Antioxidant Activity of Sesamol Derivatives and Their Drug Delivery via C60 Nanocage: a Theoretical Study
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摘要
The antioxidant activity of sesamol derivatives and their drug delivery via fullerene were investigated. Fullerene can interact with sesamol derivatives, and their adsorptions were possible from the energetic viewpoint. Adding the NH_2 group to sesamol can improve the sensitivity of sesamol toward fullerene surface. The NH_2 and OMe substitutions increase the antioxidant activity of sesamol. The results can also be used to select novel sesamol derivatives with higher antioxidant activity and higher drug delivery ability.
The antioxidant activity of sesamol derivatives and their drug delivery via fullerene were investigated. Fullerene can interact with sesamol derivatives, and their adsorptions were possible from the energetic viewpoint. Adding the NH_2 group to sesamol can improve the sensitivity of sesamol toward fullerene surface. The NH_2 and OMe substitutions increase the antioxidant activity of sesamol. The results can also be used to select novel sesamol derivatives with higher antioxidant activity and higher drug delivery ability.
The antioxidant activity of sesamol derivatives and their drug delivery via fullerene were investigated. Fullerene can interact with sesamol derivatives, and their adsorptions were possible from the energetic viewpoint. Adding the NH_2 group to sesamol can improve the sensitivity of sesamol toward fullerene surface. The NH_2 and OMe substitutions increase the antioxidant activity of sesamol. The results can also be used to select novel sesamol derivatives with higher antioxidant activity and higher drug delivery ability.
引文
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(6)Chanda, S.; Dave, R. In vitro models for antioxidant activity evaluation and some medicinal plants possessing antioxidant properties:an overview.Afr. J. Microbiol. Res. 2009, 3, 981–996.
(7)Srisayam, M.; Weerapreeyakul, N.; Barusrux, S.; Kanokmedhakul, K. Antioxidant, antimelanogenic, and skin-protective effect of sesamol. J. Cosm.Sci. 2014, 65, 69–79.
(8)Furumoto, T.; Nishimoto, K. Identification of a characteristic antioxidant, anthrasesamone F, in black sesame seeds and its accumulation at different seed developmental stages. Bio. Scie. Biotech. Biochem. 2016, 80, 350–355.
(9)Xu,P.;Cai,F.;Liu,X.;Guo,L.Sesamininhibitslipopolysaccharide-inducedproliferationandinvasionthroughthep38-MAPKandNF-κB signaling pathways in prostate cancer cells. Oncol. Reports 2015, 33, 3117–3123.
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(14)Wang, L. F.; Zhang, H. Y. A theoretical study of the different radical-scavenging activities of catechin, quercetin, and a rationally designed planar catechin. Bioorg. Chem. 2005, 33, 108–115.
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(17)Machado, M.; Mota, R.; Piquini, P. Electronic properties of BN nanocones under electric fields. Microelectron. J. 2003, 34, 545–547.
(18)Halpern, J. B.; Bello, A.; Gilcrease, A.; Harris, G. L.; He, M.; Biphasic GaN nanowires:growth mechanism and properties. Microelectron. J. 2009,40, 316–318.
(19)Masoudipour, E.; Kashanian, S.; Maleki, N. A targeted drug delivery system based on dopamine functionalized nano graphene oxide. Chem. Phys.Lett. 2017, 668, 56–63.
(20)Akbar, S.; Anwar, A.; Ayish, A. Phytantriol based smart nano-carriers for drug delivery applications. Europ. J. Pharm. Scie. 2017, 101, 31–42.
(21)Beheshtian, J.; Kamfiroozi, M.; Bagheri, Z.; Ahmadi A. B12N12 nano-cage as potential sensor for NO2 detection. Chin. J. Chem. Phys. 2012, 25,60–64.
(22)Ahmadi, A.; Beheshtian, J.; Kamfiroozi, M. Benchmarking of ONIOM method for the study of NH3 dissociation at open ends of BNNTs. J. Mol.Model 2012, 18, 1729–1734.
(23)Najafi,M.;Najafi,M.;Najafi,H.DFT/B3LYPstudyofthesubstituenteffectsonthereactionenthalpiesoftheantioxidantmechanismsof indole-3-carbinol derivatives in the gas-phase and water. Comp. Theor. Chem. 2012, 999, 34–42.
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(25)Koroleva, M. Y.; Nagovitsina, T. Y.; Bidanov, D. Y.; Gorbachevski, O. S.; Yurtov, E. V. Nano and microcapsules as drug-delivery systems. Reso.Effi. Techn. 2016, 2, 233–239.
(26)Neeraj, V.; Taehong, M.; Manish, B.; Aakruti, G.; Indrajit, R. Neutrophil targeted nano-drug delivery system for chronic obstructive lung diseases.Biol. Med. 2016, 12, 2415–2427.
(27)Dinadayalane,T.C.;Murray,J.S.;Conch,M.C.Reactivitiesofsiteson(5,5)single-walledcarbonnanotubeswithandwithoutaStoneWales defect. J. Chem. Theory Comp. 2010, 6, 1351–1357.
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(29)Grimme, S. Accurate description of van der Waals complexes by density functional theory including empirical corrections. J. Comput. Chem. 2004,25, 1463–1471.
(30)Shokuhi, A.; Ayub, K. Ni adsorption on Al12P12 nano-cage:a DFT study. J. Alloy. Comp. 2016, 678, 317–324.
(31)Andzelm, J.; Kolmel, C. Incorporation of solvent effects into density functional calculations of molecular energies and geometries. J. Chem. Phys.1995, 103, 9312–9320.
(32)Gan, L. H.; Zhao, J. Q. Theoretica l investigation of[5, 5],[9, 0] and[10, 10] closed WCNTs. Physica. E 2009, 41, 1249–1252.
(33)Beheshtian,J.;Peyghan,A.A.;Bagheri,A.AdsorptionanddissociationofCl2moleculeonZnOnanocluster.Appl.Surf.Sci.2012,258,8171–8176.
(34)Boys, S. F.; Bernardi, F. The calculation of small molecular interact ions by the separate total energies Mol. Phys. 1970, 19, 553–566.
(35)Arab, A.; Habibzadeh, M. Comparative hydrogen adsorption on the pure Al and mixed Al–Si nano clusters:a first principle DFT study. Comput.Theor. Chem. 2015, 1068, 52–56.
(36)Bahrami,A.;Seidi,S.;Baheri,T.Afirst-principlesstudyontheadsorptionbehaviorofamphetamineonpristine,P-andAl-dopedB12N12nano-cages. Superl. Micros. 2013, 64, 265–273.
(37)Najafi, M.; Najafi, M.; Najafi, H. Theoretical study of the substituent effects on the reaction enthalpies of the antioxidant mechanisms of stobadine derivatives in the gas-phase and water, J. Theor. Comput. Chem. 2013, 12, 1250116.
(38)Najafi, M.; Najafi, M.; Najafi, H. DFT/B3LYP study of the substituent effects on the reaction enthalpies of the antioxidant mechanisms of sesamol derivatives in the gas phase and water. Can. J. Chem. 2012, 90, 915–926.
(39)Mahdavinia, G. H.; Amani, A. M.; Sepehrian, H. MCM-41-SO3H as a highly efficient sulfonic acid nanoreactor for the rapid and green synthesis of some novel highly substituted imidazoles under solvent-free condition. Chin. J. Chem.2102,03, 703–708.
(40)Rostamizadeh,S.;Amani,A.M.;Aryan,R.;Ghaieni,H.R.;Norouzi,L.Veryfastandefficientsynthesisofsomenovelsubstituted2-arylbenzimidazoles in water using ZrOCl2 NH2O on montmorillonite K10 as catalyst. Monatsh. Chem. 2009, 140, 547–552.
(41)Rostamizadeh,S.;Amani,A.M.;Mahdavinia,G.H.;Shadjou,N.Silicasupportedammoniumdihydrogenphosphate(NH4H2PO4/SiO2):amild,reusable and highly efficient heterogeneous catalyst for the synthesis of 14-aryl-14-H-dibenzo[a,j]xanthenes. Chin. Chem. Lett. 2009, 20,779–783.
(42)Rostamizadeh, S.; Aryan, R.; Ghaieni, H. R.; Amani, A. M. Aqueous NaHSO4 catalyzed regioselective and versatile synthesis of 2-thiazolamines.Monatsh. Chem. 2008, 139, 1241–1245.
(43)Mahdavinia,G.H.;Rostamizadeh,S.;Amani,A.M.;Sepehrian,H.Fastandefficientmethodforthesynthesisof2-arylbenzimidazolesusing MCM-41-SO3H. Heterocycl. Commun. 2012, 18, 33–37.
(44)Rostamizadeh, S.; Aryan, R.; Ghaieni, H. R.; Amani, A. M. An efficient one-pot procedure for the preparation of 1,3,4-thiadiazoles in ionic liquid[Bmim]BF4 as dual solvent and catalyst. Heteroat. Chem. 2008, 19, 320–324.
(45)Rostamizadeh,S.;Aryan,R.;Ghaieni,H.R.;Amani,A.M.Efficientsynthesisof1,3,4-thiadiazolesusinghydrogenbonddonor(thio)urea derivatives as organocatalysts. J. Heterocycl. Chem. 2010, 47, 616–623.
(46)Rostamizadeh, S.; Abdollahi, F.; Shadjou, N.; Amani, A. M. MCM-41-SO3H:a novel reusable nanocatalyst for synthesis of amidoalkyl naphthols under solvent-free conditions. Monatsh. Chem. 2013, 144, 1191–1196.
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