D0260

N⁶,2′-O-Dibutyryladenosine 3′,5′-cyclic monophosphate sodium salt

≥97% (HPLC), powder

• Synonym(s): Bucladesine sodium salt, Dibutyryl cAMP sodium salt, Dibutyryl cyclic-AMP sodium salt
• Linear Formula: C₁₈H₂₃N₅O₈PNa
• CAS Number: 16980-89-5
• Molecular Weight: 491.37
• EC Number: 241-059-4
• MDL number: MFCD00005843
• UNSPSC Code: 41106305
• PubChem Substance ID: 24893221
• NACRES: NA.77

Properties

• Assay: ≥97% (HPLC)
• form: powder
• impurities: ≤0.5% cyclic AMP and 2′-O-monobutyryl-cyclic AMP; ≤3% N⁶-monobutyryl-cyclic AMP
• color: white
• solubility: H₂O: 100 mg/mL
• storage temp.: −20°C
• SMILES string: [Na+].CCCC(=O)Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4COP([O-])(=O)O[C@H]4[C@H]3OC(=O)CCC
• InChI: 1S/C18H24N5O8P.Na/c1-3-5-11(24)22-16-13-17(20-8-19-16)23(9-21-13)18-15(30-12(25)6-4-2)14-10(29-18)7-28-32(26,27)31-14;/h8-10,14-15,18H,3-7H2,1-2H3,(H,26,27)(H,19,20,22,24);/q;+1/p-1/t10-,14-,15-,18-;/m1./s1
• InChI key: KRBZRVBLIUDQNG-JBVYASIDSA-M

Description

General description

Dibutyrylcyclic adenosine monophosphate (cAMP) mimics the activity of endogenous cAMP.It is lipophilic, allows it to be more cell-permeable, and has higherresistance towards hydrolysis by cAMP phosphodiesterase. Dibutyryl cAMPinhibits phosphodiesterases and plays a vital role as a probe in signaltransduction pathways.

Application

It has been used as a component of the differentiation medium to induce differentiationof dopaminergic neurons from floor plate progenitors. It has also been usedasa supplement in DMEM: F12 to culture neuronal cells from human pluripotent stemcells.

N⁶,2′-O-Dibutyryladenosine 3′,5′-cyclic monophosphate sodium salt has been used:

• as a medium supplement for neural crest stem cells (NCSCs) differentiation
• as a component of thawing medium for cryopreserved human iPSC (induced pluripotent stem cell)-derived neurons
• in serum-free Dulbecco′s modified eagle′s medium (DMEM) to induce astrocyte differentiation

Biochem/physiol Actions

Cell-permeable cAMP analog that activates cAMP dependent protein kinase (PKA).

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Caution

Loses 2′-O-butyryl group at pH 8.5

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves