Reactions of 4-hydroxy-2(E)-nonenal and related aldehydes with proteins studied by carbon-13 nuclear magnetic resonance spectroscopy

Chemical Research in Toxicology
V AmarnathD G Graham

Abstract

In order to understand the modifications of proteins produced by aldehydes of lipid peroxidation, [1-13C]-2(E)-hexenal, [1-13C]-4-oxopentanal, and a mixture of [1-13C]- and [2-13C]-4-hydroxynon-2(E)-enal were synthesized and the reaction of each of the labeled aldehydes with bovine serum albumin was analyzed by 13C NMR spectroscopy. Protein nucleophiles add to the 3-position of hexenal, and the resulting propanal moieties appear to undergo aldol condensation, form imine cross-links with lysyl residues, or lead to pyridinium rings. During the reaction of 4-oxopentanal with the lysyl residues of bovine serum albumin, only 1-alkyl-2-methylpyrrole and a possible intermediate leading to the pyrrole were observed. Hydroxypyrrolidine cross-links such as 25 could not be detected, leaving the pyrrole as the mediator of protein cross-linking. The Michael adducts are the major products in the reaction between 4-hydroxynon-2-enal and proteins. They exist almost exclusively in the cyclic hemiacetal form and do not appear to cross-link through imine formation with lysyl residues. A minor pathway involves the reaction of 4-hydroxynon-2-enal with the lysyl amino groups of protein resulting in 2-pentylpyrrole adducts that may mediate protein cr...Continue Reading

References

Jan 1, 1991·Free Radical Biology & Medicine·H EsterbauerH Zollner
Jan 1, 1995·Chemical Research in Toxicology·E DiFrancoR G Salomon
Mar 1, 1995·Chemical Research in Toxicology·V AmarnathD G Graham
Jan 1, 1994·Chemical Research in Toxicology·V AmarnathD G Graham
Jan 1, 1993·Chemical Research in Toxicology·L M SayreR G Salomon

❮ Previous
Next ❯

Citations

Apr 15, 2004·Free Radical Biology & Medicine·Sean S DaviesL Jackson Roberts
Jun 19, 2013·Journal of Proteomics·Rosário M DominguesCorinne M Spickett
Jul 5, 2005·Journal of Neurochemistry·Irene Zagol-IkapitteJohn A Oates
May 26, 2005·Brain Pathology·Olivier BoutaudJohn A Oates
Mar 5, 2003·Journal of Neurochemistry·Tonya C MurphyMatthew J Picklo
Jan 18, 2006·Journal of Neurochemistry·Olivier BoutaudJohn A Oates
Sep 6, 2005·Free Radical Biology & Medicine·Ales HonzatkoMatthew J Picklo
Feb 27, 2003·Chemico-biological Interactions·Tonya MurphyMatthew J Picklo
May 7, 2015·Journal of Agricultural and Food Chemistry·Martin GlobischThomas Henle
May 9, 2001·Biochimica Et Biophysica Acta·M J Picklo, T J Montine
Mar 31, 1999·Journal of Neurochemistry·M J PickloT J Montine
Jul 11, 2001·Journal of Neuropathology and Experimental Neurology·M J PickloT J Montine
Dec 17, 2020·Comprehensive Reviews in Food Science and Food Safety·Xuxia ZhouYongning Wu
Jul 21, 2009·Chemical Research in Toxicology·Richard M LoPachinDavid S Barber
Dec 10, 1999·Journal of Agricultural and Food Chemistry·S NoëlS Collin
Jul 6, 2021·EMBO Molecular Medicine·Caitlin W BrownArthur M Mercurio
Jul 31, 2007·Chemical Research in Toxicology·Carlos A O SigoloMarisa H G Medeiros
Feb 28, 2007·Journal of Agricultural and Food Chemistry·Kyung MyungDouglas D Archbold

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.