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C7344

Sigma-Aldrich

Cyclic adenosine diphosphate-ribose

≥90% (HPLC), lyophilized powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C15H21N5O13P2
CAS Number:
119340-53-3
Molecular Weight:
541.30
UNSPSC Code:
41106305
NACRES:
NA.51

biological source

(Ovotestis from sea hare)

Assay

≥90% (HPLC)

form

lyophilized powder

storage temp.

−20°C

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

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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
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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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
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
Tami Khazma et al.
Cell reports, 42(9), 113026-113026 (2023-08-28)
Wallerian axonal degeneration (WD) does not occur in the nematode C. elegans, in contrast to other model animals. However, WD depends on the NADase activity of SARM1, a protein that is also expressed in C. elegans (ceSARM/ceTIR-1). We hypothesized that
Transfer of mitochondria from astrocytes to neurons after stroke
Hayakawa K, et al.
Nature, 535(7613), 551-551 (2016)
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
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