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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
Hiroto Okuda et al.
Glia, 58(14), 1757-1765 (2010-07-21)
Nucleotides and nucleosides play important roles by maintaining brain homeostasis, and their extracellular concentrations are mainly regulated by ectonucleotidases and nucleoside transporters expressed by astrocytes. Extracellularly applied NAD(+) prevents astrocyte death caused by excessive activation of poly(ADP-ribose) polymerase-1, of which
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