Abstract
Molecules acting as antioxidants capable of scavenging reactive oxygen species (ROS) are of utmost importance in the living cell. Vitamin C is known to be one of these molecules. In this study we have analyzed the reactivity of vitamin C toward the \( \cdot OH \) and \( \cdot OOH \) ROS species, in all acidic, neutral and basic media. In order to do so, density functional theory (DFT) have been used. More concretely, the meta-GGA functional MPW1B95 have been used. Two reaction types have been studied in each case: addition to the ring atoms, and hydrogen/proton abstraction. Our results show that \( \cdot OH \) is the most reactive species, while \( \cdot OOH \) displays low reactivity. In all three media, vitamin C reactions with two hydroxyl radicals show a wide variety of possible products.
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References
Niki E (2001) Free Radic Res 33:693
Halliwell B, Gutteridge JM, Cross CE (1992) J Lab Clin Med 119:598
Young LS, Woodside JV (2001) J Clin Pathol 54:176
Ames BN, Shigenaga MK, Hagen TM (1993) Proc Nat Ac Sci USA 90:7915
Gey KF, Brubacher GB, Stahelin HB (1987) Am J Clin Nutr 45:1368
Frei B, Stocker R, Ames BN (1988) Proc Nat Ac Sci USA 85:9748
Berlett BS, Stadtman ER (1997) J Biol Chem 272:20313
Halliwell B, Gutteridge JMC (1999) Free radicals in biology and medicine, 3rd edn. Oxford University Press, Oxford, and references therein
Stocker P, Lesgards JF, Vidal N, Chalier F, Prost M (2003) Biochim Biophys Acta 1621:1
Padayyaty SJ, Katz A, Wang Y, Eck P, Kwon O, Lee JH, Chen S, Corpe C, Dutta A, Dutta SK, Levine M (2003) J Am Coll Nutr 18:22
Mitsuta K, Mizuta Y, Kohno M, Hiramatsu M, Mori A (1990) Bull Chem Soc Jpn 63:187
Gershoff SN (1993) Nutr Rev 51:313
Buettner GR, Moseley PL (1993) Free Radic Res Commun 19:589
Bielski BH, Richter HW, Chan PC (1975) Ann NY Acad Sci 258:231
Meister A (1994) J Biol Chem 269:9397
Tolbert BM, Ward JB (1982) In: Tolbert BM (ed) Ascorbic acid: chemistry, metabolism and uses. American Chemical Society, Washington D.C., p 101
Buettner GR (1993) Arch Biochem Biophys 300:535
Halliwell B (1999) Trends Biochem Sci 24:255
Buettner GR and Jurkiewicz BH (1996) In: Cadenas E, Packer L (eds) Handbook of antioxidants. Dekker, New York, p 91
Bendich A, Machlin JL, Scandurra O, Burton GW, Wayner DD (1986) Adv Free Radic Biol Med 2:419
Fraga S, Saxena KMS, Lo BWN (1971) Atom Data Nucl Data 3:323
Lutsenko EA, Carcamo JM, Golde DW (2002) J Biol Chem 227:16895
Martensson J, Meister A (1991) Proc Nat Ac Sci USA 88:4656
Laroff GP, Fessnden RW, Schler RH (1972) J Am Chem Soc 94:9062
Wilson C, Gisvolds O (1998) Textbook of organic medicinal and pharmaceutical chemistry. Lippincott-Raven, Philadelphia, p 915
Allen RN, Shukla MK, Reed D, Leszczynski J (2006) Int J Quant Chem 106:2934
Shukla MK, Mishra PC (1995) J Mol Struct 377:277
Hvoslef J (1969) J Acta Crystallogr B 25:2214
Zhao Y, Lynch BJ, Truhlar DG (2004) J Phys Chem A 108:2715
Zhao Y, Lynch BJ, Truhlar DG (2004) J Phys Chem A 108:4786
Zhao Y, Pu J, Lynch BJ, and TruhlarD (2004) G Phys Chem Chem Phys 673
Zhao Y, Truhlar DG (2004) J Phys Chem A 108:6908
Hohenberg P, Kohn W (1964) Phys Rev 136:B864
Kohn W, Sham LJ (1965) Phys Rev 140:A1133
Gonzalez C, Schlegel HB (1989) J Chem Phys 90:2154
Gonzalez C, Schlegel HB (1990) J Phys Chem 94:5523
Mennucci B, Tomasi J (1997) J Chem Phys 106:5151
Tomasi J, Mennucci B, Cances E (1999) J Mol Struct (THEOCHEM) 464:211
Tejero I, Gonzalez-Lafont A, Lluch JM, Eriksson LA (2004) Chem Phys Lett 398:336
Matxain JM, Ristila M, Strid Å, Eriksson LA (2006) J Phys Chem A 110:13068
Matxain JM, Ristila M, Strid Å̊ et al. (2007) Chem Eur J 13:4636–4642
Frisch MJ, Trucks GW, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Jr Montgomery JA (2004) Pople, Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford, CT
Acknowledgments
This research was funded by Eusko Jaurlaritza (GIC 07/85 IT-330-07) and the Spanish Office for Scientific Research (CTQ2011-27374). The SGI/IZO-SGIker UPV/EHU (supported by Fondo Social Europeo and MCyT) is gratefully acknowledged for generous allocation of computational resources. JMM would like to thank Spanish Ministry of Science and Innovation for funding through a Ramon y Cajal fellow position (RYC 2008-03216).
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Mujika, J.I., Matxain, J.M. Theoretical study of the pH-dependent antioxidant properties of vitamin C. J Mol Model 19, 1945–1952 (2013). https://doi.org/10.1007/s00894-012-1465-5
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DOI: https://doi.org/10.1007/s00894-012-1465-5