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SML0789

Sigma-Aldrich

GI254023X

≥98% (HPLC)

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Synonym(s):
(2R)-N-[(1S)-2,2-Dimethyl-1-[(methylamino)carbonyl]-propyl]-2-[(1S)-1-[formyl(hydroxy)amino]ethyl]-5-phenylpentanamide, GI4023
Empirical Formula (Hill Notation):
C21H33N3O4
CAS Number:
260264-93-5
Molecular Weight:
391.50
MDL number:
MFCD19381832
UNSPSC Code:
12352200
PubChem Substance ID:
329825599
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

2-8°C

SMILES string

ON(C=O)[C@@H](C)[C@@H](CCCC1=CC=CC=C1)C(N[C@@H](C(C)(C)C)C(NC)=O)=O

InChI

1S/C21H33N3O4/c1-15(24(28)14-25)17(13-9-12-16-10-7-6-8-11-16)19(26)23-18(20(27)22-5)21(2,3)4/h6-8,10-11,14-15,17-18,28H,9,12-13H2,1-5H3,(H,22,27)(H,23,26)/t15-,17+,18+/m0/s1

InChI key

GHVMTHKJUAOZJP-CGTJXYLNSA-N

Application

GI254023X has been used to inhibit ADAM10 (ADAM metallopeptidase domain 10).

Biochem/physiol Actions

GI254023X blocks ADAM10 (ADAM metallopeptidase domain 10) activity and decreases human leukocyte antigen (HLA)-mediated cytotoxicity and cleavage of extracellular E-cadherin in epithelial and endothelial cells.
GI254023X is a potent and selective ADAM10 metalloproteinase inhibitor with 100-fold selectivity for the α-secretase ADAM10 over ADAM17 (TACE). In a study using recombinant TACE and ADAM10 ectodomain, the IC50 for GI254023X was 5.3 nM for ADAM10 vs 541 nM for TACE.
GI254023X is a potent and selective ADAM10 metalloproteinase inhibitor.

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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Ezekwe E A D, et al.
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Developmental cell, 43(3), 305-317 (2017-11-08)
The biophysical framework of collective cell migration has been extensively investigated in recent years; however, it remains elusive how chemical inputs from neighboring cells are integrated to coordinate the collective movement. Here, we provide evidence that propagation waves of extracellular
Laura S Christian et al.
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As a critical machinery for rapid pathogen removal, resident memory T cells (TRMs) are locally generated after the initial encounter. However, their development accompanying tumorigenesis remains elusive. Using a murine breast cancer model, we show that TRMs develop in the tumor
Joshua A Kulas et al.
American journal of physiology. Endocrinology and metabolism, 316(1), E106-E120 (2018-11-14)
The amyloid precursor protein (APP) is a type I transmembrane glycoprotein widely studied for its role as the source of β-amyloid peptide, accumulation of which is causal in at least some cases of Alzheimer's disease (AD). APP is expressed ubiquitously
Paul M Jordan et al.
Cell reports, 33(2), 108247-108247 (2020-10-15)
Underlying mechanisms of how infectious inflammation is resolved by the host are incompletely understood. One hallmark of inflammation resolution is the activation of specialized pro-resolving mediators (SPMs) that enhance bacterial clearance and promote tissue repair. Here, we reveal α-hemolysin (Hla)
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