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SML1918

Sigma-Aldrich

ML349

≥98% (HPLC)

Synonym(s):

ML349, (5,5-Dioxido-4H-thieno[3,2-c][1]benzothiopyran-2-yl)[4-(4-methoxyphenyl)-1-piperazinyl]methanone, ML 349, ML-349, (5,5-Dioxo-4H-thieno[4,5-c]thiochromen-2-yl)-[4-(4-methoxyphenyl)piperazin-1-yl]methanone

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About This Item

Empirical Formula (Hill Notation):
C23H22N2O4S2
CAS Number:
890819-86-0
Molecular Weight:
454.56
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 3 mg/mL, clear (warmed)

storage temp.

2-8°C

InChI

1S/C23H22N2O4S2/c1-29-18-8-6-17(7-9-18)24-10-12-25(13-11-24)23(26)20-14-16-15-31(27,28)21-5-3-2-4-19(21)22(16)30-20/h2-9,14H,10-13,15H2,1H3

InChI key

YVIJPELUPZUEJX-UHFFFAOYSA-N

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Biochem/physiol Actions

ML349 is a substrate-competitive, reversible and APT2-selective acyl-protein thioesterase (APT) inhibitor (IC50/Ki = 510 nM/230 nM against APT2; IC50 & Ki >10 μM against APT1). ML349 effectively inhibits cellular APT2 activity in cultures (by >95% in HEK293T & mouse T cells; 5 μM for 4 h) and in mice in vivo (by >90% in lung/heart/kidney and by ~50% in brain tissue 4 h post 50 mg/kg i.p. dosing) without affecting more than 15 cellular serine hydrolases and APT1. ML349 treatment (5 μM) is shown to restore palmitoylation and membrane localization of the multidomain scaffolding protein Scribble (Scrib) in MDCK cells overexpressing the epithelial-to-mesenchymal transcription factor (EMT-TF) Snail.

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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Alexander Adibekian et al.
Journal of the American Chemical Society, 134(25), 10345-10348 (2012-06-14)
The development of small-molecule inhibitors for perturbing enzyme function requires assays to confirm that the inhibitors interact with their enzymatic targets in vivo. Determining target engagement in vivo can be particularly challenging for poorly characterized enzymes that lack known biomarkers
Jeannie L Hernandez et al.
Cell chemical biology, 24(1), 87-97 (2017-01-10)
The multidomain scaffolding protein Scribble (Scrib) organizes key signaling complexes to specify basolateral cell polarity and suppress aberrant growth. In many human cancers, genetically normal Scrib mislocalizes from cell-cell junctions to the cytosol, correlating with enhanced growth signaling and malignancy.
Rahul S Kathayat et al.
Nature chemical biology, 13(2), 150-152 (2016-12-20)
Hundreds of human proteins are modified by reversible palmitoylation of cysteine residues (S-palmitoylation), but the regulation of depalmitoylation is poorly understood. Here, we develop 'depalmitoylation probes' (DPPs), small-molecule fluorophores, to monitor the endogenous activity levels of 'erasers' of S-palmitoylation, acylprotein

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