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SML1128

Sigma-Aldrich

NMS-873

≥98% (HPLC)

Synonyme(s) :

3-[3-(Cyclopentylthio)-5-[[[2-methyl-4′-(methylsulfonyl)[1,1′-biphenyl]-4-yl]oxy]methyl]-4H-1,2,4-triazol-4-yl]-pyridine, 3-[3-Cyclopentylsulfanyl-5-(4′-methanesulfonyl-2-methylbiphenyl-4-yloxymethyl)-[1,2,4]triazol-4-yl]-pyridine

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About This Item

Formule empirique (notation de Hill):
C27H28N4O3S2
Numéro CAS:
1418013-75-8
Poids moléculaire :
520.67
Numéro MDL:
MFCD28009371
Code UNSPSC :
12352200
ID de substance PubChem :
329825666
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 25 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

CC1=CC(OCC2=NN=C(SC3CCCC3)N2C4=CN=CC=C4)=CC=C1C5=CC=C(S(C)(=O)=O)C=C5

InChI

1S/C27H28N4O3S2/c1-19-16-22(11-14-25(19)20-9-12-24(13-10-20)36(2,32)33)34-18-26-29-30-27(35-23-7-3-4-8-23)31(26)21-6-5-15-28-17-21/h5-6,9-17,23H,3-4,7-8,18H2,1-2H3

Clé InChI

UJGTUKMAJVCBIS-UHFFFAOYSA-N

Application

MS-873 has been used as an allosteric inhibitor of ATPase valosin-containing protein (VCP)/p97.

Actions biochimiques/physiologiques

NMS-873 is a selective allosteric non–ATP-competitive inhibitor of the AAA ATPase family member valosine containing protein (VCP), also known as p97 (VCP/p97), an integral component of the ubiquitin fusion degradation (UFD) pathway. VCP/p97 plays a role in degradation of misfolded proteins, Golgi membrane reassembly, membrane transport, myofibril assembly, autophagosome maturation, and cell division, and is overexpressed in many tumor types. NMS-873 is the most potent and specific VCP inhibitor described to date. NMS-873 has an IC50 of 30 nM for VCP/p97 compared to IC50 >10 μM against all of the AAA ATPases, HSP90 or the 53 kinases analyzed. NMS-873 inhibited proliferation of HCT116 cancer cell line cells with an IC50 value of 400 nM.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Replication-dependent unhooking of DNA interstrand cross-links by the NEIL3 glycosylase.
Semlow D R, et al.
Cell, 167(2), 498-511 (2016)
Haixia Zhou et al.
Nucleic acids research, 49(22), 13194-13206 (2021-12-02)
When vertebrate replisomes from neighboring origins converge, the Mcm7 subunit of the replicative helicase, CMG, is ubiquitylated by the E3 ubiquitin ligase, CRL2Lrr1. Polyubiquitylated CMG is then disassembled by the p97 ATPase, leading to replication termination. To avoid premature replisome
Mike Blueggel et al.
Nature communications, 14(1), 3258-3258 (2023-06-06)
The AAA+ ATPase p97/VCP together with different sets of substrate-delivery adapters and accessory cofactor proteins unfolds ubiquitinated substrates to facilitate degradation by the proteasome. The UBXD1 cofactor is connected to p97-associated multisystem proteinopathy but its biochemical function and structural organization
Sahradha Albert et al.
Proceedings of the National Academy of Sciences of the United States of America, 117(2), 1069-1080 (2019-12-29)
To promote the biochemical reactions of life, cells can compartmentalize molecular interaction partners together within separated non-membrane-bound regions. It is unknown whether this strategy is used to facilitate protein degradation at specific locations within the cell. Leveraging in situ cryo-electron
Tycho E T Mevissen et al.
Cell reports, 42(2), 112125-112125 (2023-02-23)
Tripartite motif-containing protein 21 (TRIM21) is a cytosolic antibody receptor and E3 ubiquitin ligase that promotes destruction of a broad range of pathogens. TRIM21 also underlies the antibody-dependent protein targeting method Trim-Away. Current evidence suggests that TRIM21 binding to antibodies
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