加巴喷丁、安替比林与多巴胺盐酸盐的相互作用研究
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摘要
使用循环伏安法、密度泛函理论、分子中的原子理论及自然键轨道分析分别研究了多巴胺盐酸盐(DH)与加巴喷丁、安替比林的相互作用。水溶液及PBS缓冲溶液中的电化学结果表明:加巴喷丁和安替比林均可与DH形成氢键,使DH的电氧化过程难以进行。理论计算也进一步证明了上述混合体系中氢键作用的存在,其主要作用位点为加巴喷丁中的氮/氧原子、安替比林中的氧原子及DH酚羟基上的氢原子。
The interactions of gabapentin and antipyrine respectively with dopamine hydrochloride(DH)were studied by cyclic?voltammetry,density functional theory methods,atoms in molecules and natural bond orbital analyses.The electrochemical results of DH in aqueous solution and phosphate buffer saline solution showed that the hydrogen bonding were formed in the two mixed systems,which resulting in the electro-oxidation reaction of DH become more difficult.The existence of hydrogen bonding in above mixed systems were further confirmed by quantum chemical calculations,in addition,the main interaction sites are N/O atoms of gabapentin,the O atom of antipyrine and the H atom on the phenolic hydroxyl of DH.
The interactions of gabapentin and antipyrine respectively with dopamine hydrochloride(DH)were studied by cyclic?voltammetry,density functional theory methods,atoms in molecules and natural bond orbital analyses.The electrochemical results of DH in aqueous solution and phosphate buffer saline solution showed that the hydrogen bonding were formed in the two mixed systems,which resulting in the electro-oxidation reaction of DH become more difficult.The existence of hydrogen bonding in above mixed systems were further confirmed by quantum chemical calculations,in addition,the main interaction sites are N/O atoms of gabapentin,the O atom of antipyrine and the H atom on the phenolic hydroxyl of DH.
引文
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[2]Hao F R,Wang S Y,Xiao Z,et al.Pharmacokinetic-pharmacodynamic modeling of the anti-tumor effect of sunitinib combined with dopamine in the human non-small cell lung cancer xenograft[J].Pharm Res,2017,34(2):408-418.
[3]Citarella M R,Choi M R,Gironacci M M,et al.Urodilatin and dopamine:a new interaction in the kidney[J].Regul Pept,2009,153(1):19-24.
[4]Chen Y W,Chiu C C,Lin H T,et al.Adding dopamine to proxymetacaine or oxybuprocaine solutions potentiates and prolongs the cutaneous antinociception in rats[J].Anesth Analg,2018,126(5):1721-1728.
[5]Hung C H,Chiu C C,Liu K S,et al.Synergistic effects of serotonin or dopamine combined with lidocaine at producing nociceptive block in rats[J].Region Anesth Pain M,2017,42(3):351-356.
[6]Tzeng J I,Wang J N,Wang J J,et al.Cutaneous synergistic analgesia of bupivacaine in combination with dopamine in rats[J].Neurosci Lett,2016,620:88-92.
[7]Liu H,Li N,Zhang H Q,et al.A simple and convenient fluorescent strategy for the highly sensitive detection of dopamine and ascorbic acid based on graphene quantum dots[J].Talanta,2018,189:190-195.
[8]Prabhu1A A M,Fatiha M,Leila N,et al.Investigation of 3D contour map and intermolecular interaction of dopamine with β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin[J].J Solution Chem,2018,47(3):409-429.
[9]Zhai C P,Sun F,Zhang P,et al.Interactions of dopamine and dopamine hydrochloride with ethanol[J].J Mol Liq,2016,223:420-426.
[10]Skúpa K,Melicher■ík M,Urban J.A computational study of the interaction between dopamine and DNA/RNA nucleosides[J].J Mol Model,2015,21(9):241.
[11]Zhai C P,Ma H T,Sun F,et al.Experimental and theoretical study on the interaction of dopamine hydrochloride with H2O[J].J Mol Liq,2016,215:481-485.
[12]Zhai C P,Li D,Li L N,et al.Experimental and theoretical study on the hydrogen bonding between dopamine hydrochloride and N,N-dimethyl formamide[J].Spectrochim Acta,Part A,2015,145:500-504.
[13]Zhai C P,Peng P,Liu X J,et al.Experimental and theoretical study on the interactions between dopamine hydrochloride and nicotinamide[J].J Mol Struct,2019,1178:599-605.
[14]Gujral R S,Haque S M,Shanker P.A sensitive UV spectrophotometric method for the determination of gabapentin[J].J Chem,2009,6(1):163-170.
[15]Moore A,Derry S,Wiffen P.Gabapentin for chronic neuropathic pain[J].JAMA.2018,319(8):818-819.
[16]Ortega-varela L F,Herrera J E,Caramsalas N L,et al.Isobolographic analyses of the gabapentin-metamizol combination after local peripheral,intrathecal and oral administration in the rat[J].Pharmacol,2007,79(4):214-222.
[17]Luszczki J J,Czuczwar S J.Isobolographic profile of interactions between tiagabine and gabapentin:a preclinical study[J].N-S Arch Pharmacol,2004,369(4):434-446.
[18]Eckhardt K,Ammon S,Hofmann U,et al.Gabapentin enhances the analgesic effect of morphine in healthy volunteers[J].Anesth Analg,2000,91(1):185-191.
[19]De S G,Spagnolo C,Gareri P,et al.Gabapentin potentiates the antiseizure activity of certain anticonvulsants in DBA/2 mice[J].Eur J Pharmacol,1998,349(2-3):179-185.
[20]Luszczki J J,Andres M M,Czuczwar S J.Synergistic interaction of gabapentin and oxcarbazepine in the mouse maximal electroshock seizure model-an isobolographic analysis[J].Eur J Pharmacol,2005,515(1-3):54-61.
[21]Jalali F,Dorraji P S,Mahdiuni H.Binding of the neuroleptic drug,gabapentin,to bovine serum albumin:Insights from experimental and computational studies[J].J Lumin,2014,148:347-352.
[22]Jalali F,Dorraji P S.Electrochemical and spectroscopic studies of the interaction between the neuroleptic drug,gabapentin,and DNA[J].J Pharm Biomed Anal,2012,70:598-601.
[23]Wenger M,Bernstein J.An alternate crystal form of gabapentin:a cocrystal with oxalic acid[J].Cryst Growth Des,2008,8(5):1595-1598.
[24]Fowler D A,Tian J,Barnes C,et al.Cocrystallization of C-butyl pyrogallol[4]arene and C-propan-3-ol pyrogallol[4]arene with gabapentin[J].CrystEngComm,2011,13(5):1446-1449.
[25]Fujii M,Takeda Y,Yoshida M,et al.Enhancement effect of p-menthane-3,8-diol on in vitro permeation of antipyrine and indomethacin through yucatan micropig skin[J].Drug Dev Ind Pharm,2004,30(6):673-677.
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[27]Chan S L,Yeung J H.Modulation of antipyrine clearance by polysaccharide peptide(PSP)isolated from Coriolus versicolor in the rat[J].Food Chem Toxicol,2006,44(9):1607-1612.
[28]Vinagre A M,Collares E F.Effect of selective β-adrenoceptor blockade and surgical resection of theceliac-superior mesenteric ganglion complex on delayed liquid gastric emptyinginduced by dipyrone,4-aminoantipyrine,and antipyrine in rats[J].Braz J Med Biol Res,2016,49(3):e5011.
[29]Szakács T,Veres Z,Vereczkey L.Effect of phenobarbital and spironolactone treatment on the oxidative metabolism of antipyrine by rat liver microsomes[J].Pol J Pharmacol,2001,53(1):11-19.
[30]Tan C Q,Gao N Y,Deng Y,et al.Kinetic oxidation of antipyrine in heat-activated persulfate[J].Desalin Water Treat,2015,53(1):263-271.
[31]Meng X M,Xu Z N,Wang M,et al.Electrochemical behavior of antipyrine at a Bi2S3 modified glassy carbon electrode and its determination in pharmaceutical formulations[J].Anal Methods,2012,4:1736-1741.
[32]Gannimani R,Perumal A,Ramesh M,et al.Antipyrine-gamma cyclodextrin inclusion complex:molecular modeling,preparation,characterization and cytotoxicity studies[J].J Mol Struct,2015,1089:38-47.
[33]Frisch M J,Trucks G W,Schlegel H B,et al.Gaussian 09,Revision D.01,Gaussian,Inc,Wallingford,CT,2009.
[34]Boys S F,Bernardi F.The calculation of small molecular interactions by the differences of separate total energies.Some procedures with reduced errors[J].Mol Phys,1970,19(4):553-566.
[35]Lu T,Chen F W.Multiwfn:A multifunctional wavefunction analyzer[J].J Comput Chem,2012,33(5):580-592.
[36]Huo J,Li J,Li Q M.Study on electrochemical behaviors and the reaction mechanisms of dopamine and epinephrine at the pre-anodized inlaying ultrathin carbon paste electrode with nichrome as a substrate[J].Mat Sci Eng C-Mate,2013,33:507-511.
[37]Kamel M M,Abdalla E M,Ibrahim M S,et al.Electrochemical studies of ascorbic acid,dopamine,and uric acid at a dl-norvaline-deposited glassy carbon electrode[J].Can J Chem,2014,92:329-336.
[38]Koch U,Popelier P L A.Characterization of C-H-O hydrogen bonds on the basis of the charge density[J].J Phys Chem,1995,99(24):9747-9754.
[39]Zahedi-Tabrizi M,Ektefa F.A computational evidence of the intermolecular/intramolecular hydrogen bonding in salicylsalicylic acid:chemical shielding tensors and AIM analysis[J].Monatsh Chem,2015,146(11):1837-1843.
[40]Rozas I,Alkorta I,Elguero J.Behavior of ylides containing N,O,and C atoms as hydrogen bond acceptors[J].J Am Chem Soc,2000,122(45):11154-11161.
[41]Tavakkoli H,Farhadipour A.Mononuclear gallium(iii)complexes based on salicylaldoximes:theoretical study of structures,topological and NBO analysis of hydrogen bonding interactions involving O-H…O bonds[J].Arab J Chem,2016;9:S361-S372.