Ki16425
featured

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

MedKoo CAT#: 526788

CAS#: 355025-24-0

Description: Ki16425 is a LPA receptor antagonist with selectivity for LPA1 and LPA3. It exhibits Ki values of 0.34, 6.5, and 0.93 µM for the human LPA1, LPA2, and LPA3 receptors, respectively. Ki16425 reduces nerve growth factor-induced neurite outgrowth in pheochromocytoma 12 cells. ki16425 blunts abdominal and systemic inflammation in a mouse model of peritoneal sepsis.


Chemical Structure

img
Ki16425
CAS# 355025-24-0

Theoretical Analysis

MedKoo Cat#: 526788
Name: Ki16425
CAS#: 355025-24-0
Chemical Formula: C23H23ClN2O5S
Exact Mass: 474.10
Molecular Weight: 474.956
Elemental Analysis: C, 58.16; H, 4.88; Cl, 7.46; N, 5.90; O, 16.84; S, 6.75

Price and Availability

Size Price Availability Quantity
50mg USD 450 2 Weeks
100mg USD 750 2 Weeks
250mg USD 1450 2 Weeks
500mg USD 2350 2 Weeks
Bulk inquiry

Synonym: Ki16425; Ki-16425; Ki 16425.

IUPAC/Chemical Name: 3-((4-(4-(((1-(2-chlorophenyl)ethoxy)carbonyl)amino)-3-methylisoxazol-5-yl)benzyl)thio)propanoic acid

InChi Key: LLIFMNUXGDHTRO-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H23ClN2O5S/c1-14-21(25-23(29)30-15(2)18-5-3-4-6-19(18)24)22(31-26-14)17-9-7-16(8-10-17)13-32-12-11-20(27)28/h3-10,15H,11-13H2,1-2H3,(H,25,29)(H,27,28)

SMILES Code: O=C(O)CCSCC1=CC=C(C2=C(NC(OC(C3=CC=CC=C3Cl)C)=O)C(C)=NO2)C=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:
Biological target: Ki16425 (Debio 0719) is a subtype-selective, competitive antagonist of the EDG-family receptors, LPA1 and LPA3 with Kis of 0.34 μM and 0.93 μM, respectively.
In vitro activity: Ki16425 reduced the LPA-induced activation of p42/p44 mitogen activated protein kinase (MAPK), while acting as a weak stimulator of p42/p44 MAPK on its own, properties typical of a protean agonist. Significantly, Ki16425 also reduced the NGF-induced stimulation of p42/p44 MAPK and inhibited NGF-stimulated neurite outgrowth. Reference: J Neurochem. 2006 Sep;98(6):1920-9. https://pubmed.ncbi.nlm.nih.gov/16945108/
In vivo activity: The blockade of nerve injury-induced neuropathic pain by Ki-16425 was maximum as late as 3 h after the injury but not after this critical period. The administration of Ki-16425 at 3 h but not at 6 h after injury also blocked neurochemical changes, including up-regulation of voltage-gated calcium channel alpha(2)delta-1 subunit expression in dorsal root ganglion and reduction of substance P expression in the spinal dorsal horn. All of these results using Ki-16425 suggest that lysophosphatidic acid 1 receptor-mediated signaling which underlies the development of neuropathic pain works at an early stage of the critical period after nerve injury. Reference: J Neurochem. 2009 Apr;109(2):603-10. https://pubmed.ncbi.nlm.nih.gov/19222705/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 12.0 25.27
DMSO 62.9 132.38
DMSO:PBS (pH 7.2) (1:4) 0.2 0.42
Ethanol 52.0 109.48

Preparing Stock Solutions

The following data is based on the product molecular weight 474.96 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. Moughal NA, Waters CM, Valentine WJ, Connell M, Richardson JC, Tigyi G, Pyne S, Pyne NJ. Protean agonism of the lysophosphatidic acid receptor-1 with Ki16425 reduces nerve growth factor-induced neurite outgrowth in pheochromocytoma 12 cells. J Neurochem. 2006 Sep;98(6):1920-9. doi: 10.1111/j.1471-4159.2006.04009.x. PMID: 16945108. 2. Yamada T, Sato K, Komachi M, Malchinkhuu E, Tobo M, Kimura T, Kuwabara A, Yanagita Y, Ikeya T, Tanahashi Y, Ogawa T, Ohwada S, Morishita Y, Ohta H, Im DS, Tamoto K, Tomura H, Okajima F. Lysophosphatidic acid (LPA) in malignant ascites stimulates motility of human pancreatic cancer cells through LPA1. J Biol Chem. 2004 Feb 20;279(8):6595-605. doi: 10.1074/jbc.M308133200. Epub 2003 Dec 3. PMID: 14660630. 3. Ma L, Matsumoto M, Xie W, Inoue M, Ueda H. Evidence for lysophosphatidic acid 1 receptor signaling in the early phase of neuropathic pain mechanisms in experiments using Ki-16425, a lysophosphatidic acid 1 receptor antagonist. J Neurochem. 2009 Apr;109(2):603-10. doi: 10.1111/j.1471-4159.2009.05987.x. Epub 2009 Feb 13. PMID: 19222705. 4. Sánchez-Marín L, Ladrón de Guevara-Miranda D, Mañas-Padilla MC, Alén F, Moreno-Fernández RD, Díaz-Navarro C, Pérez-Del Palacio J, García-Fernández M, Pedraza C, Pavón FJ, Rodríguez de Fonseca F, Santín LJ, Serrano A, Castilla-Ortega E. Systemic blockade of LPA1/3 lysophosphatidic acid receptors by ki16425 modulates the effects of ethanol on the brain and behavior. Neuropharmacology. 2018 May 1;133:189-201. doi: 10.1016/j.neuropharm.2018.01.033. Epub 2018 Jan 31. PMID: 29378212.
In vitro protocol: 1. Moughal NA, Waters CM, Valentine WJ, Connell M, Richardson JC, Tigyi G, Pyne S, Pyne NJ. Protean agonism of the lysophosphatidic acid receptor-1 with Ki16425 reduces nerve growth factor-induced neurite outgrowth in pheochromocytoma 12 cells. J Neurochem. 2006 Sep;98(6):1920-9. doi: 10.1111/j.1471-4159.2006.04009.x. PMID: 16945108. 2. Yamada T, Sato K, Komachi M, Malchinkhuu E, Tobo M, Kimura T, Kuwabara A, Yanagita Y, Ikeya T, Tanahashi Y, Ogawa T, Ohwada S, Morishita Y, Ohta H, Im DS, Tamoto K, Tomura H, Okajima F. Lysophosphatidic acid (LPA) in malignant ascites stimulates motility of human pancreatic cancer cells through LPA1. J Biol Chem. 2004 Feb 20;279(8):6595-605. doi: 10.1074/jbc.M308133200. Epub 2003 Dec 3. PMID: 14660630.
In vivo protocol: 1. Ma L, Matsumoto M, Xie W, Inoue M, Ueda H. Evidence for lysophosphatidic acid 1 receptor signaling in the early phase of neuropathic pain mechanisms in experiments using Ki-16425, a lysophosphatidic acid 1 receptor antagonist. J Neurochem. 2009 Apr;109(2):603-10. doi: 10.1111/j.1471-4159.2009.05987.x. Epub 2009 Feb 13. PMID: 19222705. 2. Sánchez-Marín L, Ladrón de Guevara-Miranda D, Mañas-Padilla MC, Alén F, Moreno-Fernández RD, Díaz-Navarro C, Pérez-Del Palacio J, García-Fernández M, Pedraza C, Pavón FJ, Rodríguez de Fonseca F, Santín LJ, Serrano A, Castilla-Ortega E. Systemic blockade of LPA1/3 lysophosphatidic acid receptors by ki16425 modulates the effects of ethanol on the brain and behavior. Neuropharmacology. 2018 May 1;133:189-201. doi: 10.1016/j.neuropharm.2018.01.033. Epub 2018 Jan 31. PMID: 29378212.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Zhao J, Wei J, Weathington N, Jacko AM, Huang H, Tsung A, Zhao Y. Lysophosphatidic acid receptor 1 antagonist ki16425 blunts abdominal and systemic inflammation in a mouse model of peritoneal sepsis. Transl Res. 2015 Jul;166(1):80-8. doi: 10.1016/j.trsl.2015.01.008. Epub 2015 Jan 31. PubMed PMID: 25701366; PubMed Central PMCID: PMC4458421.

2: Sato T, Sugimoto K, Inoue A, Okudaira S, Aoki J, Tokuyama H. Synthesis and biological evaluation of optically active Ki16425. Bioorg Med Chem Lett. 2012 Jul 1;22(13):4323-6. doi: 10.1016/j.bmcl.2012.05.012. Epub 2012 May 11. PubMed PMID: 22658556.

3: Kim K, Kim HL, Lee YK, Han M, Sacket SJ, Jo JY, Kim YL, Im DS. Lysophosphatidylserine induces calcium signaling through Ki16425/VPC32183-sensitive GPCR in bone marrow-derived mast cells and in C6 glioma and colon cancer cells. Arch Pharm Res. 2008 Mar;31(3):310-7. doi: 10.1007/s12272-001-1157-x. Epub 2008 Apr 13. PubMed PMID: 18409043.

4: Moughal NA, Waters CM, Valentine WJ, Connell M, Richardson JC, Tigyi G, Pyne S, Pyne NJ. Protean agonism of the lysophosphatidic acid receptor-1 with Ki16425 reduces nerve growth factor-induced neurite outgrowth in pheochromocytoma 12 cells. J Neurochem. 2006 Sep;98(6):1920-9. PubMed PMID: 16945108.

5: Ohta H, Sato K, Murata N, Damirin A, Malchinkhuu E, Kon J, Kimura T, Tobo M, Yamazaki Y, Watanabe T, Yagi M, Sato M, Suzuki R, Murooka H, Sakai T, Nishitoba T, Im DS, Nochi H, Tamoto K, Tomura H, Okajima F. Ki16425, a subtype-selective antagonist for EDG-family lysophosphatidic acid receptors. Mol Pharmacol. 2003 Oct;64(4):994-1005. PubMed PMID: 14500756.