Effects of curcumin and related compounds on processes involving α-hydroxyethyl radicals

Free Radical Research

Volumn 46, Issue 3, 2012, Pages 295-302

  Brinkevich, Sviatoslav Dmitrievich ^a   Ostrovskaya, Natalia Ivanovna ^a   Parkhach, Margaret Evgenievna ^a   Samovich, Svetlana Nikolaevna ^a   Shadyro, Oleg I ^a  

^a BELARUSIAN STATE UNIVERSITY   (Belarus)

Author keywords

hydroxyl containing carbon centered radicals; Bond dissociation enthalpy (BDE); Curcumin; Radical regulatory properties; Steady state radiolysis

Indexed keywords

ALCOHOL; CURCUMIN; HYDROGEN; OXYGEN; RADICAL;

ARTICLE; DRUG EFFECT; ENTHALPY; HYDROGEN BOND; RADIOLYSIS;

ALDEHYDES; ANTIOXIDANTS; CHALCONE; CURCUMIN; ETHANOL; FREE RADICALS; GUAIACOL; HEXANONES; HYDROGEN; MOLECULAR STRUCTURE; OXYGEN; PENTANONES; PULSE RADIOLYSIS; STRUCTURE-ACTIVITY RELATIONSHIP; STYRENES; THERMODYNAMICS;

EID: 84857309755     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.3109/10715762.2011.653966     Document Type: Article

References (45)

1. Preetha A, Sherin GT, Ajaikumar BK, Chitra S, Kuzhuvelil BH, Bokyung S, et al. Biological activities of curcumin and its analogues (Congeners) made by man and Mother Nature. Biochem Pharmacol 2008;76:1590-1611.
2. Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB. Bioavailability of curcumin: problems and promises. Mol Pharm 2007;4:807-818.
3. Sandur SK, Pandey MK, Sung B, Ahn KS, Murakami A, Sethi G, et al. Curcumin, demethoxycurcumin, bisdemeth-oxycurcumin, tetrahydrocurcumin and turmerones differentially regulate anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism. J Car-cinogenesis 2007;28:1765-1773. (Pubitemid 47289040)
4. Adams BK, Cai J, Armstrong J, Herold M, Lu YJ, Sun A, et al. EF24, a novel synthetic curcumin analog, induces apop-tosis in cancer cells via a redox-dependent mechanism. Anti-cancer Drugs 2005;16:263-275. (Pubitemid 40283941)
5. Anto RJ, George J, Babu KVD, Rajasekharan KN, Kuttan R. Antimutagenic and anticarcinogenic activity of natural and synthetic curcuminoids. Mutation Res 1996;370:127-131. (Pubitemid 26343824)
6. Ramsewak RS, DeWitt DL, Nair MG. Cytotoxicity, antioxi-dant and anti-inflammatory activities of curcumins I-III from Curcuma longa. Phytomedicine 2000;7:303-308. (Pubitemid 30618495)
7. Awasthi S, Srivastava SK, Piper JT, Singhal SS, Chaubey M, Awasthi YC. Curcumin protects against 4-hydroxy-2-trans-nonenal-induced cataract formation in rat lenses. Am J Clin Nutr 1996;64:761-766. (Pubitemid 26398280)
8. Vietri M, Pietrabissa A, Mosca F, Spisni R, Pacifici GM. Cur-cumin is a potent inhibitor of phenol sulfotransferase (SULT1A1) in human liver and extrahepatic tissues. Xenobi-otica 2003;33:357-363. (Pubitemid 36688113)
9. Deeb D, Xu YX, Jiang H, Gao X, Janakiraman N, Chapman RA, Gautam SC. Curcumin (diferuloyl-methane) enhances tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis in LNCaP prostate cancer cells. J Mol Cancer Ther 2003;2:95-103.
10. Somparn P, Phisalaphong C, Nakornchai S, Unchern S, Morales NP. Comparative antioxidant activities of curcumin and its dimethoxy and hydrogenated derivatives. Biol Pharm Bull 2007;30:74-78. (Pubitemid 46066323)
11. Rukkumani R, Aruna K, Varma PS, Rajasekaran KN, Menon V P. Comparative effects of curcumin and an analog of curcumin on alcohol and PUFA induced oxidative stress. J Pharm Sci 2004;7:274-283. (Pubitemid 41528902)
12. Chen WF, Deng SL, Yang BZL, Liu ZL. Curcumin and its analogues as potent inhibitors of low density lipoprotein oxidation: H-atom abstraction from the phenolic groups and possible involvement of the 4-hydroxy-3-methoxyphenyl groups. Free Radic Biol Med 2006;40:526-535.
13. Weber WM, Hunsaker LA, Abcouwer SF, Deck LM, Jagt DLV. Anti-oxidant activities of curcumin and related enones. Bioorg Med Chem 2005;13:3811-3820. (Pubitemid 40615931)
14. Sreejayan N, Rao MN. Free radical scavenging activity of cur-cuminoids. Arzneimittelforschung 1996;46:169-171. (Pubitemid 26079147)
15. Barik A, Mishra B, Shen L, Mohan H, Kadam RM, Dutta S, et al. Evaluation of a new copper (II)-curcumin complex as superoxide dismutase mimic and free radical reactions. Free Radic Biol Med 2005;39:811-822. (Pubitemid 41139894)
16. Shadyro OI. Radiation-induced free radical fragmentation of cell membrane components and the respective model compounds. In: Minisci F, editor. Free radicals in biology and environment. Dordrecht: Kluwer Academic Publishers; 1997. pp 317-329.
17. Edimecheva IP, Kisel RM, Shadyro OI, Kazem K, Murase H, Kagiya TJ. Homolytic cleavage of the O-gly oside bond in carbohydrates: a steady-state radiolysis study. Radiat Res 2005;46:319-324. (Pubitemid 43086302)
18. Shadyro O, Yurkova I, Kisel M, Brede O, Arnhold J. Formation of phosphatidic acid, ceramide, and diglyceride on radiolysis of lipids: identification by MALDI-TOF mass spectrometry. Free Rad Biol Med 2004;36:1612-1624. (Pubitemid 38746567)
19. Shadyro OI, Sosnovskaya AA, Vrublevskaya ON. C-N bond cleavage reactions on the radiolysis of amino-containing organic compounds and their derivatives in aqueous solutions. Int J Radiat Biol 2003;79:269-279. (Pubitemid 36774204)
20. Von Sonntag C. Free-radical-induced DNA damage and its repair. Berlin: Springer-Verlag; 2006.
21. Shadyro OI, Glushonok GK, Glushonok TG, Edimicheva IP, Moroz AG, Sosnovskaya AA, et al. Quinones as free-radical fragmentation inhibitors in biologically important molecules. Free Radic Res 2002;36:859-867. (Pubitemid 34830819)
22. Shadyro OI, Sosnovskaya AA, Edimecheva IP, Grintsevich IB, Lagutin PYu, Alekseev AV, Kazem K. Effects of various vitamins and coenzymes Q on reactions involving a-hydroxyl-containing radicals. Free Radic Res 2005;39:713-718. (Pubitemid 40959658)
23. Brinkevich SD, Shadyro OI. The effects of ascorbic acid on homolytic processes involving a-hydroxyl-containing carbon-centered radicals. Bioorg Med Chem Lett 2008;18: 6448-6450.
24. Organicum. Practical handbook of organic chemistry. Ongley PA, editor. Berlin: Deutscher Verlag der Wissenschaf-ten; 1973.
25. Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ. Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem 1994;98:11623-11627.
26. Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 1993;98:5648-5652.
27. http://classic.chem.msu.su/gran/firefly/index.html
28. Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordon MS, Jensen JH, et al. General atomic and molecular electronic structure. J Comput Chem 1993;14:1347-1363.
29. Wright JS, Carpenter DJ, McKay DJ, Ingold KU. Theoretical calculation of substituent effects on the O-H bond strength of phenolic antioxidants related to vitamin E. J Am Chem Soc 1997;119:4245-4252. (Pubitemid 27239976)
30. Wright JS, Johnson ER, DiLabio GA. Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects, and application to major families of antioxidants. J Am Chem Soc 2001;123:1173-1183. (Pubitemid 32148182)
31. Bakalbassis EG, Lithoxoidou AT, Vafiadis AP Theoretical calculation of accurate absolute and relative gas-and liquid-phase O-H bond dissociation enthalpies of 2-mono-and 2,6-disubstituted phenols, using DFT/B3LYP. J Phys Chem A 2003;107:8594-8606.
32. Chandra AK, Uchimaru T. The O-H bond dissociation energies of substituted phenols and proton affinities of substituted phenoxide ions: a DFT study. Int J Mol Sci 2002;3:407-422. (Pubitemid 38977683)
33. Atkins PW, de Paula J. Physical chemistry. 8-th ed. Oxford: Oxford University Press; 2006.
34. http://cccbdb.nist.gov/vibscalejust.asp
35. Foti MC, Johnson ER, Vinqvist MR, Write JS, Barclay LRC, Ingold KU. Naphthalene diols: a new class of antioxidants intramolecular hydrogen bonding in catechols, naphthalene diols, and their aryloxyl radicals. J Org Chem 2002;67: 5190-5196. (Pubitemid 34793186)
36. Klein E, Lukes V. DFT/B3LYP study of O-H bond dissociation enthalpies of para and meta substituted phenols: correlation with the phenolic C-O bond length. J Mol Struct: THEOCHEM 2006;767:43-50.
37. Luzhov VB. Mechanisms of antioxidant activity: a DFT study of hydrogen abstraction from phenol and toluene by the hydroperoxyl radical. Chem Phys 2005;314:211-217.
38. Hussain HH, Babic G, Durst T, Wright JS, Flueraru M, Chich-irau A, Chepelev LL. Development of novel antioxidants: design, synthesis, and reactivity. J Org Chem 2003;68:7023-7032. (Pubitemid 37071783)
39. Klein E, Lukes V. Study of gas-phase OH-bond dissociation enthalpies and ionization potentials of substituted phenols-aplicability of ab initio and DFT/B3LYP methods. Chem Phys 2006;330:515-525.
40. Khlestov NM, Shendrik AN. Quantum-chemical DFT calculations of the energies of the O-H bond of phenols. Theor Experim Chem 2010;46:279-283.
41. Lu Z, Nie G, Belton PS, Tang H, Zhao B. Structure-activity relationship analysis of antioxidant ability and neuroprotective effect of gallic acid derivatives. Neurochem Int 2006;48: 263-274. (Pubitemid 43177148)
42. Calliste CA, Kozlowski D, Duroux JL, Champavier Y, Chulia AJ, Trouillas P. A new antioxidant from wild nutmeg. Food Chem 2009;118:489-496.
43. Shadyro OI, Sosnovskaya AA, Edimecheva IP, Ostrovskaya NI, Kazem KM, Hryntsevich IB, Alekseev AV. Effects of qui-nones on free-radical processes of oxidation and fragmentation of hydroxyl-containing organic compounds. Bioorg Med Chem Lett 2007;17:6383-6386. (Pubitemid 47552803)
44. Hryntsevich IB, Shadyro OI. Reactions of α-hydroxyethyl radicals with flavonoids of various structures. Bioorg Med Chem Lett 2005;15:4252-4255. (Pubitemid 41187996)
45. Freeman GR. Radiation chemistry of ethanol. Washington: NBS; 1974.