C1081

8-Chloroadenosine 3′,5′-cyclic-monophosphate

Name: 8-Chloroadenosine 3′,5′-cyclic-monophosphate
Brand: SIGMA
Price: 152 EUR

≥85%

Synonym(s):

8-Chloro-cAMP, 8-Chloroadenosine 3′,5′-monophosphate, 8-Cl-cAMP

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5 MG

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₁ClN₅O₆P

CAS Number:

41941-56-4

Molecular Weight:

363.65

NACRES:

NA.77

PubChem Substance ID:

24892338

UNSPSC Code:

41106305

MDL number:

MFCD00153938

Key Documents

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Product Name

8-Chloroadenosine 3′,5′-cyclic-monophosphate, ≥85%

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

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Chemistry & Biochemicals

Phosphates

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Show Differences

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This Item	C8988	A9501	C5438
Sigma-Aldrich C1081 8-Chloroadenosine 3′,5′-cyclic-monophosphate	Sigma-Aldrich C8988 8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic monophosphate monosodium hydrate	Sigma-Aldrich A9501 Adenosine 3′,5′-cyclic monophosphate	Sigma-Aldrich C5438 8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphate sodium salt
form powder	form powder	form powder	form powder
assay ≥85%	assay ≥98% (HPLC)	assay ≥98.5% (HPLC)	assay ≥95% (HPLC)
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C
solubility aqueous base: soluble	solubility H₂O: >10 mg/mL	solubility H₂O: 10 mg/mL, clear, colorless (pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20× more soluble.)	solubility H₂O: 25 mg/mL

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)

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The combination of gamma ionizing radiation and 8-Cl-cAMP induces synergistic cell growth inhibition and induction of apoptosis in human prostate cancer cells.

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

8-Phenylthio-adenines stimulate the expression of steroid hydroxylases, Cav3.2 Ca²⁺ channels, and cortisol synthesis by a cAMP-independent mechanism.

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

Targeting the mitogen‑activated protein kinase kinase and protein kinase A pathways overcomes acquired resistance to Selumetinib in low‑grade glioma cells.

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

Protein kinase A-independent inhibition of proliferation and induction of apoptosis in human thyroid cancer cells by 8-Cl-adenosine.

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

8-Chloro-cyclic AMP-induced growth inhibition and apoptosis is mediated by p38 mitogen-activated protein kinase activation in HL60 cells.

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

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8-Chloroadenosine 3′,5′-cyclic-monophosphate