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Merck

N5655

Sigma-Aldrich

Nicotinic acid adenine dinucleotide phosphate sodium salt

≥92.5%

Synonym(e):

β-NAADP

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About This Item

Empirische Formel (Hill-System):
C21H27N6O18P3 · xNa+
CAS-Nummer:
Molekulargewicht:
744.39 (free acid basis)
MDL-Nummer:
UNSPSC-Code:
12352106
PubChem Substanz-ID:
NACRES:
NA.77

Qualitätsniveau

Assay

≥92.5%

Form

solid

Lagertemp.

−20°C

SMILES String

[Na+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP([O-])(=O)OP([O-])(=O)OCC4O[C@@H]([C@@H](O)[C@H]4O)[n+]5cccc(c5)C(O)=O)[C@@H](O)[C@H]3OP(O)(O)=O

InChI

1S/C21H27N6O18P3.Na/c22-17-12-18(24-7-23-17)27(8-25-12)20-16(44-46(33,34)35)14(29)11(43-20)6-41-48(38,39)45-47(36,37)40-5-10-13(28)15(30)19(42-10)26-3-1-2-9(4-26)21(31)32;/h1-4,7-8,10-11,13-16,19-20,28-30H,5-6H2,(H6-,22,23,24,31,32,33,34,35,36,37,38,39);/q;+1/p-1/t10?,11-,13+,14-,15+,16-,19+,20-;/m1./s1

InChIKey

KKCRODBDXQTAPI-NZNNTXIPSA-M

Allgemeine Beschreibung

NAADP induces Ca2+ release from the eggs of sea urchin, when injected into the cell. It can be enzymatically produced from nicotinamide adenine dinucleotide phosphate (β-NADP) with the help of ADP-ribosyl cyclase.

Anwendung

Nicotinic acid adenine dinucleotide phosphate sodium salt has been used for agonist injection into unfertilized eggs and embryos.

Biochem./physiol. Wirkung

Potent activator of intracellular Ca2+ release via an IP3 and cyclic ADP ribose-independent mechanism.

Sonstige Hinweise

Note: Should not be confused with nicotinamide adenine dinucleotide phosphate (NADP).

Angaben zur Herstellung

Enzymatically prepared analog of β-NADP+.

Piktogramme

Exclamation mark

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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Slow calcium waves mediate furrow microtubule reorganization and germ plasm compaction in the early zebrafish embryo
Eno C, et al.
Development (2018)
Yong-Liang Jiang et al.
The Journal of biological chemistry, 288(15), 10381-10394 (2013-02-28)
Nicotinic acid adenine dinucleotide phosphate (NAADP) is the most potent Ca(2+)-mobilizing messenger that releases Ca(2+) from endolysosomal organelles. Recent studies showed that NAADP-induced Ca(2+) release is mediated by the two-pore channels (TPCs) TPC1 and TPC2. However, the expression of TPCs
Patricia Gómez-Suaga et al.
Autophagy, 8(4), 692-693 (2012-03-24)
Alterations in autophagy are thought to underlie various neurodegenerative diseases including Parkinson disease (PD). Previous studies have indicated that the PD gene leucine rich repeat kinase 2 (LRRK2) is involved in this process, but its mechanism of action has remained
H C Lee et al.
The Journal of biological chemistry, 270(5), 2152-2157 (1995-02-03)
We have previously shown that alkaline treatment of NADP generates a derivative which can mobilize Ca2+ from sea urchin egg homogenates (Clapper, D. L., Walseth, T. F., Dargie, P. J., and Lee, H. C. (1987) J. Biol. Chem. 262, 9561-9568).
Parvinder K Aley et al.
The Journal of biological chemistry, 288(16), 10986-10993 (2013-03-08)
Nicotinic acid adenine dinucleotide phosphate (NAADP) is increasingly being demonstrated to be involved in calcium signaling in many cell types and species. Although it has been shown to play a role in smooth muscle cell contraction in several tissues, nothing

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