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Original Articles

Autoxidation and photooxidation of tetrahydrobiopterin: a theoretical study

ORCID Icon, ORCID Icon, ORCID Icon & ORCID Icon
Pages 499-509 | Received 30 Aug 2020, Accepted 02 Dec 2020, Published online: 17 Sep 2021

References

  • Thöny B, Auerbach G, Blau N. Tetrahydrobiopterin biosynthesis, regeneration and functions. Biochem J. 2000;347 Pt 1:1–16.
  • Scott-Burden T. Regulation of nitric oxide production by tetrahydrobiopterin. Circulation. 1995;91:248–250.
  • Werner ER, Gorren AC, Heller R, et al. Tetrahydrobiopterin and nitric oxide: mechanistic and pharmacological aspects. Exp Biol Med (Maywood). 2003;228:1291–1302.
  • Watschinger K, Keller MA, Golderer G, et al. Identification of the gene encoding alkylglycerol monooxygenase defines a third class of tetrahydrobiopterin-dependent enzymes. Proc Natl Acad Sci USA. 2010;107:13672–13677.
  • Fitzpatrick PF. Mechanism of aromatic amino acid hydroxylation. Biochemistry. 2003;42:14083–14091.
  • Wei CC, Wang ZQ, Tejero J, et al. Catalytic reduction of a tetrahydrobiopterin radical within nitric-oxide synthase. J Biol Chem. 2008;283:11734–11742.
  • Daff S. NO synthase: structures and mechanisms. Nitric Oxide. 2010;23:1–11.
  • Buglak AA, Telegina TA, Lyudnikova TA, et al. Photooxidation of tetrahydrobiopterin under UV irradiation: possible pathways and mechanisms. Photochem Photobiol. 2014;90:1017–1026.
  • Telegina TA, Lyudnikova TA, Buglak AA, et al. Transformation of 6-tetrahydrobiopterin in aqueous solutions under UV-irradiation. J Photochem Photobiol A. 2018;354:155–162.
  • Lee HW, Oh CH, Geyer A, et al. Characterization of a novel unconjugated pteridine glycoside, cyanopterin, in Synechocystis sp. PCC 6803. Biochim Biophys Acta. 1999;1410:61–70.
  • Moon YJ, Lee EM, Park YM, et al. The role of cyanopterin in UV/blue light signal transduction of cyanobacterium Synechocystis sp. PCC 6803 phototaxis. Plant Cell Physiol. 2010;51:969–980.
  • Buglak AA, Telegina TAA. A theoretical study of 5,6,7,8-tetrahydro-6-hydroxymethylpterin: insight into intrinsic photoreceptor properties of 6-substituted tetrahydropterins. Photochem Photobiol Sci. 2019;18:516–523.
  • Nishikimi M. The generation of superoxide anion in the reaction of tetrahydropteridines with molecular oxygen. Arch Biochem Biophys. 1975;166:273–279.
  • Kirsch M, Korth HG, Stenert V, et al. The autoxidation of tetrahydrobiopterin revisited. Proof of superoxide formation from reaction of tetrahydrobiopterin with molecular oxygenJ Biol Chem. 2003;278:24481–24490.
  • Blair JA, Pearson AJ. Kinetics and mechanism of the autoxidation of the 2- amino-4-hydroxy-5,6,7,8-tetrahydropteridines. J Chem Soc Perkin Trans 2. 1974;1:80–88.
  • Davis MD, Kaufman S, Milstien S. The auto-oxidation of tetrahydrobiopterin. Eur J Biochem. 1988;173:345–351.
  • Lindsay A, Gieseg SP. Pterins as diagnostic markers of exercise-induced stress: a systematic review. J Sci Med Sport. 2020;23:53–62.
  • Wakabayashi I, Nakanishi M, Ohki M, et al. A simple and useful method for evaluation of oxidative stress in vivo by spectrofluorometric estimation of urinary pteridines. Sci Rep. 2020;10:11223.
  • Castillo JJ, Rozo CE, Bertel L, et al. Orientation of pterin-6-carboxylic acid on gold capped silicon nanopillars platforms: surface enhanced raman spectroscopy and density functional theory studies. J Braz Chem Soc. 2016;27:971–977.
  • Guibal P, Lo A, Maitre P, et al. Pterin determination in cerebrospinal fluid: state of the art. Pteridines. 2017;28:83–89.
  • Serrano MP, Lorente C, Vieyra FE, et al. Photosensitizing properties of biopterin and its photoproducts using 2'-deoxyguanosine 5'-monophosphate as an oxidizable target. Phys Chem Chem Phys. 2012;14:11657–11665.
  • Swarna S, Lorente C, Thomas AH, et al. Rate constants of quenching of the fluorescence of pterins by the iodide anion in aqueous solution. Chem Phys Lett. 2012;542:62–65.
  • Dántola ML, Vignoni M, González C, et al. Electron-transfer processes induced by the triplet state of pterins in aqueous solutions. Free Radic Biol Med. 2010;49:1014–1022.
  • Buglak AA, Telegina TA, Vorotelyak EA, et al. Theoretical study of photoreactions between oxidized pterins and molecular oxygen. J Photochem Photobiol A. 2019;372:254–259.
  • Serrano MP, Lorente C, Borsarelli CD, et al. Unraveling the degradation mechanism of purine nucleotides photosensitized by pterins: the role of charge-transfer steps. Chemphyschem. 2015;16:2244–2252.
  • Castaño C, Serrano MP, Lorente C, et al. Quenching of the singlet and triplet excited states of pterin by amino acids. Photochem Photobiol. 2019;95:220–226.
  • Castaño C, Thomas AH, Lorente C. Type I photosensitized oxidation of methionine. Photochem Photobiol. 2020.
  • Estébanez S, Lorente C, Gaspar Tosato M, et al. Photochemical formation of a fluorescent thymidine-pterin adduct in DNA. Dyes Pigm. 2019;160:624–632.
  • Dántola ML, Reid LO, Castaño C, et al. Photosensitization of peptides and proteins by pterin derivatives. Pteridines. 2017;28:105–114.
  • Tosato MG, Schilardi P, Lorenzo de Mele MF, et al. Synergistic effect of carboxypterin and methylene blue applied to antimicrobial photodynamic therapy against mature biofilm of Klebsiella pneumoniae. Heliyon. 2020;6:e03522
  • Serrano MP, Vignoni M, Lorente C, et al. Thymidine radical formation via one-electron transfer oxidation photoinduced by pterin: mechanism and products characterization. Free Radic Biol Med. 2016;96:418–431.
  • Dántola LM, Gojanovich AD, Thomas AH. Inactivation of tyrosinase photoinduced by pterin. Biochem Biophys Res Commun. 2012;424:568–572.
  • Schallreuter KU, Chavan B, Rokos H, et al. Decreased phenylalanine uptake and turnover in patients with vitiligo. Mol Genet Metab. 2005;86 Suppl 1:S27–S33.
  • Davis MD, Kaufman S, Milstien S. Conversion of 6-substituted tetrahydropterins to 7-isomers via phenylalanine hydroxylase-generated intermediates. Proc Natl Acad Sci U S A. 1991;88:385–389.
  • Wood JM, Schallreuter-Wood KU, Lindsey NJ, et al. A specific tetrahydrobiopterin binding domain on tyrosinase controls melanogenesis. Biochem Biophys Res Commun. 1995;206:480–485.
  • Schallreuter KU, Wood JM, Körner C, et al. 6-Tetrahydrobiopterin functions as a UVB-light switch for de novo melanogenesis. Biochim Biophys Acta. 1998;1382:339–344.
  • Jain A, Mal J, Mehndiratta V, et al. Study of oxidative stress in vitiligo. Ind J Clin Biochem. 2011;26:78–81.
  • Wood JM, Chavan B, Hafeez I, et al. Regulation of tyrosinase by tetrahydropteridines and H2O2. Biochem Biophys Res Commun. 2004;325:1412–1417.
  • Schallreuter KU, Moore J, Wood JM, et al. Epidermal H(2)O(2) accumulation alters tetrahydrobiopterin (6BH4) recycling in vitiligo: identification of a general mechanism in regulation of all 6BH4-dependent processes? J Invest Dermatol. 2001;116:167–174.
  • Rebrin I, Bailey SW, Boerth SR, et al. Catalytic characterization of 4a-hydroxytetrahydropterin dehydratase. Biochemistry. 1995;34:5801–5810.
  • Haavik J, Doskeland AP, Flatmark T. Stereoselective effects in the interactions of pterin cofactors with rat-liver phenylalanine 4-monooxygenase. Eur J Biochem. 1986;160:1–8.
  • Davis MD, Ribeiro P, Tipper J, et al. “7-tetrahydrobiopterin,” a naturally occurring analogue of tetrahydrobiopterin, is a cofactor for and a potential inhibitor of the aromatic amino acid hydroxylases. Proc Natl Acad Sci U S A. 1992;89:10109–10113.
  • Schallreuter KU, Wood JM, Pittelkow MR, et al. Regulation of melanin biosynthesis in the human epidermis by tetrahydrobiopterin. Science. 1994;263:1444–1446.
  • Halgren TA. Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. J Comput Chem. 1996;17:490–519.
  • Zhao Y, Truhlar DG. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor Chem Account. 2008;120:215–241.
  • Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 16, revision C.01. Wallingford (CT): Gaussian; 2016.
  • Gour NK, Mishra BK, Singh HJ. Theoretical study on mechanism, kinetics, and thermochemistry of the gas phase reaction of 2,2,2-trifluoroethyl butyrate with OH radicals at 298 K. J Chem Sci. 2015;127:1015–1023.
  • Yamaguchi K, Jensen F, Dorigo A, et al. A spin correction procedure for unrestricted Hartree-Fock and Møller-Plesset wavefunctions for singlet diradicals and polyradicals. Chem Phys Lett. 1988;149:537–542.
  • Gogonea V, Shy JM 2nd, Biswas PK. Electronic structure, ionization potential, and electron affinity of the enzyme cofactor (6R)-5,6,7,8-tetrahydrobiopterin in the gas phase, solution, and protein environments. J Phys Chem B. 2006;110:22861–22871.
  • Goebbert DJ, Sanov AJ. Photodetachment, photofragmentation and fragment autodetachment of [O2n(H2O)m]- clusters: Core-anion structures and fragment energy partitioning. J Chem Phys. 2009;131:104308.
  • Filip C, editor. Reactive oxygen species (ROS) in living cells. London (UK): IntechOpen; 2018.
  • Braga LS, Leal DHS, Kuca K, et al. Perspectives on the role of the Frontier Effective-for-Reaction Molecular Orbital (FERMO) in the study of chemical reactivity: an updated review. COC. 2020;24:314–331.

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