8-CPT-2Me-cAMP, sodium saltEPAC agonist, selective CAS# 634207-53-7 |
- PI 828
Catalog No.:BCC7494
CAS No.:942289-87-4
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 634207-53-7 | SDF | Download SDF |
PubChem ID | 23679067 | Appearance | Powder |
Formula | C17H18ClN5NaO7PS | M.Wt | 525.8 |
Type of Compound | N/A | Storage | Desiccate at -20°C |
Solubility | Soluble to 100 mM in water | ||
Chemical Name | sodium;9-[(4aR,6R,7R,7aR)-7-methoxy-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-8-(4-chlorophenyl)sulfanylpurin-6-amine;hydrate | ||
SMILES | COC1C2C(COP(=O)(O2)[O-])OC1N3C4=C(C(=NC=N4)N)N=C3SC5=CC=C(C=C5)Cl.O.[Na+] | ||
Standard InChIKey | NVPSOXGMFVFZIS-IPBMGFFTSA-M | ||
Standard InChI | InChI=1S/C17H17ClN5O6PS.Na.H2O/c1-26-13-12-10(6-27-30(24,25)29-12)28-16(13)23-15-11(14(19)20-7-21-15)22-17(23)31-9-4-2-8(18)3-5-9;;/h2-5,7,10,12-13,16H,6H2,1H3,(H,24,25)(H2,19,20,21);;1H2/q;+1;/p-1/t10-,12-,13-,16-;;/m1../s1 | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Description | Selective activator of Epac, the cAMP-sensitive guanine nucleotide-exchange factor for Rap1 and Rap2. Activates Epac1 (EC50 = 2.2 μM), but not PKA (EC50 > 10 μM). Stimulates Epac-mediated Ca2+-mediated Ca2+ release in pancreatic β-cells in vitro.Cell permeable analog also available. |
8-CPT-2Me-cAMP, sodium salt Dilution Calculator
8-CPT-2Me-cAMP, sodium salt Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 1.9019 mL | 9.5093 mL | 19.0186 mL | 38.0373 mL | 47.5466 mL |
5 mM | 0.3804 mL | 1.9019 mL | 3.8037 mL | 7.6075 mL | 9.5093 mL |
10 mM | 0.1902 mL | 0.9509 mL | 1.9019 mL | 3.8037 mL | 4.7547 mL |
50 mM | 0.038 mL | 0.1902 mL | 0.3804 mL | 0.7607 mL | 0.9509 mL |
100 mM | 0.019 mL | 0.0951 mL | 0.1902 mL | 0.3804 mL | 0.4755 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
8-CPT-2Me-cAMP, sodium salt is a selective agonist of EPAC [1].
Cyclic AMP guanine nucleotide exchange factors (EPACs) are intracellular sensors for cAMP and function as nucleotide exchange factors for the Ras GTPase homologues Rap1 and Rap2 [1].
8-CPT-2Me-cAMP, sodium salt is a selective EPAC agonist. 8-CPT-2Me-cAMP increased Rap1 activation by EPAC1. Meantime, light chain 2 (LC2) of the microtubule-associated protein MAP1A increased this response. In LC2- and EPAC1-transfected cells, 8-CPT-2Me-cAMP increased cell adhesion to laminin [1]. In Jurkat Tcells, 8-CPT-2Me-cAMP (100 μM) activated Rap1, which was not affected by H-89, a PKA inhibitor [2]. In 1-LN prostate cancer cells, 8-CPT-2Me-cAMP increased Epac1, p-AktS473 and p-AktT308 in a dose-dependent way. 8-CPT-2Me-cAMP increased p-AktS473 and AktS473 kinase activity by two-three fold. Also, 8-CPT-2Me-cAMP activated mTORC1 and mTORC2 [3].
In human prostate cancer cells, 8-CPT-2Me-cAMP increased the levels of p-cPLA2S505, COX-2 and PGE2. However, COX-2, EP4 or mTOR inhibitors inhibited this effect and reduced protein and DNA synthesis induced by Epac1. These results suggested Epac1 was a pro-inflammatory modulator and promoted cell proliferation [4].
References:
[1]. Gupta M, Yarwood SJ. MAP1A light chain 2 interacts with exchange protein activated by cyclic AMP 1 (EPAC1) to enhance Rap1 GTPase activity and cell adhesion. J Biol Chem, 2005, 280(9): 8109-8116.
[2]. Fuld S, Borland G, Yarwood SJ. Elevation of cyclic AMP in Jurkat T-cells provokes distinct transcriptional responses through the protein kinase A (PKA) and exchange protein activated by cyclic AMP (EPAC) pathways. Exp Cell Res, 2005, 309(1): 161-173.
[3]. Misra UK, Pizzo SV. Upregulation of mTORC2 activation by the selective agonist of EPAC, 8-CPT-2Me-cAMP, in prostate cancer cells: assembly of a multiprotein signaling complex. J Cell Biochem, 2012, 113(5): 1488-1500.
[4]. Misra UK, Pizzo SV. Evidence for a pro-proliferative feedback loop in prostate cancer: the role of Epac1 and COX-2-dependent pathways. PLoS One, 2013, 8(4): e63150.
- Alepterolic acid
Catalog No.:BCN4172
CAS No.:63399-38-2
- 3-Acetoxy-8(17),13E-labdadien-15-oic acid
Catalog No.:BCN1390
CAS No.:63399-37-1
- SJB2-043
Catalog No.:BCC1952
CAS No.:63388-44-3
- (+)-Isolariciresinol 9'-O-glucoside
Catalog No.:BCN7014
CAS No.:63358-12-3
- Bromethalin
Catalog No.:BCC5472
CAS No.:63333-35-7
- VU 10010
Catalog No.:BCC7577
CAS No.:633283-39-3
- Secoisolariciresinol monoglucoside
Catalog No.:BCN6990
CAS No.:63320-67-2
- Jacoumaric acid
Catalog No.:BCN3245
CAS No.:63303-42-4
- Azaphen dihydrochloride monohydrate
Catalog No.:BCC1391
CAS No.:63302-99-8
- Berberine hydrogen sulphate
Catalog No.:BCN2574
CAS No.:633-66-9
- Berberine hydrochloride
Catalog No.:BCN6319
CAS No.:633-65-8
- Echiumine
Catalog No.:BCN1972
CAS No.:633-16-9
- Corollin
Catalog No.:BCC8754
CAS No.:63461-31-4
- TBPB
Catalog No.:BCC5517
CAS No.:634616-95-8
- WAY-100635 maleate salt
Catalog No.:BCC2054
CAS No.:634908-75-1
- Lithospermoside
Catalog No.:BCN1270
CAS No.:63492-69-3
- ANR 94
Catalog No.:BCC7815
CAS No.:634924-89-3
- Bilirubin
Catalog No.:BCN1047
CAS No.:635-65-4
- 4,2'-Dihydroxy-4'-methoxychalcone
Catalog No.:BCN7704
CAS No.:63529-06-6
- LY404039
Catalog No.:BCC4592
CAS No.:635318-11-5
- 24,25-Epoxydammar-20(21)-en-3-one
Catalog No.:BCN4173
CAS No.:63543-52-2
- 24,25-Dihydroxydammar-20-en-3-one
Catalog No.:BCN4174
CAS No.:63543-53-3
- Adrafinil
Catalog No.:BCC4166
CAS No.:63547-13-7
- Rebaudioside C
Catalog No.:BCN2404
CAS No.:63550-99-2
Epac-selective cAMP analog 8-pCPT-2'-O-Me-cAMP as a stimulus for Ca2+-induced Ca2+ release and exocytosis in pancreatic beta-cells.[Pubmed:12496249]
J Biol Chem. 2003 Mar 7;278(10):8279-85.
The second messenger cAMP exerts powerful stimulatory effects on Ca(2+) signaling and insulin secretion in pancreatic beta-cells. Previous studies of beta-cells focused on protein kinase A (PKA) as a downstream effector of cAMP action. However, it is now apparent that cAMP also exerts its effects by binding to cAMP-regulated guanine nucleotide exchange factors (Epac). Although one effector of Epac is the Ras-related G protein Rap1, it is not fully understood what the functional consequences of Epac-mediated signal transduction are at the cellular level. 8-(4-chloro-phenylthio)-2'-O-methyladenosine-3'-5'-cyclic monophosphate (8-pCPT-2'-O-Me-cAMP) is a newly described cAMP analog, and it activates Epac but not PKA. Here we demonstrate that 8-pCPT-2'-O-Me-cAMP acts in human pancreatic beta-cells and INS-1 insulin-secreting cells to mobilize Ca(2+) from intracellular Ca(2+) stores via Epac-mediated Ca(2+)-induced Ca(2+) release (CICR). The cAMP-dependent increase of [Ca(2+)](i) that accompanies CICR is shown to be coupled to exocytosis. We propose that the interaction of cAMP and Epac to trigger CICR explains, at least in part, the blood glucose-lowering properties of an insulinotropic hormone (glucagon-like peptide-1, also known as GLP-1) now under investigation for use in the treatment of type-2 diabetes mellitus.
A novel Epac-specific cAMP analogue demonstrates independent regulation of Rap1 and ERK.[Pubmed:12402047]
Nat Cell Biol. 2002 Nov;4(11):901-6.
cAMP is involved in a wide variety of cellular processes that were thought to be mediated by protein kinase A (PKA). However, cAMP also directly regulates Epac1 and Epac2, guanine nucleotide-exchange factors (GEFs) for the small GTPases Rap1 and Rap2 (refs 2,3). Unfortunately, there is an absence of tools to discriminate between PKA- and Epac-mediated effects. Therefore, through rational drug design we have developed a novel cAMP analogue, 8-(4-chloro-phenylthio)-2'-O-methyladenosine-3',5'-cyclic monophosphate (8CPT-2Me-cAMP), which activates Epac, but not PKA, both in vitro and in vivo. Using this analogue, we tested the widespread model that Rap1 mediates cAMP-induced regulation of the extracellular signal-regulated kinase (ERK). However, both in cell lines in which cAMP inhibits growth-factor-induced ERK activation and in which cAMP activates ERK, 8CPT-2Me-cAMP did not affect ERK activity. Moreover, in cell lines in which cAMP activates ERK, inhibition of PKA and Ras, but not Rap1, abolished cAMP-mediated ERK activation. We conclude that cAMP-induced regulation of ERK and activation of Rap1 are independent processes.
A family of cAMP-binding proteins that directly activate Rap1.[Pubmed:9856955]
Science. 1998 Dec 18;282(5397):2275-9.
cAMP (3',5' cyclic adenosine monophosphate) is a second messenger that in eukaryotic cells induces physiological responses ranging from growth, differentiation, and gene expression to secretion and neurotransmission. Most of these effects have been attributed to the binding of cAMP to cAMP-dependent protein kinase A (PKA). Here, a family of cAMP-binding proteins that are differentially distributed in the mammalian brain and body organs and that exhibit both cAMP-binding and guanine nucleotide exchange factor (GEF) domains is reported. These cAMP-regulated GEFs (cAMP-GEFs) bind cAMP and selectively activate the Ras superfamily guanine nucleotide binding protein Rap1A in a cAMP-dependent but PKA-independent manner. Our findings suggest the need to reformulate concepts of cAMP-mediated signaling to include direct coupling to Ras superfamily signaling.