Isoketals: highly reactive gamma-ketoaldehydes formed from the H2-isoprostane pathway - PubMed (original) (raw)

Review

Isoketals: highly reactive gamma-ketoaldehydes formed from the H2-isoprostane pathway

Sean S Davies et al. Chem Phys Lipids. 2004 Mar.

Abstract

Oxidation of arachidonic acid leads to the formation of highly reactive gamma-ketoaldehydes now termed isoketals. Isoketals react with proteins at a rate that far exceeds other well studied products of lipid peroxidation such as 4-hydroxynonenal and demonstrate a remarkable proclivity to crosslink these proteins. For these reasons, isoketals have the potential to significantly alter protein function and contribute to disease processes. This article reviews the chemistry of isoketal formation, of their adduction to proteins, and of their proclivity to crosslink proteins, as well as their effects on protein function, and their potential role in diseases associated with oxidative injury.

PubMed Disclaimer

Similar articles

• Covalent binding of isoketals to ethanolamine phospholipids.
  Bernoud-Hubac N, Fay LB, Armarnath V, Guichardant M, Bacot S, Davies SS, Roberts LJ 2nd, Lagarde M. Bernoud-Hubac N, et al. Free Radic Biol Med. 2004 Nov 15;37(10):1604-11. doi: 10.1016/j.freeradbiomed.2004.07.031. Free Radic Biol Med. 2004. PMID: 15477011
• Localization of isoketal adducts in vivo using a single-chain antibody.
  Davies SS, Talati M, Wang X, Mernaugh RL, Amarnath V, Fessel J, Meyrick BO, Sheller J, Roberts LJ 2nd. Davies SS, et al. Free Radic Biol Med. 2004 May 1;36(9):1163-74. doi: 10.1016/j.freeradbiomed.2004.02.014. Free Radic Biol Med. 2004. PMID: 15082070
• Pyridoxamine analogues scavenge lipid-derived gamma-ketoaldehydes and protect against H2O2-mediated cytotoxicity.
  Davies SS, Brantley EJ, Voziyan PA, Amarnath V, Zagol-Ikapitte I, Boutaud O, Hudson BG, Oates JA, Roberts LJ 2nd. Davies SS, et al. Biochemistry. 2006 Dec 26;45(51):15756-67. doi: 10.1021/bi061860g. Epub 2006 Dec 6. Biochemistry. 2006. PMID: 17176098 Free PMC article.
• Modulation of protein function by isoketals and levuglandins.
  Davies SS. Davies SS. Subcell Biochem. 2008;49:49-70. doi: 10.1007/978-1-4020-8831-5_2. Subcell Biochem. 2008. PMID: 18751907 Review.
• The biochemistry of the isoprostane, neuroprostane, and isofuran pathways of lipid peroxidation.
  Roberts LJ 2nd, Fessel JP. Roberts LJ 2nd, et al. Chem Phys Lipids. 2004 Mar;128(1-2):173-86. doi: 10.1016/j.chemphyslip.2003.09.016. Chem Phys Lipids. 2004. PMID: 15037162 Review.

Cited by

• A Paal-Knorr agent for chemoproteomic profiling of targets of isoketals in cells.
  Wang MR, He JY, He JX, Liu KK, Yang J. Wang MR, et al. Chem Sci. 2021 Oct 15;12(43):14557-14563. doi: 10.1039/d1sc02230j. eCollection 2021 Nov 10. Chem Sci. 2021. PMID: 34881007 Free PMC article.
• Scavenging 4-Oxo-2-nonenal.
  Amarnath V, Amarnath K. Amarnath V, et al. Chem Res Toxicol. 2015 Oct 19;28(10):1888-90. doi: 10.1021/acs.chemrestox.5b00301. Epub 2015 Sep 11. Chem Res Toxicol. 2015. PMID: 26355561 Free PMC article.
• Targeting Oxidative Stress in Central Nervous System Disorders.
  Patel M. Patel M. Trends Pharmacol Sci. 2016 Sep;37(9):768-778. doi: 10.1016/j.tips.2016.06.007. Epub 2016 Aug 1. Trends Pharmacol Sci. 2016. PMID: 27491897 Free PMC article. Review.
• Isoprostane generation and function.
  Milne GL, Yin H, Hardy KD, Davies SS, Roberts LJ 2nd. Milne GL, et al. Chem Rev. 2011 Oct 12;111(10):5973-96. doi: 10.1021/cr200160h. Epub 2011 Aug 18. Chem Rev. 2011. PMID: 21848345 Free PMC article. Review. No abstract available.
• Mitochondrial Isolevuglandins Contribute to Vascular Oxidative Stress and Mitochondria-Targeted Scavenger of Isolevuglandins Reduces Mitochondrial Dysfunction and Hypertension.
  Dikalova A, Mayorov V, Xiao L, Panov A, Amarnath V, Zagol-Ikapitte I, Vergeade A, Ao M, Yermalitsky V, Nazarewicz RR, Boutaud O, Lopez MG, Billings FT 4th, Davies S, Roberts LJ 2nd, Harrison DG, Dikalov S. Dikalova A, et al. Hypertension. 2020 Dec;76(6):1980-1991. doi: 10.1161/HYPERTENSIONAHA.120.15236. Epub 2020 Oct 5. Hypertension. 2020. PMID: 33012204 Free PMC article.

Publication types

MeSH terms

Substances

LinkOut - more resources

• Full Text Sources

  • Elsevier Science

• Other Literature Sources

  • The Lens - Patent Citations Database