Unveiling Photodegradation and Photosensitization Mechanisms of Unconjugated Pterins.
DFT calculations
ab initio calculations
photodegradation
pterin
vitiligo
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
22 May 2023
22 May 2023
Historique:
received:
16
02
2023
medline:
24
5
2023
pubmed:
18
3
2023
entrez:
17
3
2023
Statut:
ppublish
Résumé
Unconjugated pterins are ubiquitous molecules that participate in countless enzymatic processes and are potentially involved in the photosensitization of singlet oxygen, amino acids, and nucleotides. Following electronic excitation with UV-A light, some of these pterins degrade, producing hydrogen peroxide as the main side product. This process, which is known to take place in vivo, contributes to oxidative stress and melanocyte destruction in vitiligo. In this work, we present for the first time mechanistic insight into the formation of transient triplet species that simultaneously trigger Type I and Type II photosensitizing processes and the initiation of degradation processes. Our calculations reveal that photodegradation of 6-biopterin, which accumulates in the skin of vitiligo patients, leads to 6-formylpterin through a retro-aldol reaction, and subsequently to 6-carboxypterin through a water-mediated aldehyde oxidation. Additionally, we show that the changes in the photosensitizing potential of these systems with pH come from the modulation of their excited-state redox potentials.
Identifiants
pubmed: 36929221
doi: 10.1002/chem.202300519
doi:
Substances chimiques
Photosensitizing Agents
0
Pterins
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300519Subventions
Organisme : Ministerio de Ciencia, Innovación y Universidades
ID : PID2021-125207NB-C31
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
N. Feirer, C. Fuqua, Pteridines 2017, 28, 23-36.
M. Lucock, Mol. Genet. Metab. 2000, 71, 121-138.
H. J. Powers, Am. J. Clin. Nutr. 2003, 77, 1352-1360.
K. V. Rajagopalan, J. L. Johnson, J. Biol. Chem. 1992, 267, 10199-10202.
C. Murr, B. Widner, B. Wirleitner, Curr. Drug Metab. 2002, 3, 175-187.
E. Werner, N. Blau, B. Thöny, Biochem. J. 2011, 438, 397-414.
B. Wijnen, H. L. Leertouwer, D. G. Stavenga, J. Insect Physiol. 2007, 53, 1206-1217.
P. Cipriani, P. Ruscitti, F. Carubbi, V. Liakouli, Expert Rev. Clin. Immunol. 2014, 10, 1519-1530.
C. Chahidi, M. Aubailly, A. Momzikoff, M. Bazin, R. Santus, Photochem. Photobiol. 1981, 33, 641-649.
C. Lorente, A. H. Thomas, Acc. Chem. Res. 2006, 39, 395-402.
A. H. Thomas, C. Lorente, A. L. Capparelli, M. K. Pokhrel, A. M. Braun, E. Oliveros, Photochem. Photobiol. Sci. 2002, 2, 421-426.
A. H. Thomas, C. Lorente, A. L. Capparelli, C. G. Martínez, A. M. Braun, E. Oliveros, Photochem. Photobiol. Sci. 2003, 2, 245-250.
C. Lorente, M. P. Serrano, M. Vignoni, M. L. Dántola, A. H. Thomas, J. Photochem. Photobiol. 2021, 7, 100045.
J. J. Farías, P. Lizondo-Aranda, A. H. Thomas, V. Lhiaubet-Vallet, M. L. Dántola, Photochem. Photobiol. Sci. 2022, 21, 1647-1657.
C. Castaño, M. L. Dántola, E. Oliveros, A. H. Thomas, C. Lorente, Photochem. Photobiol. 2013, 89, 1448-1455.
A. H. Thomas, M. P. Serrano, V. Rahal, P. Vicendo, C. Claparols, E. Oliveros, C. Lorente, Free Radical Biol. Med. 2013, 63, 467-475.
C. Castaño, E. Oliveros, A. H. Thomas, C. Lorente, J. Photochem. Photobiol. B 2015, 153, 483-489.
M. L. Dántola, L. O. Reid, C. Castaño, C. Lorente, E. Oliveros, A. H. Thomas, Pteridines 2017, 28, 105-114.
C. Lorente, A. H. Thomas, L. S. Villata, D. Hozbor, A. Lagares, A. Capparelli, Pteridines 2000, 11, 100-105.
G. Petroselli, R. Erra-Balsells, F. M. Cabrerizo, C. Lorente, A. L. Capparelli, A. M. Braun, E. Oliveros, A. H. Thomas, Org. Biomol. Chem. 2007, 5, 2792-2799.
G. Petroselli, M. L. Dántola, F. M. Cabrerizo, A. L. Capparelli, C. Lorente, E. Oliveros, A. H. Thomas, J. Am. Chem. Soc. 2008, 130, 3001-3011.
M. P. Serrano, C. Lorente, F. E. Morán Vieyra, C. D. Borsarelli, A. H. Thomas, Phys. Chem. Chem. Phys. 2012, 14, 11657-11665.
A. H. Thomas, G. Suárez, F. M. Cabrerizo, R. Martino, A. L. Capparelli, J. Photochem. Photobiol. A 2000, 135, 147-154.
M. Vignoni, F. M. Cabrerizo, C. Lorente, A. H. Thomas, Photochem. Photobiol. 2009, 85, 365-373.
A. Ipiña, C. Castaño, M. L. Dántola, A. H. Thomas, Sol. Energy 2014, 109, 45-53.
R. Mengel, W. Pfleiderer, W.-R. Knappe, Tetrahedron Lett. 1977, 18, 2817-2820.
M. Vignoni, M. L. Salum, R. Erra-Balsells, A. H. Thomas, F. M. Cabrerizo, Chem. Phys. Lett. 2010, 484, 330-332.
G. Suárez, F. M. Cabrerizo, C. Lorente, A. H. Thomas, A. L. Capparelli, J. Photochem. Photobiol. A 2000, 132, 53-57.
R. M. DiScipio, R. Y. Santiago, D. Taylor, C. E. Crespo-Hernández, Phys. Chem. Chem. Phys. 2017, 19, 12720-12729.
X. Chen, X. Xu, Z. Cao, J. Phys. Chem. A 2007, 111, 9255-9262.
K. U. Schallreuter in Autoimmune Diseases of the Skin: Pathogenesis, Diagnosis, Management (Ed.: M. Hertl), Springer, 2011, Chapter 19.
K. U. Schallreuter, G. Büttner, M. R. Pittelkow, J. M. Wood, N. N. Swanson, C. Körner, Biochem. Biophys. Res. Commun. 1994, 204, 43-48.
H. Rokos, W. D. Beazley, K. U. Schallreuter, Biochem. Biophys. Res. Commun. 2002, 292, 805-811.
Minimal discrepancies with respect to Table arise from the different number of states and size of the active spaces.
S. Estébanez, C. Lorente, T. S. Kaufman, E. L. Larghi, A. H. Thomas, M. P. Serrano, Photochem. Photobiol. 2018, 94, 881-889.
R. P. Wayne in Advances in Photochemistry, Vol. 7 (Eds.: J. N. Pitts Jr., G. S. Hammond, W. A. Noyes Jr.), Wiley, 1969, Chapter 4.
T. B. Demissie, K. Ruud, J. H. Hansen, Organometallics 2015, 34, 4218-4228.
N. J. Turro, V. Ramamurthy, J. C. Scaiano, Modern Molecular Photochemistry of Organic Molecules, University Science Books, 2010.
C.-H. Wu, L. J. Karas, H. Ottosson, J. I. Wu, Proc. Natl. Acad. Sci. USA 2019, 116, 20303-20308.
L. J. Karas, C.-H. Wu, H. Ottosson, J. I. Wu, Chem. Sci. 2020, 11, 10071-10077.
A. Stanger, J. Org. Chem. 2006, 71, 883-893.
E. M. Arpa, B. Durbeej, Phys. Chem. Chem. Phys. 2022, 24, 11496-11500.
M. Hajimohammadi, N. Safari, H. Mofakham, A. Shaabani, Tetrahedron Lett. 2010, 51, 4061-4065.
Z. Yuan, Y. Ni, A. R. P. van Heiningen, Can. J. Chem. Eng. 1997, 75, 42-47.
C. Lehtinen, V. Nevalainen, G. Brunow, Tetrahedron 2001, 57, 4741-4745.