CAY10590

Cayman Chemical Item Number 13181

(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 $29.00 $0.00
5 mg $131.00 $0.00
10 mg $232.00 $0.00
50 mg $943.00 $0.00
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Pricing updated 2015-04-01. Prices are subject to change without notice.

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Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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Ann Arbor, Michigan 48108 USA

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