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MedKoo Cat#: 584619 | Name: LY311727
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

LY311727 is a potent & selective inhibitor of human non-pancreatic secretory phospholipase A2.

Chemical Structure

LY311727
LY311727
CAS#164083-84-5

Theoretical Analysis

MedKoo Cat#: 584619

Name: LY311727

CAS#: 164083-84-5

Chemical Formula: C22H27N2O5P

Exact Mass: 430.1658

Molecular Weight: 430.44

Elemental Analysis: C, 61.39; H, 6.32; N, 6.51; O, 18.58; P, 7.20

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 weeks
10mg USD 650.00 2 weeks
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Related CAS #
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Synonym
LY311727; LY 311727
IUPAC/Chemical Name
Phosphonic acid, (3-((3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl)oxy)propyl)-
InChi Key
OPWQYOUZRHDKBR-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H27N2O5P/c1-2-20-19(14-22(23)25)18-13-17(29-11-6-12-30(26,27)28)9-10-21(18)24(20)15-16-7-4-3-5-8-16/h3-5,7-10,13H,2,6,11-12,14-15H2,1H3,(H2,23,25)(H2,26,27,28)
SMILES Code
CCC(N1CC2=CC=CC=C2)=C(CC(N)=O)C3=C1C=CC(OCCCP(O)(O)=O)=C3
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
LY-311727 is a potent secretory non-pancreatic phospholipase A2 (sPLA2) inhibitor (IC50 <1 μM for group IIA sPLA2).
In vitro activity:
Furthermore, the optimized structure (LY311727) displayed 1,500-fold selectivity when assayed against porcine pancreatic s-PLA2. Reference: Nat Struct Biol. 1995 Jun;2(6):458-65. https://pubmed.ncbi.nlm.nih.gov/7664108/
In vivo activity:
Inhibition of gVPLA2 with either the PLA2 inhibitor, LY311727, or with a specific monoclonal antibody, attenuated the barrier disruption caused by HK-MRSA. LY311727 also reduced HK-MRSA-induced permeability in mouse lung EC isolated from WT but not gVPLA2-KO mice. Reference: Cells. 2021 Jul 8;10(7):1731. https://pubmed.ncbi.nlm.nih.gov/34359901/
Solvent mg/mL mM
Solubility
DMF 30.0 69.70
DMSO 30.0 69.70
PBS (pH 7.2) 2.0 4.65
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 430.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Ha JS, Dho SH, Youm TH, Kwon KS, Park SS. Astrocytic phospholipase A2 contributes to neuronal glutamate toxicity. Brain Res. 2014 Nov 24;1590:97-106. doi: 10.1016/j.brainres.2014.10.015. Epub 2014 Oct 18. PMID: 25451090. 2. Schevitz RW, Bach NJ, Carlson DG, Chirgadze NY, Clawson DK, Dillard RD, Draheim SE, Hartley LW, Jones ND, Mihelich ED, et al. Structure-based design of the first potent and selective inhibitor of human non-pancreatic secretory phospholipase A2. Nat Struct Biol. 1995 Jun;2(6):458-65. doi: 10.1038/nsb0695-458. PMID: 7664108; PMCID: PMC7097651. 3. Htwe YM, Wang H, Belvitch P, Meliton L, Bandela M, Letsiou E, Dudek SM. Group V Phospholipase A2 Mediates Endothelial Dysfunction and Acute Lung Injury Caused by Methicillin-Resistant Staphylococcus Aureus. Cells. 2021 Jul 8;10(7):1731. doi: 10.3390/cells10071731. PMID: 34359901; PMCID: PMC8304832. 4. Blache D, Gautier T, Tietge UJ, Lagrost L. Activated platelets contribute to oxidized low-density lipoproteins and dysfunctional high-density lipoproteins through a phospholipase A2-dependent mechanism. FASEB J. 2012 Feb;26(2):927-37. doi: 10.1096/fj.11-191593. Epub 2011 Oct 31. PMID: 22042222.
In vitro protocol:
1. Ha JS, Dho SH, Youm TH, Kwon KS, Park SS. Astrocytic phospholipase A2 contributes to neuronal glutamate toxicity. Brain Res. 2014 Nov 24;1590:97-106. doi: 10.1016/j.brainres.2014.10.015. Epub 2014 Oct 18. PMID: 25451090. 2. Schevitz RW, Bach NJ, Carlson DG, Chirgadze NY, Clawson DK, Dillard RD, Draheim SE, Hartley LW, Jones ND, Mihelich ED, et al. Structure-based design of the first potent and selective inhibitor of human non-pancreatic secretory phospholipase A2. Nat Struct Biol. 1995 Jun;2(6):458-65. doi: 10.1038/nsb0695-458. PMID: 7664108; PMCID: PMC7097651.
In vivo protocol:
1. Htwe YM, Wang H, Belvitch P, Meliton L, Bandela M, Letsiou E, Dudek SM. Group V Phospholipase A2 Mediates Endothelial Dysfunction and Acute Lung Injury Caused by Methicillin-Resistant Staphylococcus Aureus. Cells. 2021 Jul 8;10(7):1731. doi: 10.3390/cells10071731. PMID: 34359901; PMCID: PMC8304832. 2. Blache D, Gautier T, Tietge UJ, Lagrost L. Activated platelets contribute to oxidized low-density lipoproteins and dysfunctional high-density lipoproteins through a phospholipase A2-dependent mechanism. FASEB J. 2012 Feb;26(2):927-37. doi: 10.1096/fj.11-191593. Epub 2011 Oct 31. PMID: 22042222.
1: Buitrago-Rey R, Olarte J, Gomez-Marin JE. Evaluation of two inhibitors of invasion: LY311727 [3-(3-acetamide-1-benzyl-2-ethyl-indolyl-5-oxy)propane phosphonic acid] and AEBSF [4-(2-aminoethyl)-benzenesulphonyl fluoride] in acute murine toxoplasmosis. J Antimicrob Chemother. 2002 May;49(5):871-4. PubMed PMID: 12003987. 2: Svensson CI, Lucas KK, Hua XY, Powell HC, Dennis EA, Yaksh TL. Spinal phospholipase A2 in inflammatory hyperalgesia: role of the small, secretory phospholipase A2. Neuroscience. 2005;133(2):543-53. PubMed PMID: 15885922. 3: Pawlak JM, Khau VV, Hutchison DR, Martinelli MJ. A Practical, Nenitzescu-Based Synthesis of LY311727, the First Potent and Selective s-PLA(2) Inhibitor. J Org Chem. 1996 Dec 13;61(25):9055-9059. PubMed PMID: 11667899. 4: Balsinde J. Roles of various phospholipases A2 in providing lysophospholipid acceptors for fatty acid phospholipid incorporation and remodelling. Biochem J. 2002 Jun 15;364(Pt 3):695-702. PubMed PMID: 12049633; PubMed Central PMCID: PMC1222618. 5: Beck GCh, Yard BA, Schulte J, Oberacker R, van Ackern K, van Der Woude FJ, Krimsky M, Kaszkin M, Yedgar S. Inhibition of LPS-induced chemokine production in human lung endothelial cells by lipid conjugates anchored to the membrane. Br J Pharmacol. 2002 Apr;135(7):1665-74. PubMed PMID: 11934806; PubMed Central PMCID: PMC1573284. 6: Bernatchez PN, Winstead MV, Dennis EA, Sirois MG. VEGF stimulation of endothelial cell PAF synthesis is mediated by group V 14 kDa secretory phospholipase A2. Br J Pharmacol. 2001 Sep;134(1):197-205. PubMed PMID: 11522612; PubMed Central PMCID: PMC1572915. 7: Boilard E, Bourgoin SG, Bernatchez C, Surette ME. Identification of an autoantigen on the surface of apoptotic human T cells as a new protein interacting with inflammatory group IIA phospholipase A2. Blood. 2003 Oct 15;102(8):2901-9. Epub 2003 Jun 26. PubMed PMID: 12829607. 8: Meliton AY, Muñoz NM, Meliton LN, Birukova AA, Leff AR, Birukov KG. Mechanical induction of group V phospholipase A(2) causes lung inflammation and acute lung injury. Am J Physiol Lung Cell Mol Physiol. 2013 May 15;304(10):L689-700. doi: 10.1152/ajplung.00047.2013. Epub 2013 Mar 22. PubMed PMID: 23525785; PubMed Central PMCID: PMC3652060. 9: Thommesen L, Sjursen W, Gåsvik K, Hanssen W, Brekke OL, Skattebøl L, Holmeide AK, Espevik T, Johansen B, Laegreid A. Selective inhibitors of cytosolic or secretory phospholipase A2 block TNF-induced activation of transcription factor nuclear factor-kappa B and expression of ICAM-1. J Immunol. 1998 Oct 1;161(7):3421-30. PubMed PMID: 9759860. 10: Fox N, Song M, Schrementi J, Sharp JD, White DL, Snyder DW, Hartley LW, Carlson DG, Bach NJ, Dillard RD, Draheim SE, Bobbitt JL, Fisher L, Mihelich ED. Transgenic model for the discovery of novel human secretory non-pancreatic phospholipase A2 inhibitors. Eur J Pharmacol. 1996 Jul 18;308(2):195-203. PubMed PMID: 8840132. 11: Blache D, Gautier T, Tietge UJ, Lagrost L. Activated platelets contribute to oxidized low-density lipoproteins and dysfunctional high-density lipoproteins through a phospholipase A2-dependent mechanism. FASEB J. 2012 Feb;26(2):927-37. doi: 10.1096/fj.11-191593. Epub 2011 Oct 31. PubMed PMID: 22042222. 12: Pilitsis JG, Diaz FG, O'Regan MH, Phillis JW. Differential effects of phospholipase inhibitors on free fatty acid efflux in rat cerebral cortex during ischemia-reperfusion injury. Brain Res. 2002 Sep 27;951(1):96-106. PubMed PMID: 12231462. 13: Ha JS, Dho SH, Youm TH, Kwon KS, Park SS. Astrocytic phospholipase A2 contributes to neuronal glutamate toxicity. Brain Res. 2014 Nov 24;1590:97-106. doi: 10.1016/j.brainres.2014.10.015. Epub 2014 Oct 18. PubMed PMID: 25451090. 14: Marshall J, Krump E, Lindsay T, Downey G, Ford DA, Zhu P, Walker P, Rubin B. Involvement of cytosolic phospholipase A2 and secretory phospholipase A2 in arachidonic acid release from human neutrophils. J Immunol. 2000 Feb 15;164(4):2084-91. PubMed PMID: 10657662. 15: Schevitz RW, Bach NJ, Carlson DG, Chirgadze NY, Clawson DK, Dillard RD, Draheim SE, Hartley LW, Jones ND, Mihelich ED, et al. Structure-based design of the first potent and selective inhibitor of human non-pancreatic secretory phospholipase A2. Nat Struct Biol. 1995 Jun;2(6):458-65. PubMed PMID: 7664108. 16: Fleisch JH, Armstrong CT, Roman CR, Mihelich ED, Spaethe SM, Jackson WT, Bobbitt JL, Draheim S, Bach NJ, Dillard RD, Martinelli M, Fouts R, Snyder DW. Recombinant human secretory phospholipase A2 released thromboxane from guinea pig bronchoalveolar lavage cells: in vitro and ex vivo evaluation of a novel secretory phospholipase A2 inhibitor. J Pharmacol Exp Ther. 1996 Jul;278(1):252-7. PubMed PMID: 8764358. 17: Tibes U, Friebe WG. Phospholipase A2 inhibitors in development. Expert Opin Investig Drugs. 1997 Mar;6(3):279-98. PubMed PMID: 15989628. 18: Bidgood MJ, Jamal OS, Cunningham AM, Brooks PM, Scott KF. Type IIA secretory phospholipase A2 up-regulates cyclooxygenase-2 and amplifies cytokine-mediated prostaglandin production in human rheumatoid synoviocytes. J Immunol. 2000 Sep 1;165(5):2790-7. PubMed PMID: 10946311. 19: Pawliczak R, Han C, Huang XL, Demetris AJ, Shelhamer JH, Wu T. 85-kDa cytosolic phospholipase A2 mediates peroxisome proliferator-activated receptor gamma activation in human lung epithelial cells. J Biol Chem. 2002 Sep 6;277(36):33153-63. Epub 2002 Jun 20. PubMed PMID: 12077117. 20: Bezzine S, Koduri RS, Valentin E, Murakami M, Kudo I, Ghomashchi F, Sadilek M, Lambeau G, Gelb MH. Exogenously added human group X secreted phospholipase A(2) but not the group IB, IIA, and V enzymes efficiently release arachidonic acid from adherent mammalian cells. J Biol Chem. 2000 Feb 4;275(5):3179-91. PubMed PMID: 10652303.