ChemicalBook--->CAS DataBase List--->1101136-50-8

1101136-50-8

1101136-50-8 Structure

1101136-50-8 Structure
IdentificationBack Directory
[Name]

CAY10590
[CAS]

1101136-50-8
[Synonyms]

CAY10590
ANTPELWBOPVWPH-LJQANCHMSA-N
4-[(1-Oxo-7-phenylheptyl)amino]-(4R)-octanoic acid
Octanoic acid, 4-[(1-oxo-7-phenylheptyl)amino]-, (4R)-
[Molecular Formula]

C21H33NO3
[MDL Number]

MFCD18382098
[MOL File]

1101136-50-8.mol
[Molecular Weight]

347.49
Chemical PropertiesBack Directory
[Melting point ]

73-75 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
[Boiling point ]

567.8±43.0 °C(Predicted)
[density ]

1.028±0.06 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

DMF: 25 mg/ml; DMSO: 20 mg/ml; Ethanol: 30 mg/ml
[form ]

A crystalline solid
[pka]

4.60±0.10(Predicted)
[color ]

White to off-white
Hazard InformationBack Directory
[Description]

Phospholipase A2 (PLA2) catalyzes the hydrolysis of fatty acids at the sn-2 position of glycerophospholipids, liberating arachidonic acid for subsequent eicosanoid synthesis.1 Three primary types of PLA2 exist: secretory (sPLA2), calcium-dependent cytosolic (cPLA2), and calcium-independent cytosolic (iPLA2).2 Of these three enzymes, cPLA2 is the rate-limiting stimulus for release of arachidonic acid whereas sPLA2 amplifies the action of cPLA2 and regulates phagocytosis and foam cell formation.3 CAY10590, a simple amide based on (R)-γ-norleucine, is a potent and selective inhibitor of sPLA2. It exhibits 95% inhibition (XI(50) = 0.003) of sPLA2 at 0.091 mole fraction without affecting the activities of cPLA2 or iPLA2.4
[References]

1. Dennis, E.A. Phospholipases The Enzymes XVI,(1983).
2. Dennis, E.A. Diversity of group types, regulation, and function of phospholipase A2 J. Biol. Chem. 269,13057-13060(1994).
3. Balestrieri, B., and Arm, J.P. Group V sPLA2: Classical and novel functions Biochim. Biophys. Acta 1761,1280-1288(2006).
4. Antonopoulou, G., Barbayianni, E., Magrioti, V., et al. Structure-activity relationships of natural and non-natural amino acid-based amide and 2-oxoamide inhibitors of human phospholipase A2 enzymes Bioorg. Med. Chem. 16,10257-10269(2008).
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