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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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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 H Guse et al.
Journal of immunology (Baltimore, Md. : 1950), 155(7), 3353-3359 (1995-10-01)
Ca2+ release from intracellular stores is one of the major events transducing extracellular signals into living cells. Recently, a metabolite of nicotinamide adenine dinucleotide+ (NAD+), termed "cyclic adenosine diphosphate-ribose" (cADPr), has been described to release Ca2+ from caffeine-sensitive internal stores
Patrice Meimoun et al.
Plant signaling & behavior, 4(9), 830-835 (2009-10-23)
In Arabidopsis thaliana cell suspension, abscisic acid (ABA) induces changes in cytosolic calcium concentration ([Ca(2+)](cyt)) which are the trigger for ABA-induced plasma membrane anion current activation, H(+)-ATPase inhibition, and subsequent plasma membrane depolarization. In the present study, we took advantage
S Iino et al.
Circulation research, 81(5), 879-884 (1997-11-14)
Although it is becoming widely accepted that cADP-ribose (cADPR) can regulate calcium release from the endoplasmic reticulum in sea urchin eggs and in a variety of mammalian cell types, it remains controversial whether this substance might influence calcium release during
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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