the
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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