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Photochemistry of tyrosine dimer: when an oxidative lesion of proteins is able to photoinduce further damage

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Abstract

The tyrosine dimer (Tyr2), a covalent bond between two tyrosines (Tyr), is one of the most important modifications of the oxidative damage of proteins. This compound is increasingly used as a marker of aging, stress and pathogenesis. At physiological pH, Tyr2 is able to absorb radiation at wavelengths significantly present in the solar radiation and artificial sources of light. As a result, when Tyr2 is formed in vivo, a new chromophore appears in the proteins. Despite the biomedical importance of Tyr2, the information of its photochemical properties is limited due to the drawbacks of its synthesis. Therefore, in this work we demonstrate that at physiological pH, Tyr2 undergoes oxidation upon UV excitation yielding different products which conserve the dimeric structure. During its photodegradation different reactive oxygen species, like hydrogen peroxide, superoxide anion and singlet oxygen, are produced. Otherwise, we demonstrated that Tyr2 is able to sensitize the photodegradation of tyrosine. The results presented in this work confirm that Tyr2 can act as a potential photosensitizer, contributing to the harmful effects of UV-A radiation on biological systems.

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Abbreviations

A:

Absorbance

\(q_{{\rm{n,p}}}^{{\rm{a}},v}\) :

Absorbed photon flux density

Cyt:

Cytochrome c

D2O:

Deuterium water

DOPA:

3,4-Dihydroxy-L-phenylalanine

ESI:

Electrospray ionization source

I:

Emission intensities

ED:

Experimental-difference spectra

FL:

Fluorescence detector

HCOOH:

Formic acid

HPLC:

High-performance liquid chromatography

H2O2:

Hydrogen peroxide

\(q_{{\rm{n,p}}}^{{\rm{o}},v}\) :

Incident photon flux densitity

\(q_{{\rm{n,p}}}^{\rm{o}}\) :

Incident photons per time interval

NIR:

Near-infrared

Tyr2:

o,o′-Dityrosine or tyrosine dimer

PDA:

Photodiode array detector

Ptr:

Pterin

Φ−Tyr2:

Quantum yield of tyrosine dimer consumption

ROS:

Reactive oxygen species

tR:

Retention times

1O2:

Singlet oxygen

τΔ:

Singlet oxygen lifetime

SOSG:

Singlet oxygen sensor green

SOSG-EP:

Singlet oxygen sensor green endoperoxide

ΦΔ:

Singlet oxygen quantum yields

O2•−:

Superoxide anion radical

SOD:

Superoxide dismutase

Tyr(-H)•:

Tyrosyl radical

V:

Volume

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Authors and Affiliations

  1. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, CCT La Plata-CONICET, Casilla de Correo 16, Sucursal 4, La Plata, 1900, Argentina

    Lara O. Reid, Mariana Vignoni, Andrés H. Thomas & M. Laura Dántola

  2. Service Commun de Spectrométrie de Masse (FR2599), Université de Toulouse III (Paul Sabatier), 118, route de Narbonne, Toulouse cédex 9, F-31062, France

    Nathalie Martins-Froment

Authors
  1. Lara O. Reid
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  2. Mariana Vignoni
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  3. Nathalie Martins-Froment
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  4. Andrés H. Thomas
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  5. M. Laura Dántola
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Correspondence to M. Laura Dántola.

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Electronic supplementary information (ESI) available. See DOI: 10.1039/c9pp00182d

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Reid, L.O., Vignoni, M., Martins-Froment, N. et al. Photochemistry of tyrosine dimer: when an oxidative lesion of proteins is able to photoinduce further damage. Photochem Photobiol Sci 18, 1732–1741 (2019). https://doi.org/10.1039/c9pp00182d

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