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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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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, 209(3), 1039-1045 (2006-09-15)
8-Cl-cAMP, which is known to induce differentiation, growth inhibition, and apoptosis in various cancer cells, has been investigated as a putative anti-cancer drug. Previously, we reported that 8-Cl-cAMP and its metabolite 8-Cl-adenosine induce growth inhibition and apoptosis through p38 mitogen-activated
R G Halgren et al.
Blood, 92(8), 2893-2898 (1998-10-09)
We have examined the cytotoxic effects of cyclic adenosine-3', 5'-monophosphate (cAMP) derivatives on multiple myeloma cells lines and determined that the 8-Chloro substituted derivative (8Cl-cAMP) is one of the most potent. We report here that 8Cl-cAMP is cytotoxic to both
Milica Pesić et al.
Investigational new drugs, 28(4), 482-492 (2009-06-18)
The resistant cell line NCI-H460/R and its counterpart NCI-H460 were used to investigate the ability of purine analogs to overcome multidrug resistance (MDR) that seriously limit the efficacy of lung cancer regimens with chemotherapeutic agents. Two purine analogs, sulfinosine (SF)
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