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Merck

D0260

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

≥97% (HPLC), PKA activator, powder

동의어(들):

Bucladesine sodium salt, Dibutyryl cAMP sodium salt, Dibutyryl cyclic-AMP sodium salt

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제품정보 (DICE 배송 시 비용 별도)

Linear Formula:
C18H23N5O8PNa
CAS 번호:
Molecular Weight:
491.37
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
241-059-4
MDL number:
Assay:
≥97% (HPLC)
Form:
powder
Quality level:
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제품 이름

N6,2′-O-Dibutyryladenosine 3′,5′-cyclic monophosphate sodium salt, ≥97% (HPLC), powder

Quality Level

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

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.

Disclaimer

Loses 2′-O-butyryl group at pH 8.5


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저장 등급

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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문서 라이브러리에서 최근에 구매한 제품에 대한 문서를 찾아보세요.

문서 라이브러리 방문


문서

고리형 AMP(cAMP), 고리형 GMP(cGMP), 고리형 ADP-리보스를 포함하여 고리형 뉴클레오타이드는 GPCR 활성화에 의해 개시된 세포내 이벤트의 2차 전달자로서 광범위하게 연구되었습니다. cAMP는 주로 cAMP 의존성 단백질 인산화효소(PKA)의 활성화를 통해 모든 진핵생물 세포에서 세포 기능을 변형시키지만 cAMP 개폐 이온 채널 및 cAMP에 의해 직접 활성화되는 구아닌 뉴클레오타이드 교환 인자를 통해서도 변형시킵니다.

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.


F Schwede et al.
Pharmacology & therapeutics, 87(2-3), 199-226 (2000-09-29)
Cyclic AMP (cAMP) and cyclic GMP (cGMP) are key second messengers involved in a multitude of cellular events. From the wealth of synthetic analogs of cAMP and cGMP, only a few have been explored with regard to their therapeutic potential.
Han Zhao et al.
The Science of the total environment, 908, 168307-168307 (2023-11-11)
Atrazine (ATZ) is one of the most used herbicides in the US and a known endocrine disruptor. ATZ is frequently detected in drinking water, especially in Midwestern regions of the United States, exceeding the EPA regulation of maximum contamination level
Differentiation of human induced pluripotent stem cell (hiPSC)-derived neurons in mouse hippocampal slice cultures
Hiragi T, et al.
Frontiers in Cellular Neuroscience, 11, 143-143 (2017)