拉曼光谱技术在药物分析领域的研究进展
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摘要
拉曼光谱技术因其可有效避免样品中水的干扰、样品前处理简单、可快速无损分析以及表面增强拉曼可极大增强检测灵敏度等显著特点,在药物分析领域中的应用逐渐增多。本文旨在概述十几年来拉曼光谱技术在药物鉴别、药物定量分析、药物晶型分析、药物生产质控过程监测、药代动力学等方面的具体研究实例,对拉曼光谱技术在药物分析领域中的研究应用进行一次较为全面的综述,为之后该领域研究提供必要参考。
Raman spectroscopy has been widely used in pharmaceutical analysis due to its remarkable characteristics such as avoiding the interference of water in samples,simplicity of sample pretreatment,rapid nondestructive analysis,and greatly enhancing the sensitivity of detection by Surface Enhanced Raman Spectroscopy.The purpose of this paper is to summarize the specific research examples of Raman spectroscopy in drug identification,drug quantitative analysis,drug crystal analysis,quality control process monitoring of drug production,pharmacokinetics and so on in the past ten years,and to make a comprehensive review of the research and application of Raman spectroscopy in the field of drug analysis,so as to provide necessary reference for future research in this field.
Raman spectroscopy has been widely used in pharmaceutical analysis due to its remarkable characteristics such as avoiding the interference of water in samples,simplicity of sample pretreatment,rapid nondestructive analysis,and greatly enhancing the sensitivity of detection by Surface Enhanced Raman Spectroscopy.The purpose of this paper is to summarize the specific research examples of Raman spectroscopy in drug identification,drug quantitative analysis,drug crystal analysis,quality control process monitoring of drug production,pharmacokinetics and so on in the past ten years,and to make a comprehensive review of the research and application of Raman spectroscopy in the field of drug analysis,so as to provide necessary reference for future research in this field.
引文
[1] ALI E M A,EDWARDS H G M,HARGREAVES M D,et al.In situ detection of cocaine hydrochloride in clothing impregnated with the drug using benchtop and portable Raman spectroscopy[J].J Raman Spectrosc,2010,41:938-943.
[2] ALI E M Ai,EDWARDS H G M.Screening of textiles for contraband drugs using portable Raman spectroscopy and chemometrics[J].J Raman Spectrosc,2014,45,253-258.
[3] ALI E M Ai,EDWARDS H G M,COX R.Forensic and security applications of a longwavelength dispersive Raman system[J].J Raman Spectrosc,2015,46,322-326.
[4] TSUBOI M,BENEVIDES J M,JR G J T.The Complex of Ethidium Bromide with Genomic DNA:Structure Analysis by Polarized Raman Spectroscopy[J].Biophys J,2007,92(3):928-934.
[5] GUIRGUIS A,GIROTTO S,BERTI B,et al.Identification of new psychoactive substances (NPS)using handheld Raman spectroscopy employing both 785 and 1064nm laser sources[J].Forensic Sci Int,2017,273:113-123.
[6] HARGREAVES M D,PAGE K,MUNSHI T,et al.Analysis of seized drugs using portable Raman spectroscopy in an airport environment-a proof of principle study[J].J Raman Spectrosc,2008,39:873-880.
[7] WEYERMANN C,MIMOUNE Y,ANGLADAET F,et al.Applications of a transportable Raman spectrometer for the in situ detection of controlled substances at border controls[J].Forensic Sci Int,2011,209(1-3):21-28.
[8] WEST M J,WENT M J.The spectroscopic detection of drugs of abuse on textile fibres after recovery with adhesive lifters[J].Forensic Sci Int,2009,189(1-3),100-103.
[9] DIES H,RAVEENDRAN J,ESCOBEDO C,et al.Rapid identification and quantification of illicit drugs on nanodendritic surface-enhanced Raman scattering substrates[J].Sensor Actuat B-Chem,2018,257,382-388.
[10] MORENO V M,LOPEZ-LOPEZ M,ATOCHE J C,et al.Raman identification of drug of abuse particles collected with colored and transparent tapes[J].Sci Justice,2014,54(2):164-169.
[11] DEGARDIN K,DESPONDS A,ROGGO Y,et al.Protein-based medicines analysis by Raman spectroscopy for the detection of counterfeits[J].Forensic Sci Int,2017,278:313-325.
[12] LAWSON L S,RODRIGUEZ J D.Raman Barcode for Counterfeit Drug Product Detection[J].Anal Chem,2016,88(9):4706-4713.
[13] ROGGO Y,DEGARDIN K,MARGOT P,et al.Identification of pharmaceutical tablets by Raman spectroscopy and chemometrics[J].Talanta,2010,81(3):988-995.
[14] VEIJ M D,VANDENABEELE P,HALL K A,et al.Fast detection and identification of counterfeit antimalarial tablets by Raman spectroscopy[J].J Raman Spectrosc,2007,38,181-187.
[15] Fox J.D,Waverka K.N,Verbeck G.F,et al.Gold-plating of Mylar lift films to capitalize on surface enhanced Raman spectroscopy for chemical extraction of drug residues[J].Forensic Sci Int,2012,216(1-3):141-145.
[16] LE L M M,BERGE M,TFAYLI A,et al.Rapid discrimination and quantification analysis of five antineoplastic drugs in aqueous solutions using Raman spectroscopy[J].Eur J Pharm Sci,2018,111,158-166.
[17] PENIDO C A F D O,PACHECO M T T,NOVOTNY E H,et al.Quantification of cocaine in ternary mixtures using partial least squares regression applied to Raman and Fourier transform infrared spectroscopy[J].J Raman Spectrosc,2017,48:1732-1743.
[18] TONDEPU C,TOTH R,NAVIN C V,et al.Screening of unapproved drugs using portable Raman spectroscopy[J].Anal Chim Acta,2017,973,75-81.
[19] REBIERE H,MARTIN M,GHYSELINCK C,et al.Raman chemical imaging for spectroscopic screening and direct quantification of falsified drugs[J].J Pharm Biomed Anal,148:316-323.
[20] FRANZEN L,SELZER D,FLUHR J.W,et al.Towards drug quantification in human skin with confocal Raman microscopy[J].Eur J Pharm Biopharm,2013,84(2):437-444.
[21] LI X,CHEN H,ZHU Q,et al.Analysis of low active-pharmaceutical-ingredient signal drugs based on thin layer chromatography and surface-enhanced Raman spectroscopy[J].2016,J Pharm Biomed Anal,131:410-419.
[22] FROSCH T,YAN D,POPP J.Ultrasensitive fiber enhanced UV resonance Raman sensing of drugs[J].Anal Chem,2013,85(13):6264-6271.
[23] SCHMIDT A G,WARTEWIG S,PICKER K M.Polyethylene oxides:protection potential against polymorphic transitions of drugs[J].J Raman Spectrosc,2004,35:360-367.
[24] YING Y,BECK C,WU A,et al.Polymorph formation in fenofibrate in the absence and presence of polymer stabilizers:a low wavenumber Raman and differential scanning calorimetry study[J].J Raman Spectrosc,2017,48,750-757.
[25] WABUYELE B W,SOTTHIVIRAT S,ZHOU G X,et al.Dispersive Raman Spectroscopy for Quantifying Amorphous Drug Content in Intact Tablets[J].J Pharm Sci,2017,106(2):579-588.
[26] STRACHAN C J,PRATIWI D,GORDON K C,et al.Quantitative analysis of polymorphic mixtures of carbamazepine by Raman spectroscopy and principal components analysis[J].J Raman Spectrosc,2004,35:347-352.
[27] ZIMPER U,AALTONEN J,MCGOVERIN C M,et al.Quantification of Process Induced Disorder in Milled Samples Using Different Analytical Techniques[J].Pharmaceutics,2010,2(1):30-49.
[28] UEDA H,IDA Y,KADOTA K,et al.Raman mapping for kinetic analysis of crystallization of amorphous drug based on distributional images[J].Int J Pharm,2014,462(1-2):115-122.
[29] BONAWI-TAN W,WILLIAMS J A S.Online Quality Control with Raman Spectroscopy in Pharmaceutical Tablet Manufacturing[J].J Manuf Syst,2004,23(4):299-308.
[30] WIRGES M,MULLER J,KASA P,et al.From Mini to Micro Scale-Feasibility of Raman Spectroscopy as a Process Analytical Tool (PAT)[J].Pharmaceutics,2011,3(4):723-730.
[31] MOORE S S,VILLAUMIE J.A transferable non-destructive method for the quantification of coronary stent coating components using Raman spectroscopy[J].J Raman Spectrosc,2015,46,353-360.
[32] SHENDE C,SMITH W,BROUILLETTE C,et al.Drug stability analysis by Raman spectroscopy[J].Pharmaceutics,2014,6(4):651-662.
[33] GIL O M,ROCHA M A,L V R.Constantino,et al.Modified drug release system based on Sulindac and layered double hydroxide:An in vivo Raman investigation[J].Vib Spectrosc,2016,87,60-66.
[34] ZONG S,WANG Z,CHEN H,et al.Surface enhanced Raman scattering traceable and glutathione responsive nanocarrier for the intracellular drug delivery[J].Anal Chem,2013,85(4):2223-2230.
[35] FARQUHARSON S,SHENDE C,INSCORE F E,et al.Analysis of 5-fluorouracil in saliva using surface-enhanced Raman spectroscopy[J].J Raman Spectrosc,2005,36:208-212.
[36] PU Y,MEDENDORP J P,YONZON C R.Real-time monitoring of active ingredient dispersion in a pharmaceutical aqueous suspension using Raman spectroscopy[J].J Raman Spectrosc,2011,42,1994-1999.
[37] SAHOO S,CHAKRABORTI C,BEHERA P,et al.FTIR and Raman Spectroscopic Investigations of a Norfloxacin/Carbopol934 Polymeric Suspension[J].J Young Pharm,2012,4(3):138-145.
[38] FABRICIOVA G,SANCHEZ-CORTES S,GARCIA-RAMOS J V,et al.Joint application of micro-Raman and surface-enhanced Raman spectroscopy to the interaction study of the antitumoral anthraquinone drugs danthron and quinizarin with albumins[J].J Raman Spectrosc,2004,35:384-389.
[39] BENEVIDES J M,KAWAKAMI J,JR G J T.Mechanisms of drug-DNA recognition distinguished by Raman spectroscopy[J].J Raman Spectrosc,2008,39:1627-1634.
[40] FOX C B,HARRIS J M.Confocal Raman microscopy for simultaneous monitoring of partitioning and disordering of tricyclic antidepressants in phospholipid vesicle membranes[J].J Raman Spectrosc,2010,41,498-507.
[41] FROSCH T,KUSTNER B,SCHLUCKER S,et al.In vitro polarization-resolved resonance Raman studies of the interaction of hematin with the antimalarial drug chloroquine[J].J Raman Spectrosc,2004,35:819-821.
[42] C?NT?-P?NZARU S,PEICA N,KUSTNER B,et al.FT-Raman and NIR-SERS characterization of the antimalarial drugs chloroquine and mefloquine and their interaction with hematin[J].J Raman Spectrosc,2006,37:326-334.
[43] NEUGEBAUER U,ROSCH P,POPP J.Raman spectroscopy towards clinical application:drug monitoring and pathogen identification[J].Int J Antimicrob Agents,2015,46 Suppl 1:S35-39.
[44] SAHA A,YAKOVLEV V V.Towards a rational drug design:Raman micro-spectroscopy analysis of prostate cancer cells treated with an aqueous extract of Nerium Oleander[J].J Raman Spectrosc,2009,40,1459-1460.
[45] REKHA P,ARUNA P,BHARANIDHARAN G,et al.Ganesan Bharanidharan,Near infrared Raman spectroscopic characterization of blood plasma of normal,oral premalignant and malignant conditions-a pilot study[J].J Raman Spectrosc,2015,46,735-743.
[46] PABLO J G,ARMISTEAD F J,PEYMAN S A,et al.Peyman,Biochemical fingerprint of colorectal cancer cell lines using label‐free live single‐cell Raman spectroscopy[J].J Raman Spectrosc,2018,49:1323-1332.
[47] LIU R,XIONG Y,GUO Y,et al.Label-free and non-invasive BS-SERS detection of liver cancer based on the solid device of silver nanofilm[J].J Raman Spectrosc,2018,49:1426-1434
[2] ALI E M Ai,EDWARDS H G M.Screening of textiles for contraband drugs using portable Raman spectroscopy and chemometrics[J].J Raman Spectrosc,2014,45,253-258.
[3] ALI E M Ai,EDWARDS H G M,COX R.Forensic and security applications of a longwavelength dispersive Raman system[J].J Raman Spectrosc,2015,46,322-326.
[4] TSUBOI M,BENEVIDES J M,JR G J T.The Complex of Ethidium Bromide with Genomic DNA:Structure Analysis by Polarized Raman Spectroscopy[J].Biophys J,2007,92(3):928-934.
[5] GUIRGUIS A,GIROTTO S,BERTI B,et al.Identification of new psychoactive substances (NPS)using handheld Raman spectroscopy employing both 785 and 1064nm laser sources[J].Forensic Sci Int,2017,273:113-123.
[6] HARGREAVES M D,PAGE K,MUNSHI T,et al.Analysis of seized drugs using portable Raman spectroscopy in an airport environment-a proof of principle study[J].J Raman Spectrosc,2008,39:873-880.
[7] WEYERMANN C,MIMOUNE Y,ANGLADAET F,et al.Applications of a transportable Raman spectrometer for the in situ detection of controlled substances at border controls[J].Forensic Sci Int,2011,209(1-3):21-28.
[8] WEST M J,WENT M J.The spectroscopic detection of drugs of abuse on textile fibres after recovery with adhesive lifters[J].Forensic Sci Int,2009,189(1-3),100-103.
[9] DIES H,RAVEENDRAN J,ESCOBEDO C,et al.Rapid identification and quantification of illicit drugs on nanodendritic surface-enhanced Raman scattering substrates[J].Sensor Actuat B-Chem,2018,257,382-388.
[10] MORENO V M,LOPEZ-LOPEZ M,ATOCHE J C,et al.Raman identification of drug of abuse particles collected with colored and transparent tapes[J].Sci Justice,2014,54(2):164-169.
[11] DEGARDIN K,DESPONDS A,ROGGO Y,et al.Protein-based medicines analysis by Raman spectroscopy for the detection of counterfeits[J].Forensic Sci Int,2017,278:313-325.
[12] LAWSON L S,RODRIGUEZ J D.Raman Barcode for Counterfeit Drug Product Detection[J].Anal Chem,2016,88(9):4706-4713.
[13] ROGGO Y,DEGARDIN K,MARGOT P,et al.Identification of pharmaceutical tablets by Raman spectroscopy and chemometrics[J].Talanta,2010,81(3):988-995.
[14] VEIJ M D,VANDENABEELE P,HALL K A,et al.Fast detection and identification of counterfeit antimalarial tablets by Raman spectroscopy[J].J Raman Spectrosc,2007,38,181-187.
[15] Fox J.D,Waverka K.N,Verbeck G.F,et al.Gold-plating of Mylar lift films to capitalize on surface enhanced Raman spectroscopy for chemical extraction of drug residues[J].Forensic Sci Int,2012,216(1-3):141-145.
[16] LE L M M,BERGE M,TFAYLI A,et al.Rapid discrimination and quantification analysis of five antineoplastic drugs in aqueous solutions using Raman spectroscopy[J].Eur J Pharm Sci,2018,111,158-166.
[17] PENIDO C A F D O,PACHECO M T T,NOVOTNY E H,et al.Quantification of cocaine in ternary mixtures using partial least squares regression applied to Raman and Fourier transform infrared spectroscopy[J].J Raman Spectrosc,2017,48:1732-1743.
[18] TONDEPU C,TOTH R,NAVIN C V,et al.Screening of unapproved drugs using portable Raman spectroscopy[J].Anal Chim Acta,2017,973,75-81.
[19] REBIERE H,MARTIN M,GHYSELINCK C,et al.Raman chemical imaging for spectroscopic screening and direct quantification of falsified drugs[J].J Pharm Biomed Anal,148:316-323.
[20] FRANZEN L,SELZER D,FLUHR J.W,et al.Towards drug quantification in human skin with confocal Raman microscopy[J].Eur J Pharm Biopharm,2013,84(2):437-444.
[21] LI X,CHEN H,ZHU Q,et al.Analysis of low active-pharmaceutical-ingredient signal drugs based on thin layer chromatography and surface-enhanced Raman spectroscopy[J].2016,J Pharm Biomed Anal,131:410-419.
[22] FROSCH T,YAN D,POPP J.Ultrasensitive fiber enhanced UV resonance Raman sensing of drugs[J].Anal Chem,2013,85(13):6264-6271.
[23] SCHMIDT A G,WARTEWIG S,PICKER K M.Polyethylene oxides:protection potential against polymorphic transitions of drugs[J].J Raman Spectrosc,2004,35:360-367.
[24] YING Y,BECK C,WU A,et al.Polymorph formation in fenofibrate in the absence and presence of polymer stabilizers:a low wavenumber Raman and differential scanning calorimetry study[J].J Raman Spectrosc,2017,48,750-757.
[25] WABUYELE B W,SOTTHIVIRAT S,ZHOU G X,et al.Dispersive Raman Spectroscopy for Quantifying Amorphous Drug Content in Intact Tablets[J].J Pharm Sci,2017,106(2):579-588.
[26] STRACHAN C J,PRATIWI D,GORDON K C,et al.Quantitative analysis of polymorphic mixtures of carbamazepine by Raman spectroscopy and principal components analysis[J].J Raman Spectrosc,2004,35:347-352.
[27] ZIMPER U,AALTONEN J,MCGOVERIN C M,et al.Quantification of Process Induced Disorder in Milled Samples Using Different Analytical Techniques[J].Pharmaceutics,2010,2(1):30-49.
[28] UEDA H,IDA Y,KADOTA K,et al.Raman mapping for kinetic analysis of crystallization of amorphous drug based on distributional images[J].Int J Pharm,2014,462(1-2):115-122.
[29] BONAWI-TAN W,WILLIAMS J A S.Online Quality Control with Raman Spectroscopy in Pharmaceutical Tablet Manufacturing[J].J Manuf Syst,2004,23(4):299-308.
[30] WIRGES M,MULLER J,KASA P,et al.From Mini to Micro Scale-Feasibility of Raman Spectroscopy as a Process Analytical Tool (PAT)[J].Pharmaceutics,2011,3(4):723-730.
[31] MOORE S S,VILLAUMIE J.A transferable non-destructive method for the quantification of coronary stent coating components using Raman spectroscopy[J].J Raman Spectrosc,2015,46,353-360.
[32] SHENDE C,SMITH W,BROUILLETTE C,et al.Drug stability analysis by Raman spectroscopy[J].Pharmaceutics,2014,6(4):651-662.
[33] GIL O M,ROCHA M A,L V R.Constantino,et al.Modified drug release system based on Sulindac and layered double hydroxide:An in vivo Raman investigation[J].Vib Spectrosc,2016,87,60-66.
[34] ZONG S,WANG Z,CHEN H,et al.Surface enhanced Raman scattering traceable and glutathione responsive nanocarrier for the intracellular drug delivery[J].Anal Chem,2013,85(4):2223-2230.
[35] FARQUHARSON S,SHENDE C,INSCORE F E,et al.Analysis of 5-fluorouracil in saliva using surface-enhanced Raman spectroscopy[J].J Raman Spectrosc,2005,36:208-212.
[36] PU Y,MEDENDORP J P,YONZON C R.Real-time monitoring of active ingredient dispersion in a pharmaceutical aqueous suspension using Raman spectroscopy[J].J Raman Spectrosc,2011,42,1994-1999.
[37] SAHOO S,CHAKRABORTI C,BEHERA P,et al.FTIR and Raman Spectroscopic Investigations of a Norfloxacin/Carbopol934 Polymeric Suspension[J].J Young Pharm,2012,4(3):138-145.
[38] FABRICIOVA G,SANCHEZ-CORTES S,GARCIA-RAMOS J V,et al.Joint application of micro-Raman and surface-enhanced Raman spectroscopy to the interaction study of the antitumoral anthraquinone drugs danthron and quinizarin with albumins[J].J Raman Spectrosc,2004,35:384-389.
[39] BENEVIDES J M,KAWAKAMI J,JR G J T.Mechanisms of drug-DNA recognition distinguished by Raman spectroscopy[J].J Raman Spectrosc,2008,39:1627-1634.
[40] FOX C B,HARRIS J M.Confocal Raman microscopy for simultaneous monitoring of partitioning and disordering of tricyclic antidepressants in phospholipid vesicle membranes[J].J Raman Spectrosc,2010,41,498-507.
[41] FROSCH T,KUSTNER B,SCHLUCKER S,et al.In vitro polarization-resolved resonance Raman studies of the interaction of hematin with the antimalarial drug chloroquine[J].J Raman Spectrosc,2004,35:819-821.
[42] C?NT?-P?NZARU S,PEICA N,KUSTNER B,et al.FT-Raman and NIR-SERS characterization of the antimalarial drugs chloroquine and mefloquine and their interaction with hematin[J].J Raman Spectrosc,2006,37:326-334.
[43] NEUGEBAUER U,ROSCH P,POPP J.Raman spectroscopy towards clinical application:drug monitoring and pathogen identification[J].Int J Antimicrob Agents,2015,46 Suppl 1:S35-39.
[44] SAHA A,YAKOVLEV V V.Towards a rational drug design:Raman micro-spectroscopy analysis of prostate cancer cells treated with an aqueous extract of Nerium Oleander[J].J Raman Spectrosc,2009,40,1459-1460.
[45] REKHA P,ARUNA P,BHARANIDHARAN G,et al.Ganesan Bharanidharan,Near infrared Raman spectroscopic characterization of blood plasma of normal,oral premalignant and malignant conditions-a pilot study[J].J Raman Spectrosc,2015,46,735-743.
[46] PABLO J G,ARMISTEAD F J,PEYMAN S A,et al.Peyman,Biochemical fingerprint of colorectal cancer cell lines using label‐free live single‐cell Raman spectroscopy[J].J Raman Spectrosc,2018,49:1323-1332.
[47] LIU R,XIONG Y,GUO Y,et al.Label-free and non-invasive BS-SERS detection of liver cancer based on the solid device of silver nanofilm[J].J Raman Spectrosc,2018,49:1426-1434
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