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SML2279

Sigma-Aldrich

VU0155069

≥98% (HPLC)

Synonym(s):

(S)-N-(1-(4-(5-Chloro-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidin-1-yl)propan-2-yl)-2-naphthamide, CAY10593, N-[(1S)-2-[4-(5-Chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]-1-methylethyl]-2-naphthalenecarboxamide

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About This Item

Empirical Formula (Hill Notation):
C26H27ClN4O2
CAS Number:
1130067-06-9
Molecular Weight:
462.97
MDL number:
MFCD23160355
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

storage temp.

2-8°C

SMILES string

O=C(C1=CC=C2C=CC=CC2=C1)N[C@@H](C)CN3CCC(N4C5=CC=C(Cl)C=C5NC4=O)CC3

InChI

1S/C26H27ClN4O2.ClH/c1-17(28-25(32)20-7-6-18-4-2-3-5-19(18)14-20)16-30-12-10-22(11-13-30)31-24-9-8-21(27)15-23(24)29-26(31)33;/h2-9,14-15,17,22H,10-13,16H2,1H3,(H,28,32)(H,29,33);1H/t17-;/m0./s1

InChI key

RQULTQQAHGYYDG-LMOVPXPDSA-N

Biochem/physiol Actions

VU0155069 is a PLD1-selective catalytic site-targeting phospholipase D inhibitor (PLD1/2 IC50 = 46 nM/933 nM by cell-free enzymatic assays; substrate = di-palmitoyl-PLC) that selectively suppresses the cellular PLD activity in PMA-stimulated non-small-cell lung cancer (NSCLC) Calu-1 cells with predominant PLD1 activity over GFP-PLD2-overexpressing HEK293 cells (IC50 = 11 nM and 1.8 μM, respectively). Note: VU0155069 is reported to impair P2X7-induced pore formation in human RPMI 8226 B cells lacking PLD1 expression.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Li-Da Luo et al.
Scientific reports, 7(1), 6035-6035 (2017-07-22)
Synapses are the basic units of information transmission, processing and integration in the nervous system. Dysfunction of the synaptic development has been recognized as one of the main reasons for mental dementia and psychiatric diseases such as Alzheimer's disease and
Dong Woo Kang et al.
Cancer research, 77(1), 142-152 (2016-10-30)
The RB1/E2F1 signaling pathway is frequently deregulated in colorectal cancer and has been suggested to intersect with Wnt/β-catenin and PI3K/Akt pathways, but molecular evidence for this link is lacking. In this study, we demonstrate that phospholipase D1 (PLD1), a transcriptional
Dong Woo Kang et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 23(23), 7340-7350 (2017-09-25)
Purpose: Dysregulated expression of PLD1 has emerged as a hallmark feature of colorectal cancer, which remains a major cause of mortality worldwide. Aberrant activation of Wnt/β-catenin signaling is a critical event in the development of colorectal cancer. Here, we investigated
A Pupovac et al.
Purinergic signalling, 9(4), 609-619 (2013-06-25)
The P2X7 receptor is a trimeric ATP-gated cation channel important in health and disease. We have observed that the specific phospholipase D (PLD)1 antagonist, CAY10593 impairs P2X7-induced shedding of the 'low affinity' IgE receptor, CD23. The current study investigated the
Menglin Cheng et al.
Neoplasia (New York, N.Y.), 19(8), 617-627 (2017-06-28)
Abnormal choline phospholipid metabolism is a hallmark of cancer. The magnetic resonance spectroscopy (MRS) detected total choline (tCho) signal can serve as an early noninvasive imaging biomarker of chemotherapy response in breast cancer. We have quantified the individual components of
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