CAS 73208-40-9

Adenosine cyclic 3′,5′-[hydrogen [P(R)]-phosphorothioate]

Description:

Adenosine cyclic 3′,5′-[hydrogen [P(R)]-phosphorothioate], commonly referred to as 3',5'-cyclic adenosine monophosphate (cAMP) phosphorothioate, is a nucleotide derivative characterized by its cyclic structure and the presence of a phosphorothioate group. This compound plays a crucial role in cellular signaling as a second messenger, mediating various physiological processes such as metabolism, gene expression, and cell proliferation. The phosphorothioate modification enhances its stability against enzymatic degradation, making it a valuable tool in biochemical research and therapeutic applications. The compound exhibits a polar nature due to its phosphate group, which contributes to its solubility in aqueous environments. Additionally, it can interact with specific receptors and proteins, influencing intracellular signaling pathways. Its stereochemistry, particularly the configuration of the phosphorothioate moiety, is significant for its biological activity. Overall, this compound serves as an important model for studying nucleotide signaling and the development of pharmacological agents targeting related pathways.

Formula: C₁₀H₁₂N₅O₅PS

InChI: InChI=1S/C10H12N5O5PS/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(19-10)1-18-21(17,22)20-7/h2-4,6-7,10,16H,1H2,(H,17,22)(H2,11,12,13)/t4-,6-,7-,10-,21-/m1/s1

InChI key: InChIKey=SMPNJFHAPJOHPP-PUHOFUEYSA-N

SMILES: O[C@H]1[C@H](N2C=3C(N=C2)=C(N)N=CN3)O[C@]4([C@]1(OP(=O)(S)OC4)[H])[H]

Synonyms:

• (4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-2-sulfanyltetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-ium
• 4H-Furo[3,2-d]-1,3,2-dioxaphosphorin, adenosine deriv.
• Adenosine cyclic 3′,5′-[hydrogen [P(R)]-phosphorothioate]
• Adenosine, cyclic 3',5'-(hydrogen (P(R))-phosphorothioate)
• Adenosine, cyclic 3′,5′-(hydrogen phosphorothioate), (R)-

Rp-cAMPS

CAS: 73208-40-9

Rp-cAMPS competitively inhibits the cAMP-induced activation of cAMP-dependent protein kinase (PKA).

Formula: C₁₀H₁₂N₅O₅PS

Purity: 98%

Color and Shape: Solid

Molecular weight: 345.27

Ref: TM-T22621

Adenosine 3'',5''-cyclic monophosphothioate Rp-isomer triethylammonium salt

CAS: 73208-40-9

Ref: 7W-GN7145

Adenosine 3',5'-cyclic monophosphothioate Rp-isomer sodium salt

CAS: 73208-40-9

Adenosine 3',5'-cyclic monophosphothioate Rp-isomer sodium salt is a neurotrophic factor that has been shown to have neuroprotective properties in different animal models of Parkinson's disease. It has been shown to promote the synthesis of dopamine, glutamate, and other neurotransmitters in dopaminergic neurons. Adenosine 3',5'-cyclic monophosphothioate Rp-isomer sodium salt also promotes protein production by stimulating the synthesis of intracellular proteins such as cytosolic Ca2+ and IGF-I. This drug may be effective in pharmacological treatment for Parkinson's disease. Adenosine 3',5'-cyclic monophosphothioate Rp-isomer sodium salt is a potent inhibitor of phosphodiesterase type 4 (PDE4) with a Ki value of 0.07 μM. This inhibition leads to the accumulation of cAMP, which activates protein kinase A (PKA

Formula: C₁₀H₁₁N₅O₅PS·Na

Purity: Min. 95%

Molecular weight: 367.25 g/mol

Ref: 3D-NA58197