3-(5-[1,2]DITHIOLAN-3YL-PENTANOYLAMINO)-PROPYL-AMIDE Chemical Properties

Melting point:

79-81 °C

Boiling point:

702.1±43.0 °C(Predicted)

Density 

1.178±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMF: 10 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2)(1:4): .15 mg/ml; Ethanol: 2 mg/ml

form 

A crystalline solid

pka

15.86±0.46(Predicted)

3-(5-[1,2]DITHIOLAN-3YL-PENTANOYLAMINO)-PROPYL-AMIDE Usage And Synthesis

Description

α-Lipoic acid is a cyclic disulfide antioxidant that interconverts with its reduced dithiol form. It is an essential cofactor for decarboxylation reactions of the citric acid cycle and acts as a general antioxidant.¹ AN-7 is a more lipophilic analog of α-lipoic acid with enhanced potency and 1.5-fold increased maximal capacity to stimulate glucose transport into myocytes.² This identifies the analogs of lipoic acid as potential new treatments for diabetes.

Uses

α-Lipoic Acid Derivative 1 (Compound AN-7) is an α-lipoic acid derivative that enhances glucose transport in skeletal muscle by releasing active α-lipoic acid (LA), significantly improving glucose metabolism. In L6 skeletal muscle cells, α-Lipoic Acid Derivative 1 significantly increases glucose transport rates, approximately 12 times more potent than the parent compound α-lipoic acid (HY-N0492). In a mild diabetic mouse model, 10 mg/kg of α-Lipoic Acid Derivative 1 administered for two weeks significantly reduced blood glucose levels by 39%. α-Lipoic Acid Derivative 1 shows significant potential in research related to glucose metabolism in diabetes[1].

References

1. Biewenga, G.P., Haenen, G.R.M.M., and Bast, A. The pharmacology of the antioxidant lipoic acid Gen. Pharmacol. 29(3),315-331(1997).
2. Gruzman, A., Hidmi, A., Katzhendler, J., et al. Synthesis and characterization of new and potent α-lipoic acid derivatives Bioorg. Med. Chem. 12,1183-1190(2004).