ChemicalBook CAS DataBase List 139262-76-3

139262-76-3

Name	4,4′-[1,3-Phenylenebis(oxy-4,1-phenyleneimino)]bis[4-oxo-2-Butenoic acid
CAS	139262-76-3
Molecular Formula	C26H20N2O8
Molecular Weight	488.45
MOL File	139262-76-3.mol

Chemical Properties

storage temp.	2-8°C
solubility	DMSO: soluble25mg/mL, clear
form	powder
color	white to beige
Stability:	Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
InChIKey	HZFPOTBCYPWQSH-DZDAAMPGSA-N
SMILES	N(c1ccc(cc1)Oc2cc(ccc2)Oc3ccc(cc3)NC(=O)\C=C/C(=O)O)C(=O)\C=C/C(=O)O

Safety Data

WGK Germany	3
Storage Class	11 - Combustible Solids

Hazard Information

Description

H2L5186303 (139262-76-3) is a potent and selective lysophosphatidic acid 2 (LPA2) receptor antagonist.? IC50?= 8.9 nM, 1230 nM and 27.35 μM for LPA2, LPA3, and LPA1 respectively.1,2

Uses

H2L5186303 is an antidepressant acting on the LPA1 (lysophosphatidic acid receptor 1) and induce insulin-like growth factor-I receptor transactivation as well as causing enhanced cell proliferation.

Biochem/physiol Actions

H2L5186303 is specific antagonist of the lysophosphatidic acid receptor LPA2 (Ki = 7.2 nM). The compound H2L5186303 displays 40- to 1800-fold selectivity over other LPA receptors.

in vivo

H2L5186303 (0-50 mg/kg, given by intraperitoneal injection, single dose) suppresses the levels of eosinophils and lymphocytes in OVA-sensitized mice, and has the trachea inflammation inhibitory effect^[2].
H2L5186303 (10 mg/kg, given by intraperitoneal injection, three times every other day, 6 days) inhibits cell proliferation in Lpar5f/f Villin-Cre mice intestinal crypts and promotes apoptosis^[3].

Animal Model:	Ovalbumin-Induced allergic asthma in BALB/c mice^[2]
Dosage:	1 mg/kg, single dose; 0, 6.25, 12.5, 25, 50 mg/mL, single dose
Administration:	Intraperitoneal injection (i.p.)
Result:	Showed strong inhibitory effects, reducing airway hyper-responsiveness, levels of inflammatory cytokines, mucus production, and the number of eosinophils before sensitization and toxin exposure in OVA. Lowered AHR and inflammation scores. Suppressed mRNA levels of IL-4, IL-13, and IFN-γ, but did not inhibit IgE levels.

Animal Model:	Lpar5f/f Villin-Cre mice^[3]
Dosage:	10 mg/kg, every other day for three times, 6 days
Administration:	Intraperitoneal injection (i.p.)
Result:	Reduced the number of proliferating cells in the intestinal crypts of mice and increased cell apoptosis.

IC 50

LPA₂ Receptor: 9 nM (IC₅₀)

storage

Store at -20°C

References

1) Fells?et al. (2008)?Identification of non-lipid LPA3 antagonists by virtual screening; Bioorg. Med. Chem.?16?6207 2) Fells?et al. (2009)?Structure-based drug design identifies novel LPA3 antagonists; Bioorg. Med. Chem. 17?7457

Spectrum Detail

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