An antagonist of NAADP receptors
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trans-Ned-19

Item No. 17527

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(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
CAS Number
1354235-96-3
Molecular Formula
C30H31FN4O3
Formula Weight
514.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:1): 0.5 mg/mlDMSO: 2 mg/ml
λmax
222, 272 nm
SMILES
FC1=CC=CC=C1N2CCN(CC3=CC([C@H]4N[C@H](C(O)=O)CC5=C4NC6=C5C=CC=C6)=CC=C3OC)CC2
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Nicotinic acid adenine dinucleotide phosphate (NAADP) is a dinucleotide second messenger that triggers the release of calcium from lysosomes and related cellular compartments.1 trans-Ned-19 is a structural analog of NAADP that blocks NAADP-dependent calcium release (IC50 = 6 nM) as well as NAADP binding to sea urchin egg homogenate (IC50 = 0.4 nM).2 The trans form of Ned-19 is significantly more potent than the cis isomer in both assays.2 Ned-19 does not affect either IP3-mediated calcium release or cyclic ADP-ribose-mediated calcium release.2 It directly binds NAADP receptors on lysosomes in mouse pancreatic beta cells and competitively antagonizes activation by NAADP.2,3 It inhibits glucose-induced calcium oscillations in pancreatic islets and insulin-induced calcium increases in 3T3-L1 adipocytes.2,4 Ned-19 also blocks calcium signaling induced by endothelin-1 or norepinephrine in renal afferent arterioles.5 Ned-19 dose-dependently reduces infection of host cells by Ebola virus.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lam, A.K.M., and Galione, A. The endoplasmic reticulum and junctional membrane communication during calcium signaling. Biochim. Biophys. Acta 1833(11), 2542-2559 (2013).

    2. Naylor, E., Arredouani, A., Vasudevan, S.R., et al. Identification of a chemical probe for NAADP by virtual screening. Nat. Chem. Biol. 5(4), 220-226 (2009).

    3. Rosen, D., Lewis, A.M., Mizote, A., et al. Analogues of the nicotinic acid adenine dinucleotide phosphate (NAADP) antagonist Ned-19 indicate two binding sites on the NAADP receptor. The Journal of Biological Chemisty 284(50), 34930-34934 (2009).

    4. Song, E.K., Lee, Y.R., Kim, Y.R., et al. NAADP mediates insulin-stimulated glucose uptake and insulin sensitization by PPARγ in adipocytes. Cell Rep. 2(6), 1607-1619 (2012).

    5. Sakurai, Y., Kolokoltsov, A.A., Chen, C.C., et al. Two-pore channels control Ebola virus host cell entry and are drug targets for disease treatment. Science 347(6225), 995-998 (2015).

    6. Thai, T.L., Churchill, G.C., and Arendshorst, W.J. NAADP receptors mediate calcium signaling stimulated by endothelin-1 and norepinephrine in renal afferent arterioles. Am. J. Physiol. Renal. Physiol. 297(2), F510-F516 (2009).