Synonym
CI-201, VB-201, CI 201; VB 201, CI201; VB201
IUPAC/Chemical Name
(R)-2-(4-carboxybutoxy)-3-(hexadecyloxy)propyl (2-(trimethylammonio)ethyl) phosphate
InChi Key
JGGNOCUEWOGWPL-MUUNZHRXSA-N
InChi Code
InChI=1S/C29H60NO8P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-19-23-35-26-28(36-24-20-18-21-29(31)32)27-38-39(33,34)37-25-22-30(2,3)4/h28H,5-27H2,1-4H3,(H-,31,32,33,34)/t28-/m1/s1
SMILES Code
O=P(OC[C@H](OCCCCC(O)=O)COCCCCCCCCCCCCCCCC)([O-])OCC[N+](C)(C)C
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
581.77
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 |
1: Mendel I, Feige E, Yacov N, Salem Y, Levi I, Propheta-Meiran O, Shoham A, Ishai E, George J, Harats D, Breitbart E. VB-201, an oxidized phospholipid small molecule, inhibits CD14- and Toll-like receptor-2-dependent innate cell activation and constrains atherosclerosis. Clin Exp Immunol. 2014 Jan;175(1):126-37. doi: 10.1111/cei.12212. PubMed PMID: 24116867; PubMed Central PMCID: PMC3898561.
2: Feige E, Yacov N, Salem Y, Levi I, Mendel I, Propheta-Meiran O, Shoham A, Hait-Darshan R, Polonsky O, George J, Harats D, Breitbart E. Inhibition of monocyte chemotaxis by VB-201, a small molecule lecinoxoid, hinders atherosclerosis development in ApoE⁻/⁻ mice. Atherosclerosis. 2013 Aug;229(2):430-9. doi: 10.1016/j.atherosclerosis.2013.06.005. PubMed PMID: 23880199.
3: Mendel I, Shoham A, Propheta-Meiran O, Ishai E, Halperin G, Feige E, Breitbart E. A Lecinoxoid, an oxidized phospholipid small molecule, constrains CNS autoimmune disease. J Neuroimmunol. 2010 Sep 14;226(1-2):126-35. doi: 10.1016/j.jneuroim.2010.06.011. PubMed PMID: 20663571.
4: Mendel I, Yacov N, Shoham A, Ishai E, Breitbart E. Treatment with Oxidized Phospholipids Directly Inhibits Nonalcoholic Steatohepatitis and Liver Fibrosis Without Affecting Steatosis. Dig Dis Sci. 2016 Sep;61(9):2545-53. doi: 10.1007/s10620-016-4159-5. PubMed PMID: 27074921; PubMed Central PMCID: PMC4980417.
5: Feige E, Mendel I, George J, Yacov N, Harats D. Modified phospholipids as anti-inflammatory compounds. Curr Opin Lipidol. 2010 Dec;21(6):525-9. doi: 10.1097/MOL.0b013e32833f2fcb. Review. PubMed PMID: 20827191.
