Synonym
18:1-2:0 DG; 1-oleoyl-2-acetyl-sn-glycerol; PYN 90774; PYN-90774; PYN90774
IUPAC/Chemical Name
(S)-2-acetoxy-3-hydroxypropyl oleate
InChi Key
PWTCCMJTPHCGMS-YRBAHSOBSA-N
InChi Code
InChI=1S/C23H42O5/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)27-20-22(19-24)28-21(2)25/h10-11,22,24H,3-9,12-20H2,1-2H3/b11-10-/t22-/m0/s1
SMILES Code
OC[C@]([H])(OC(C)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O
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 and DMF
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
2934.99.9001
Biological target:
PYN90774 is a cell-permeable analog of the PKC-activating second messenger DAG. It activates PKC in platelets, resulting in the phosphorylation of a 40 kDa protein. PYN90774 is metabolized to its corresponding phosphatidic acid (1-oleoyl-2-acetyl-3-phosphoglycerol), most likely through the action of a diglycerol kinase.
In vitro activity:
PYN90774 was studied in ascites tumor cells. PYN90774treatment led to transient increases in inositol 1,4-bis- and inositol 1,4,5-trisphosphate liberation with peaks at 30 minutes, followed by sustained inositol phosphate accumulation at 30 minutes. Phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate showed transient activity profiles, while PtdIns exhibited sustained high activity levels at 30 minutes after PYN90774treatment. These findings suggest that PYN90774affects phosphoinositide metabolism by modulating PLC and phosphoinositide kinase activities.
Reference: J Lipid Mediat. 1993 Jul;7(3):239-52. https://pubmed.ncbi.nlm.nih.gov/8219004/
In vivo activity:
Patients with essential hypertension exhibited increased TRPC3 and TRPC5. PYN90774-induced calcium influx was heightened in these patients and could be mitigated by TRPC3 and TRPC5 knockdown. These findings suggest that PYN90774 contributes to the activation of monocytes in patients with essential hypertension, potentially promoting vascular disease.
Reference: J Hypertens. 2007 Apr;25(4):799-808. https://pubmed.ncbi.nlm.nih.gov/17351372/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
20.0 |
50.18 |
| DMSO |
20.0 |
50.18 |
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
398.58
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.
| 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. Haeffner EW. Transient temporal relationship between 1-oleoyl-2-acetyl-sn-glycerol (OAG)-activated synthesis and hydrolysis of polyphosphoinositides: desensitization of phospholipase C and the inositol lipid kinases upon long-term treatment of ascites cells by exogenous OAG. J Lipid Mediat. 1993 Jul;7(3):239-52. PMID: 8219004.
2. Marchetti C, Brown AM. Protein kinase activator 1-oleoyl-2-acetyl-sn-glycerol inhibits two types of calcium currents in GH3 cells. Am J Physiol. 1988 Jan;254(1 Pt 1):C206-10. doi: 10.1152/ajpcell.1988.254.1.C206. PMID: 2447796.
3. Liu DY, Thilo F, Scholze A, Wittstock A, Zhao ZG, Harteneck C, Zidek W, Zhu ZM, Tepel M. Increased store-operated and 1-oleoyl-2-acetyl-sn-glycerol-induced calcium influx in monocytes is mediated by transient receptor potential canonical channels in human essential hypertension. J Hypertens. 2007 Apr;25(4):799-808. doi: 10.1097/HJH.0b013e32803cae2b. PMID: 17351372.
In vitro protocol:
1. Haeffner EW. Transient temporal relationship between 1-oleoyl-2-acetyl-sn-glycerol (OAG)-activated synthesis and hydrolysis of polyphosphoinositides: desensitization of phospholipase C and the inositol lipid kinases upon long-term treatment of ascites cells by exogenous OAG. J Lipid Mediat. 1993 Jul;7(3):239-52. PMID: 8219004.
2. Marchetti C, Brown AM. Protein kinase activator 1-oleoyl-2-acetyl-sn-glycerol inhibits two types of calcium currents in GH3 cells. Am J Physiol. 1988 Jan;254(1 Pt 1):C206-10. doi: 10.1152/ajpcell.1988.254.1.C206. PMID: 2447796.
In vivo protocol:
1. Liu DY, Thilo F, Scholze A, Wittstock A, Zhao ZG, Harteneck C, Zidek W, Zhu ZM, Tepel M. Increased store-operated and 1-oleoyl-2-acetyl-sn-glycerol-induced calcium influx in monocytes is mediated by transient receptor potential canonical channels in human essential hypertension. J Hypertens. 2007 Apr;25(4):799-808. doi: 10.1097/HJH.0b013e32803cae2b. PMID: 17351372.
1. Ebeling, J.G., Vandenbark, G.R., Kuhn, L., Ganong, B., Bell, R.M. & Niedel, J.E. (1985) Diacylglycerols and Phorbol Diesters Induce Leukemic Cell Differentiation via a Common Mechanism. Proc. Natl. Acad. Sci. USA 82:815-819. Davis, R.J., Ganong, B.R., Bell, R.M. & Czech, M.P. (1985) sn-1,2-dioctanoylglycerol: a Cell Permeable Diacylglycerol That Mimics Phorbol Diester Action on the Epidermal Growth Factor Receptor and Mitogenesis. J. Biol. Chem. 260:1562-1566. Lapetina, E.G., Reep, B., Ganong, B.R. & Bell, R.M. (1985) Exogenous sn-1,2-diacylglycerols Containing Saturated Fatty Acids Functions as Bioregulators of Protein Kinase C in Human Platelets. J. Biol. Chem. 260:1358-1361. Ganong, B.R., Loomis, C.R., Hannun, Y.A. & Bell, R.M. (1986) Specificity and Mechanism of Protein Kinase C Activation by sn-1,2-diacylglycerols. Proc. Natl. Acad. Sci. USA 83:1184-1188.
