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MedKoo Cat#: 598749 | Name: Levuglandin E2

Description:

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

Levuglandin E2 is a secoprostanoid from prostaglandin endoperoxide; gamma-ketoaldehyde cpd; related to prostaglandin E2.

Chemical Structure

Levuglandin E2
CAS#91712-41-3

Theoretical Analysis

MedKoo Cat#: 598749

Name: Levuglandin E2

CAS#: 91712-41-3

Chemical Formula: C20H32O5

Exact Mass: 352.2250

Molecular Weight: 352.47

Elemental Analysis: C, 68.15; H, 9.15; O, 22.70

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Levuglandin E2;
IUPAC/Chemical Name
(5Z,8R,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid
InChi Key
WJWAORNTZNRHBP-QNUMDXCLSA-N
InChi Code
InChI=1S/C20H32O5/c1-3-4-7-10-18(23)14-13-17(15-21)19(16(2)22)11-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19-/m0/s1
SMILES Code
CCCCC[C@H](O)/C=C/[C@@H](C=O)[C@H](C(C)=O)C/C=C\CCCC(O)=O
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:
Levuglandin E2 is a secoprostanoid from prostaglandin endoperoxide.
In vitro activity:
Levuglandin E2 (LGE2), a rearrangement product derived from the prostaglandin endoperoxide, PGH2, causes repair-resistant DNA-protein cross-links and cell death (LD50 = 230 nM) in V79 Chinese hamster lung fibroblasts. Reference: Biochemistry. 1993 Apr 20;32(15):4090-7. https://pubmed.ncbi.nlm.nih.gov/8471616/
In vivo activity:
Treatment of LDL with LGE2 (Levuglandin E2) leads to uptake and degradation by mouse peritoneal macrophages. Oxidized LDL, but not acetyl LDL efficiently competed for binding and uptake of LGE2-modified 125I-LDL. This result suggests that LGE2-modified LDL was recognized by a class of scavenger receptor that demonstrated ligand specificity for oxidized LDL but not for acetyl LDL. Reference: Biochim Biophys Acta. 1997 Jan 7;1344(1):1-5. https://pubmed.ncbi.nlm.nih.gov/9022751/

Preparing Stock Solutions

The following data is based on the product molecular weight 352.47 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. Murthi KK, Friedman LR, Oleinick NL, Salomon RG. Formation of DNA-protein cross-links in mammalian cells by levuglandin E2. Biochemistry. 1993 Apr 20;32(15):4090-7. doi: 10.1021/bi00066a034. PMID: 8471616. 2. Murthi KK, Salomon RG, Sternlicht H. Levuglandin E2 inhibits mitosis and microtubule assembly. Prostaglandins. 1990 Jun;39(6):611-22. doi: 10.1016/0090-6980(90)90022-n. PMID: 2115185. 3. Hoppe G, Subbanagounder G, O'Neil J, Salomon RG, Hoff HF. Macrophage recognition of LDL modified by levuglandin E2, an oxidation product of arachidonic acid. Biochim Biophys Acta. 1997 Jan 7;1344(1):1-5. doi: 10.1016/s0005-2760(96)00160-9. PMID: 9022751.
In vitro protocol:
1. Murthi KK, Friedman LR, Oleinick NL, Salomon RG. Formation of DNA-protein cross-links in mammalian cells by levuglandin E2. Biochemistry. 1993 Apr 20;32(15):4090-7. doi: 10.1021/bi00066a034. PMID: 8471616. 2. Murthi KK, Salomon RG, Sternlicht H. Levuglandin E2 inhibits mitosis and microtubule assembly. Prostaglandins. 1990 Jun;39(6):611-22. doi: 10.1016/0090-6980(90)90022-n. PMID: 2115185.
In vivo protocol:
1. Hoppe G, Subbanagounder G, O'Neil J, Salomon RG, Hoff HF. Macrophage recognition of LDL modified by levuglandin E2, an oxidation product of arachidonic acid. Biochim Biophys Acta. 1997 Jan 7;1344(1):1-5. doi: 10.1016/s0005-2760(96)00160-9. PMID: 9022751.
1: Iyer RS, Ghosh S, Salomon RG. Levuglandin E2 crosslinks proteins. Prostaglandins. 1989 Apr;37(4):471-80. PubMed PMID: 2762557. 2: Murthi KK, Salomon RG, Sternlicht H. Levuglandin E2 inhibits mitosis and microtubule assembly. Prostaglandins. 1990 Jun;39(6):611-22. PubMed PMID: 2115185. 3: Hoppe G, Subbanagounder G, O'Neil J, Salomon RG, Hoff HF. Macrophage recognition of LDL modified by levuglandin E2, an oxidation product of arachidonic acid. Biochim Biophys Acta. 1997 Jan 7;1344(1):1-5. PubMed PMID: 9022751. 4: Salomon RG, Jirousek MR, Ghosh S, Sharma RB. Prostaglandin endoperoxides 21. Covalent binding of levuglandin E2 with proteins. Prostaglandins. 1987 Nov;34(5):643-56. PubMed PMID: 3481092. 5: Jirousek MR, Murthi KK, Salomon RG. Electrophilic levuglandin E2-protein adducts bind glycine: a model for protein crosslinking. Prostaglandins. 1990 Aug;40(2):187-203. PubMed PMID: 2217833. 6: Carrier EJ, Zagol-Ikapitte I, Amarnath V, Boutaud O, Oates JA. Levuglandin forms adducts with histone h4 in a cyclooxygenase-2-dependent manner, altering its interaction with DNA. Biochemistry. 2014 Apr 22;53(15):2436-41. doi: 10.1021/bi401673b. Epub 2014 Apr 11. PubMed PMID: 24684440; PubMed Central PMCID: PMC4004227. 7: DiFranco E, Subbanagounder G, Kim S, Murthi K, Taneda S, Monnier VM, Salomon RG. Formation and stability of pyrrole adducts in the reaction of levuglandin E2 with proteins. Chem Res Toxicol. 1995 Jan-Feb;8(1):61-7. PubMed PMID: 7703368. 8: Murthi KK, Friedman LR, Oleinick NL, Salomon RG. Formation of DNA-protein cross-links in mammalian cells by levuglandin E2. Biochemistry. 1993 Apr 20;32(15):4090-7. PubMed PMID: 8471616. 9: Salomon RG, Sha W, Brame C, Kaur K, Subbanagounder G, O'Neil J, Hoff HF, Roberts LJ 2nd. Protein adducts of iso[4]levuglandin E2, a product of the isoprostane pathway, in oxidized low density lipoprotein. J Biol Chem. 1999 Jul 16;274(29):20271-80. PubMed PMID: 10400646. 10: Salomon RG, Subbanagounder G, O'Neil J, Kaur K, Smith MA, Hoff HF, Perry G, Monnier VM. Levuglandin E2-protein adducts in human plasma and vasculature. Chem Res Toxicol. 1997 May;10(5):536-45. PubMed PMID: 9168251. 11: Boutaud O, Brame CJ, Chaurand P, Li J, Rowlinson SW, Crews BC, Ji C, Marnett LJ, Caprioli RM, Roberts LJ 2nd, Oates JA. Characterization of the lysyl adducts of prostaglandin H-synthases that are derived from oxygenation of arachidonic acid. Biochemistry. 2001 Jun 12;40(23):6948-55. PubMed PMID: 11389610. 12: Davies SS, Amarnath V, Brame CJ, Boutaud O, Roberts LJ 2nd. Measurement of chronic oxidative and inflammatory stress by quantification of isoketal/levuglandin gamma-ketoaldehyde protein adducts using liquid chromatography tandem mass spectrometry. Nat Protoc. 2007;2(9):2079-91. PubMed PMID: 17853863. 13: Boutaud O, Brame CJ, Salomon RG, Roberts LJ 2nd, Oates JA. Characterization of the lysyl adducts formed from prostaglandin H2 via the levuglandin pathway. Biochemistry. 1999 Jul 20;38(29):9389-96. PubMed PMID: 10413514. 14: Carrier EJ, Amarnath V, Oates JA, Boutaud O. Characterization of covalent adducts of nucleosides and DNA formed by reaction with levuglandin. Biochemistry. 2009 Nov 17;48(45):10775-81. doi: 10.1021/bi9015132. PubMed PMID: 19824699; PubMed Central PMCID: PMC2824920. 15: Boutaud O, Montine TJ, Chang L, Klein WL, Oates JA. PGH2-derived levuglandin adducts increase the neurotoxicity of amyloid beta1-42. J Neurochem. 2006 Feb;96(4):917-23. Epub 2006 Jan 12. PubMed PMID: 16412101; PubMed Central PMCID: PMC1621054. 16: Foreman D, Solomon RG. Evidence that the prostaglandin E2 receptor and the anhydrolevuglandin E2 receptor in the rat uterus are the same receptor. Prostaglandins. 1992 Mar;43(3):263-70. PubMed PMID: 1321465. 17: Salomon RG, Subbanagounder G, Singh U, O'Neil J, Hoff HF. Oxidation of low-density lipoproteins produces levuglandin-protein adducts. Chem Res Toxicol. 1997 Jul;10(7):750-9. PubMed PMID: 9250408. 18: Schmidley JW, Dadson J, Iyer RS, Salomon RG. Brain tissue injury and blood-brain barrier opening induced by injection of LGE2 or PGE2. Prostaglandins Leukot Essent Fatty Acids. 1992 Oct;47(2):105-10. PubMed PMID: 1461920. 19: Zhang M, Li W, Li T. Generation and detection of levuglandins and isolevuglandins in vitro and in vivo. Molecules. 2011 Jun 24;16(7):5333-48. doi: 10.3390/molecules16075333. Review. PubMed PMID: 21705973. 20: Davies SS, Brantley EJ, Voziyan PA, Amarnath V, Zagol-Ikapitte I, Boutaud O, Hudson BG, Oates JA, Roberts LJ 2nd. Pyridoxamine analogues scavenge lipid-derived gamma-ketoaldehydes and protect against H2O2-mediated cytotoxicity. Biochemistry. 2006 Dec 26;45(51):15756-67. Epub 2006 Dec 6. PubMed PMID: 17176098; PubMed Central PMCID: PMC2597444.