DG 051 (HCl salt) Chemical Properties

storage temp. 

Store at -20°C

solubility 

DMF: 20 mg/ml; DMSO: 12.5 mg/ml; Ethanol: 12.5 mg/ml; PBS (pH 7.2): 2 mg/ml

form 

Solid

color 

White to light yellow

InChI

InChI=1/C21H24ClNO4.ClH/c22-16-5-7-19(8-6-16)27-20-11-9-18(10-12-20)26-15-17-3-1-13-23(17)14-2-4-21(24)25;/h5-12,17H,1-4,13-15H2,(H,24,25);1H/t17-;/s3

InChIKey

UCPVOTSNNAVKNE-VOPAOICTNA-N

SMILES

C(O)(=O)CCCN1CCC[C@H]1COC1=CC=C(OC2=CC=C(Cl)C=C2)C=C1.Cl |&1:10,r|

DG 051 (HCl salt) Usage And Synthesis

Description

DG-051 is a potent, orally bioavailable leukotriene A₄ hydrolase (LTA₄H) inhibitor (K_d = 25 nM; IC₅₀ = 47 nM), the enzyme that catalyzes the rate-determining step in the synthesis of LTB₄ . However, it also inhibits the aminopeptidase activity of LTA₄H with IC₅₀ values of 72 and 150 nM when tested using the substrates L-alanine p-nitroanaline and prolyl-glycyl-proline peptide (PGP; ), respectively, potentially leading to PGP accumulation in vivo. DG-051 does not show any inhibitory activity against a panel of more than 50 additional aminopeptidases, ion channels, or HERG.

Uses

(2S)?-2-?[[4-?(4-Chlorophenoxy)?phenoxy]?methyl]?-1-?pyrrolidinebutanoic Acid Hydrochloride is a potent inhibitor leukotriene A4 hydrolase (LTA4H), which is a therapeutic target for developing treatments for cardiovascular diseases and cancers.

References

[1] VINCENT SANDANAYAKA. Discovery of 4-[(2S)-2-{[4-(4-Chlorophenoxy)phenoxy]methyl}-1-pyrrolidinyl]butanoic Acid (DG-051) as a Novel Leukotriene A4 Hydrolase Inhibitor of Leukotriene B4 Biosynthesis[J]. Journal of Medicinal Chemistry, 2009, 53 2: 573-585. DOI: 10.1021/jm900838g
[2] CAROLINE M LOW. The development of novel LTA4H modulators to selectively target LTB4 generation.[J]. Scientific Reports, 2017: 44449. DOI: 10.1038/srep44449