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MedKoo Cat#: 532063 | Name: L659989

Description:

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

L659989 is a PAF receptor antagonist.

Chemical Structure

L659989
L659989
CAS#113787-28-3

Theoretical Analysis

MedKoo Cat#: 532063

Name: L659989

CAS#: 113787-28-3

Chemical Formula: C24H32O8S

Exact Mass: 480.1818

Molecular Weight: 480.57

Elemental Analysis: C, 59.98; H, 6.71; O, 26.63; S, 6.67

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Related CAS #
No Data
Synonym
L659989; L 659989; L-659989.
IUPAC/Chemical Name
(2S,5S)-2-(3-methoxy-5-methylsulfonyl-4-propoxyphenyl)-5-(3,4,5-trimethoxyphenyl)oxolane
InChi Key
NZWPFJNQOZFEDT-ROUUACIJSA-N
InChi Code
InChI=1S/C24H32O8S/c1-7-10-31-24-21(29-4)13-16(14-22(24)33(6,25)26)18-9-8-17(32-18)15-11-19(27-2)23(30-5)20(12-15)28-3/h11-14,17-18H,7-10H2,1-6H3/t17-,18-/m0/s1
SMILES Code
COC1=C(OC)C(OC)=CC([C@@H]2CC[C@@H](C3=CC(S(=O)(C)=O)=C(OCCC)C(OC)=C3)O2)=C1
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
>2 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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
L659989 is a PAF receptor antagonist.
In vitro activity:
At concentrations of 30 micrograms/ml, L-659,989 inhibited basal and agonist-stimulated phospholipase D activity by about 55% and 70-100% respectively, through a mechanism that may involve the generation of intracellular ceramides. Furthermore, L-659,989 directly inhibited the activity of bacterial PLD in vitro. Reference: Biochim Biophys Acta. 1999 May 18;1438(2):247-52. https://pubmed.ncbi.nlm.nih.gov/10320807/
In vivo activity:
The specific platelet-activating factor receptor antagonist L-659,989 is beneficial to the survival of both pig muscle and skin flap components, a single, prereperfusion local dose of this lipophilic drug remains concentrated within the flap during the early inflammatory phase of reperfusion, and during reperfusion, platelet-activating factor antagonism is able to directly or indirectly diminish the accumulation of acute inflammatory cells in musculocutaneous flaps. Reference: Plast Reconstr Surg. 1997 Jun;99(7):1989-99; discussion 2000-1. https://pubmed.ncbi.nlm.nih.gov/9180723/

Preparing Stock Solutions

The following data is based on the product molecular weight 480.57 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. Gómez-Muñoz A, O'Brien L, Steinbrecher UP. The platelet-activating factor receptor antagonist L-659,989 inhibits phospholipase D activity. Biochim Biophys Acta. 1999 May 18;1438(2):247-52. doi: 10.1016/s1388-1981(99)00056-6. PMID: 10320807. 2. Parker AL, Likar LL, Dawicki DD, Rounds S. Mechanism of ATP-induced leukocyte adherence to cultured pulmonary artery endothelial cells. Am J Physiol. 1996 May;270(5 Pt 1):L695-703. doi: 10.1152/ajplung.1996.270.5.L695. PMID: 8967502. 3. Stotland MA, Kerrigan CL. The role of platelet-activating factor in musculocutaneous flap reperfusion injury. Plast Reconstr Surg. 1997 Jun;99(7):1989-99; discussion 2000-1. doi: 10.1097/00006534-199706000-00026. PMID: 9180723. 4. Herbertson MJ, Werner HA, Walley KR. Platelet-activating factor antagonism improves ventricular contractility in endotoxemia. Crit Care Med. 1997 Feb;25(2):221-6. doi: 10.1097/00003246-199702000-00004. PMID: 9034254.
In vitro protocol:
1. Gómez-Muñoz A, O'Brien L, Steinbrecher UP. The platelet-activating factor receptor antagonist L-659,989 inhibits phospholipase D activity. Biochim Biophys Acta. 1999 May 18;1438(2):247-52. doi: 10.1016/s1388-1981(99)00056-6. PMID: 10320807. 2. Parker AL, Likar LL, Dawicki DD, Rounds S. Mechanism of ATP-induced leukocyte adherence to cultured pulmonary artery endothelial cells. Am J Physiol. 1996 May;270(5 Pt 1):L695-703. doi: 10.1152/ajplung.1996.270.5.L695. PMID: 8967502.
In vivo protocol:
1. Stotland MA, Kerrigan CL. The role of platelet-activating factor in musculocutaneous flap reperfusion injury. Plast Reconstr Surg. 1997 Jun;99(7):1989-99; discussion 2000-1. doi: 10.1097/00006534-199706000-00026. PMID: 9180723. 2. Herbertson MJ, Werner HA, Walley KR. Platelet-activating factor antagonism improves ventricular contractility in endotoxemia. Crit Care Med. 1997 Feb;25(2):221-6. doi: 10.1097/00003246-199702000-00004. PMID: 9034254.
1: Chen J, Giris N. Species differences in PAF receptor binding in the lungs between hamster and guinea pig. J Lipid Mediat Cell Signal. 1997 Jun;16(2):63-74. PubMed PMID: 9172049. 2: Lin Y, Jamieson D. Are leukotrienes or PAF involved in hyperbaric oxygen toxicity? Agents Actions. 1993 Jan;38(1-2):66-75. PubMed PMID: 8386902. 3: Lefkowith JB, Morrison A, Lee V, Rogers M. Manipulation of the acute inflammatory response by dietary polyunsaturated fatty acid modulation. J Immunol. 1990 Sep 1;145(5):1523-9. PubMed PMID: 2166763.

View History

NSC-407436

NSC-407436