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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 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

Certificates of Analysis (COA)

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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
Linda Melotti et al.
Oncology reports, 45(2), 752-763 (2021-01-09)
The Ras/Raf/MEK/MAPK signaling cascade is frequently activated in human cancer and serves a crucial role in the oncogenesis of pediatric low‑grade gliomas (PLGGs). Therefore, drugs targeting kinases among the mitogen‑activated protein kinase (MAPK) effectors of receptor tyrosine kinase signaling may represent promising
Dragana Janković et al.
Investigational new drugs, 24(1), 15-25 (2005-12-28)
To identify purine analogs that could be effective in treating neuroblastomas, we tested the anticancer properties of sulfinosine, 8-Cl-cAMP and 8-Cl-adenosine in the SK-N-SH cell line. First we examined the effects of these three agents on cell growth inhibition and
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
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