2-Alkenal modification of hemoglobin: Identification of a novel hemoglobin-specific alkanoic acid-histidine adduct

Redox Biology
Jun YoshitakeKoji Uchida

Abstract

α,β-Unsaturated aldehydes generated during lipid peroxidation, such as 2-alkenals, give rise to protein degeneration in a variety of pathological states. 2-Alkenals are highly reactive toward nucleophilic amino acid residues, such as histidine and lysine, to form Schiff base adducts or Michael addition adducts. In this study, upon the reaction of hemoglobin with 2-octenal, we unexpectedly detected a product corresponding to the reduced form of the 2-octenal-histidine Michael adduct plus 14 mass unit. Based on the LC-ESI-MS/MS analysis of synthetic adduct candidates, the adduct was identified to be Nτ-(1-carboxyheptan-2-yl)-histidine (CHH), a novel alkanoic acid-type histidine adduct. The alkanoic acid-histidine adducts were detected in the 2-alkenal-treated hemoglobin and myoglobin, but not in the 2-alkenal-treated cytochrome c and transferrin. The addition of hemin to the reaction mixture, containing a non-heme protein and 2-alkenals, resulted in the formation of the alkanoic acid-histidine adducts, suggesting that a heme iron may play a role in the oxidation of covalently modified proteins. Moreover, using the stable isotope dilution method, we showed evidence for the endogenous formation of CHH in red blood cells exposed to ...Continue Reading

References

Jun 1, 1976·The Journal of Clinical Investigation·H F BunnP M Gallop
Oct 1, 1992·Respiration Physiology·C PoyartJ Kister
Jan 1, 1991·Free Radical Biology & Medicine·H EsterbauerH Zollner
Apr 1, 1990·Trends in Biochemical Sciences·J M Gutteridge, B Halliwell
Jan 1, 1989·Free Radical Biology & Medicine·G Witz
Aug 22, 1969·Biochemical and Biophysical Research Communications·S RahbarH M Ranney
Feb 1, 1981·The Journal of Clinical Investigation·V J StevensC M Peterson
May 1, 1993·Toxicology and Applied Pharmacology·E BergmarkL G Costa
Jun 6, 1998·Proceedings of the National Academy of Sciences of the United States of America·K UchidaT Osawa
Aug 18, 2000·Free Radical Biology & Medicine·K Uchida
Apr 3, 2001·The Journal of Biological Chemistry·K IchihashiK Uchida
Oct 12, 2002·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·M TörnqvistP Rydberg
Sep 25, 2003·The Journal of Biological Chemistry·Atsunori FuruhataKoji Uchida
Dec 17, 2008·Revista brasileira de anestesiologia·Tatiana Souza do NascimentoJosé Costa
Mar 5, 2010·The New England Journal of Medicine·Elizabeth SelvinFrederick L Brancati
Mar 11, 2010·The Journal of Biological Chemistry·Kousuke IshinoKoji Uchida
Mar 1, 2009·Journal of Diabetes·Emily Jane GallagherZachary Bloomgarden
Jul 10, 2012·Nature Chemical Biology·Motohiro NishidaTakaaki Akaike
Aug 3, 2013·Science·Raymond E Moellering, Benjamin F Cravatt
Oct 29, 2014·Chemical Research in Toxicology·Henrik CarlssonMargareta Törnqvist
Mar 28, 2017·The Journal of Biological Chemistry·Takahiro ShibataKoji Uchida

❮ Previous
Next ❯

Citations

Mar 12, 2019·Free Radical Biology & Medicine·Takahiro Shibata, Koji Uchida
Mar 18, 2021·Antioxidants & Redox Signaling·Marilene DemasiLeonor Thomson
Jun 11, 2021·Chemical Research in Toxicology·Andrew T RajczewskiNatalia Y Tretyakova

❮ 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.