稳定同位素氘标记试剂的研究进展
|
摘要
稳定同位素氘标记试剂是科研工作中必不可少的试剂。氘代溶剂可有效避免普通溶剂氢原子干扰,被大量用于核磁共振仪溶剂。氘标记内标试剂具有优良的示踪效果,广泛地应用于食品领域的农残检测、兽残检测、非法添加剂、药物残留检测等方面。此外,由于氘原子良好的化学惰性,氘标记试剂还用于新药研发领域。稳定同位素氘标记试剂的合成方法主要有化学合成法及物理交换法。从核磁检测、食品安全、生命科学、药物研发等方面阐述国内外近几年稳定同位素氘标记试剂的研发新技术以及应用展望。
Stable isotope deuterium labeling reagent is an essential reagent in our scientific research.Deuterium substituted solvents which can effectively avoid the interference of hydrogen atoms in common solvents are used in NMR solvents in large quantities.Deuterium labeled internal standard reagents are widely used in the field of agricultural residue detection,animal residue detection,illegal additives detection,drug residue detection because of its excellent tracer effects.In addition,deuterium labeled reagents are also used in the field of new drug development due to their excellent chemical inertia.The main synthetic methods of stable isotope deuterium labeled reagents are chemical synthesis and physical exchange.In this paper,the new technology and application prospect of stable isotope deuterium labeling reagents at home and abroad in recent years are described from the aspects of nuclear magnetic detection,food safety,life science and drug research and development.
Stable isotope deuterium labeling reagent is an essential reagent in our scientific research.Deuterium substituted solvents which can effectively avoid the interference of hydrogen atoms in common solvents are used in NMR solvents in large quantities.Deuterium labeled internal standard reagents are widely used in the field of agricultural residue detection,animal residue detection,illegal additives detection,drug residue detection because of its excellent tracer effects.In addition,deuterium labeled reagents are also used in the field of new drug development due to their excellent chemical inertia.The main synthetic methods of stable isotope deuterium labeled reagents are chemical synthesis and physical exchange.In this paper,the new technology and application prospect of stable isotope deuterium labeling reagents at home and abroad in recent years are described from the aspects of nuclear magnetic detection,food safety,life science and drug research and development.
引文
[1]杨维成,罗勇,宋家龙,等.同位素标记D6-苯的合成研究[J].化学试剂,2011,33(10):887-888.
[2]盛怀禹,陈耀焕,袁群,等.同位素有机化学[M].浙江:浙江教育出版社,1994:63-101.
[3]王雪婷,王伟,杜晓宁,等.丙酮与重水氢-氘交换反应催化剂的考察研究[J].化学试剂,2017,39(6):647-650.
[4]FRASER R R,RENAUD R N.The steric effect in the platinum-catalyzed exchange reaction between aromatic ring protons and deuterium oxide[J].J.Am.Chem.Soc.,1966,88(19):4 365-4 370.
[5]RYLANDER P N,TARBELL D S.Cleavage of the carbon-sulfur bond.Rates of hydrolysis of some alkyl acetates and the corresponding thiolacetates in aqueous acetone[J].J.Am.Chem.Soc.,1997,79(4):842-846.
[6]CONDIRSTON D A,LAPOSA J D.Vibrational spectra of styrene-H8,-D3,-D5,and-D8[J].J.Mol.Spectrosc.,1976,63(3):466-477.
[7]陈建平,何淡云.乙苯氘标记物的合成[J].厦门大学学报:自然科学版,1985,(4):527-531.
[8]SAWAMA Y,YAMADA T,YABE Y,et al.Platinum on carbon-catalyzed H—D exchange reaction of aromatic nuclei due to isopropyl alcohol-mediated self-activation of platinum metal in deuterium oxide[J].Adv.Synth.Catal.,2013,355(8):1 529-1 534.
[9]CAMPOS J,ESQUEDA A C,LOPEZ-SERRANO J,et al.A cationic Rh(Ⅲ) complex that efficiently catalyzes hydrogen isotope exchange in hydrosilanes[J].J.Am.Chem.Soc.,2010,132(47):16 765-16 767.
[10]FORTMAN G C,JACOBSEN H,CAVALLO L,et al.Catalytic deuteration of silanes mediated by N-heterocyclic carbene-Ir(ⅲ) complexes[J].Chem.Commun.,2011,47(34):9 723-9 725.
[11]SMART K A,EMMANUELLE M M,ANNAKA T,et al.Silane deuteration catalyzed by ruthenium bis(dihydrogen) complexes or simple metal salts[J].Adv.Syn.Catal.,2014,356(4):759-764.
[12]张林,高文德,肖淑兴.新法氘代溴苯-D5的合成与表征[J].化学世界,2000,(2):75-78.
[13]杨超,杨维成,潘洁.稳定同位素标记卤代苯-D5的合成[J].化学试剂,2019,41(1):89-92.
[14]肖淑兴,高文德,刘维铭,等.高氘代率乙醛的制备[J].四川大学学报,1998,35(4):645-647.
[15]贾献彬,罗炫,常冠军,等.氘代聚乙烯的合成与表征[J].核化学与放射化学,2009,31(3):163-167.
[16]徐仲杰,涂亚辉,孙雯.稳定同位素标记六六六-D6的合成[J].广东化工,2014,41(22):206-207.
[17]杨维成,吕靖,齐庆瑞,等.同位素标记敌百虫-甲氧基-D6和敌敌畏-甲氧基-D6的合成[J].同位素,2014,27(1):8-14.
[18]徐建飞,卢伟京,杜晓宁.甲萘威-(甲基-D3)的合成[J].化学试剂,2013,35(9):845-850.
[19]杜鸿雁,宋歌,董颖,等.甲基对硫磷-D6的合成[J].合成化学,2018,26(11):856-858.
[20]解龙,王伟,杨超,等.稳定同位素标记溴布特罗-D9的合成[J].化学试剂,2016,38(5):468-472.
[21]SU F,WU F,TANG H,et al.Efficient and facile synthesis of novel stable monodeuterium labeled ractopamine[J].J.Label.Compd.Radiopharm.,2015,58(13/14):479-482.
[22]SUN K,FANG C,YANG W C,et al.Efficient synthesis of D6-clenproperol and D6-cimaterol using deuterium isopropylamine as labelled precursor[J].J.Label.Compd.Radiopharm.,2016,59(13):552-556.
[23]TU Y H,ZHONG J Q,WANG H R,et al.Synthesis of stable isotope labeled D9-mabuterol,D9-bambuterol,and D9-cimbuterol[J].J.Label.Compd.Radiopharm.,2016,59(13):546-551.
[24]CHEN W L,ZHAO C M,DENG X J.Synthesis of deuterium-labeled 2-quinoxalinecarboxylic acid and 3-methylquinoxaline-2-carboxylic acid from deuterium aniline[J].J.Label.Compd.Radiopharm.,2018,61(14):1-5.
[25]NINO A D,DONNA L D,MAIUOLO L,et al.Synthesis of deuterium-labeled azo dyes of the Sudan family[J].Synthesis,2008,2 008(3):459-463.
[26]卢浩,孙雯,徐仲杰.稳定同位素标记苏丹红Ⅰ-D5的合成研究[J].化学试剂,2017,39(11):1 225-1 228.
[27]徐仲杰,卢伟京,孙雯,等.碱性橙Ⅱ-D5的合成研究[J].化学试剂,2014,36(1):83-85.
[28]王浩然,杨维成,杨超,等.稳定同位素标记D6-二甲基黄的合成[J].化学世界,2016,(10):649-652.
[29]徐仲杰,卢伟京,孙雯,等.邻苯二甲酸二甲酯-D6的合成[J].同位素,2014,27(2):72-76.
[30]徐仲杰,孙雯,罗勇.一锅法合成稳定同位素标记邻苯二甲酸丁苄酯-D4[J].食品科技,2016,41(1):247-250.
[31]徐仲杰,孙雯,钟佳琪,等.稳定同位素内标试剂邻苯二甲酸二(2-乙基己)酯-D4的合成[J].化学试剂,2016,38(2):178-180.
[32]杨维成,齐庆瑞,李美华,等.稳定同位素氘标记D6-结晶紫的合成及表征[J].应用化学,2014,31(3):262-267.
[33]杜晓宁,王伟,雷雯.稳定性同位素标记试剂的研发及应用展望[J].化学试剂,2015,37(9):769-775.
[34]徐仲杰,卢伟京,卢浩.稳定同位素标记恩诺沙星-D5的合成[J].精细化工,2012,29(11):1 050-1 052.
[35]杜鸿雁,宋歌,董颖,等.地西泮-D5中间体的简便合成[J].合成化学,2017,25(12):1 017-1 019.
[36]FENTIMAN A F,RODGER L.Synthesis of deuterium labelled drugs of abuse for used as internal standardsion monitoring Ⅱ.Deuterium-labelled benzodiazepam:chlordiazepoxide,demethyldiazepam,diazepam,and oxazepam[J].J.Label.Compd.Radiopharm.,1976,8(4):579-585.
[37]AHLBURG A,LINDHARDT A T,TAANING R H,et al.An air-tolerant approach to the carbonylative Suzuki-Miyaura coupling:applications in isotope labeling[J].J.Org.Chem.,2013,78(20):10 310-10 318.
[38]GANT T G.Using deuterium in drug discovery:leaving the label in the drug[J].J.Med.Chem.,2014,57(9):3 595-3 611.
[39]宋瑞捧,刘佳麟,李贝,等.氘标记药物分子的合成进展[J].中国医药工业杂志,2017,48(6):809-815.
[40]李雪莹,费嘉,张伟波.氘代药物的专利技术进展[J].药学进展,2017,41(11):833-845.
[41]GANT T G,SARSHAR S,WOO S H.Substituted phenethylamines with serotoninergic and/or norepinephrinergic activity and their preparation:US 20 080 234 257[P].2008-09-25.
[42]TUNG R.Benzo[d][1,3]dioxole isotopologue derivatives as selective serotonin reuptake inhibitors,their preparation,pharmaceutical compositions,and use in therapy:WO 2 007 016 431A2[P].2007-02-08.
[43]XING L D,SHENG Z L.Preparation of deuterium-substituted ω-diphenylurea derivatives as antitumor agents:WO 2 011 113 203A1[P].2011-09-22.
[44]SHAH P,SAKS S.Benzoquinolines as inhibitors of vesicular monoamine transporter 2 and their preparation:WO 2 015 077 521A1[P].2015-05-28.
[2]盛怀禹,陈耀焕,袁群,等.同位素有机化学[M].浙江:浙江教育出版社,1994:63-101.
[3]王雪婷,王伟,杜晓宁,等.丙酮与重水氢-氘交换反应催化剂的考察研究[J].化学试剂,2017,39(6):647-650.
[4]FRASER R R,RENAUD R N.The steric effect in the platinum-catalyzed exchange reaction between aromatic ring protons and deuterium oxide[J].J.Am.Chem.Soc.,1966,88(19):4 365-4 370.
[5]RYLANDER P N,TARBELL D S.Cleavage of the carbon-sulfur bond.Rates of hydrolysis of some alkyl acetates and the corresponding thiolacetates in aqueous acetone[J].J.Am.Chem.Soc.,1997,79(4):842-846.
[6]CONDIRSTON D A,LAPOSA J D.Vibrational spectra of styrene-H8,-D3,-D5,and-D8[J].J.Mol.Spectrosc.,1976,63(3):466-477.
[7]陈建平,何淡云.乙苯氘标记物的合成[J].厦门大学学报:自然科学版,1985,(4):527-531.
[8]SAWAMA Y,YAMADA T,YABE Y,et al.Platinum on carbon-catalyzed H—D exchange reaction of aromatic nuclei due to isopropyl alcohol-mediated self-activation of platinum metal in deuterium oxide[J].Adv.Synth.Catal.,2013,355(8):1 529-1 534.
[9]CAMPOS J,ESQUEDA A C,LOPEZ-SERRANO J,et al.A cationic Rh(Ⅲ) complex that efficiently catalyzes hydrogen isotope exchange in hydrosilanes[J].J.Am.Chem.Soc.,2010,132(47):16 765-16 767.
[10]FORTMAN G C,JACOBSEN H,CAVALLO L,et al.Catalytic deuteration of silanes mediated by N-heterocyclic carbene-Ir(ⅲ) complexes[J].Chem.Commun.,2011,47(34):9 723-9 725.
[11]SMART K A,EMMANUELLE M M,ANNAKA T,et al.Silane deuteration catalyzed by ruthenium bis(dihydrogen) complexes or simple metal salts[J].Adv.Syn.Catal.,2014,356(4):759-764.
[12]张林,高文德,肖淑兴.新法氘代溴苯-D5的合成与表征[J].化学世界,2000,(2):75-78.
[13]杨超,杨维成,潘洁.稳定同位素标记卤代苯-D5的合成[J].化学试剂,2019,41(1):89-92.
[14]肖淑兴,高文德,刘维铭,等.高氘代率乙醛的制备[J].四川大学学报,1998,35(4):645-647.
[15]贾献彬,罗炫,常冠军,等.氘代聚乙烯的合成与表征[J].核化学与放射化学,2009,31(3):163-167.
[16]徐仲杰,涂亚辉,孙雯.稳定同位素标记六六六-D6的合成[J].广东化工,2014,41(22):206-207.
[17]杨维成,吕靖,齐庆瑞,等.同位素标记敌百虫-甲氧基-D6和敌敌畏-甲氧基-D6的合成[J].同位素,2014,27(1):8-14.
[18]徐建飞,卢伟京,杜晓宁.甲萘威-(甲基-D3)的合成[J].化学试剂,2013,35(9):845-850.
[19]杜鸿雁,宋歌,董颖,等.甲基对硫磷-D6的合成[J].合成化学,2018,26(11):856-858.
[20]解龙,王伟,杨超,等.稳定同位素标记溴布特罗-D9的合成[J].化学试剂,2016,38(5):468-472.
[21]SU F,WU F,TANG H,et al.Efficient and facile synthesis of novel stable monodeuterium labeled ractopamine[J].J.Label.Compd.Radiopharm.,2015,58(13/14):479-482.
[22]SUN K,FANG C,YANG W C,et al.Efficient synthesis of D6-clenproperol and D6-cimaterol using deuterium isopropylamine as labelled precursor[J].J.Label.Compd.Radiopharm.,2016,59(13):552-556.
[23]TU Y H,ZHONG J Q,WANG H R,et al.Synthesis of stable isotope labeled D9-mabuterol,D9-bambuterol,and D9-cimbuterol[J].J.Label.Compd.Radiopharm.,2016,59(13):546-551.
[24]CHEN W L,ZHAO C M,DENG X J.Synthesis of deuterium-labeled 2-quinoxalinecarboxylic acid and 3-methylquinoxaline-2-carboxylic acid from deuterium aniline[J].J.Label.Compd.Radiopharm.,2018,61(14):1-5.
[25]NINO A D,DONNA L D,MAIUOLO L,et al.Synthesis of deuterium-labeled azo dyes of the Sudan family[J].Synthesis,2008,2 008(3):459-463.
[26]卢浩,孙雯,徐仲杰.稳定同位素标记苏丹红Ⅰ-D5的合成研究[J].化学试剂,2017,39(11):1 225-1 228.
[27]徐仲杰,卢伟京,孙雯,等.碱性橙Ⅱ-D5的合成研究[J].化学试剂,2014,36(1):83-85.
[28]王浩然,杨维成,杨超,等.稳定同位素标记D6-二甲基黄的合成[J].化学世界,2016,(10):649-652.
[29]徐仲杰,卢伟京,孙雯,等.邻苯二甲酸二甲酯-D6的合成[J].同位素,2014,27(2):72-76.
[30]徐仲杰,孙雯,罗勇.一锅法合成稳定同位素标记邻苯二甲酸丁苄酯-D4[J].食品科技,2016,41(1):247-250.
[31]徐仲杰,孙雯,钟佳琪,等.稳定同位素内标试剂邻苯二甲酸二(2-乙基己)酯-D4的合成[J].化学试剂,2016,38(2):178-180.
[32]杨维成,齐庆瑞,李美华,等.稳定同位素氘标记D6-结晶紫的合成及表征[J].应用化学,2014,31(3):262-267.
[33]杜晓宁,王伟,雷雯.稳定性同位素标记试剂的研发及应用展望[J].化学试剂,2015,37(9):769-775.
[34]徐仲杰,卢伟京,卢浩.稳定同位素标记恩诺沙星-D5的合成[J].精细化工,2012,29(11):1 050-1 052.
[35]杜鸿雁,宋歌,董颖,等.地西泮-D5中间体的简便合成[J].合成化学,2017,25(12):1 017-1 019.
[36]FENTIMAN A F,RODGER L.Synthesis of deuterium labelled drugs of abuse for used as internal standardsion monitoring Ⅱ.Deuterium-labelled benzodiazepam:chlordiazepoxide,demethyldiazepam,diazepam,and oxazepam[J].J.Label.Compd.Radiopharm.,1976,8(4):579-585.
[37]AHLBURG A,LINDHARDT A T,TAANING R H,et al.An air-tolerant approach to the carbonylative Suzuki-Miyaura coupling:applications in isotope labeling[J].J.Org.Chem.,2013,78(20):10 310-10 318.
[38]GANT T G.Using deuterium in drug discovery:leaving the label in the drug[J].J.Med.Chem.,2014,57(9):3 595-3 611.
[39]宋瑞捧,刘佳麟,李贝,等.氘标记药物分子的合成进展[J].中国医药工业杂志,2017,48(6):809-815.
[40]李雪莹,费嘉,张伟波.氘代药物的专利技术进展[J].药学进展,2017,41(11):833-845.
[41]GANT T G,SARSHAR S,WOO S H.Substituted phenethylamines with serotoninergic and/or norepinephrinergic activity and their preparation:US 20 080 234 257[P].2008-09-25.
[42]TUNG R.Benzo[d][1,3]dioxole isotopologue derivatives as selective serotonin reuptake inhibitors,their preparation,pharmaceutical compositions,and use in therapy:WO 2 007 016 431A2[P].2007-02-08.
[43]XING L D,SHENG Z L.Preparation of deuterium-substituted ω-diphenylurea derivatives as antitumor agents:WO 2 011 113 203A1[P].2011-09-22.
[44]SHAH P,SAKS S.Benzoquinolines as inhibitors of vesicular monoamine transporter 2 and their preparation:WO 2 015 077 521A1[P].2015-05-28.