Page last updated: 2024-12-07

dityrosine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Dityrosine is a dimer of tyrosine, formed by oxidative coupling of two tyrosine residues. It is a naturally occurring compound found in various organisms, including humans, where it is formed in response to oxidative stress. Dityrosine is synthesized through the action of enzymes such as tyrosinase, laccases, and peroxidases, which catalyze the oxidation of tyrosine to tyrosyl radical. These radicals then combine to form dityrosine. Dityrosine plays a role in various biological processes, including protein cross-linking, pigmentation, and defense against oxidative stress. In proteins, dityrosine cross-links contribute to the structural integrity and stability of collagen, elastin, and other proteins. Dityrosine is also a biomarker of oxidative stress, and its presence in biological samples can indicate the level of oxidative damage. Its formation is also associated with several diseases, including Alzheimer's disease, Parkinson's disease, and cancer. Due to its relevance in various biological processes and its potential as a biomarker, dityrosine has been extensively studied in research. Researchers are investigating the mechanisms of dityrosine formation, its biological functions, and its potential as a therapeutic target for various diseases.'

dityrosine: o,o'-biphenol analog of tyrosine; isolated from insoluble protein of human cataractous lenses; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

dityrosine : A biphenyl compound comprising two tyrosine residues linked at carbon-3 of their benzene rings. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID107904
CHEBI ID50607
SCHEMBL ID338068
MeSH IDM0050810

Synonyms (19)

Synonym
bityrosine
dityrosine
alpha,alpha'-diamino-6,6'-dihydroxy-(1,1'-biphenyl)-3,3'-dipropanoic acid
980-21-2
o,o-dityrosine
3,3'-(6,6'-dihydroxybiphenyl-3,3'-diyl)bis(2-aminopropanoic acid)
CHEBI:50607
2-amino-3-[3-[5-(2-amino-3-hydroxy-3-oxopropyl)-2-hydroxyphenyl]-4-hydroxyphenyl]propanoic acid
(1,1'-biphenyl)-3,3'-dipropanoic acid, alpha,alpha'-diamino-6,6'-dihydroxy-
SCHEMBL338068
3,3'-(6,6'-dihydroxy-[1,1'-biphenyl]-3,3'-diyl)bis(2-aminopropanoic acid)
2-amino-3-[5'-(2-amino-2-carboxy-ethyl)-6,2'-dihydroxy-biphenyl-3-yl]-propionic acid
Q15889293
2-amino-3-[3-[5-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-4-hydroxyphenyl]propanoic acid
bityrosine pound>>o,o-dityrosine pound>>3,3'-dityrosine
BCP31111
SB40342
3,3'-(6,6'-dihydroxy-[1,1'-biphenyl]-3,3'-diyl)bis(2-aminopropanoicacid)
DTXSID101318376

Research Excerpts

Overview

Dityrosine (DT) is a protein oxidation marker present in many high-protein foods, such as dairy and meat products. Dityrosin is a fluorescent molecule formed as a result of normal posttranslational processing.

ExcerptReferenceRelevance
"Dityrosine (DT) is a protein oxidation marker present in many high-protein foods, such as dairy and meat products. "( Dietary Dityrosine Induces Oxidative Stress and Mitochondrial-Lipid Imbalance in Mouse Liver via MiR-144-3p-Mediated Downregulation of Nrf2.
Chen, A; Lu, N; Lyu, Y; Tang, X; Wang, J; Yu, R; Zeng, F; Zhou, Z, 2023
)
2.79
"Dityrosine (Dityr) is a typical oxidized tyrosine product."( Dityrosine administration induces dysfunction of insulin secretion accompanied by diminished thyroid hormones T3 function in pancreas of mice.
Cheng, XR; Ding, YY; Le, G; Li, ZQ; Ran, YM; Shi, Y; Wu, SJ, 2017
)
2.62
"Dityrosine is a marker of tyrosine oxidation. "( [Studies on the oxidation of tyrosine induced by hydroxyl radical with fluorescence spectroscopic method].
Jia, XL; Sun, YH; Wang, WL; Wu, LS, 2011
)
1.81
"The dityrosine bond (DT) is an oxidative covalent cross-link between two tyrosines. "( Molecular pathology of dityrosine cross-links in proteins: structural and functional analysis of four proteins.
Balasubramanian, D; Kanwar, R,
)
1
"Dityrosine is a fluorescent molecule formed as a result of normal posttranslational processing. "( Current analytical methods for the detection of dityrosine, a biomarker of oxidative stress, in biological samples.
DiMarco, T; Giulivi, C,
)
1.83
"Dityrosine is a substance frequently found in structural proteins. "( A fluorescent compound in bovine dental enamel matrix compared with synthetic dityrosine.
Booij, M; ten Bosch, JJ, 1982
)
1.94
"Dityrosine is a sporulation-specific component of the yeast ascospore wall that is essential for the resistance of the spores to adverse environmental conditions. "( The sporulation-specific enzymes encoded by the DIT1 and DIT2 genes catalyze a two-step reaction leading to a soluble LL-dityrosine-containing precursor of the yeast spore wall.
Breitenbach, M; Briza, P; Eckerstorfer, M, 1994
)
1.94

Effects

Dityrosine cross-linking has been shown in Aβ plaques in AD and α-synuclein aggregates in Lewy bodies in ex vivo tissue sections. This modification may increase the insolubility of these aggregates and their resistance to degradation.

ExcerptReferenceRelevance
"Dityrosine cross-linking has been shown in Aβ plaques in AD and α-synuclein aggregates in Lewy bodies in ex vivo tissue sections, and this modification may increase the insolubility of these aggregates and their resistance to degradation."( Dityrosine Cross-links are Present in Alzheimer's Disease-derived Tau Oligomers and Paired Helical Filaments (PHF) which Promotes the Stability of the PHF-core Tau (297-391) In Vitro.
Al-Hilaly, YK; Biasetti, L; Burra, G; Harrington, CR; Khanom, T; Maina, MB; Marshall, K; Mengham, K; Oakley, S; Serpell, LC; Wischik, CM, 2022
)
2.89
"Dityrosine has also been found in oxidative/nitrative stress under a variety of conditions and biological systems."( Current analytical methods for the detection of dityrosine, a biomarker of oxidative stress, in biological samples.
DiMarco, T; Giulivi, C,
)
1.11
"Dityrosine has been detected in the cuticle of nematodes and of insects; formation of dityrosine bridges may be one of the cross-linking mechanisms contributing to the insolubility of cuticlins."( The role of dityrosine formation in the crosslinking of CUT-2, the product of a second cuticlin gene of Caenorhabditis elegans.
Bazzicalupo, P; Lassandro, F; Sebastiano, M; Zei, F, 1994
)
1.39
"Dityrosine crosslinking has been suspected to occur in the crystallins of the eye lens during cataract."( Structure and stability of the dityrosine-linked dimer of gammaB-crystallin.
Balasubramanian, D; Kanwar, R, 1999
)
1.31

Pharmacokinetics

ExcerptReferenceRelevance
"To determine the pharmacokinetic properties of advanced oxidation protein products (AOPP), we prepared oxidized human serum albumin (oxi-HSA) using chloramine-T (a hypochlorite analogue) in vitro."( The structural and pharmacokinetic properties of oxidized human serum albumin, advanced oxidation protein products (AOPP).
Anraku, M; Hiraike, M; Iwao, Y; Kai, T; Kawai, K; Nakajou, K; Otagiri, M; Suenaga, A, 2006
)
0.33

Bioavailability

ExcerptReferenceRelevance
"We conclude that cholesterol-enriched diet-induced hyperlipidemia leads to an increase in cardiac ONOO(-) formation and a decrease in the bioavailability of NO which contributes to the deterioration of cardiac performance and may lead to further cardiac pathologies."( Hyperlipidemia induced by a cholesterol-rich diet leads to enhanced peroxynitrite formation in rat hearts.
Csonka, C; Ferdinandy, P; Giricz, Z; Onody, A, 2003
)
0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
biomarkerA substance used as an indicator of a biological state.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
biphenylsBenzenoid aromatic compounds containing two phenyl or substituted-phenyl groups which are joined together by a single bond.
tyrosine derivativeAn amino acid derivative resulting from reaction of tyrosine at the amino group or the carboxy group, any substitution of phenyl hydrogens, or from the replacement of any hydrogen of tyrosine by a heteroatom. The definition normally excludes peptides containing tyrosine residues.
non-proteinogenic alpha-amino acidAny alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (367)

TimeframeStudies, This Drug (%)All Drugs %
pre-199024 (6.54)18.7374
1990's83 (22.62)18.2507
2000's133 (36.24)29.6817
2010's100 (27.25)24.3611
2020's27 (7.36)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.70

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index30.70 (24.57)
Research Supply Index5.95 (2.92)
Research Growth Index4.95 (4.65)
Search Engine Demand Index40.78 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.70)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials6 (1.60%)5.53%
Reviews10 (2.66%)6.00%
Case Studies0 (0.00%)4.05%
Observational2 (0.53%)0.25%
Other358 (95.21%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]