3-Indolepropionic acid explained

Verifiedrevid:685380927
Drug Name:3-indolepropionic acid
Iupac Name:3-(1H-Indol-3-yl)propanoic acid
Tradename:Oxigon[1]
Legal Us:Unscheduled
Legal Un:unscheduled
Cas Number:830-96-6
Atc Prefix:none
Pubchem:3744
Iuphar Ligand:4709
Chemspiderid:3613
Unii:JF49U1Q7KN
Chebi:43580
Synonyms:Conjugate acid:


Conjugate base:
C:11
H:11
N:1
O:2
Smiles:C1=CC=C2C(=C1)C(=CN2)CCC(=O)O
Stdinchi:1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)
Stdinchikey:GOLXRNDWAUTYKT-UHFFFAOYSA-N
Melting Point:134
Melting High:135

3-Indolepropionic acid (IPA), or indole-3-propionic acid, has been studied for its therapeutic value in the treatment of Alzheimer's disease. As of 2022[2] IPA shows potential in the treatment of this disease, though the therapeutic effect of IPA depends on dose and time of therapy initiation.

Though promising in some historical clinical trials, IPA is not clinically listed as a useful therapeutic in managing Alzheimer's as of 2023.[3]

This compound endogenously produced by human microbiota and has only been detected in vivo when the species Clostridium sporogenes is present in the gastrointestinal tract.[4], C. sporogenes, which uses tryptophan to synthesize IPA, is the only species of bacteria known to synthesize IPA in vivo at levels which are subsequently detectable in the blood plasma of the host.

IPA is an even more potent scavenger of hydroxyl radicals than melatonin, the most potent scavenger of hydroxyl radicals that is synthesized by human enzymes. Similar to melatonin but unlike other antioxidants, it scavenges radicals without subsequently generating reactive and pro-oxidant intermediate compounds.[5] In 2017, elevated concentrations of IPA in human blood plasma were found to be correlated with a lower risk of type 2 diabetes and higher consumption of fiber-rich foods.[6] [7]

Biosynthesis in humans and cellular effects

Metabolism

IPA can be converted in the liver or kidneys to 3-indoleacrylic acid, which is subsequently conjugated with glycine, forming indolylacryloyl glycine.[8]

History

The neuroprotective, antioxidant, and anti-amyloid properties of IPA were first reported in 1999.[9] [10] [11]

See also

Notes and References

  1. Bendheim PE, Poeggeler B, Neria E, Ziv V, Pappolla MA, Chain DG . Development of indole-3-propionic acid (OXIGON) for Alzheimer's disease . Journal of Molecular Neuroscience . 19 . 1–2 . 213–217 . October 2002 . 12212784 . 10.1007/s12031-002-0036-0 . The accumulation of amyloid-beta and concomitant oxidative stress are major pathogenic events in Alzheimer's disease. Indole-3-propionic acid (IPA, OXIGON) is a potent anti-oxidant devoid of pro-oxidant activity. IPA has been demonstrated to be an inhibitor of beta-amyloid fibril formation and to be a potent neuroprotectant against a variety of oxidotoxins. This review will summarize the known properties of IPA and outline the rationale behind its selection as a potential disease-modifying therapy for Alzheimer's disease. . 31107810 .
  2. Jiang H, Chen C, Gao J . Extensive Summary of the Important Roles of Indole Propionic Acid, a Gut Microbial Metabolite in Host Health and Disease . Nutrients . 15 . 1 . 151 . December 2022 . 36615808 . 9824871 . 10.3390/nu15010151 . free .
  3. Web site: How Alzheimer's drugs help manage symptoms . 2023-11-03 . Mayo Clinic . en.
  4. Attwood G, Li D, Pacheco D, Tavendale M . Production of indolic compounds by rumen bacteria isolated from grazing ruminants . Journal of Applied Microbiology . 100 . 6 . 1261–1271 . June 2006 . 16696673 . 10.1111/j.1365-2672.2006.02896.x . 35673610 . free .
  5. Reiter RJ, Guerrero JM, Garcia JJ, Acuña-Castroviejo D . Reactive oxygen intermediates, molecular damage, and aging. Relation to melatonin . Annals of the New York Academy of Sciences . 854 . 1 . 410–424 . November 1998 . 9928448 . 10.1111/j.1749-6632.1998.tb09920.x . 29333394 . 1998NYASA.854..410R .
  6. de Mello VD, Paananen J, Lindström J, Lankinen MA, Shi L, Kuusisto J, Pihlajamäki J, Auriola S, Lehtonen M, Rolandsson O, Bergdahl IA, Nordin E, Ilanne-Parikka P, Keinänen-Kiukaanniemi S, Landberg R, Eriksson JG, Tuomilehto J, Hanhineva K, Uusitupa M . 6 . Indolepropionic acid and novel lipid metabolites are associated with a lower risk of type 2 diabetes in the Finnish Diabetes Prevention Study . Scientific Reports . 7 . 46337 . April 2017 . 28397877 . 5387722 . 10.1038/srep46337 . 2017NatSR...746337D .
  7. Tuomainen M, Lindström J, Lehtonen M, Auriola S, Pihlajamäki J, Peltonen M, Tuomilehto J, Uusitupa M, de Mello VD, Hanhineva K . 6 . Associations of serum indolepropionic acid, a gut microbiota metabolite, with type 2 diabetes and low-grade inflammation in high-risk individuals . Nutrition & Diabetes . 8 . 1 . 35 . May 2018 . 29795366 . 5968030 . 10.1038/s41387-018-0046-9 .
  8. Keszthelyi D, Troost FJ, Masclee AA . Understanding the role of tryptophan and serotonin metabolism in gastrointestinal function . Neurogastroenterology and Motility . 21 . 12 . 1239–1249 . December 2009 . 19650771 . 10.1111/j.1365-2982.2009.01370.x . Indolylpropionic acid can be further converted in the liver or kidney into indolyl acrylic acid (IAcrA) and conjugated with glycine to produce indolylacryloyl glycine (IAcrGly). ... Also, indolyl propionic acid has been shown to be a powerful antioxidant, and is currently being investigated as a possible treatment for Alzheimer's disease.40 . 23568813 .
  9. Poeggeler B, Sambamurti K, Siedlak SL, Perry G, Smith MA, Pappolla MA . A novel endogenous indole protects rodent mitochondria and extends rotifer lifespan . PLOS ONE . 5 . 4 . e10206 . April 2010 . 20421998 . 2858081 . 10.1371/journal.pone.0010206 . free . 2010PLoSO...510206P .
  10. Karbownik M, Reiter RJ, Garcia JJ, Cabrera J, Burkhardt S, Osuna C, Lewiński A . Indole-3-propionic acid, a melatonin-related molecule, protects hepatic microsomal membranes from iron-induced oxidative damage: relevance to cancer reduction . Journal of Cellular Biochemistry . 81 . 3 . 507–513 . 2001 . 11255233 . 10.1002/1097-4644(20010601)81:3<507::AID-JCB1064>3.0.CO;2-M . 27462000 .
  11. Reiter RJ, Tan DX, Osuna C, Gitto E . Actions of melatonin in the reduction of oxidative stress. A review . Journal of Biomedical Science . 7 . 6 . 444–458 . 2000 . 11060493 . 10.1007/bf02253360 .

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