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SML0181

Sigma-Aldrich

S 17092

≥98% (HPLC)

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Synonym(s):
(2S,3aS,7aS)-1-(((R,R)-2-Phenylcyclopropyl)carbonyl)-2-((thiazolidin-3-yl)carbonyl)octahydro-1H-indole, [(2S,3aS,7aS)-Octahydro-1-[[(1R,2R)-2-phenylcyclopropyl]carbonyl]-1H-indol-2-yl]-3-thiazolidinyl--methanone
Empirical Formula (Hill Notation):
C22H28N2O2S
CAS Number:
176797-26-5
Molecular Weight:
384.53
MDL number:
MFCD00948255
UNSPSC Code:
12352200
PubChem Substance ID:
329825210
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -140 to -170° in dichloromethane

color

white to tan

solubility

DMSO: ≥10 mg/mL

storage temp.

2-8°C

SMILES string

O=C([C@@H]1C[C@@H]2CCCC[C@@H]2N1C(=O)[C@@H]3C[C@H]3c4ccccc4)N5CCSC5

InChI

1S/C22H28N2O2S/c25-21(18-13-17(18)15-6-2-1-3-7-15)24-19-9-5-4-8-16(19)12-20(24)22(26)23-10-11-27-14-23/h1-3,6-7,16-20H,4-5,8-14H2/t16-,17-,18+,19-,20-/m0/s1

InChI key

NXSXRIHXEQSYEZ-KNJMJIDISA-N

Related Categories

Application

S 17092 may be used in prolyl endopeptidase-mediated cell signaling studies.

Biochem/physiol Actions

S-17092 is a potent, selective inhibitor of Prolyl oligopeptidase (POP), also known as prolyl endopeptidase (PEP or PE). Ki=1.5 nM. Nootropic.

S-17092 inhibition of POP prevents breakdown and thus increases the activity of a number of neuropeptides, which is likely the basis for its nootropic activity. S 17092 has been shown to improve cognition. It improved cognitive task performance in chronic low dose MPTP-treated monkeys. S-17092 was recently used to inhibit the formation of AcSDKP from its precursor 43-mer thymosin ?4 (T?4). Ac-SDKP is involved in hemopoietic stem cell differentiation, is pro-angiogenic and antifibrogenic.

Features and Benefits

This compound is featured on the Neuropeptidases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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

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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Sokrates Stein et al.
Cardiovascular research, 117(4), 1060-1069 (2020-05-14)
Fibroblast activation protein (FAP) is upregulated at sites of tissue remodelling including chronic arthritis, solid tumours, and fibrotic hearts. It has also been associated with human coronary atherosclerotic plaques. Yet, the causal role of FAP in atherosclerosis remains unknown. To
Tommi P Kilpeläinen et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 128, 110253-110253 (2020-05-25)
Previous studies have shown that prolyl oligopeptidase (PREP) negatively regulates autophagy and increases the aggregation of alpha-synuclein (αSyn), linking it to the pathophysiology of Parkinson's disease. Our earlier results have revealed that the potent small molecular PREP inhibitor KYP-2047 is
Hypothalamic prolyl endopeptidase (PREP) regulates pancreatic insulin and glucagon secretion in mice.
Kim JD, Toda C, D'Agostino G, et al.
Proceedings of the National Academy of Sciences of the USA, 111(32), 11876-11881 (2014)

Articles

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