CAY10590

Cayman Chemical Item Number 13181

(CAS 1101136-50-8)

CAY10590 (CAS 1101136-50-8)

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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

1 Dennis, E.A. Phospholipases. Enzymes XVI 307-353 (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).

Formal Name 4-​[(1-​oxo-​7-​phenylheptyl)amino]-​(4R)-​octanoic acid
CAS Number 1101136-50-8
Molecular Formula C21H33NO3
Formula Weight 347.5
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=C(N[C@H]​(CCCC)​CCC(O)​=O)​CCCCCCC1=CC=CC=C1
InCHI Code
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​1S/C21H33NO3/c1-2-3-14-19(16-17-21(24)​25)​22-20(23)​15-10-5-4-7-11-18-12-8-6-9-13-18/h6,8-9,12-13,19H,2-5,7,10-11,14-17H2,1H3,(H,22,23)​(H,24,25)​/t19-/m1/s1
InCHI Key
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ANTPELWBOPVWPH-LJQANCHMSA-N

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CAY10590 is available in the following screening library:

Size Price Quantity Subtotal
1 mg $26.00 $0.00
5 mg $117.00 $0.00
10 mg $208.00 $0.00
50 mg $910.00 $0.00
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Cart Total $0.00

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Pricing updated 2014-04-24. Prices are subject to change without notice.

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