| Identification | Back Directory | [Name]
3-(5-[1,2]DITHIOLAN-3YL-PENTANOYLAMINO)-PROPYL-AMIDE | [CAS]
691410-93-2 | [Synonyms]
AN-7
AN7,AN 7
α-lipoic acid derivatives
3-(5-[1,2]DITHIOLAN-3YL-PENTANOYLAMINO)-PROPYL-AMIDE
5-(dithiolan-3-yl)-N-[3-[5-(dithiolan-3-yl)pentanoylamino]propyl]pentanamide | [Molecular Formula]
C11H20N2O2S2 | [MDL Number]
MFCD23380216 | [MOL File]
691410-93-2.mol | [Molecular Weight]
276.42 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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). |
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