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
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
41106305
MDL number:
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)
SMILES string
Nc1ncnc2n(C3OC4COP(O)(=O)OC4C3O)c(Cl)nc12
InChI key
CLLFEJLEDNXZNR-UHFFFAOYSA-N
assay
≥85%
form
powder
solubility
aqueous base: soluble
storage temp.
−20°C
Related Categories
Biochem/physiol Actions
Membrane-permeable cAMP analog; resistant to hydrolysis by phosphodiesterases.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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D J Propper et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 5(7), 1682-1689 (1999-08-03)
The cyclic AMP (cAMP)-dependent protein kinase regulatory subunit RI is overexpressed in cancer cells. 8-Chloro-cAMP (8-Cl-cAMP) is an RII site-specific analogue that down-regulates RI and inhibits the growth of a wide range of cancer cells in vitro and in vivo.
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
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
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
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
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