M9131

Sigma-Aldrich

2′-O-Monosuccinyladenosine 3′:5′-cyclic monophosphate

≥98%

Empirical Formula (Hill Notation):
C14H16N5O9P
CAS Number:
Molecular Weight:
429.28
EC Number:
PubChem Substance ID:

Quality Level

biological source

synthetic (organic)

assay

≥98%

form

powder

solubility

1 M NH4OH: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

[H][C@@]1(C2)[C@@](O[C@@H](N3C=NC4=C(N)N=CN=C43)[C@@H]1OC(CCC(O)=O)=O)([H])CCP2(O)=O

InChI

1S/C14H16N5O9P/c15-12-9-13(17-4-16-12)19(5-18-9)14-11(27-8(22)2-1-7(20)21)10-6(26-14)3-25-29(23,24)28-10/h4-6,10-11,14H,1-3H2,(H,20,21)(H,23,24)(H2,15,16,17)

InChI key

QNPSLGPIZRJDAN-UHFFFAOYSA-N

Packaging

25, 100 mg in poly bottle

Application

2′-O-Monosuccinyladenosine 3′:5′-cyclic monophosphate is a cAMP analog that may be used with other cAMP analogs to evaluate cAMP mediate processes within cells.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
S C Wen et al.
Endocrinology, 116(3), 935-944 (1985-03-01)
Adrenal cortical cells are known to export cAMP and have binding proteins and cAMP-dependent protein kinase activity associated with their plasma membranes. Because these properties suggest a function for extracellular cAMP, we have undertaken a search for specific cell surface...
R A Richman et al.
Journal of cyclic nucleotide research, 6(6), 461-468 (1980-01-01)
Antisera to cyclic AMP and cyclic GMP were obtained by immunizing rabbits with antigens prepared by conjugating the 2'0-succinyl derivative of the cyclic nucleotides to thyroglobulin. The cyclic nucleotide-thyroglobulin conjugates were injected intradermally into multiple sites on the backs of...
Michael Newton et al.
Analytical biochemistry, 402(2), 129-136 (2010-04-08)
Nitric oxide (NO) mediates intercellular signaling through activation of its receptor, soluble guanylyl cyclase (sGC), leading to elevation of intracellular guanosine 3',5'-cyclic monophosphate (cGMP) levels. Through this signal transduction pathway, NO regulates a diverse range of physiological effects, from vasodilatation...
Vinay Bulusu et al.
Biochimica et biophysica acta, 1794(4), 642-654 (2008-12-30)
Adenylosuccinate lyase (ASL) catalyzes two distinct but chemically similar reactions in purine biosynthesis. The first, exclusive to the de novo pathway involves the cleavage of 5-aminoimidazole-4-(N-succinylcarboxamide) ribonucleotide (SAICAR) to 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR) and fumarate and the second common to both...
D Moreno-Delgado et al.
Neuroscience, 164(3), 1244-1251 (2009-09-09)
Histamine H(3) autoreceptors induce a negative feedback on histamine synthesis and release. While it is known that cAMP/cAMP dependent protein kinase (PKA) and Ca(2+)/CaMKII transduction pathways mediate H(3) effects on histamine synthesis, the pathways regulating neuronal histamine release are poorly...

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