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SML1621

Sigma-Aldrich

OSMI-1

≥98% (HPLC)

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Synonym(s):
(αR)-α-[[(1,2-Dihydro-2-oxo-6-quinolinyl)sulfonyl]amino]-N-(2-furanylmethyl)-2-methoxy-N-(2-thienylmethyl)-benzeneacetamide, OSMI 1
Empirical Formula (Hill Notation):
C28H25N3O6S2
CAS Number:
1681056-61-0
Molecular Weight:
563.64
UNSPSC Code:
12352200
PubChem Substance ID:
329825506
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(N1)C=CC2=C1C=CC(S(N[C@H](C3=C(OC)C=CC=C3)C(N(CC4=CC=CS4)CC5=CC=CO5)=O)(=O)=O)=C2

InChI

1S/C28H25N3O6S2/c1-36-25-9-3-2-8-23(25)27(28(33)31(17-20-6-4-14-37-20)18-21-7-5-15-38-21)30-39(34,35)22-11-12-24-19(16-22)10-13-26(32)29-24/h2-16,27,30H,17-18H2,1H3,(H,29,32)/t27-/m1/s1

InChI key

IYIGLWQQAMROOF-HHHXNRCGSA-N

Application

OSMI-1 (OGT with a small molecule inhibitor) has been used in proximal ligation assay, Sox2 (SRY (sex determining region Y)-Box 2 ) dual luciferase reporter assay, Sox2 ELISA (enzyme linked immunosorbent assay) and other in vivo approaches, to study the O-Linked β-N-acetylglucosamine (O-GlcNAc) mediated regulation of self-renewal genes in cancer. It has also been used to study the Hippo pathway regulation mediated by O-GlcNAc transferase.

Biochem/physiol Actions

OGT catalyses the attachment of N-acetylglucosamine moieties to a number proteins during post-translational modification. Inhibition of OGT activity might hinder the rate of viral replication in infections such as Herpes simplex viral disease.
OSMI-1 is a cell permeable inhibitor of OGT (O-GlcNAc transferase).

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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O-GlcNAc transferase inhibitors: current tools and future challenges.
Trapannone R, et al.
Biochemical Society Transactions, 44(1), 88-93 (2016)
O-GlcNAc modification of oncogenic transcription factor Sox2 promotes protein stability and regulates self-renewal in pancreatic cancer.
Sharma N, et al.
bioRxiv, 345223-345223 (2018)
Regulation of the hippo-YAP pathway by glucose sensor O-GlcNAcylation.
Peng C, et al.
Molecular Cell, 68(3), 591-604 (2018)
Hye-Yeon Kim et al.
Bioprocess and biosystems engineering, 43(5), 863-875 (2020-01-26)
O-Glycosylation occurs in recombinant proteins produced by CHO cells, but this phenomenon has not been studied extensively. Here, we report that rituximab is an O-linked N-acetyl-glucosaminylated (O-GlcNAcylated) protein and the production of rituximab is increased by thiamet G, an inhibitor
Nikita S Sharma et al.
Theranostics, 9(12), 3410-3424 (2019-07-10)
Pancreatic adenocarcinoma (PDAC) claims more than 90% of the patients diagnosed with the disease owing to its aggressive biology that is manifested by high rate of tumor recurrence. Aberrant upregulation in the transcriptional activity of proteins involved in self-renewal like
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