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SML2238

Sigma-Aldrich

NAV-2729

≥98% (HPLC)

Synonym(s):

3-(4-Chlorophenyl)-5-(4-nitrophenyl)-2-(phenylmethyl)-pyrazolo[1,5-a]pyrimidin-7(4H)-one, NAV 2729, NAV2729

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About This Item

Empirical Formula (Hill Notation):
C25H17ClN4O3
CAS Number:
419547-11-8
Molecular Weight:
456.88
MDL number:
MFCD01455625
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C1C=C(C2=CC=C([N+]([O-])=O)C=C2)NC3=C(C4=CC=C(Cl)C=C4)C(CC5=CC=CC=C5)=NN31

Biochem/physiol Actions

NAV-2729 (IC50 of 1.5 μM) has a therapeutic benefit in reducing the adverse effect of diabetic retinopathy in animal models.
Originally characterized as a non-nucleotide-competitive and reversible ARF6-selective inhibitor (IC50 = 1.4 μM without GEF and 2.4 μM with 100 nM ARNO or BRAG2/GEP100) that targets ARF6 GEF-binding region, NAV-2729 prevents GEF-dependent ARF1 & ARF6 activity (% inhibition of BRAG2Sec7PH-stimulated GTPase activity/[NAV-2729] = 50% Δ17Arf1/10 μM and 15% Δ13Arf6/25 μM) with higher potency against BRAG2- than ARNO-dependent ARF1 activity (64% vs. 20% Δ17Arf1 inhibition at 25 μM in the presence of respective GEF sec7 domain). NAV-2729 treatment effectively inhibits G-alpha-q downstream signaling pathways and anchorage-independent colony growth of Mel92.1 & Mel202 melanoma cells in vitro (10 μM) as well as uveal melanoma tumor establishment in Mel202 xenograft mice in vivo (30 mg/kg/day i.p.).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Yohei Yamauchi et al.
Advances in biological regulation, 63, 115-121 (2016-10-26)
The Small GTPase ADP-ribosylation factor 6 (Arf6) functions as the molecular switch in cellular signaling pathways by cycling between GDP-bound inactive and GTP-bound active form, which is precisely regulated by two regulators, guanine nucleotide exchange factors (GEFs) and GTPase-activating proteins
Jae Hyuk Yoo et al.
Cancer cell, 29(6), 889-904 (2016-06-07)
Activating mutations in Gαq proteins, which form the α subunit of certain heterotrimeric G proteins, drive uveal melanoma oncogenesis by triggering multiple downstream signaling pathways, including PLC/PKC, Rho/Rac, and YAP. Here we show that the small GTPase ARF6 acts as
Weiquan Zhu et al.
The Journal of clinical investigation, 127(12), 4569-4582 (2017-10-24)
The devastating sequelae of diabetes mellitus include microvascular permeability, which results in retinopathy. Despite clinical and scientific advances, there remains a need for new approaches to treat retinopathy. Here, we have presented a possible treatment strategy, whereby targeting the small
Sarah Benabdi et al.
Biochemistry, 56(38), 5125-5133 (2017-09-01)
Arf GTPases and their guanine nucleotide exchange factors (ArfGEFs) are major regulators of membrane traffic and organelle structure in cells. They are associated with a variety of diseases and are thus attractive therapeutic targets for inhibition by small molecules. Several

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