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Merck

B1381

8-Bromoguanosine 3′,5′-cyclic monophosphate sodium salt

≥98% (HPLC), cGMP analog, powder

동의어(들):

8-Br-cGMP, 8-Bromo-cyclic GMP

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제품정보 (DICE 배송 시 비용 별도)

실험식(Hill 표기법):
C10H10BrN5NaO7P
CAS 번호:
Molecular Weight:
446.08
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
256-993-8
MDL number:
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제품 이름

8-Bromoguanosine 3′,5′-cyclic monophosphate sodium salt, ≥98% (HPLC), powder

InChI key

ZJRFCXHKYQVNFK-YEOHUATISA-M

InChI

1S/C10H11BrN5O7P.Na/c11-9-13-3-6(14-10(12)15-7(3)18)16(9)8-4(17)5-2(22-8)1-21-24(19,20)23-5;/h2,4-5,8,17H,1H2,(H,19,20)(H3,12,14,15,18);/q;+1/p-1/t2-,4-,5-,8-;/m1./s1

SMILES string

[Na+].NC1=Nc2c(nc(Br)n2[C@@H]3O[C@@H]4COP([O-])(=O)O[C@H]4[C@H]3O)C(=O)N1

assay

≥98% (HPLC)

form

powder

solubility

H2O: 50 mg/mL

storage temp.

−20°C

Quality Level

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General description

8-Bromoguanosine 3′,5′-cyclic monophosphate is a cell-permeable cGMP analog of cyclic guanosine 3′:5′-monophosphate (cGMP). It is a lipid-soluble analog used in cGMP based contraction studies in cardiomyocytes.

Application

8-Bromoguanosine 3′,5′-cyclic monophosphate sodium salt has been used:
  • as a cyclic guanosine 3′:5′-monophosphate (cGMP) agonist in the collapse assay in retinal ganglion axons(10)
  • as a component of reaction buffer in in vitro kinase activity assay of recombinant protein kinase (PKG)(11)
  • as a cyclic nucleotide analog for the induction of cyclic nucleotide-gated channel (CNGA and CNGC) expression in human embryonic kidney cells(12)

Biochem/physiol Actions

8-Bromoguanosine 3′,5′-cyclic monophosphate has greater resistance to hydrolysis by phosphodiesterases than cGMP. Activates cGMP-dependent protein kinase. It slows or inhibits the intracellular calcium oscillations of tracheal smooth muscle cells in response to acetylcholine. 8-Bromoguanosine 3′,5′-cyclic monophosphate sodium salt mimics the effect of nitric oxide generating drugs. It modulates circadian rhythms and increases optic nerve impulses. In the eye 8-Bromoguanosine 3′,5′-cyclic monophosphate may favour transduction of non-R-type photoreceptors.
Cell-permeable cGMP analog having greater resistance to hydrolysis by phosphodiesterases than cGMP. Activates cGMP-dependent protein kinase. Slows or inhibits the intracellular calcium oscillations of tracheal smooth muscle cells in response to acetylcholine. Reported to mimic the effect of nitric oxide generating drugs.

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.
This compound is featured on the PKA & PKG page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

저장 등급

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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시험 성적서(COA)

Lot/Batch Number

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이 제품을 이미 가지고 계십니까?

문서 라이브러리에서 최근에 구매한 제품에 대한 문서를 찾아보세요.

문서 라이브러리 방문

U C Garg et al.
The Journal of clinical investigation, 83(5), 1774-1777 (1989-05-01)
Endothelium-derived relaxing factor has been recently identified as nitric oxide. The purpose of this study was to determine if vasodilator drugs that generate nitric oxide inhibit vascular smooth muscle mitogenesis and proliferation in culture. Three chemically dissimilar vasodilators, sodium nitroprusside
Cyclic guanosine 3': 5'-monophosphate mimics the effects of light on a circadian pacemaker in the eye of aplysia
Eskin A, et al.
The Journal of Neuroscience, 4(10), 2466-2471 (1984)
8-bromo-cGMP reduces the myofilament response to Ca2+ in intact cardiac myocytes.
Shah AM, et al.
Circulation Research, 74(5), 970-978 (1994)
Arun Govindapillai et al.
Scientific reports, 8(1), 6939-6939 (2018-05-04)
Patients born with congenital heart defects frequently encounter arrhythmias due to defects in the ventricular conduction system (VCS) development. Although recent studies identified transcriptional networks essential for the heart development, there is scant information on the mechanisms regulating VCS development.
Nadine Suffee et al.
Proceedings of the National Academy of Sciences of the United States of America, 114(5), E771-E780 (2017-01-18)
The abundance of epicardial adipose tissue (EAT) is associated with atrial fibrillation (AF), the most frequent cardiac arrhythmia. However, both the origin and the factors involved in EAT expansion are unknown. Here, we found that adult human atrial epicardial cells

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.

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