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Merck

C7344

Cyclic adenosine diphosphate-ribose

≥90% (HPLC), from Ovotestis from sea hare, lyophilized powder

Synonyme(s) :

ADP-cyclo[N1:1′′]-ribose, Cyclic ADPR, cADP-ribose, cADPR

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A propos de cet article

Formule empirique (notation de Hill) :
C15H21N5O13P2
Numéro CAS:
Poids moléculaire :
541.30
MDL number:
UNSPSC Code:
41106305
NACRES:
NA.51
Assay:
≥90% (HPLC)
Biological source:
(Ovotestis from sea hare)
Form:
lyophilized powder
Solubility:
water: 5 mg/mL, clear, colorless
Storage temp.:
−20°C
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Nom du produit

Cyclic adenosine diphosphate-ribose, ≥90% (HPLC), lyophilized powder

SMILES string

O[C@H]1[C@@H](O)[C@H]2O[C@@H]1COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)[n@H]4cnc5C(=N)[N@@H]2C=Nc45

InChI

1S/C15H21N5O13P2/c16-12-7-13-18-4-19(12)14-10(23)8(21)5(31-14)1-29-34(25,26)33-35(27,28)30-2-6-9(22)11(24)15(32-6)20(13)3-17-7/h3-6,8-11,14-16,21-24H,1-2H2,(H,25,26)(H,27,28)/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1

InChI key

BQOHYSXSASDCEA-KEOHHSTQSA-N

biological source

(Ovotestis from sea hare)

assay

≥90% (HPLC)

form

lyophilized powder

solubility

water: 5 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

Application

Cyclic adenosine diphosphate-ribose (cADPR) is an intracellular second messenger that mobilizes intracellular Ca2+ release from the sarcoplasmic reticulum through ryanodine receptors. CADPR is also a second messenger for glucose-induced insulin release from endocrine pancreas and for abscisic acid-induced calcium release in plants.
Cyclic adenosine diphosphate-ribose has been used to stimulate astrocytes to activate CD38 signaling. It has also been used as a supplement in buffered peptone water to recover S. enteritidis.

Biochem/physiol Actions

Mobilizes intracellular Ca2+; regulates Ca2+-induced Ca2+ release specifically blocked by ryanodine; second messenger for glucose-induced insulin release from the endocrine pancreas and for abscisic acid-induced calcium release in plants.

Packaging

Package size based on nucleotide content.

Physical form

Lyophilized powder

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Consulter la Bibliothèque de documents

Hon Cheung Lee
Science China. Life sciences, 54(8), 699-711 (2011-07-26)
The concept advanced by Berridge and colleagues that intracellular Ca(2+)-stores can be mobilized in an agonist-dependent and messenger (IP(3))-mediated manner has put Ca(2+)-mobilization at the center stage of signal transduction mechanisms. During the late 1980s, we showed that Ca(2+)-stores can
Shunichi Kajioka et al.
The Journal of urology, 186(2), 736-744 (2011-06-21)
To clarify the properties of adenosine triphosphate sensitive K+ channel in human detrusor smooth muscle we examined the effect of the representative nicotinic acid derivatives β-nicotinamide adenine dinucleotide, cyclic adenosine diphosphate ribose and nicotinic acid adenine dinucleotide phosphate (Sigma-Aldrich®) on
Y Wu et al.
Science (New York, N.Y.), 278(5346), 2126-2130 (1998-02-12)
Abscisic acid (ABA) is the primary hormone that mediates plant responses to stresses such as cold, drought, and salinity. Single-cell microinjection experiments in tomato were used to identify possible intermediates involved in ABA signal transduction. Cyclic ADP-ribose (cADPR) was identified
Asif Iqbal Shawl et al.
Islets, 1(3), 216-223 (2010-11-26)
Insulin has an autocrine/paracrine role through insulin receptors in pancreatic β-cells. Herein, we show the insulin receptor signaling pathway underlying CD38/ADPR-cyclase activation for NAADP/cADPR formation to induce Ca2+ rise, ultimately resulting in β-cell proliferation. Binding of insulin on insulin receptors
Transfer of mitochondria from astrocytes to neurons after stroke
Hayakawa K, et al.
Nature, 535(7613), 551-551 (2016)

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