{[(4aR,6R,7R,7aR)-6-{6-Amino-8-[(4-chlorophenyl)sulfanyl]-9H-purin-9-yl}-7-methoxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-yl]oxy}methyl acetate

Modify Date: 2024-03-10 13:32:31

{[(4aR,6R,7R,7aR)-6-{6-Amino-8-[(4-chlorophenyl)sulfanyl]-9H-purin-9-yl}-7-methoxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-yl]oxy}methyl acetate structure	Common Name	{[(4aR,6R,7R,7aR)-6-{6-Amino-8-[(4-chlorophenyl)sulfanyl]-9H-purin-9-yl}-7-methoxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-yl]oxy}methyl acetate
	CAS Number	1152197-23-3	Molecular Weight	557.901
	Density	1.8±0.1 g/cm3	Boiling Point	757.2±70.0 °C at 760 mmHg
	Molecular Formula	C₂₀H₂₁ClN₅O₈PS	Melting Point	N/A
	MSDS	N/A	Flash Point	411.7±35.7 °C

Use of {[(4aR,6R,7R,7aR)-6-{6-Amino-8-[(4-chlorophenyl)sulfanyl]-9H-purin-9-yl}-7-methoxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-yl]oxy}methyl acetate

8-pCPT-2'-O-Me-cAMP-AM is a cyclic AMP analogue, selectively activates Epac-Rap signaling pathway. 8-pCPT-2'-O-Me-cAMP-AM protects renal function by activating Epac from ischemia injury. 8-pCPT-2'-O-Me-cAMP-AM also stimulates insulin secretion by interaction with PKA pathway[1][2].

Name	{[(4aR,6R,7R,7aR)-6-{6-Amino-8-[(4-chlorophenyl)sulfanyl]-9H-purin-9-yl}-7-methoxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-yl]oxy}methyl acetate
Synonym	More Synonyms

Description	8-pCPT-2'-O-Me-cAMP-AM is a cyclic AMP analogue, selectively activates Epac-Rap signaling pathway. 8-pCPT-2'-O-Me-cAMP-AM protects renal function by activating Epac from ischemia injury. 8-pCPT-2'-O-Me-cAMP-AM also stimulates insulin secretion by interaction with PKA pathway[1][2].
Related Catalog	Signaling Pathways >> Protein Tyrosine Kinase/RTK >> PKA Signaling Pathways >> Stem Cell/Wnt >> PKA Research Areas >> Metabolic Disease
In Vitro	8-pCPT-2'-O-Me-cAMP-AM (2.5 μM; 30 min) activates Epac and prevents adherens junction disassembly during hypoxia (60 min)[1]. 8-pCPT-2'-O-Me-cAMP-AM can cross the plasma membrane and is able to alter diverse cellular functions that include Rap1 GTPase activity, PKB, and ERK1/2 protein kinase activity, phospholipase C activity, Ca2+ signaling, ion channel activity, exocytosis, cell adhesion, and gene expression[2]. 8-pCPT-2'-O-Me-cAMP-AM stimulates insulin secretion with dose-dependent and glucose metabolism-dependent (0.1 or 1.11 mM) actions[2]. 8-pCPT-2'-O-Me-cAMP-AM (20 μM) activates the cAMP reporter Epac1-camps, while 8-pCPT-2'-O-Me-cAMP doesn’t in INS-1 cells[2]. 8-pCPT-2'-O-Me-cAMP-AM (0.3-3.0 μM; 0-300 sec) activates Epac1-camps in a dose- and time-dependent manner in high throughput assay[2].
In Vivo	8-pCPT-2'-O-Me-cAMP-AM (intrarenal injection; ) activates renal Rap1 and likely is caused by activation of Epac in the tubular epithelium[1]. 8-pCPT-2'-O-Me-cAMP-AM preserves renal function by Epac activation and reduces tubular epithelial-cell stress during ischemia[1]. Animal Model: IR injuried mouse model[1] Dosage: 1.45 mM Administration: Intrarenal injection; mice were sacrificed at 24, 48, or 72 hours after ischemia Result: Protected renal injury during ischemia.
References	[1]. Stokman G, et al. Epac-Rap signaling reduces cellular stress and ischemia-induced kidney failure. J Am Soc Nephrol. 2011 May;22(5):859-72. [2]. Chepurny OG, et al. Enhanced Rap1 activation and insulin secretagogue properties of an acetoxymethyl ester of an Epac-selective cyclic AMP analog in rat INS-1 cells: studies with 8-pCPT-2'-O-Me-cAMP-AM. J Biol Chem. 2009 Apr 17;284(16):10728-36.

Density	1.8±0.1 g/cm3
Boiling Point	757.2±70.0 °C at 760 mmHg
Molecular Formula	C₂₀H₂₁ClN₅O₈PS
Molecular Weight	557.901
Flash Point	411.7±35.7 °C
Exact Mass	557.053711
LogP	2.51
Vapour Pressure	0.0±2.5 mmHg at 25°C
Index of Refraction	1.750

Methanol, 1-[[(4aR,6R,7R,7aR)-6-[6-amino-8-[(4-chlorophenyl)thio]-9H-purin-9-yl]tetrahydro-7-methoxy-2-oxido-4H-furo[3,2-d]-1,3,2-dioxaphosphorin-2-yl]oxy]-, acetate (ester)

{[(4aR,6R,7R,7aR)-6-{6-Amino-8-[(4-chlorophenyl)sulfanyl]-9H-purin-9-yl}-7-methoxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-yl]oxy}methyl acetate

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{[(4aR,6R,7R,7aR)-6-{6-Amino-8-[(4-chlorophenyl)sulfanyl]-9H-purin-9-yl}-7-methoxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-yl]oxy}methyl acetate

Use of {[(4aR,6R,7R,7aR)-6-{6-Amino-8-[(4-chlorophenyl)sulfanyl]-9H-purin-9-yl}-7-methoxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-yl]oxy}methyl acetate

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Biological Activity

Chemical & Physical Properties

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The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.