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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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
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
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.
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