Alfa lipoic acid

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Vinayak Khairnar α-Lipoic Acid


It is as sulfur-containing fatty acid. It is found inside every cell of the body, where it helps as cofactor to generate the energy that keeps us alive and functioning. Lipoic acid is a key part of the metabolic machinery that turns glucose (blood sugar) into energy for the body's needs. History and chemistry Generic Name- Lipoic Acid (Thioctic acid) Mol. Formula -C8H14S2O2 Mol.Wt.-206.317 g/mol Log P- 1.89


Antioxidants – These are a bit like kamikaze pilots, sacrificing themselves to knock out free radicals( naturally occurring harmful chemicals) Lipoic acid is an universal antioxidant Broad spectrum of antioxidant action Unlike other antioxidants, which work only in water or fatty tissues (eg. vitamin E, vitamin C), lipoic acid is unusual in that it functions in both water and fat. Regeneration of other antioxidants Lipoic acid may help to regenerate other antioxidants (Vit-C, Vit-E, glutathione) that have been used up. In addition, lipoic acid may be able to do the work of other antioxidants when the body is deficient in them. Augments the body’s entire antioxidant network, including glutathione & coenzyme Q10. Crosses blood-brain barrier (protects nervous system) . Directly and indirectly reduces DNA damage. THE Universal Antioxidant


One stone & multi Hunts Alpha lipoic acid is used in treatements of ……. Blood sugar control Lipoic acid is a key part of the metabolic machinery that turns glucose (blood sugar) into energy for the body's needs. Ultimately used in the treatment of diabetes mellitus. Diabetic peripheral neuropathy. This is a condition caused by diabetes in which nerves leading to the arms and legs become damaged, resulting in numbness, pain, and other symptoms. Free radicals are hypothesized to play a role in neuropathy, and, on this basis, lipoic acid has been tried as a treatment. Cardiac autonomic neuropathy Autonomic nerves that control internal organs may become damaged in diabetes. When this occurs in the heart (cardiac autonomic neuro- pathy), it leads to irregularities of heart rhythm. There is some evidence that lipoic acid supplements may be helpful for this condition.


Burning mouth syndrome (BMS) It is a condition characterized by unexplained scalding sensations in the mouth. Lipoic acid may be helpful for treating this. Migraine headaches Weak evidence hints that use of lipoic acid might help prevent migraine headaches. Sun-damaged skin A cream containing 5% lipoic acid has shown promise for the treatment of sun-damaged skin. Age-related hearing loss One animal study suggests that lipoic acid might help prevent age- related hearing loss. Glaucoma Similarly weak evidence hints that lipoic acid might be helpful for glaucoma. Other For reducing the side effects (specifically, cardiac toxicity) of the cancer chemotherapy drug doxorubicin Other uses for which lipoic acid has been proposed include preventing cancer and heart disease, and treating or preventing cataracts


Pharmacology and hypothesis for the treatement of Autism , amalgam poisoning,Diabetes α-lipoic acid is able to pass the blood-brain barrier and is putatively used for detoxification of mercury attached to the brain cells. It can mobilise bound mercury into the blood stream as it is a mercaptan (sulfur compound which readily binds to the mercury). In the blood stream, another chelator such as dimercaptosuccinic acid (DMSA) or methylsulfonylmethane (MSM) is used to transfer mercury safely into the urine for excretion. Neither DMSA nor MSM can cross the blood- brain barrier, which is why both lipoic acid and DMSA are used. Most medicines and vitamin supplements do not penetrate the blood- brain barrier,however α-lipoic acid and perhaps vitamin B12 could making it possible for other chelators to remove mercury safely out of the body and could perhaps one day be used as a treatment for autism. Because lipoic acid is related to cellular uptake of glucose and it is both soluble in water and fat, it is being used for treatment in diabetes. It may be helpful for people with Alzheimer's disease or Parkinson's disease.


Lipoic Acid is generally involved in oxidative decarboxylations of keto acids and is presented as a growth factor for some organisms. Lipoic acid exists as two enantiomers, the R-enantiomer and the S-enantiomer. Normally only the R-enantiomer of an amino acid is biologically active, but for lipoic acid the S-enantiomer assists in the reduction of the R-enantiomer when a racemic mixture is given. Some recent studies have suggested that the S-enantiomer in fact has an inhibiting effect on the R-enantiomer, reducing its biological activity substantially and actually adding to oxidative stress rather than reducing it. Furthermore, the S-enantiomer has been found to reduce the expression of GLUT-4s in cells, responsible for glucose uptake, and hence reduce insulin sensitivity Natural Selection of Enantiomers Why R and why not S ? R R –(alpha) Lipoic Acid is a biologically active enantiomer.


HOW ? How is the lipoic acid functions as multiceutics?


Lipoic acid is a co-factor found in pyruvate dehydrogenase and a-ketoglutarate dehydrogenase, two multienzymes involved in a-keto acid oxidation. Lipoic acid functions to couple acyl group transfer and electron transfer during oxidation and decarboxylation of a-ketoacids No evidence exists of a dietary lipoic acid requirement in humans; therefore it is not considered a vitamin Expression in body


Mitochondrial Matrix Cellular Cytoplasm Mitochondrial Outer Membrane Inner Membrane Intermembrane Space V I II III IV CytC CoQ Pyruvate Dehydrogenase complex Citrate Synthase -Ketoglutarate Dehydrogenase Complex Fumarate L-Malate Oxaloacetate Acetyl-Co-A Citrate Isocitrate -Ketoglutarate Succinyl-Co-A Succinate FAD FADH2 H2O O2 ADP ATP ATP NADH NADH NADH NAD+ NADH NADH 9


Krebs Cycle


Engineered microorganisms that produce at least 200 .mug alpha-lipoic acid (ALA) per g dry cell weight and engineered microorganisms that secrete at least a 2-fold greater amount of ALA than an amount of ALA found intracellularly, are described. Synthesis of Lipoic acid in cells


Lipoic acid exists in 2 forms: a closed-ring disulfide form and an open-chain reduced form; oxidation-reduction cycles interconvert these 2 species; lipoic acid exists covalently attached in an amide linkage with lysine residues on enzymes Existance in Body


R--Lipoic Acid (LA) in mitochondria LA reduced to dihydrolipoic acid, a potent antioxidant, & chelator of Fe & Cu Coenzyme of pyruvate and -ketoglutarate dehydrogenases Involved with carbohydrate utilization for ATP production


As an antioxidant


Bruce N. Ames Children’s Hospital Oakland Research Institute Professor, University of California, Berkeley Delaying (or Accelerating) the Degenerative Diseases of Aging 24JN07 Timiras


“The Perpetrators” 2-5% of the oxygen used by mitochondria is diverted to produce free radicals! Mitochondria


Free radical damage from oxidative stress (Reactive oxygen species, ROS) has long been thought to play an important role in age-related neurodegenerative disorders Free radicals are produced by the mitochondria in cells as a side effect of energy production from food. Emerging consensus that free radicals play a causative role in many diseases Free radical-mediated damage to neuronal membrane is implicated in the etiology of Alzheimer’s disease. Free Radical !


1. Enzymes ● superoxide dismutase-SOD (Zn, Cu, Mn) ● glutathione peroxidase (Se) ● catalase (Fe) 2. Dietary Anti-Oxidants ● vitamin C for aqueous compartments ● vitamin E for lipid compartments 3. Other Factors ● Coenzyme Q10, carnitine, lipoic acid How Does the Body Protect Itself from Reactive Oxygen Species ?


● Mitochondrial DNA is 20X more susceptible to oxidative damage than cellular damage ● Little evidence of self-repair ● Without adequate energy production, all functional systems are impaired Oxidatic Damage of DNA

DNA Attack: 

Antioxidants are good for our body as they “catch” bad free radicals before they can hurt us. DNA Attack

Extent of DNA Damage: 

73,000 DNA damage events per cell every day! DNA repair enzymes, fix most of the damage Extent of DNA Damage


In Therapy of Diabetes


Use Of alpha-lipoic acid in treatment of dibetes


Cardiac Diseases

Cardiovascular Benefits: 

Over 20 Antioxidants: protect blood lipids (LDL) from oxidation by free radicals Cardiovascular Benefits



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