(R)-(+)--Lipoic acid - CAS 1200-22-2
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
(R)-(+)--Lipoic acid
Catalog Number:
1200-22-2
Synonyms:
(R)-6,8-Dithiooctanoic acid, (R)-6,8-Thioctic acid, (R)-(+)-1,2-Dithiolane-3-pentanoic acid
CAS Number:
1200-22-2
Description:
Lipoic Acid, an organosulfur compound, is widely used as dietary supplements and antioxidant. It has been also found to influence the activity of nuclear factor kappa-B.
Molecular Weight:
206.33
Molecular Formula:
C8H14O2S2
Quantity:
Grams-Kilos
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
C1CSSC1CCCCC(=O)O
InChI:
InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1
InChIKey:
AGBQKNBQESQNJD-SSDOTTSWSA-N
Targets:
NF-κB
Chemical Structure
CAS 1200-22-2 (R)-(+)--Lipoic acid

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Reference Reading


1.Increasing bioavailability of (R)-alpha-lipoic acid to boost antioxidant activity in the treatment of neuropathic pain.
Maglione E1, Marrese C, Migliaro E, Marcuccio F, Panico C, Salvati C, Citro G, Quercio M, Roncagliolo F, Torello C, Brufani M. Acta Biomed. 2015 Dec 14;86(3):226-33.
a-lipoic acid (a-LA) is a potent natural antioxidant because it has a broad spectrum of action towards a great many free radical species and boosts the endogenous antioxidant systems.Although it is a multi-functional molecule, its pharmacokinetic characteristics pose restrictions to its use in the treatment of oxidative stress-dependent illnesses. Formulations that increase the bioavailability of a-LA have a better potential efficacy as adjuvants for the treatment of these conditions.This objective was achieved with a liquid formulation for oral use containing only R-aLA, the natural enantiomeric and most active form of a-lipoic acid.For the first time, the effects of this formulation were evaluated on neuropathic pain, a symptom caused by an increase in oxidative stress, regardless of the underlying cause. Neuropathic patients who have used this dietary supplement noticed an improvement in their quality of life and a significant reduction was observed in a number of certain descriptive pain parameters (intensity, burning, unpleasantness, superficial pain).
2.α-Lipoic Acid in Soluplus® Polymeric Nanomicelles for Ocular Treatment of Diabetes-Associated Corneal Diseases.
Alvarez-Rivera F1, Fernández-Villanueva D1, Concheiro A1, Alvarez-Lorenzo C2. J Pharm Sci. 2016 Apr 19. pii: S0022-3549(16)00434-2. doi: 10.1016/j.xphs.2016.03.006. [Epub ahead of print]
α-Lipoic acid (ALA) is a powerful antioxidant valuable for prevention and treatment of ophthalmic complications such as diabetic keratopathy and retinopathy. The aim of this work was to develop micelle-based formulations that can enhance the solubility, stability, and corneal permeability of ALA. Compared to a conventional surfactant (sodium dioctylsulfosuccinate), Soluplus® (polyvinyl caprolactam-polyvinyl acetate-polyethylene glycol copolymer) led to smaller micelles (70-80 vs. 240-528 nm) with improved ability to solubilize ALA, maintaining ocular compatibility (Hens Egg Test on the Chorio-Allantoic Membrane). Soluplus nanomicelles enhanced more than 10-fold ALA solubility compared to common eye drops and withstood strong dilution in lachrymal fluid, filtration through sterilizing membranes, and freeze-drying. Interestingly, Soluplus nanomicelle formulation prepared with 1 or 2 mM block copolymer concentration exhibited in situ gelling capability and transformed into weak gels at 35°C, which is expected to increase corneal residence time.
3.Binary-copolymer system base on low-density lipoprotein-coupled N-succinyl chitosan lipoic acid micelles for co-delivery MDR1 siRNA and paclitaxel, enhances antitumor effects via reducing drug.
Yang SD1, Zhu WJ1, Zhu QL1,2, Chen WL1, Ren ZX3, Li F1, Yuan ZQ1, Li JZ1, Liu Y1, Zhou XF4,5, Liu C6, Zhang XN1. J Biomed Mater Res B Appl Biomater. 2016 Mar 23. doi: 10.1002/jbm.b.33636. [Epub ahead of print]
The development of effective and stable carriers of small interfering RNA (siRNA) is important for treating cancer with multidrug resistance (MDR). We developed a new gene and drug co-delivery system and checked its characteristics. Low-density lipoprotein (LDL) was coupled with N-succinyl chitosan (NSC) Lipoic acid (LA) micelles and co-delivered MDR1 siRNA and paclitaxel (PTX-siRNA/LDL-NSC-LA) to enhance antitumor effects by silencing the MDR gene of tumors (Li et al., Adv Mater 2014;26:8217-8224). In our study, we developed a new type of containing paclitaxel-loaded micelles and siRNA-loaded LDL nanoparticle. This "binary polymer" is pH and reduction dual-sensitive core-crosslinked micelles. PTX-siRNA/LDL-NSC-LA had an average particle size of (171.6 ± 6.42) nm, entrapment efficiency of (93.92 ± 1.06) %, and drug-loading amount of (12.35% ± 0.87) %. In vitro, MCF-7 cells, high expressed LDL receptor, were more sensitive to this delivery system than to taxol® and cell activity was inhibited significantly.
4.Investigation of Enantioselective Membrane Permeability of α-Lipoic Acid in Caco-2 and MDCKII Cell.
Uchida R1, Okamoto H2,3, Ikuta N4, Terao K5,6, Hirota T7. Int J Mol Sci. 2016 Jan 26;17(2). pii: E155. doi: 10.3390/ijms17020155.
α-Lipoic acid (LA) contains a chiral carbon and exists as two enantiomers (R-α-lipoic acid (RLA) and S-α-lipoic acid (SLA)). We previously demonstrated that oral bioavailability of RLA is better than that of SLA. This difference arose from the fraction absorbed multiplied by gastrointestinal availability (Fa × Fg) and hepatic availability (Fh) in the absorption phase. However, it remains unclear whether Fa and/or Fg are involved in enantioselectivity. In this study, Caco-2 cells and Madin-Darby canine kidney strain II cells were used to assess the enantioselectivity of membrane permeability. LA was actively transported from the apical side to basal side, regardless of the differences in its steric structure. Permeability rates were proportionally increased in the range of 10-250 µg LA/mL, and the permeability coefficient did not differ significantly between enantiomers. Hence, we conclude that enantioselective pharmacokinetics arose from the metabolism (Fh or Fg × Fh), and definitely not from the membrane permeation (Fa) in the absorption phase.