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

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

≥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

NACRES:

NA.77

PubChem Substance ID:

24892338

UNSPSC Code:

41106305

MDL number:

MFCD00153938

Assay:

≥85%

Form:

powder

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Properties

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

Description

Biochem/physiol Actions

Membrane-permeable cAMP analog; resistant to hydrolysis by phosphodiesterases.

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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
assay ≥85%	assay ≥98% (HPLC)	assay ≥98.5% (HPLC)	assay ≥95% (HPLC)
form powder	form powder	form powder	form powder
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

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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Involvement of AMP-activated protein kinase and p38 mitogen-activated protein kinase in 8-Cl-cAMP-induced growth inhibition.

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

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

Inhibition of B16 mouse melanoma cell growth and induction of apoptotic cell death with 8-chloroadenosine-3',5'-monophosphate and tiazofurin.

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

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Global Trade Item Number

SKU	GTIN
SAB1306256-400UL	04061835632527
C1081-10MG	04061832897592
C1081-5MG	04061832897608

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

≥85%

Select a Size

About This Item

assay

form

solubility

storage temp.

SMILES string

InChI

InChI key

Biochem/physiol Actions

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This Item

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Storage Class

wgk

flash_point_f

flash_point_c

ppe

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