H2L5186303
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MedKoo CAT#: 531950

CAS#: 139262-76-3

Description: H2L5186303 is a potent and selective lysophosphatidic acid 2 (LPA2) receptor antagonist (IC50 values are 8.9, 1230 and 27354 nM).


Chemical Structure

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H2L5186303
CAS# 139262-76-3

Theoretical Analysis

MedKoo Cat#: 531950
Name: H2L5186303
CAS#: 139262-76-3
Chemical Formula: C26H20N2O8
Exact Mass: 488.12
Molecular Weight: 488.450
Elemental Analysis: C, 63.93; H, 4.13; N, 5.74; O, 26.20

Price and Availability

Size Price Availability Quantity
10mg USD 200 Ready to ship
25mg USD 350 Ready to ship
50mg USD 550 Ready to ship
100mg USD 950 Ready to ship
200mg USD 1650 Ready to ship
500mg USD 3450 Ready to ship
1g USD 5250 Ready to ship
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Synonym: H2L5186303; H2L 5186303; H2L-5186303.

IUPAC/Chemical Name: (2Z,2'Z)-4,4'-(((1,3-phenylenebis(oxy))bis(4,1-phenylene))bis(azanediyl))bis(4-oxobut-2-enoic acid)

InChi Key: HZFPOTBCYPWQSH-DZDAAMPGSA-N

InChi Code: InChI=1S/C26H20N2O8/c29-23(12-14-25(31)32)27-17-4-8-19(9-5-17)35-21-2-1-3-22(16-21)36-20-10-6-18(7-11-20)28-24(30)13-15-26(33)34/h1-16H,(H,27,29)(H,28,30)(H,31,32)(H,33,34)/b14-12-,15-13-

SMILES Code: O(C1=CC(OC2=CC=C(NC(/C=C\C(O)=O)=O)C=C2)=CC=C1)C3=CC=C(NC(/C=C\C(O)=O)=O)C=C3

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:

Biological target: H2L5186303 is a selective lysophosphatidic acid 2 (LPA2) receptor antagonist (IC50 = 9 nM in a LPA-elicited calcium mobilization assay). It inhibits LPA1 and LPA3 at much higher concentrations (IC50s = 27,354 and 4,504 nM, respectively).
In vitro activity: The high cell invasion activity of human fibrosarcoma HT1080-M6 cells was significantly suppressed by H2L5186303, suggesting that LPA2 acts as a key regulator of malignant properties in HT1080 cells. Reference: Biochem Biophys Res Commun. 2018 Sep 18;503(4):2698-2703. https://pubmed.ncbi.nlm.nih.gov/30093116/
In vivo activity: H2L5186303 showed strong suppressive efficacy in a single experimental protocol of ovalbumin (OVA)-induced allergic asthma when administered before OVA sensitization and challenge, such as suppression of airway hyper responsiveness, inflammatory cytokine levels, mucin production, and eosinophil numbers. Reference: Int J Mol Sci. 2022 Aug 28;23(17):9745. https://pubmed.ncbi.nlm.nih.gov/36077141/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 48.8 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 488.45 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. Takahashi K, Minami K, Otagaki S, Ishimoto K, Fukushima K, Fukushima N, Honoki K, Tsujiuchi T. Lysophosphatidic acid receptor-2 (LPA2) and LPA5 regulate cellular functions during tumor progression in fibrosarcoma HT1080 cells. Biochem Biophys Res Commun. 2018 Sep 18;503(4):2698-2703. doi: 10.1016/j.bbrc.2018.08.026. Epub 2018 Aug 7. PMID: 30093116. 2. Olianas MC, Dedoni S, Onali P. LPA1 is a key mediator of intracellular signalling and neuroprotection triggered by tetracyclic antidepressants in hippocampal neurons. J Neurochem. 2017 Oct;143(2):183-197. doi: 10.1111/jnc.14150. Epub 2017 Sep 11. PMID: 28815598. 3. Lee YJ, Im DS. Efficacy Comparison of LPA2 Antagonist H2L5186303 and Agonist GRI977143 on Ovalbumin-Induced Allergic Asthma in BALB/c Mice. Int J Mol Sci. 2022 Aug 28;23(17):9745. doi: 10.3390/ijms23179745. PMID: 36077141; PMCID: PMC9456302.
In vitro protocol: 1. Takahashi K, Minami K, Otagaki S, Ishimoto K, Fukushima K, Fukushima N, Honoki K, Tsujiuchi T. Lysophosphatidic acid receptor-2 (LPA2) and LPA5 regulate cellular functions during tumor progression in fibrosarcoma HT1080 cells. Biochem Biophys Res Commun. 2018 Sep 18;503(4):2698-2703. doi: 10.1016/j.bbrc.2018.08.026. Epub 2018 Aug 7. PMID: 30093116. 2. Olianas MC, Dedoni S, Onali P. LPA1 is a key mediator of intracellular signalling and neuroprotection triggered by tetracyclic antidepressants in hippocampal neurons. J Neurochem. 2017 Oct;143(2):183-197. doi: 10.1111/jnc.14150. Epub 2017 Sep 11. PMID: 28815598.
In vivo protocol: 1. Lee YJ, Im DS. Efficacy Comparison of LPA2 Antagonist H2L5186303 and Agonist GRI977143 on Ovalbumin-Induced Allergic Asthma in BALB/c Mice. Int J Mol Sci. 2022 Aug 28;23(17):9745. doi: 10.3390/ijms23179745. PMID: 36077141; PMCID: PMC9456302.

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1: Fells JI, Tsukahara R, Liu J, Tigyi G, Parrill AL. Structure-based drug design identifies novel LPA3 antagonists. Bioorg Med Chem. 2009 Nov 1;17(21):7457-64. doi: 10.1016/j.bmc.2009.09.022. PubMed PMID: 19800804; PubMed Central PMCID: PMC2771199.