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Merck

B5386

Sigma-Aldrich

8-Bromoadenosine 3′,5′-cyclic monophosphate

≥97% (HPLC), powder, protein kinase A activator

Synonym(s):

8-Br-A-3:5-MP, 8-Br-cAMP, 8-Bromo-cAMP

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About This Item

Empirical Formula (Hill Notation):
C10H11BrN5O6P
CAS Number:
23583-48-4
Molecular Weight:
408.10
Beilstein:
591930
EC Number:
245-760-6
MDL number:
MFCD00075580
UNSPSC Code:
41106305
PubChem Substance ID:
24891835
NACRES:
NA.77

Key Documents

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Product Name

8-Bromoadenosine 3′,5′-cyclic monophosphate, ≥97% (HPLC)

Quality Level

200

Assay

≥97% (HPLC)

form

powder

mp

254 °C (dec.) (lit.)

solubility

aqueous base: soluble, clear

storage temp.

−20°C

SMILES string

Nc1ncnc2n([C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O)c(Br)nc12

InChI

1S/C10H11BrN5O6P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,17H,1H2,(H,18,19)(H2,12,13,14)/t3-,5-,6-,9-/m1/s1

InChI key

DVKQVRZMKBDMDH-UUOKFMHZSA-N

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Application

8-Bromoadenosine 3′,5′-cyclic monophosphate has been used:
  • to treat H295R cells as positive controls for CYP19 induction
  • as a membrane permeable cAMP analog to study its effect on short-circuit current (Isc)
  • to investigate its potential as an inducer of differentiation in Wharton′s jelly-derived mesenchymal stem cells (WJ-MSCs)

Biochem/physiol Actions

8-Bromoadenosine 3′,5′-cyclic monophosphate is a cell-permeable cAMP analog having greater resistance to hydrolysis by phosphodiesterases than cAMP. 8-Bromoadenosine 3′,5′-cyclic monophosphate activates protein kinase A, inhibits growth, decreases proliferation, increases differentiation, and induces apoptosis of cultured cells.
8-bromo-adenosine 3′,5′-cyclic monophosphate (8-bromo-cAMP), added to hepatocytes during plating helps to increase the acquisition of beta-adrenoceptors.
Cell-permeable cAMP analog having greater resistance to hydrolysis by phosphodiesterases than cAMP.

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.

Other Notes

8-Bromoadenosine 3′,5′-cyclic monophosphate is a membrane-permeable cAMP analog.
Sensitive to light and moisture

Disclaimer

Sensitive to light and moisture.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000276013
0000276015
0000276013
0000276015
SLCC7982

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Dopamine increases Na+ absorption in the Reissner's membrane of the gerbil cochlea
Kim C H, et al.
Auris, Nasus, Larynx, 40(3), 266-272 (2013)
Differentiation of human umbilical cord Wharton?s jelly-derived mesenchymal stem cells into endometrial cells
Shi Q, et al.
Stem Cell Research & Therapy, 8(1), 246-246 (2017)
8-Bromo-cAMP and 8-CPT-cAMP Increase the Density of beta-Adrenoceptors in Hepatocytes by a Mechanism Not Mimicking the Effect of cAMP
Sandnes D, et al.
Pharmacology & Toxicology, 79(1), 15-22 (1996)
2, 3, 7, 8-Tetrachlorodibenzo-p-dioxin and diindolylmethanes differentially induce cytochrome P450 1A1, 1B1, and 19 in H295R human adrenocortical carcinoma cells
Sanderson J T, et al.
Toxicological Sciences, 61(1), 40-48 (2001)
Hisayuu Cho et al.
Fertility and sterility, 99(1), 248-255 (2012-10-06)
To investigate whether heart and neural crest derivatives expressed transcript 2 (HAND2) regulates fibulin-1 (FBLN1) expression during decidualization of human endometrial stromal cells (ESCs). In vitro experiment. Research laboratory. Twenty-four patients undergoing hysterectomy for benign reasons. ESCs were cultured with various
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고리형 뉴클레오타이드를 위한 생체 활성 저분자

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.

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