Липоинска киселина

Lipoinska kiselina
Nazivi
	IUPAC naziv (R)-5-(1,2-ditiolan-3-il)pentanska kiselina
	Drugi nazivi α-Lipoinska kiselina (alfa lipoinska kiselina); Tioktinska kiselina; 6,8-Ditiooktanska kiselina
Identifikacija
CAS broj	1200-22-2 ;
3D model (Jmol)	interaktivna slika;
ChEBI	CHEBI:30314 ;
ChemSpider	5886 ;
DrugBank	DB00166 ;
ECHA InfoCard	100.012.793
KEGG	C16241 ;
MeSH	Lipoic+acid
PubChem C ID	6112;
	SMILES O=C(O)CCCC[C@H]1SSCC1; ; ; ; ; ;
Svojstva
Hemijska formula	C8H14O2S2
Molarna masa	206,32 g·mol−1
Agregatno stanje	Žuti igličasti kristali
Rastvorljivost u vodi	Rastvorna kao natrijumova so
Rastvorljivost u etanol	Rastvorna
Farmakologija
	Farmakokinetika:
Bioraspoloživost	30% (oralno)
Srodna jedinjenja
Srodna jedinjenja	Lipoamid; Asparagusna kiselina
	Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa).
	verifikuj (šta je ?)
	Reference infokutije

Lipoinska kiselina (LA, α-lipoinska kiselina^[5] i alfa lipoinska kiselina, ALA^[6]) je organosumporno jedinjenje izvedeno iz oktanske kiseline. Lipoinska kiselina sadrži dva atoma sumpora (između C6 i C8) povezana disulfidnom vezom i stoga se smatra oksidovanim molekulom (mada atomi sumpora mogu da postoje u višim oksidacionim stanjima). Atom ugljenika u C6 poziciji je hiralan, te se molekul se javlja u obliku dva enantiomera (R)-(+)-lipoinska kiselina (RLA) i (S)-(-)-lipoinska kiselina (SLA), kao i u obliku racemske smeše (R/S)-lipoinske kiseline (R/S-LA). Jedino se (R)-(+)-enantiomer javlja u prirodi i on je esencijalni kofaktor za četiri mitohondrijska enzimska kompleksa.^[7] Endogeno sintetisana RLA je esencijalna za život i aerobni metabolizam.

RLA i R/S-LA su dostupne na slobodno kao nutricioni suplementi. One su u prehrambenoj i kliničkoj upotrebi od 1950-tih za razne bolesti i poremećaje. Lipoinska kiselina je žuta čvrsta materija.

Reference

^ Joanne Wixon; Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast. 17 (1): 48—55. doi:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
^ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди
^ Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.
^ Teichert J, Hermann R, Ruus P, Preiss R (2003). „Plasma kinetics, metabolism, and urinary excretion of alpha-lipoic acid following oral administration in healthy volunteers”. J Clin Pharmacol. 43 (11): 1257—67. PMID 14551180. doi:10.1177/0091270003258654.
^ Petersen Shay, K; Moreau, RF; Smith, EJ; Hagen, TM (2008). „Is alpha-lipoic acid a scavenger of reactive oxygen species in vivo? Evidence for its initiation of stress signaling pathways that promote endogenous antioxidant capacity”. IUBMB life. 60 (6): 362—7. PMID 18409172. doi:10.1002/iub.40.
^ Reljanovic M; Reichel G; Rett K; et al. (1999). „Treatment of diabetic polyneuropathy with the antioxidant thioctic acid (alpha-lipoic acid): a two year multicenter randomized double-blind placebo-controlled trial (ALADIN II). Alpha Lipoic Acid in Diabetic Neuropathy”. Free Radic. Res. 31 (3): 171—9. PMID 10499773.
^ Raddatz, G; Bisswanger, H (1997). „Receptor site and stereospecifity of dihydrolipoamide dehydrogenase for R- and S-lipoamide: a molecular modeling study”. Journal of Biotechnology. 58 (2): 89—100. PMID 9383983. doi:10.1016/S0168-1656(97)00135-1.

Literatura

Packer, Lester; Patel, Mulchand S., ур. (2008). Lipoic acid: energy production, antioxidant activity and health effects. Boca Raton: CRC Press. ISBN 1-4200-4537-7.

Spoljašnje veze

Jane Higdon, "Lipoic Acid", Micronutrient Information Center, Linus Pauling Institute, Oregon State University

Molimo Vas, obratite pažnju na važno upozorenje
u vezi sa temama iz oblasti medicine (zdravlja).

[1] Joanne Wixon; Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast. 17 (1): 48—55. doi:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[2] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди

[3] Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.

[4] Teichert J, Hermann R, Ruus P, Preiss R (2003). „Plasma kinetics, metabolism, and urinary excretion of alpha-lipoic acid following oral administration in healthy volunteers”. J Clin Pharmacol. 43 (11): 1257—67. PMID 14551180. doi:10.1177/0091270003258654.

[PetersenShay08-5] Petersen Shay, K; Moreau, RF; Smith, EJ; Hagen, TM (2008). „Is alpha-lipoic acid a scavenger of reactive oxygen species in vivo? Evidence for its initiation of stress signaling pathways that promote endogenous antioxidant capacity”. IUBMB life. 60 (6): 362—7. PMID 18409172. doi:10.1002/iub.40.

[6] Reljanovic M; Reichel G; Rett K; et al. (1999). „Treatment of diabetic polyneuropathy with the antioxidant thioctic acid (alpha-lipoic acid): a two year multicenter randomized double-blind placebo-controlled trial (ALADIN II). Alpha Lipoic Acid in Diabetic Neuropathy”. Free Radic. Res. 31 (3): 171—9. PMID 10499773.

[7] Raddatz, G; Bisswanger, H (1997). „Receptor site and stereospecifity of dihydrolipoamide dehydrogenase for R- and S-lipoamide: a molecular modeling study”. Journal of Biotechnology. 58 (2): 89—100. PMID 9383983. doi:10.1016/S0168-1656(97)00135-1.

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