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B5416

Sigma-Aldrich

8-Bromo-cyclic adenosine diphosphate ribose

85% (HPLC), lyophilized powder

Synonym(s):

Br-cADP-ribose, Br-cADPR

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About This Item

Empirical Formula (Hill Notation):
C15H20BrN5O13P2
CAS Number:
151898-26-9
Molecular Weight:
620.20
MDL number:
MFCD00274402
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
329773258
NACRES:
NA.51

Quality Level

200

assay

85% (HPLC)

form

lyophilized powder

color

white

solubility

H2O: 5 mg/mL

storage temp.

−20°C

SMILES string

Nc1ncnc2n([C@@H]3O[C@@H]4COP(O)(=O)OP(=O)(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H]5O)O[C@H]4[C@H]3O)c(Br)nc12

InChI

1S/C15H20BrN5O13P2/c16-15-20-6-11(17)18-3-19-12(6)21(15)13-9(25)10-5(30-13)2-29-35(26,27)34-36(28,32-10)33-14-8(24)7(23)4(1-22)31-14/h3-5,7-10,13-14,22-25H,1-2H2,(H,26,27)(H2,17,18,19)/t4-,5-,7-,8-,9-,10-,13-,14+,36?/m1/s1

InChI key

PLQQKRPSINJWTK-VNMBDIRDSA-N

Biochem/physiol Actions

An antagonist of cyclic ADP-ribose (cADPR), and an endogenous metabolite of β-NAD+. cADPR has been shown to regulate calcium release from the endoplasmic and sarcoplasmic reticulum. In cells, cADPR is synthesized by ADP-ribosyl cyclase or CD38, a lymphocyte differentiation antigen.

Physical form

Lyophilized powder containing 10-20% sodium phosphate buffer salts

Preparation Note

Prepared enzymatically

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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H C Lee et al.
Advances in experimental medicine and biology, 419, 411-419 (1997-01-01)
Mobilization of internal Ca+2 is an important signaling mechanism in cells. In addition to the inositol trisphosphate pathway, cyclic ADP-ribose (cADPR) and nicotinic acid adenine dinucleotide (NAADP) have been shown to mobilize Ca+2 via independent mechanisms. Although the structures of
A De Flora et al.
The international journal of biochemistry & cell biology, 29(10), 1149-1166 (1998-01-23)
CD38 was first identified as a lymphocyte differentiation antigen that showed typical properties of an orphan receptor involved in many programs of cell proliferation and activation. However, CD38 proved also to be a bifunctional ectoenzyme that catalyzes the transient formation
H C Lee
Cell biochemistry and biophysics, 28(1), 1-17 (1997-12-05)
Ca2+ mobilization as a signaling mechanism has been placed on center stage with the discovery of the first Ca2+ messenger, inositol trisphosphate (IP3). This article focuses on two new Ca2+ release activators, which mobilize internal Ca2+ stores via mechanisms totally
P Lahouratate et al.
The American journal of physiology, 273(3 Pt 2), H1082-H1089 (1997-10-10)
Cyclic ADP-ribose (cADPR), an endogenous metabolite of beta-NAD+, activates Ca2+ release from endoplasmic reticulum in sea urchin eggs via the ryanodine receptor (RyR) pathway. A similar role has been proposed in cardiac sarcoplasmic reticulum (SR), although this remains controversial. We
Susan K Fellner et al.
American journal of physiology. Heart and circulatory physiology, 298(1), H144-H151 (2009-11-03)
Little is known about the effects of nitric oxide (NO) and the cyclic GMP (cGMP)/protein kinase G (PKG) system on Ca(2+) signaling in vascular smooth muscle cells (VSMC) of resistance vessels in general and afferent arterioles in particular. We tested
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