SML2989
OSMI-2
≥98% (HPLC)
Synonym(s):
(R)-Methyl 2-(2-(2-methoxyphenyl)-2-(2-oxo-1,2-dihydroquinoline-6-sulfonamido)-N-(thiophen-2-ylmethyl)acetamido)acetate, OSMI 2, OSMI2
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About This Item
Empirical Formula (Hill Notation):
C26H25N3O7S2
CAS Number:
Molecular Weight:
555.62
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Quality Segment
assay
≥98% (HPLC)
form
powder
optical activity
[α]/D -175.0 to -135.0°, c = 1.0 in chloroform-d
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
−20°C
SMILES string
O=C(N1)C=CC2=C1C=CC(S(N[C@@H](C(N(CC3=CC=CS3)CC(OC)=O)=O)C4=C(C=CC=C4)OC)(=O)=O)=C2
Biochem/physiol Actions
Cell-permeable precursor of an active-site O-GlcNAc transferase (OGT) inhibitor that effectively downregulates cellular protein O-GlcNAc level.
OSMI-2 is a cell-permeable precursor of an active site-targeting (Kd = 140 nM) O-GlcNAc transferase (OGT) inhibitor. Upon cell entry, OSMI-2 is activated by cellular esterase to the active inhibitor that effectively downregulates cellular protein O-GlcNAc level (20-40 μM for 4 h/HCT116, 50 μM for 24 h/HEK293T) and renders LNCaP prostate cancer cells dependent on CDK9 for growth (confluency post 96-hr treatment = 73% with 40 μM OSMI-2, 56% with 0.5 μM AT7519, 19% with co-treatment; control cells at 20% and 81% at 0 and 96 hr, respectively).
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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