Synonym
Velsicol VCS O-analog; Leptophos oxon; Leptophos oxygen analog; Leptophos OA; Phosvel oxon;
IUPAC/Chemical Name
4-bromo-2,5-dichlorophenyl methyl phenylphosphonate
InChi Key
MAKUYRKZFGSMMG-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H10BrCl2O3P/c1-18-20(17,9-5-3-2-4-6-9)19-13-8-11(15)10(14)7-12(13)16/h2-8H,1H3
SMILES Code
O=P(C1=CC=CC=C1)(OC)OC2=CC(Cl)=C(Br)C=C2Cl
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
Biological target:
Leptophos oxon is a phosvel analog-oxygen substituting sulfur.
In vitro activity:
In case of leptophos-oxon inhibited AChE, the best reactivation potency was achieved with methoxime, trimedoxime, obidoxime and oxime K027. The reactivation efficacy of tested oximes was lower in case of leptophos-oxon inhibited BChE.
Reference: Int J Mol Sci. 2010 Aug 3;11(8):2856-63. https://pubmed.ncbi.nlm.nih.gov/21152278/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
396.00
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. Jun D, Musilova L, Pohanka M, Jung YS, Bostik P, Kuca K. Reactivation of human acetylcholinesterase and butyrylcholinesterase inhibited by leptophos-oxon with different oxime reactivators in vitro. Int J Mol Sci. 2010 Aug 3;11(8):2856-63. doi: 10.3390/ijms11082856. PMID: 21152278; PMCID: PMC2996742.
In vitro protocol:
1. Jun D, Musilova L, Pohanka M, Jung YS, Bostik P, Kuca K. Reactivation of human acetylcholinesterase and butyrylcholinesterase inhibited by leptophos-oxon with different oxime reactivators in vitro. Int J Mol Sci. 2010 Aug 3;11(8):2856-63. doi: 10.3390/ijms11082856. PMID: 21152278; PMCID: PMC2996742.
1: Jun D, Musilova L, Pohanka M, Jung YS, Bostik P, Kuca K. Reactivation of human acetylcholinesterase and butyrylcholinesterase inhibited by leptophos-oxon with different oxime reactivators in vitro. Int J Mol Sci. 2010 Aug 3;11(8):2856-63. doi: 10.3390/ijms11082856. PubMed PMID: 21152278; PubMed Central PMCID: PMC2996742.
2: Reinders JH, Hansen LG, Metcalf RL. In vitro neurotoxic esterase assay using leptophos oxon analogs as inhibitors. Toxicol Lett. 1983 Jun;17(1-2):107-11. PubMed PMID: 6623496.
3: Preissig SH, Abou-Donia MB. The neuropathology of leptophos in the hen: a chronologic study. Environ Res. 1978 Oct;17(2):242-50. PubMed PMID: 318517.
4: Currie RA. Determination of leptophos, leptophos oxon, and a possible phenolic photoconversion metabolite in rapeseed grain. J Assoc Off Anal Chem. 1974 Sep;57(5):1056-60. PubMed PMID: 4369913.
5: Lee PW, Fukuto TR. Penetration and comparative metabolism of leptophos in susceptible and resistant houseflies. Arch Environ Contam Toxicol. 1976;4(4):443-55. PubMed PMID: 63268.
6: Jun D, Musilova L, Musilek K, Kuca K. In vitro ability of currently available oximes to reactivate organophosphate pesticide-inhibited human acetylcholinesterase and butyrylcholinesterase. Int J Mol Sci. 2011;12(3):2077-87. doi: 10.3390/ijms12032077. Epub 2011 Mar 23. PubMed PMID: 21673941; PubMed Central PMCID: PMC3111652.
7: Riskallah MR. Reduced sensitivity of cholinesterase as a factor of resistance in leptophos selected strain in the Egyptian cotton leafworm. J Environ Sci Health B. 1980;15(2):181-92. PubMed PMID: 6154073.
8: Riskallah MR, Esaac EG. Metabolism and excretion of leptophos and its phenol in S and R larvae of the Egyptian cotton leafworm. Arch Environ Contam Toxicol. 1982;11(2):253-7. PubMed PMID: 6178375.
9: Fulton MH, Chambers JE. The toxic and teratogenic effects of selected organophosphorus compounds on the embryos of three species of amphibians. Toxicol Lett. 1985 Aug;26(2-3):175-80. PubMed PMID: 4035710.
10: El-Sebae AH, Soliman SA, Ahmed NS, Curley A. Biochemical interaction of six OP delayed neurotoxicants with several neurotargets. J Environ Sci Health B. 1981;16(4):465-74. PubMed PMID: 6169754.
11: Gant DB, Eldefrawi ME, Eldefrawi AT. Action of organophosphates on GABAA receptor and voltage-dependent chloride channels. Fundam Appl Toxicol. 1987 Nov;9(4):698-704. PubMed PMID: 2446940.
12: Soliman SA, Curley A. Assay of chicken brain neurotoxic esterase activity using leptophosoxon as the selective neurotoxic inhibitor. J Anal Toxicol. 1981 Jul-Aug;5(4):183-6. PubMed PMID: 7278155.
13: Veronesi B, Ehrich M. Differential cytotoxic sensitivity in mouse and human cell lines exposed to organophosphate insecticides. Toxicol Appl Pharmacol. 1993 Jun;120(2):240-6. PubMed PMID: 8511793.
