Free-radical scavenging by tryptophan and its metabolites through electron transfer based processes

Journal of Molecular Modeling

Volumn 21, Issue 8, 2015, Pages

  Pérez González, Adriana ^a   Alvarez Idaboy, Juan Raúl ^a   Galano, Annia ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b DEPARTAMENTO DE QUÍMICA   (Mexico)

Author keywords

Free radical scavenger; Rate constants; Single electron transfer

Indexed keywords

3 HYDROXYKYNURENINE; 5 HYDROXYTRYPTOPHAN; ANTHRANILIC ACID; FREE RADICAL; INDOLEPYRUVIC ACID; KYNURENIC ACID; KYNURENINE; SCAVENGER; TROLOX C; TRYPTOPHAN; XANTHURENIC ACID;

ANTIOXIDANT ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CONFORMATIONAL TRANSITION; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT; HUMAN; PH; PRIORITY JOURNAL; PROTEIN STRUCTURE; QUANTUM MECHANICS; SOLVATION; TRYPTOPHAN METABOLISM; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; THERMODYNAMICS;

ELECTRON TRANSPORT; FREE RADICAL SCAVENGERS; KINETICS; KYNURENIC ACID; MODELS, MOLECULAR; THERMODYNAMICS; TRYPTOPHAN; XANTHURENATES;

EID: 84938363639     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-015-2758-2     Document Type: Article

References (72)

1. Wang J, Li JZ, Lu AX et al (2014) Anticancer effect of salidroside on A549 lung cancer cells through inhibition of oxidative stress and phospho-p38 expression. Oncol Lett 7:1159–1164
2. Granados-Principal S, El-Azem N, Pamplona R et al (2014) Hydroxytyrosol ameliorates oxidative stress and mitochondrial dysfunction in doxorubicin-induced cardiotoxicity in rats with breast cancer. Biochem Pharmacol 90:25–33
3. Tekiner-Gulbas B, Westwell AD, Suzen S (2013) Oxidative stress in carcinogenesis: new synthetic compounds with dual effects upon free radicals and cancer. Curr Med Chem 20:4451–4459
4. Knekt P, Reunanen A, Takkunen H et al (1994) Body iron stores and risk of cancer. Int J Cancer 56:379–382
5. Al-Aubaidy HA, Jelinek HF (2014) Oxidative stress and triglycerides as predictors of subclinical atherosclerosis in prediabetes. Redox Rep 19:87–91
6. Şerban C, Drǎgan S (2014) The relationship between inflammatory and oxidative stress biomarkers, atherosclerosis and rheumatic diseases. Curr Pharm Design 20:585–600
7. Zampetaki A, Dudek K, Mayr M (2013) Oxidative stress in atherosclerosis: the role of microRNAs in arterial remodeling. Free Radic Biol Med 64:69–77
8. Panasenko OM, Vol’nova TV, Azizova OA et al (1991) Free radical modification of lipoproteins and cholesterol accumulation in cells upon atherosclerosis. Free Radic Biol Med 10:137–148
9. Rosini M, Simoni E, Milelli A et al (2014) Oxidative stress in Alzheimer’s disease: are we connecting the dots? J Med Chem 57:2821–2831
10. Turunc Bayrakdar E, Uyanikgil Y, Kanit L et al (2014) Nicotinamide treatment reduces the levels of oxidative stress, apoptosis, and PARP-1 activity in Aβ(1–42)-induced rat model of Alzheimer’s disease. Free Radic Res 48:146–158
11. Fay DS, Fluet A, Johnson CJ et al (1998) In vivo aggregation of β-amyloid peptide variants. J Neurochem 71:1616–1625
12. Butterfield DA (1997) β-Amyloid-associated free radical oxidative stress and neurotoxicity: implications for Alzheimer’s disease. Chem Res Toxicol 10:495–506
13. Hensley K, Carney JM, Mattson MP et al (1994) A model for β-amyloid aggregation and neurotoxicity based on free radical generation by the peptide: relevance to Alzheimer disease. Proc Natl Acad Sci USA 91:3270–3274
14. Matsuda M, Shimomura I (2014) Roles of adiponectin and oxidative stress in obesity-associated metabolic and cardiovascular diseases. Rev Endocr Metab Disord 15:1–10
15. Eren E, Ellidag HY, Cekin Y et al (2014) Heart valve disease: the role of calcidiol deficiency, elevated parathyroid hormone levels and oxidative stress in mitral and aortic valve insufficiency. Redox Rep 19:34–39
16. Stephens NG, Parsons A, Schofield PM et al (1996) Randomised controlled trial of vitamin E in patients with coronary disease: Cambridge Heart Antioxidant Study (CHAOS). Lancet 347:781–786
17. Street DA, Comstock GW, Salkeld RM et al (1994) Serum antioxidants and myocardial infarction: are low levels of carotenoids and α-tocopherol risk factors for myocardial infarction? Circulation 90:1154–1161
18. Salonen JT, Nyyssönen K, Korpela H et al (1992) High stored iron levels are associated with excess risk of myocardial infarction in Eastern Finnish men. Circulation 86:803–811
19. Ames BN, Cathcart R, Schwiers E et al (1981) Uric acid provides an antioxidant defense in humans against oxidant- and radical-caused aging and cancer: a hypothesis. Proc Natl Acad Sci USA 78:6858–6862
20. Stocker R, Yamamoto Y, McDonagh AF et al (1987) Bilirubin is an antioxidant of possible physiological importance. Science 235:1043–1046
21. DeLange RJ, Glazer AN (1989) Phycoerythrin fluorescence-based assay for peroxy radicals: a screen for biologically relevant protective agents. Anal Biochem 177:300–306
22. Richard DM, Dawes MA, Mathias CW et al (2009) L-Tryptophan: basic metabolic functions, behavioral research and therapeutic indications. Int J Tryptophan Res 2:45–60
23. Bravo R, Matito S, Cubero J et al (2013) Tryptophan-enriched cereal intake improves nocturnal sleep, melatonin, serotonin, and total antioxidant capacity levels and mood in elderly humans. Age 35:1277–1285
24. Jiang Y, Ng TB, Wang CR et al (2010) First isolation of tryptophan from edible lotus (Nelumbo nucifera Gaertn) rhizomes and demonstration of its antioxidant effects. Int J Food Sci Nutr 61:346–356
25. Bitzer-Quintero OK, Dávalos-Marín AJ, Ortiz GG et al (2010) Antioxidant activity of tryptophan in rats under experimental endotoxic shock. Biomed Pharmacother 64:77–81
26. Tsopmo A, Diehl-Jones BW, Aluko RE et al (2009) Tryptophan released from mother’s milk has antioxidant properties. Pediatr Res 66:614–618
27. Watanabe S, Togashi SI, Takahashi N et al (2002) L-Tryptophan as an antioxidant in human placenta extract. J Nutr Sci Vitaminol 48:36–39
28. Moosmann B, Behl C (2000) Cytoprotective antioxidant function of tyrosine and tryptophan residues in transmembrane proteins. Eur J Biochem 267:5687–5692
29. Domazou AS, Koppenol WH, Gebicki JM (2009) Efficient repair of protein radicals by ascorbate. Free Radic Biol Med 46:1049–1057
30. Gebicki JM, Nauser T, Domazou A et al (2010) Reduction of protein radicals by GSH and ascorbate: potential biological significance. Amino Acids 39:1131–1137
31. Perez-Gonzalez A, Muñoz-Rugeles L, Alvarez-Idaboy JR (2014) Tryptophan: antioxidant or target of oxidative stress? A quantum chemistry elucidation. RSC Adv 4:56128–56131
32. Christen S, Peterhans E, Stocker R (1990) Antioxidant activities of some tryptophan metabolites: possible implication for inflammatory diseases. Proc Natl Acad Sci USA 87:2506–2510
33. Weiss G, Diez-Ruiz A, Murr C et al (2002) Tryptophan metabolites as scavengers of reactive oxygen and chlorine species. Pteridines 13:140–144
34. Lima VLA, Dias F, Nunes RD et al (2012) The antioxidant role of xanthurenic acid in the Aedes aegypti midgut during digestion of a blood meal. PLoS ONE 7:e38349
35. Zhao Y, Schultz NE, Truhlar DG (2006) Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. J Chem Theory Comput 2:364–382
36. Marenich AV, Cramer CJ, Truhlar DG (2009) Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J Phys Chem B 113:6378–6396
37. Velez E, Quijano J, Notario R et al (2009) A computational study of stereospecifity in the thermal elimination reaction of menthyl benzoate in the gas phase. J Phys Org Chem 22:971–977
38. Ando H, Fingerhut BP, Dorfman KE et al (2014) Femtosecond stimulated Raman spectroscopy of the cyclobutane thymine dimer repair mechanism: a computational study. J Am Chem Soc 136:14801–14810
39. Black G, Simmie JM (2010) Barrier heights for H-atom abstraction by HO2 from η-butanol: a simple yet exacting test for model chemistries? J Comput Chem 31:1236–1248
40. Dargiewicz M, Biczysko M, Improta R et al (2012) Solvent effects on electron-driven proton-transfer processes: adenine–thymine base pairs. Phys Chem Chem Phys 14:8981–8989
41. Furuncuoǧlu T, Uǧur I, Degirmenci I et al (2010) Role of chain transfer agents in free radical polymerization kinetics. Macromolecules 43:1823–1835
42. Zhao Y, Truhlar DG (2008) How well can new-generation density functionals describe the energetics of bond-dissociation reactions producing radicals? J Phys Chem A 112:1095–1099
43. Galano A, Alvarez-Idaboy JR (2014) Kinetics of radical-molecule reactions in aqueous solution: a benchmark study of the performance of density functional methods. J Comput Chem 35:2019–2026
44. Frisch MJ, Trucks GW, Schlegel HB et al (2009) Gaussian 09. Gaussian, Inc., Wallingford
45. Galano A, Alvarez-Idaboy JR (2013) A computational methodology for accurate predictions of rate constants in solution: application to the assessment of primary antioxidant activity. J Comput Chem 34:2430–2445
46. Eyring H (1935) The activated complex in chemical reactions. J Chem Phys 3:63–71
47. Evans MG, Polanyi M (1935) Some applications of the transition state method to the calculation of reaction velocities, especially in solution. Trans Faraday Soc 31:875–894
48. Truhlar DG, Garrett BC, Klippenstein SJ (1996) Current status of transition-state theory. J Phys Chem 100:12771–12800
49. Marcus RA (1993) Electron transfer reactions in chemistry. Theory and experiment. Rev Modern Phys 65:599–610
50. Marcus RA (1997) Electron transfer reactions in chemistry: theory and experiment. J Electroanal Chem 438:251–259
51. Marcus RA (1997) Electron transfer reactions in chemistry. Theory and experiment. Pure Appl Chem 69:13–29
52. Collins FC, Kimball GE (1949) Diffusion-controlled reaction rates. J Colloid Sci 4:425–437
53. Smoluchowski M (1917) Mathematical theory of the kinetics of the coagulation of colloidal solutions. Z Phys Chem 92:129–168
54. Einstein A (1905) On the movement of small particles suspended in a stationary liquid demanded by the molecular-kinetic theory of heat. Ann der Phys (Leipzig) 17:559–560
55. George SG (1903) Mathematical and physical papers, vol 3. Cambridge University Press, Cambridge
56. Ho J, Coote ML (2009) A universal approach for continuum solvent pKa calculations: are we there yet? Theory Chem Acc 125:3–21
57. Shields GC, Seybold PG (2013) Nitrogen acids (Chapter 6). In: Computational approaches for the prediction of pKa values. QSAR in environmental and health sciences. CRC, Boca Raton, pp 57–72
58. Kelen M, Sanli N (2009) Determination of pKa values of some auxins in methanol–water mixtures by reversed phase liquid chromatography and potentiometric methods. J Braz Chem Soc 20:133–140
59. Liao X, Zhu J, Rubab M et al (2010) An analytical method for the measurement of acid metabolites of tryptophan-NAD pathway and related acids in urine. J Chromatogr B 878:1003–1006
60. Kelly CP, Cramer CJ, Truhlar DG (2006) Adding explicit solvent molecules to continuum solvent calculations for the calculation of aqueous acid dissociation constants. J Phys Chem A 110:2493–2499
61. Cramer CJ, Truhlar DG (2008) A universal approach to solvation modeling. Acc Chem Res 41:760–768
62. Pérez-González A, Galano A (2012) On the outstanding antioxidant capacity of edaravone derivatives through single electron transfer reactions. J Phys Chem B 116:1180–1188
63. Litwinienko G, Ingold KU (2003) Abnormal solvent effects on hydrogen atom abstractions. 1. The reactions of phenols with 2,2-diphenyl-1-picrylhydrazyl (dpph•) in alcohols. J Org Chem 68:3433–3438
64. Litwinienko G, Ingold KU (2004) Abnormal solvent effects on hydrogen atom abstraction. 2. Resolution of the curcumin antioxidant controversy. The role of sequential proton loss electron transfer. J Org Chem 69:5888–5896
65. Litwinienko G, Ingold KU (2005) Abnormal solvent effects on hydrogen atom abstraction. 3. Novel kinetics in sequential proton loss electron transfer chemistry. J Org Chem 70:8982–8990
66. Litwinienko G, Ingold KU (2007) Solvent effects on the rates and mechanisms of reaction of phenols with free radicals. Acc Chem Res 40:222–230
67. Marino T, Galano A, Russo N (2014) Radical scavenging ability of gallic acid toward OH and OOH radicals. Reaction mechanism and rate constants from the density functional theory. J Phys Chem B 118:10380–10389
68. Pérez-González A, Galano A, Alvarez-Idaboy JR (2014) Dihydroxybenzoic acids as free radical scavengers: mechanisms, kinetics, and trends in activity. New J Chem 38:2639–2652
69. Alberto ME, Russo N, Grand A et al (2013) A physicochemical examination of the free radical scavenging activity of trolox: mechanism, kinetics and influence of the environment. Phys Chem Chem Phys 15:4642–4650
70. Ulstrup J, Jortner J (1975) The effect of intramolecular quantum modes on free energy relationships for electron transfer reactions. J Chem Phys 63:4358–4368
71. Marcus RA, Sutin N (1985) Electron transfers in chemistry and biology. BBA Rev Bioenergetics 811:265–322
72. Marcus RA (1993) Electron transfer reactions in chemistry: theory and experiment (Nobel lecture). Angew Chem Int Ed Engl 32:1111–1121