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SML2830

Sigma-Aldrich

trans-Ned-19

≥98% (HPLC)

Synonym(s):

(1R,3S)-)-1-[3-[[4-(2-Fluorophenyl)-1-piperazinyl]methyl]-4-methoxyphenyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid, Ned-19, trans (1R,3S)-NED-19

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About This Item

Empirical Formula (Hill Notation):
C30H31FN4O3
CAS Number:
1354235-96-3
Molecular Weight:
514.59
MDL number:
MFCD31562774
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

InChI

1S/C30H31FN4O3/c1-38-27-11-10-19(16-20(27)18-34-12-14-35(15-13-34)26-9-5-3-7-23(26)31)28-29-22(17-25(33-28)30(36)37)21-6-2-4-8-24(21)32-29/h2-11,16,25,28,32-33H,12-15,17-18H2,1H3,(H,36,37)/t25-,28+/m0/s1

InChI key

FUHCEERDBRGPQZ-LBNVMWSVSA-N

Biochem/physiol Actions

NAADP (nicotinic acid adenine dinucleotide phosphate) has recently been recognized as a crucial Ca2+-releasing second messenger in several mammalian tissues including pancreatic, brain and cardiac. Ned-19 is a potent inhibitor of NAADP action. It is a selective blocker of cellular NAADP-induced Ca2+-release and can fluorescently label NAADP receptors. Ned-19 blocks NAADP signaling at nanomolar concentrations. In intact cells, Ned-19 blocked NAADP signaling and fluorescently labeled NAADP receptors.The trans-Ned-19 is more potent than the cis form in regard to both inhibition of Ca2+ release (IC50 of 6 nM versus 800 nM) and [32P]NAADP binding (IC50 of 0.4 nM versus 15 μM).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

Certificates of Analysis (COA)

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Edmund Naylor et al.
Nature chemical biology, 5(4), 220-226 (2009-02-24)
Research into the biological role of the Ca(2+)-releasing second messenger NAADP (nicotinic acid adenine dinucleotide phosphate) has been hampered by a lack of chemical probes. To find new chemical probes for exploring NAADP signaling, we turned to virtual screening, which
So-Young Rah et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 31(7), 3126-3137 (2017-04-08)
LPS has been shown to induce hepatocyte autophagy, but little is known about how LPS is able to do this during acute toxic liver injury. Our aim was to determine the existence of any selective Ca2+ signaling coupling to hepatocyte
Annarita Favia et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(44), E4706-E4715 (2014-10-22)
Vascular endothelial growth factor (VEGF) and its receptors VEGFR1/VEGFR2 play major roles in controlling angiogenesis, including vascularization of solid tumors. Here we describe a specific Ca(2+) signaling pathway linked to the VEGFR2 receptor subtype, controlling the critical angiogenic responses of

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