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Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1573-4064
ISSN (Online): 1875-6638

Research Article

Synthesis and Evaluation of Bis-Schiff Bases of Carbohydrazide as Antioxidant and Cytotoxic Agents

Author(s): Sarosh Iqbal*, Shumaila Kiran, Shahida Perveen, Rizwana Malik, Muhammad Taha, Khalid Mohammed Khan*, Shahnaz Perveen and M. Iqbal Choudhary*

Volume 18, Issue 6, 2022

Published on: 21 January, 2022

Page: [667 - 678] Pages: 12

DOI: 10.2174/1573406418666211220123403

Price: $65

Abstract

Introduction: Antioxidants are known to prevent oxidative stress-induced damage to the biomolecules and thus, delay the onset of cancers and many age-related diseases. Therefore, the development of novel and potent antioxidants is justified.

Methods: During this study, we synthesized symmetrical Bis-Schiff bases of carbohydrazide 1-27, and evaluated their in vitro antioxidative activity and cytotoxic activity.

Results: Among synthesized compounds, six compounds 20 (IC50 = 12.89 ± 0.02 μM), 16 (IC50 = 14.32 ± 0.43 μM), 17 (IC50 = 18.52 ± 0.83 μM), 19 (IC50 = 22.84 ± 0.62 μM), 24 (IC50 = 35.1 ± 0.82 μM) and 15 (IC50 = 40.03 ± 1.06 μM) showed an excellent 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, better than the standard butylatedhydroxyanisole (BHA) (IC50 = 44.6 ± 0.6 μM). Likewise, two compounds 16 (IC50 = 4.3 ± 1.3 μM) and 20 (IC50 = 6.6 ± 1.6 μM) showed oxidative burst scavenging activity better than the standard drug ibuprofen (IC50 = 11.2 ± 1.9 μM). Some synthesized compounds showed good to moderate toxicity against prostate cancer (PC-3) cell lines.

Conclusion: This study has identified potent antioxidants and good cytotoxic agents with the potential to further investigate.

Keywords: Bis-schiff bases, antioxidant, DPPH, radical scavenging, oxidative burst scavenging, PC-3 cancer cell line.

Graphical Abstract

[1]
Kiran, G.; Sarangapani, M.; Gouthami, T.; Rama, A.; Reddy, N. Synthesis, characterization, and antimicrobial and antioxidant activities of novel bis-isatin carbohydrazone derivatives. Toxicol. Environ. Chem., 2013, 95, 367-378.
[http://dx.doi.org/10.1080/02772248.2013.777605]
[2]
Finkel, T. Radical medicine: Treating ageing to cure disease. Nat. Rev. Mol. Cell Biol., 2005, 6(12), 971-976.
[http://dx.doi.org/10.1038/nrm1763] [PMID: 16227974]
[3]
Hussain, S.P.; Hofseth, L.J.; Harris, C.C. Radical causes of cancer. Nat. Rev. Cancer, 2003, 3(4), 276-285.
[http://dx.doi.org/10.1038/nrc1046] [PMID: 12671666]
[4]
Finkel, T.; Holbrook, N.J. Oxidants, oxidative stress and the biology of ageing. Nature, 2000, 408(6809), 239-247.
[http://dx.doi.org/10.1038/35041687] [PMID: 11089981]
[5]
Basu, C.; Chowdhury, S.R. Banerjee, Evans, H.S.; Mukherjee, S. Reactivity studies of cyclopentadienylruthenium(II), osmium(II) and pentamethylcyclopentadienyl iridium(III) complexes towards 2-(2′-pyridyl)imidazole derivatives. Polyhedron, 2007, 26, 3617-3624.
[http://dx.doi.org/10.1016/j.poly.2007.03.053]
[6]
Hipkiss, A.R. Glycation, ageing and carnosine: Are carnivorous diets beneficial? Mech. Ageing Dev., 2005, 126(10), 1034-1039.
[http://dx.doi.org/10.1016/j.mad.2005.05.002] [PMID: 15955546]
[7]
Halliwell, B.; Gutteridge, J.M.C. Free radicals in biology and medicine; Oxford University Press: Oxford, 1999.
[8]
Meyer, A.S.; Heiononen, M.; Frankel, E.N. Antioxidant interactions of catechin, cyanidin, caffeic acid, quercetin, and ellagic acid on human LDL oxidation. Food Chem., 1998, 61, 71-75.
[http://dx.doi.org/10.1016/S0308-8146(97)00100-3]
[9]
Hunt, E.J.; Lester, C.E.; Lester, E.A.; Tackett, R.L. Effect of St. John’s wort on free radical production. Life Sci., 2001, 69(2), 181-190.
[http://dx.doi.org/10.1016/S0024-3205(01)01102-X] [PMID: 11441908]
[10]
Çakmakçi, S.; Topdaş, E.F.; Kalın, P.; Han, H.; Şekerci, P.; Kose, L.P.; Gulçin, I. Antioxidant capacity and functionality of oleaster (E laeagnus angustifolia L.) flour and crust in a new kind of fruity ice cream. Int. J. Food Sci. Technol., 2015, 50, 472-481.
[http://dx.doi.org/10.1111/ijfs.12637]
[11]
Göçer, H.; Akıncıoğlu, A.; Öztaşkın, N.; Göksu, S.; Gülçin, İ. Synthesis, antioxidant, and antiacetylcholinesterase activities of sulfonamide derivatives of dopamine-related compounds. Arch. Pharm. (Weinheim), 2013, 346(11), 783-792.
[http://dx.doi.org/10.1002/ardp.201300228] [PMID: 24591156]
[12]
Aziz, A.N.; Taha, M.; Ismail, N.H.; Anouar, H.; Yousuf, S.; Jamil, W.; Awang, K.; Ahmat, N.; Khan, K.M.; Kashif, S.M. Synthesis, crystal structure, DFT studies and evaluation of the antioxidant activity of 3,4-dimethoxybenzenamine Schiff bases. Molecules, 2014, 19(6), 8414-8433.
[http://dx.doi.org/10.3390/molecules19068414] [PMID: 24950444]
[13]
Ather, A.Q.; Chaudhry, F.; Khan, M.N.; Silicz Bueno, E.A.; Khan, M.A.; Aslam, N.; Khan, K.M.; Athar, M.M.; Munawar, M.A.; Ashraf, M.; Ejaz, S.A. Synthesis, antibacterial and antioxidant properties of pyrazolylpyridazines. Asian J. Chem., 2013, 25, 7743-7748.
[http://dx.doi.org/10.14233/ajchem.2013.14590]
[14]
Ajaib, M.; Zikrea, A.; Khan, K.M.; Perveen, S.; Shah, S.; Karim, A. Rivina humilis L: A potential antimicrobial and antioxidant source. J. Chem. Soc. Pak., 2013, 35, 1384-1398.
[15]
Khan, K.M.; Khan, M.; Ali, M.; Qadir, M.I.; Perveen, S.; Karim, A.; Choudhary, M.I. Superoxide respiratory burst inhibitory activity of Bis-Schiff bases of isatins. J. Chem. Soc. Pak., 2013, 35, 987-993.
[16]
Ajaib, M.; Khan, K.M. Antimicrobial and antioxidant activities of Echinochloa colona (Linn.) link and Sporobolus coromandelianus (Retz.) kunth. J. Chem. Soc. Pak., 2013, 35, 960-965.
[17]
Shahzadi, T.; Abbasi, M.A.; Ur-Rehman, A.; Riaz, T.; Khan, K.M.; Ashraf, M.; Afzal, I.; Akhtar, M.N.; Ajaib, M. Antioxidant and lipoxygenase inhibiting new iridoid glucosides from Caryopteris odorata. Nat. Prod. Res., 2013, 27(4-5), 302-313.
[http://dx.doi.org/10.1080/14786419.2012.668692] [PMID: 22424117]
[18]
Khan, K.M.; Ali, M.; Ambreen, N.; Naz, F.; Arshad, M.; Akber, N.; Perveen, S.; Shah, Z. Free radical scavenging potential of anilinoacridines and acridinylhydrazides. J. Chem. Soc. Pak., 2013, 35, 202-205.
[19]
Makhmoor, T.; Naheed, S.; Shujaat, S.; Jalil, S.; Hayat, S.; Choudhary, M.I.; Khan, K.M.; Alam, J.M.; Nazir, S. Hepatoprotection by chemical constituents of the marine brown alga Spatoglossum variabile: A relation to free radical scavenging potential. Pharm. Biol., 2013, 51(3), 383-390.
[http://dx.doi.org/10.3109/13880209.2012.732582] [PMID: 23406359]
[20]
Riaz, T.; Abbasi, M.A.; Riaz, N.; Saleem, M.; Khan, K.M.; Ajaib, M. Isolation, structure elucidation and antioxidant screening of secondary metabolites from Rhynchosia pseudo-cajan. J. Chem. Soc. Pak., 2012, 34, 1204-1212.
[21]
Riaz, T.; Abbasi, M.A. Aziz-ur-Rehman; Rubab, K.; Shahzadi, T.; Ajaib, M.; Khan, K.M. Cotinus coggyria: A rich source of antioxidants. Pak. J. Pharm. Sci., 2012, 25(3), 679-686.
[PMID: 22713961]
[22]
Khan, K.M.; Taha, M.; Naz, F.; Siddiqui, S.; Ali, S.; Rahim, F.; Perveen, S.; Choudhary, M.I. Acylhydrazide Schiff bases: DPPH radical and superoxide anion scavengers. Med. Chem., 2012, 8(4), 705-710.
[http://dx.doi.org/10.2174/157340612801216111] [PMID: 22571188]
[23]
Laghari, A.H.; Ali Memon, A.; Memon, S.; Nelofar, A.; Khan, K.M.; Yasmin, A. Determination of free phenolic acids and antioxidant capacity of methanolic extracts obtained from leaves and flowers of camel thorn (Alhagi maurorum). Nat. Prod. Res., 2012, 26(2), 173-176.
[http://dx.doi.org/10.1080/14786419.2010.538846] [PMID: 21834635]
[24]
Riaz, T.; Abbasi, A.M.; Shahzadi, T.; Ajaib, M.; Khan, M.K. Phytochemical screening, free radical scavenging, antioxidant activity and phenolic content of Dodonaea viscosa. J. Serb. Chem. Soc., 2012, 77, 423-435.
[http://dx.doi.org/10.2298/JSC110621183R]
[25]
Khan, K.M.; Karim, A.; Saied, S.; Ambreen, N.; Saleem, M.; Perveen, S.; Ahmad, A.; Choudharya, M.I. Synthesis, antioxidant and carbonic anhydrase inhibitory potential of Schiff bases of thiazoles. J. Pharm. Res., 2012, 5, 661-663.
[26]
Mohammed, K.K.; Rani, M.; Ambreen, N.; Ejaz, A.; Perveen, S.; Moazzam, H.S.; Iqbal, C.M.; Voelter, W. Acyl hydrazides: Potent antioxidants. Lett. Drug Des. Discov., 2012, 9, 135-139.
[http://dx.doi.org/10.2174/157018012799079798]
[27]
Riaz, T.; Abbasi, M.A.; Shahzadi, T.; Qureshi, M.Z.; Khan, K.M. Antioxidant activity and radical scavenging effects of various fractions from Curcuma zedoaria. Asian J. Pharm. Biol. Res., 2011, 1, 525-533.
[28]
Khan, K.M.; Khan, M.; Ambreen, N.; Rahim, F.; Muhammad, B.; Ali, S.; Haider, S.M.; Perveen, S.; Choudhary, M.I. Bis-Schiff bases of isatins: A new class of antioxidant. J. Pharm. Res., 2011, 4, 3402-3404.
[29]
MuĞlu. H.; Yakan, H.; Bakir, T.K. Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde. Turk. J. Chem., 2020, 44(1), 237-248.
[http://dx.doi.org/10.3906/kim-1910-13] [PMID: 33488154]
[30]
Khan, K.M.; Ali, M.; Wadood, A. Zaheer-ul-Haq; Khan, M.; Lodhi, M.A.; Perveen, S.; Choudhary, M.I.; Voelter, W. Molecular modeling-based antioxidant arylidene barbiturates as urease inhibitors. J. Mol. Graph. Model., 2011, 30, 153-156.
[http://dx.doi.org/10.1016/j.jmgm.2011.07.001] [PMID: 21816644]
[31]
Khan, K.M.; Khan, M.; Ali, M.; Taha, M.; Hameed, A.; Ali, S.; Perveen, S.; Choudhary, M.I. Synthesis and DPPH radical scavenging activity of 5-arylidene-N,N-dimethylbarbiturates. Med. Chem., 2011, 7(3), 231-236.
[http://dx.doi.org/10.2174/157340611795564231] [PMID: 21486204]
[32]
Riaz, T.; Abbasi, M.A.; Umar, M.I.; Shahzadi, T.; Khan, K.M.; Ahmad, V.U. Comparison of antioxidant potential of volatile oils of Syzygium aromaticum and Illicium verum relative to conventionally used standards. J. Chem. Soc. Pak., 2011, 33, 200-204.
[33]
Laghari, A.H.; Memon, S.; Nelofar, A.; Khan, K.M.; Yasmin, A. Determination of free phenolic acids and antioxidant activity of methanolic extracts obtained from fruits and leaves of Chenopodium album. Food Chem., 2011, 126(4), 1850-1855.
[http://dx.doi.org/10.1016/j.foodchem.2010.11.165] [PMID: 25213967]
[34]
Hasan, A.; Sadiq, A.; Abbas, A.; Mughal, E.; Khan, K.M.; Ali, M. Isolation and synthesis of flavonols and comparison of their antioxidant activity. Nat. Prod. Res., 2010, 24(11), 995-1003.
[http://dx.doi.org/10.1080/14786410902847302] [PMID: 20552521]
[35]
Ashiq, U.; Jamal, R.A.; Mahroof-Tahir, M.; Maqsood, Z.T.; Khan, K.M.; Omer, I.; Choudhary, M.I. Enzyme inhibition, radical scavenging, and spectroscopic studies of vanadium(IV)-hydrazide complexes. J. Enzyme Inhib. Med. Chem., 2009, 24(6), 1336-1343.
[http://dx.doi.org/10.3109/14756360902888168] [PMID: 19912066]
[36]
Gomes, F.A.; Costa, P.A.; Campos, M.B.D.; Tanon, R.V.; Couri, S.; Carbal, L.M.C. Watermelon juice pretreatment with microfiltration process for obtaining lycopene. Int. J. Food Sci. Technol., 2013, 48, 601-608.
[http://dx.doi.org/10.1111/ijfs.12005]
[37]
Khan, K.M.; Mughal, U.R.; Omar, I.; Choudhary, M.I. Microwaves-assisted syntheses of imidazolylbenzamides and their antioxidant activities. Lett. Drug Des. Discov., 2008, 5, 152-157.
[http://dx.doi.org/10.2174/157018008784083974]
[38]
Mohammed, K.K.; Murtaza, M.G.; Ahmed, N.S.; Perveen, S.; Iqbal, C.M. An alternative method for the synthesis of tetraketones and their lipoxygenase inhibiting and antioxidant properties. Lett. Drug Des. Discov., 2007, 4, 272-278.
[http://dx.doi.org/10.2174/157018007784620004]
[39]
Khan, K.M.; Maharvi, G.M.; Abbaskhan, A.; Hayat, S.; Khan, M.T.; Makhmoor, T.; Choudhary, M.I.; Shaheen, F. Three tyrosinase inhibitors and antioxidant compounds from Salsola foetida. Helv. Chim. Acta, 2003, 86, 457-469.
[http://dx.doi.org/10.1002/hlca.200390045]
[40]
Makhmoor, T.; Choudhary, M.I.; Ngounou, F.N.; Khan, K.M. Evaluation of free radical scavenging activities of natural and synthetic compounds. Sindh Univ. Res. J., 1999, 6, 59-62.
[41]
Fehér, J.; Prónai, L. The role of free radical scavengers in gastrointestinal diseases. Orv. Hetil., 1993, 134(13), 693-696.
[PMID: 8460019]
[42]
Grossman, S.; Dovrat, S.; Bergman, M. Natural antioxidants: Just free radical scavengers or much more? Trends Cancer Res., 2011, 7, 57-73.
[43]
Guilliams, T.G. Free radicals, antioxidants and eye diseases. Stand., 1999, 116, 1640.
[44]
Sin, H.P.Y.; Liu, D.T.L.; Lam, D.S.C. Lifestyle modification, nutritional and vitamins supplements for age-related macular degeneration. Acta Ophthalmol., 2013, 91(1), 6-11.
[http://dx.doi.org/10.1111/j.1755-3768.2011.02357.x] [PMID: 22268800]
[45]
Willis, L.M.; Shukitt-Hale, B.; Joseph, J.A.J. Recent advances in berry supplementation and age-related cognitive decline. Curr. Opin. Clin. Nutr. Metab. Care, 2009, 12(1), 91-94.
[http://dx.doi.org/10.1097/MCO.0b013e32831b9c6e] [PMID: 19057194]
[46]
Rahimi, R.; Nikfar, S.; Larijani, B.; Abdollahi, M. A review on the role of antioxidants in the management of diabetes and its complications. Biomed. Pharmacother., 2005, 59(7), 365-373.
[http://dx.doi.org/10.1016/j.biopha.2005.07.002] [PMID: 16081237]
[47]
Rhone, M.; Basu, A. Phytochemicals and age-related eye diseases. Nutr. Rev., 2008, 66(8), 465-472.
[http://dx.doi.org/10.1111/j.1753-4887.2008.00078.x] [PMID: 18667008]
[48]
Montonen, J.; Knekt, P.; Järvinen, R.; Reunanen, A. Dietary antioxidant intake and risk of type 2 diabetes. Diabetes Care, 2004, 27(2), 362-366.
[http://dx.doi.org/10.2337/diacare.27.2.362] [PMID: 14747214]
[49]
Al-Amiery, A.A.; Kadhum, A.A.H.; Obayes, H.R.; Mohamad, A.B. Synthesis and antioxidant activities of novel 5-chlorocurcumin, complemented by semiempirical calculations. Bioinorg. Chem. Appl., 2013, 2013354982
[http://dx.doi.org/10.1155/2013/354982] [PMID: 24170994]
[50]
Mohana, K.N.; Kumar, C.B.P. Synthesis and antioxidant activity of 2-amino-5-methylhiazole derivatives containing 1,3,4-oxadiazole-2-thiol moiety. ISRN Org. Chem., 2013, 2013620718
[http://dx.doi.org/10.1155/2013/620718] [PMID: 24052865]
[51]
Park, K. The role of antioxidants in combating the aging process. Inq. J., 2009, 13, 1-6.
[52]
Lin, D.; Xiao, M.; Zhao, J.; Li, Z.; Xing, B.; Li, X.; Kong, M.; Li, L.; Zhang, Q.; Liu, Y.; Chen, H.; Qin, W.; Wu, H.; Chen, S. An overview of plant phenolic compounds and their importance in human nutrition and management of type 2 diabetes. Molecules, 2016, 21(10), 1374.
[http://dx.doi.org/10.3390/molecules21101374] [PMID: 27754463]
[53]
Naveen, K.; Sai, K.; Chandana, K. Synthesis, characterization and screening of novel 5, 6-dihydroacridine derivatives as potent antidiabetic and antioxidant agent. J. Basic Appl. Res., 2016, 2, 176-184.
[54]
Agte, V.; Tarwadi, K. The importance of nutrition in the prevention of ocular disease with special reference to cataract. Ophthalmic Res., 2010, 44(3), 166-172.
[http://dx.doi.org/10.1159/000316477] [PMID: 20829640]
[55]
Fletcher, A.E. Free radicals, antioxidants and eye diseases: evidence from epidemiological studies on cataract and age-related macular degeneration. Ophthalmic Res., 2010, 44(3), 191-198.
[http://dx.doi.org/10.1159/000316476] [PMID: 20829643]
[56]
Singal, A.K.; Jampana, S.C.; Weinman, S.A. Antioxidants as therapeutic agents for liver disease. Liver Int., 2011, 31(10), 1432-1448.
[http://dx.doi.org/10.1111/j.1478-3231.2011.02604.x] [PMID: 22093324]
[57]
Li, S.; Tan, H.Y.; Wang, N.; Zhang, Z.J.; Lao, L.; Wong, C.W.; Feng, Y. The role of oxidative stress and antioxidants in liver diseases. Int. J. Mol. Sci., 2015, 16(11), 26087-26124.
[http://dx.doi.org/10.3390/ijms161125942] [PMID: 26540040]
[58]
Chiruta, C.; Schubert, D.; Dargusch, R.; Maher, P. Chemical modification of the multitarget neuroprotective compound fisetin. J. Med. Chem., 2012, 55(1), 378-389.
[http://dx.doi.org/10.1021/jm2012563] [PMID: 22192055]
[59]
Albarracin, S.L.; Stab, B.; Casas, Z.; Sutachan, J.J.; Samudio, I.; Gonzalez, J.; Gonzalo, L.; Capani, F.; Morales, L.; Barreto, G.E. Effects of natural antioxidants in neurodegenerative disease. Nutr. Neurosci., 2012, 15(1), 1-9.
[http://dx.doi.org/10.1179/1476830511Y.0000000028] [PMID: 22305647]
[60]
Moghaddam, A.H.; Nabavi, S.M.; Nabavi, S.F.; Bigdellou, R.; Mohammadzadeh, S.; Ebrahimzadeh, M.A. Antioxidant, antihemolytic and nephroprotective activity of aqueous extract of Diospyros lotus seeds. Acta Pol. Pharm., 2012, 69(4), 687-692.
[PMID: 22876611]
[61]
Rodrigo, R.; González, J.; Paoletto, F. The role of oxidative stress in the pathophysiology of hypertension. Hypertens. Res., 2011, 34(4), 431-440.
[http://dx.doi.org/10.1038/hr.2010.264] [PMID: 21228777]
[62]
Leopold, J.A. Antioxidants and coronary artery disease: From pathophysiology to preventive therapy. Coron. Artery Dis., 2015, 26(2), 176-183.
[http://dx.doi.org/10.1097/MCA.0000000000000187] [PMID: 25369999]
[63]
Neha, K.; Haider, M.R.; Pathak, A.; Yar, M.S. Medicinal prospects of antioxidants: A review. Eur. J. Med. Chem., 2019, 178, 687-704.
[http://dx.doi.org/10.1016/j.ejmech.2019.06.010] [PMID: 31228811]
[64]
Hertog, M.G.; Feskens, E.J.; Hollman, P.C.; Katan, M.B.; Kromhout, D. Dietary antioxidant flavonoids and risk of coronary heart disease: The Zutphen Elderly Study. Lancet, 1993, 342(8878), 1007-1011.
[http://dx.doi.org/10.1016/0140-6736(93)92876-U] [PMID: 8105262]
[65]
Moure, A.; Cruz, J.; Franco, D.; Dominguez, M.; Sineiro, J.; Dominguez, H.; Nunez, J. Natural antioxidants from residual sources, a review. Food Chem., 2001, 72, 145-171.
[http://dx.doi.org/10.1016/S0308-8146(00)00223-5]
[66]
Hollman, P.C.; Hertog, M.G.; Katan, M.B. Analysis and health effects of flavonoids. Food Chem., 1996, 57, 43-46.
[http://dx.doi.org/10.1016/0308-8146(96)00065-9]
[67]
Fulda, S. Resveratrol and derivatives for the prevention and treatment of cancer. Drug Discov. Today, 2010, 15(17-18), 757-765.
[http://dx.doi.org/10.1016/j.drudis.2010.07.005] [PMID: 20692359]
[68]
Tian, S.; Tang, J.; Liu, H.; Wang, L.; Shen, J.; Li, J.; Gan, Y. Propyl gallate plays a nephroprotective role in early stage of diabetic nephropathy associated with suppression of glomerular endothelial cell proliferation and angiogenesis. Exp. Diabetes Res., 2012, 2012209567
[http://dx.doi.org/10.1155/2012/209567] [PMID: 22988451]
[69]
Ray, P.S.; Maulik, G.; Cordis, G.A.; Bertelli, A.A.E.; Bertelli, A.; Das, D.K. The red wine antioxidant resveratrol protects isolated rat hearts from ischemia reperfusion injury. Free Radic. Biol. Med., 1999, 27(1-2), 160-169.
[http://dx.doi.org/10.1016/S0891-5849(99)00063-5] [PMID: 10443932]
[70]
Burkitt, M.J.; Duncan, J. Effects of trans-resveratrol on copper-dependent hydroxyl-radical formation and DNA damage: Evidence for hydroxyl-radical scavenging and a novel, glutathione-sparing mechanism of action. Arch. Biochem. Biophys., 2000, 381(2), 253-263.
[http://dx.doi.org/10.1006/abbi.2000.1973] [PMID: 11032413]
[71]
Stojanović, S.; Sprinz, H.; Brede, O. Efficiency and mechanism of the antioxidant action of trans-resveratrol and its analogues in the radical liposome oxidation. Arch. Biochem. Biophys., 2001, 391(1), 79-89.
[http://dx.doi.org/10.1006/abbi.2001.2388] [PMID: 11414688]
[72]
Stojanovic, S.; Brede, O. Elementry reactions of the antioxidant action of trans-stilbene derivatives: Resveratrol, pinosylvin, and 4-hydroxystilbene. Phys. Chem. Chem. Phys., 2002, 4, 757-764.
[http://dx.doi.org/10.1039/b109063c]
[73]
Amorati, R.; Lucarini, M.; Mugnaini, V.; Pedulli, G.F.; Roberti, M.; Pizzirani, D. Antioxidant activity of hydroxystilbene derivatives in homogeneous solution. J. Org. Chem., 2004, 69(21), 7101-7107.
[http://dx.doi.org/10.1021/jo0497860] [PMID: 15471458]
[74]
Nakanishi, I.; Shimada, T.; Ohkubo, K.; Manda, S.; Shimizu, T.; Urano, S.; Okuda, H.; Miyata, N.; Ozawa, T.; Anzai, K.; Fukuzumi, S.; Ikota, N.; Fukuhara, K. Involvement of electron transfer in the radical scavenging reaction of resveratrol. Chem. Lett., 2007, 36, 1276-1277.
[http://dx.doi.org/10.1246/cl.2007.1276]
[75]
Fabris, S.; Momo, F.; Ravagnan, G.; Stevanato, R. Antioxidant properties of resveratrol and piceid on lipid peroxidation in micelles and monolamellar liposomes. Biophys. Chem., 2008, 135(1-3), 76-83.
[http://dx.doi.org/10.1016/j.bpc.2008.03.005] [PMID: 18420333]
[76]
Liu, Z-Q. How many free Radicals can be trapped by (Hydroxylphenylimino)-methylphenol in the free-radical-induced peroxidation of triolein in micelles? QSAR Comb. Sci., 2007, 26, 488-495.
[http://dx.doi.org/10.1002/qsar.200630071]
[77]
Zhao, F.; Liu, Z-Q. The protective effect of hydroxyl-substituted Schiff bases on the radical-induced oxidation of DNA. J. Phys. Org. Chem., 2009, 22, 791-798.
[http://dx.doi.org/10.1002/poc.1517]
[78]
Saiko, P.; Szakmary, A.; Jaeger, W.; Szekeres, T. Resveratrol and its analogs: Defense against cancer, coronary disease and neurodegenerative maladies or just a fad? Mutat. Res., 2008, 658(1-2), 68-94.
[http://dx.doi.org/10.1016/j.mrrev.2007.08.004] [PMID: 17890139]
[79]
Baur, J.A.; Sinclair, D.A. Therapeutic potential of resveratrol: The in vivo evidence. Nat. Rev. Drug Discov., 2006, 5(6), 493-506.
[http://dx.doi.org/10.1038/nrd2060] [PMID: 16732220]
[80]
Zia-ur-Rehman. M.; Choudhary, J.A.; Elsegood, M.R.J.; Siddiqui, H.L.; Khan, K.M. A facile synthesis of novel biologically active 4-hydroxy-N′-(benzylidene)-2H-benzo[e][1,2]thiazine-3-cabihydrazide-1,1dioxies. Eur. J. Med. Chem., 2009, 44, 1311-1316.
[http://dx.doi.org/10.1016/j.ejmech.2008.08.002] [PMID: 18804313]
[81]
Khan, K.M.; Ali, M.; Asma, A.; Perveen, S.; Choudhary, M.I. Synthesis of arylidene barbiturate: A novel class of DPPH radical scavenging. Lett. Drug Des. Discov., 2008, 5, 286-291.
[http://dx.doi.org/10.2174/157018008784619889]
[82]
Badami, S.; Gupta, M.K.; Suresh, B. Antioxidant activity of the ethanolic extract of Striga orobanchioides. J. Ethnopharmacol., 2003, 85(2-3), 227-230.
[http://dx.doi.org/10.1016/S0378-8741(03)00021-7] [PMID: 12639745]
[83]
Helfand, S.L.; Werkmeister, J.; Roder, J.C. Chemiluminescence response of human natural killer cells. I. The relationship between target cell binding, chemiluminescence, and cytolysis. J. Exp. Med., 1982, 156(2), 492-505.
[http://dx.doi.org/10.1084/jem.156.2.492] [PMID: 6178787]
[84]
Candan, F. Effect of Rhus coriaria L. (Anacardiaceae) on superoxide radical scavenging and xanthine oxidase activity. J. Enzyme Inhib. Med. Chem., 2003, 18(1), 59-62.
[http://dx.doi.org/10.1080/1475636031000069273] [PMID: 12751822]
[85]
Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods, 1983, 65(1-2), 55-63.
[http://dx.doi.org/10.1016/0022-1759(83)90303-4] [PMID: 6606682]

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