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PZ0152

Sigma-Aldrich

UK-356618

≥98% (HPLC)

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Synonym(s):
(2R)-N1-[(1S)-2,2-Dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-2-{3-[(3-methyl-4-phenyl)-phenyl]propyl}-(N4-hydroxy)butanediamide, UK-356,618
Empirical Formula (Hill Notation):
C34H43N3O4
CAS Number:
230961-08-7
Molecular Weight:
557.72
MDL number:
MFCD19443865
UNSPSC Code:
12352200
PubChem Substance ID:
329823737
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D >+25.0°, c = 0.5 in methanol

color

white to tan

solubility

DMSO: ≥25 mg/mL

storage temp.

2-8°C

SMILES string

C[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CCCc1ccc(c(C)c1)-c2ccccc2)CC(=O)NO)C(C)(C)C)c3ccccc3

InChI

1S/C34H43N3O4/c1-23-21-25(19-20-29(23)27-16-10-7-11-17-27)13-12-18-28(22-30(38)37-41)32(39)36-31(34(3,4)5)33(40)35-24(2)26-14-8-6-9-15-26/h6-11,14-17,19-21,24,28,31,41H,12-13,18,22H2,1-5H3,(H,35,40)(H,36,39)(H,37,38)/t24-,28-,31-/m1/s1

InChI key

JJHRUUKMPWUYIB-HVOSOHGQSA-N

Application

UK-356618 has been used as a specific matrix metalloproteinase 3 (MMP3) inhibitor to study its effect on amitriptyline-induced glial cell line-derived neurotrophic factor (GDNF) mRNA expression and to confirm its influence on amitriptyline-induced zymographic MMP-9 activation in rat C6 astroglial cells.

Biochem/physiol Actions

UK 356618 has the potential to inhibit interleukin (IL)-6-induced cell migration in NCI H446 small cell lung cancer cells in vitro.
UK-356,618 is a potent, selective inhibitor of Matrix metalloproteinase MMP3 (stromelysin-1). MMP-3 IC50 = 5.9 nM, selectivity is 140-fold vs MMP-1, -2, -9, and -14.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Yi Na Jiang et al.
Oncotarget, 6(38), 40719-40733 (2015-11-04)
Our previous studies show that the phosphorylation of ataxia-telangiectasia mutated (ATM) induced by interleukin 6 (IL-6) treatment contributes to multidrug resistance formation in lung cancer cells, but the exact role of ATM activation in IL-6 increased metastasis is still elusive.
Hiromi Abe et al.
Biochemical and biophysical research communications, 479(4), 907-912 (2016-09-30)
Neurotrophic/growth factors derived from glial cells, especially astrocytes, have been implicated in mood disorders and the pharmacological effects of antidepressant drugs. Previous studies demonstrated that the release of glial cell line-derived neurotrophic factor (GDNF) induced by the tricyclic antidepressant amitriptyline

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