An overview of chiral separations of pharmaceutically active substances by HPLC (2018-2020)
Status PubMed-not-MEDLINE Jazyk angličtina Země Rakousko Médium print-electronic
Typ dokumentu časopisecké články, přehledy
PubMed
34456367
PubMed Central
PMC8382579
DOI
10.1007/s00706-021-02832-5
PII: 2832
Knihovny.cz E-zdroje
- Klíčová slova
- Chiral resolution, Chiral stationary phase, HPLC, Pharmaceutical compounds,
- Publikační typ
- časopisecké články MeSH
- přehledy MeSH
This review provides a brief survey of chiral separation of pharmaceutically active substances published over the last 3 years (2018-2020). Chiral separation of drugs is an important area of research. The control of enantiomeric purity and determination of individual enantiomeric drug molecules is a necessity especially for clinical, analytical, and regulatory purposes. Among chromatographic resolution methods, high-performance liquid chromatography based on chiral stationary phases remains the most popular and effective method used for chiral separation of various drugs. In this review, attention is paid to several classes of chiral stationary phases that have been the most frequently used for drug enantioseparation during this period.
Zobrazit více v PubMed
Nag A. Asymmetric synthesis of drugs and natural products. Boca Raton: CRC Press; 2018.
McBride WG. Lancet. 1961;278:1358. doi: 10.1016/S0140-6736(61)90927-8. DOI
Witte DT. Pharm World Sci. 1993;15:283. doi: 10.1007/BF01871133. PubMed DOI
Armstrong DW, Zhang B. Anal Chem. 2001;73:557A. doi: 10.1021/ac012526n. PubMed DOI
Ward TJ, Armstrong DW. J Liq Chromatogr. 1986;9:407. doi: 10.1080/01483918608076644. DOI
Tiwari G, Tiwari R, Rai AK. J Pharm Bioallied Sci. 2010;2:72. doi: 10.4103/0975-7406.67003. PubMed DOI PMC
Szejtli J. Chem Rev. 1998;98:1743. doi: 10.1021/cr970022c. PubMed DOI
Scriba GKE. Trends Anal Chem. 2019;120:115639. doi: 10.1016/j.trac.2019.115639. DOI
Wren S. The separation of enantiomers by capillary electrophoresis. Wiesbaden: Vieweg+Teubner Verlag; 2001.
Zhang Y, Guo Z, Ye J, Xu Q, Liang X, Lei A. J Chromatogr A. 2008;1191:188. doi: 10.1016/j.chroma.2007.11.018. PubMed DOI
Sun J, Ma S, Liu B, Yu J, Guo X. Talanta. 2019;204:817. doi: 10.1016/j.talanta.2019.06.071. PubMed DOI
Sun J, Zhu Y, Lin B, Yu J. J Pharm Biomed Anal. 2020;191:113552. doi: 10.1016/j.jpba.2020.113552. PubMed DOI
Sun J, Liu B, Cai L, Yu J, Guo X. New J Chem. 2020;44:10334. doi: 10.1039/D0NJ01516D. DOI
Shuang Y, Zhang T, Li L. J Chromatogr A. 2020;1614:460702. doi: 10.1016/j.chroma.2019.460702. PubMed DOI
Naghdi E, Fakhari AR, Baca M, De Malsche W. J Chromatogr A. 2020;1615:460752. doi: 10.1016/j.chroma.2019.460752. PubMed DOI
Zhang H, Qiu X, Lv L, Sun W, Wang C, Yan J, Tong S. J Sep Sci. 2018;41:2828. doi: 10.1002/jssc.201800231. PubMed DOI
Sun W, Bao H, Qian J, Tong S. J Sep Sci. 2020;44:922. doi: 10.1002/jssc.202001118. PubMed DOI
Casado N, Valimaña-Traverso J, García MÁ, Marina ML. Crit Rev Anal Chem. 2020;50:554. doi: 10.1080/10408347.2019.1670043. PubMed DOI
Solínová V, Kasicka V, Sázelová P, Holý A. Electrophoresis. 2009;30:2245. doi: 10.1002/elps.200800790. PubMed DOI
Řezanka P, Navrátilová K, Řezanka M, Král V, Sýkora D. Electrophoresis. 2014;35:2701. doi: 10.1002/elps.201400145. PubMed DOI
Salido-Fortuna S, Marina ML, Castro-Puyana M. J Chromatogr A. 2020;1621:461085. doi: 10.1016/j.chroma.2020.461085. PubMed DOI
Azhari NR, Yahaya N, Mohd Suah FBM, Prabu S, Hui BY, Shahriman MS, Mohamad Zain NNM, Raoov M. Chirality. 2021;33:37. doi: 10.1002/chir.23285. PubMed DOI
Salido-Fortuna S, Casado N, Castro-Puyana M, Marina ML. Microchem J. 2021;160:105669. doi: 10.1016/j.microc.2020.105669. DOI
Ke J, Yang K, Bai X, Luo H, Ji Y, Chen J. Sep Purif Technol. 2021;255:117717. doi: 10.1016/j.seppur.2020.117717. DOI
León-González ME, Rosales-Conrado N. J Chromatogr A. 2017;1514:88. doi: 10.1016/j.chroma.2017.07.072. PubMed DOI
Yashima E, Okamoto Y. Bull Chem Soc Jpn. 1995;68:3289. doi: 10.1246/bcsj.68.3289. DOI
Yashima E, Yamamoto C, Okamoto Y. Synlett. 1998;1998:344. doi: 10.1055/s-1998-1675. DOI
Yashima E. J Chromatogr A. 2001;906:105. doi: 10.1016/S0021-9673(00)00501-X. PubMed DOI
Cirilli R, Carradori S, Casulli A, Pierini M. J Sep Sci. 2018;41:4014. doi: 10.1002/jssc.201800696. PubMed DOI
Merino MED, Lancioni C, Padró JM, Castells CB. J Chromatogr A. 2020;1634:461685. doi: 10.1016/j.chroma.2020.461685. PubMed DOI
Rosetti A, Ferretti R, Zanitti L, Casulli A, Villani C, Cirilli R. J Pharm Anal. 2020;10:610. doi: 10.1016/j.jpha.2020.11.002. PubMed DOI PMC
Balaji N, Gabani BB, Todmal U, Sulochana SP, Saini NK, Chandran R, Mullangi R. Biomed Chromatogr. 2019;33:e4434. doi: 10.1002/bmc.4434. PubMed DOI
Zhou Q, Gu R, Li P, Lu Y, Chen L, Gu Q. Appl Microbiol Biotechnol. 2020;104:5283. doi: 10.1007/s00253-020-10503-4. PubMed DOI
Wang LY, Qiu BL, Xia H, Xia GY, Xiao BB, Zhang JF, Zhong WC, Lin S. J Nat Prod. 2020;83:489. doi: 10.1021/acs.jnatprod.9b01155. PubMed DOI
Lun J, Ma S, Xue M, Zhao P, Song Y, Guo X. Microchem J. 2021;160:105625. doi: 10.1016/j.microc.2020.105625. DOI
Pandya PA, Shah PA, Shrivastav PS. J Chromatogr A. 2020;1625:461299. doi: 10.1016/j.chroma.2020.461299. PubMed DOI
Kozlov O, Záhoráková D, Gondová T. J Pharm Biomed Anal. 2020;190:113549. doi: 10.1016/j.jpba.2020.113549. PubMed DOI
Miyaguchi H, Kuwayama K. J Chromatogr A. 2017;1519:55. doi: 10.1016/j.chroma.2017.08.058. PubMed DOI
Catto M, Pisani L, de la Mora E, Belviso BD, Mangiatordi GF, Pinto A, Palma AD, Denora N, Caliandro R, Colletier JP, Silman I, Nicolotti O, Altomare CD. ACS Med Chem Lett. 2020;11:869. doi: 10.1021/acsmedchemlett.9b00656. PubMed DOI PMC
Tóth G, Fogarasi E, Bartalis-Fábián G, Foroughbakhshfasaei M, Boldizsár I, Darcsi A, Lohner S, Scriba GK, Szabó ZI. J Chromatogr A. 2020;1626:461388. doi: 10.1016/j.chroma.2020.461388. PubMed DOI
Choppari T, Gunnam S, Chennuru LN, Boddala ChSR, Murthy CP, Talluri KMVN. Chromatographia. 2021;84:297. doi: 10.1007/s10337-021-04004-3. DOI
Zhang J, Liu B, Jiang Z, Cui Y, Guo X. Anal Biochem. 2020;602:113791. doi: 10.1016/j.ab.2020.113791. PubMed DOI
Jiang S, Wu C, Yu J, Sun T, Guo X. Chirality. 2019;31:72. doi: 10.1002/chir.23037. PubMed DOI
Pérez-Baeza M, Escuder-Gilabert L, Martín-Biosca Y, Sagrado S, Medina-Hernández MJ. J Chromatogr A. 2020;1625:461334. doi: 10.1016/j.chroma.2020.461334. PubMed DOI
Karatt KT, Sathiq MA, Laya S. Steroids. 2020;155:108572. doi: 10.1016/j.steroids.2019.108572. PubMed DOI
Li M, Zhang J, Ma S, Jiang Z, Di X, Guo X. New J Chem. 2020;44:5819. doi: 10.1039/D0NJ00095G. DOI
Lee SB, Pham TV, Mai XL, Le TAT, Nguyen TNV, Kang JS, Mar W, Kim KH. Anal Sci Technol. 2020;33:59.
Hikita K, Saigusa S, Takeuchi Y, Matsuyama H, Nagai R, Kato K, Murata T, Tanaka H, Wagh YS, Asao N, Kaneda N. Bioorg Med Chem. 2020;28:115490. doi: 10.1016/j.bmc.2020.115490. PubMed DOI
Jalakam SP, Tambe VS, Deodhar MN, Prakya V, Waghmode J, Pawar P. Pharm Chem J. 2020;54:96. doi: 10.1007/s11094-020-02162-6. DOI
Hägele JS, Basrak M, Schmid MG. J Pharm Biomed Anal. 2020;179:112967. doi: 10.1016/j.jpba.2019.112967. PubMed DOI
Andukuri R, Drincic A, Rendell M. Diabetes Metab Syndr Obes. 2009;2:117. doi: 10.2147/DMSO.S4312. PubMed DOI PMC
Kant R, Bodla RB, Bhutani R, Kapoor G. Adv Pharm Bull. 2019;9:147. doi: 10.15171/apb.2019.018. PubMed DOI PMC
Ianni F, Carotti A, Intagliata S, Macchiarulo A, Chankvetadze B, Pittalà V, Sardella R. Chromatographia. 2020;83:1509. doi: 10.1007/s10337-020-03972-2. DOI
Ferencz E, Kovács B, Boda F, Foroughbakhshfasaei M, Kelemen VK, Tóth G, Szabó ZI. J Pharm Biomed Anal. 2020;177:112851. doi: 10.1016/j.jpba.2019.112851. PubMed DOI
Tse S, Mazzola N. Pharm Ther. 2015;40:810. PubMed PMC
Köteles I, Foroughbakhshfasaei M, Dobó M, Ádám M, Boldizsár I, Szabó ZI, Tóth G. Chromatographia. 2020;83:909. doi: 10.1007/s10337-020-03911-1. DOI
Gill BD, Indyk HE. J AOAC Int. 2020;103:12882. PubMed
Liu H, Ding W. Chirality. 2019;31:219. doi: 10.1002/chir.23050. PubMed DOI
Matarashvili I, Chelidze A, Dolidze G, Kobidze G, Zaqashvili N, Dadianidze A, Bacskay I, Felinger A, Farkas T, Chankvetadze B. J Chromatogr A. 2020;1624:461218. doi: 10.1016/j.chroma.2020.461218. PubMed DOI
Ilisz I, Bajtai A, Szatmári I, Fülöp F, Lindner W, Péter A. J Chromatogr A. 2020;1615:460771. doi: 10.1016/j.chroma.2019.460771. PubMed DOI
Li M, Liang X, Guo X, Di X, Jiang Z. Microchem J. 2020;153:104511. doi: 10.1016/j.microc.2019.104511. DOI
Zhu B, Li S, Zhou L, Li Q, Guo X. Food Chem. 2019;300:125241. doi: 10.1016/j.foodchem.2019.125241. PubMed DOI
Liu Y, Cai L, Lun J, Zhao M, Guo X. New J Chem. 2020;44:18337. doi: 10.1039/D0NJ03657A. DOI
Baksam V, Pocha SNVR, Chakka VB, Ummadi RR, Kumar P. Chirality. 2020;32:1208. doi: 10.1002/chir.23269. PubMed DOI
Ou F, Zhou Y, Lei J, Zeng S, Wu F, Zhang N, Yu L. J Pharm Anal. 2020;10:617. doi: 10.1016/j.jpha.2019.09.002. PubMed DOI PMC
Kannappan V, Kanthiah S. J Anal Chem. 2020;75:349. doi: 10.1134/S1061934820030090. DOI
Xu F, Xu Y, Liu G, Zhang M, Qiang S, Kang J. J Chromatogr A. 2020;1618:460845. doi: 10.1016/j.chroma.2019.460845. PubMed DOI
Lun J, Zhao P, Jiang Z, Song Y, Guo X. Chirality. 2020;32:1129. doi: 10.1002/chir.23257. PubMed DOI
Kenari ME, Putman JI, Singh RP, Fulton BB, Phan H, Haimour RK, Tse K, Berthod A, Lovely CJ, Armstrong DW. Molecules. 2021;26:213. doi: 10.3390/molecules26010213. PubMed DOI PMC
Tome T, Časar Z, Obreza A. Molecules. 2020;25:809. doi: 10.3390/molecules25040809. PubMed DOI PMC
Hofmann J, Fayez S, Scheiner M, Hoffmann M, Oerter S, Appelt-Menzel A, Maher P, Maurice T, Bringmann G, Decker M. Chem Eur J. 2020;26:7299. doi: 10.1002/chem.202001264. PubMed DOI PMC
Agrawal R, Belemkar S, Bonde C (2020) Microchem J 158:105320
Armstrong DW, Tang Y, Chen S, Zhou Y, Bagwill C, Chen JR. Anal Chem. 1994;66:1473. doi: 10.1021/ac00081a019. DOI
Xiao TL, Armstrong DW. Enantiomeric separations by HPLC using macrocyclic glycopeptide-based chiral stationary phases. In: Gübitz G, Schmid MG, editors. Chiral separations. Methods in molecular biology. Totowa: Humana Press; 2004. PubMed
Aboul-Enein HY, Ali I. Chromatographia. 2000;52:679. doi: 10.1007/BF02490991. DOI
Honetschlagerova-Vadinska M, Srkalova S, Bosakova Z, Coufal P, Tesarova E. J Sep Sci. 2009;32:1704. doi: 10.1002/jssc.200800725. PubMed DOI
Folprechtová D, Kalíková K, Kadkhodaei K, Reiterer C, Armstrong DW, Tesařová E, Schmid MG. J Chromatogr A. 2021;1637:461846. doi: 10.1016/j.chroma.2020.461846. PubMed DOI
D’Orazio G, Fanali C, Gentili A, Tagliaro F, Fanali S. J Chromatogr A. 2019;1605:360358. doi: 10.1016/j.chroma.2019.07.012. PubMed DOI
Li J, Liu R, Wang L, Liu X, Gao H. Chirality. 2019;31:236. doi: 10.1002/chir.23052. PubMed DOI
Luo R, Han H, Liu J, Xu D, Wang Q, Fanali S, Jiang Z. J Pharm Biomed Anal. 2020;182:113129. doi: 10.1016/j.jpba.2020.113129. PubMed DOI
Paik MJ, Kang JS, Huang BS, Carey JR, Lee W. J Chromatogr A. 2013;1274:1. doi: 10.1016/j.chroma.2012.11.086. PubMed DOI
Ali I, Suhail M, Al-Othman ZA, Al-Mohaimeed AM, Alwarthan A. Sep Purif Technol. 2020;236:116256. doi: 10.1016/j.seppur.2019.116256. DOI
Lee Y, Bang E, Lee W, Na YC. J Pharm Biomed Anal. 2021;196:113904. doi: 10.1016/j.jpba.2021.113904. PubMed DOI
Bi C, Zheng X, Azaria S, Beeram S, Li Z, Hage D. Separations. 2016;3:27. doi: 10.3390/separations3030027. PubMed DOI PMC
Mitrović M, Protić A, Malenović A, Otašević B, Zečević M. J Pharm Biomed Anal. 2020;180:113034. doi: 10.1016/j.jpba.2019.113034. PubMed DOI
Fu Y, Borrull F, Fontanals N, Marcé RM. Chirality. 2020;32:876. doi: 10.1002/chir.23198. PubMed DOI
Wang W, Guo C, Chen L, Qiu Z, Yin X, Xu J (2021) Environ Pollut 273:116424 PubMed
Zhu B, Xue M, Liu B, Li Q, Guo X. J Pharm Biomed Anal. 2019;176:112803. doi: 10.1016/j.jpba.2019.112803. PubMed DOI
Liu Y, Zhu B, Xue M, Jiang Z, Guo X. Microchem J. 2020;156:104989. doi: 10.1016/j.microc.2020.104989. DOI
Soliman SM. Chirality. 2019;31:185. doi: 10.1002/chir.23046. PubMed DOI
Iwasaki K, Iwasaki A, Sumimoto S, Matsubara T, Sato T, Nozaki T, Saito-Nakano Y, Suenaga KL. J Nat Prod. 2020;83:481. doi: 10.1021/acs.jnatprod.9b01147. PubMed DOI