Biomaterial Database

NMR study of lipoic acid binding to bovine serum albumin. 1994

V Schepkin, and T Kawabata, and L Packer

Department of Molecular & Cell Biology, University of California, Berkeley 94720-3200.

Evidence for the binding of lipoic (LA) and dihydrolipoic (DHLA) acid to bovine serum albumin (BSA) was sought as a feature for understanding the mechanism of their antioxidant activity and prevention of glycation. Experiments were performed by 1H high resolution NMR. The average binding ratio of LA, DHLA and tetranor LA to BSA were 10 +/- 2, 7.9 +/- 2 and 1.8 +/- 0.4 mol/mol BSA respectively. In this row the number of bound molecules lessens with the decrease of their hydrophobic interactions that correlates with their protective activity. Octanoic acid, the closest analog of lipoate, had a binding ratio of 4.7 +/- 0.5 mol. Lipoic acid was able to replace bound octanoic acid which points out that lipoate occupies the same binding site on BSA. Lipoate had no binding to low density lipoproteins extracted from human plasma which corresponds to its low protection of LDL against glycosylation and oxidative modification. This study indicates that lipoic acid molecules experience strong hydrophobic attraction and binding to BSA which is important part of lipoate protective mechanism.

UI	MeSH Term	Description	Entries
D008063	Thioctic Acid	An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.	Lipoic Acid,Alpha-Lipogamma,Alpha-Lipon Stada,Alpha-Liponsaure Sofotec,Alpha-Lippon AL,Alphaflam,Azulipont,Fenint,Juthiac,Liponsaure-ratiopharm,MTW-Alphaliponsaure,Neurium,Pleomix-Alpha,Pleomix-Alpha N,Thioctacid,Thioctacide T,Thiogamma Injekt,Thiogamma oral,Tromlipon,Verla-Lipon,alpha-Lipoic Acid,alpha-Liponaure Heumann,alpha-Liponsaure von ct,alpha-Vibolex,biomo-lipon,duralipon,espa-lipon,Acid, alpha-Lipoic,Alpha Lipogamma,Alpha Lipon Stada,Alpha Liponsaure Sofotec,Alpha Lippon AL,AlphaLipogamma,AlphaLipon Stada,AlphaLiponsaure Sofotec,AlphaLippon AL,Injekt, Thiogamma,Liponsaure ratiopharm,Liponsaureratiopharm,MTW Alphaliponsaure,MTWAlphaliponsaure,Pleomix Alpha,Pleomix Alpha N,PleomixAlpha,PleomixAlpha N,Verla Lipon,VerlaLipon,alpha Lipoic Acid,alpha Liponaure Heumann,alpha Liponsaure von ct,alpha Vibolex,alphaLiponaure Heumann,alphaLiponsaure von ct,alphaVibolex,biomo lipon,biomolipon,espa lipon,espalipon
D008077	Lipoproteins, LDL	A class of lipoproteins of small size (18-25 nm) and light (1.019-1.063 g/ml) particles with a core composed mainly of CHOLESTEROL ESTERS and smaller amounts of TRIGLYCERIDES. The surface monolayer consists mostly of PHOSPHOLIPIDS, a single copy of APOLIPOPROTEIN B-100, and free cholesterol molecules. The main LDL function is to transport cholesterol and cholesterol esters to extrahepatic tissues.	Low-Density Lipoprotein,Low-Density Lipoproteins,beta-Lipoprotein,beta-Lipoproteins,LDL(1),LDL(2),LDL-1,LDL-2,LDL1,LDL2,Low-Density Lipoprotein 1,Low-Density Lipoprotein 2,LDL Lipoproteins,Lipoprotein, Low-Density,Lipoproteins, Low-Density,Low Density Lipoprotein,Low Density Lipoprotein 1,Low Density Lipoprotein 2,Low Density Lipoproteins,beta Lipoprotein,beta Lipoproteins
D009682	Magnetic Resonance Spectroscopy	Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING).	In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D011485	Protein Binding	The process in which substances, either endogenous or exogenous, bind to proteins, peptides, enzymes, protein precursors, or allied compounds. Specific protein-binding measures are often used as assays in diagnostic assessments.	Plasma Protein Binding Capacity,Binding, Protein
D002210	Caprylates	Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.	Caprylate,Octanoates,Caprylic Acids,Octanoic Acids,Acids, Caprylic,Acids, Octanoic
D002417	Cattle	Domesticated bovine animals of the genus Bos, usually kept on a farm or ranch and used for the production of meat or dairy products or for heavy labor.	Beef Cow,Bos grunniens,Bos indicus,Bos indicus Cattle,Bos taurus,Cow,Cow, Domestic,Dairy Cow,Holstein Cow,Indicine Cattle,Taurine Cattle,Taurus Cattle,Yak,Zebu,Beef Cows,Bos indicus Cattles,Cattle, Bos indicus,Cattle, Indicine,Cattle, Taurine,Cattle, Taurus,Cattles, Bos indicus,Cattles, Indicine,Cattles, Taurine,Cattles, Taurus,Cow, Beef,Cow, Dairy,Cow, Holstein,Cows,Dairy Cows,Domestic Cow,Domestic Cows,Indicine Cattles,Taurine Cattles,Taurus Cattles,Yaks,Zebus
D006801	Humans	Members of the species Homo sapiens.	Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D012710	Serum Albumin, Bovine	Serum albumin from cows, commonly used in in vitro biological studies. (From Stedman, 25th ed)	Fetal Bovine Serum,Fetal Calf Serum,Albumin Bovine,Bovine Albumin,Bovine Serum Albumin,Albumin, Bovine,Albumin, Bovine Serum,Bovine Serum, Fetal,Bovine, Albumin,Calf Serum, Fetal,Serum, Fetal Bovine,Serum, Fetal Calf
D014867	Water	A clear, odorless, tasteless liquid that is essential for most animal and plant life and is an excellent solvent for many substances. The chemical formula is hydrogen oxide (H2O). (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	Hydrogen Oxide

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