{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,14]],"date-time":"2026-07-14T20:59:03Z","timestamp":1784062743149,"version":"3.55.0"},"reference-count":44,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2020,3,1]],"date-time":"2020-03-01T00:00:00Z","timestamp":1583020800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2020,3,1]],"date-time":"2020-03-01T00:00:00Z","timestamp":1583020800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2020,4,2]],"date-time":"2020-04-02T00:00:00Z","timestamp":1585785600000},"content-version":"vor","delay-in-days":32,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100005881","name":"Emberi Eroforr\u00e1sok Miniszt\u00e9riuma","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100005881","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Journal of Chromatography A"],"published-print":{"date-parts":[[2020,3]]},"DOI":"10.1016\/j.chroma.2019.460771","type":"journal-article","created":{"date-parts":[[2019,12,4]],"date-time":"2019-12-04T22:39:01Z","timestamp":1575499141000},"page":"460771","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":11,"special_numbering":"C","title":["Enantioseparation of \u00df-carboline, tetrahydroisoquinoline and benzazepine analogues of pharmaceutical importance: Utilization of chiral stationary phases based on polysaccharides and sulfonic acid modified Cinchonaalkaloids in high-performance liquid and subcritical fluid chromatography"],"prefix":"10.1016","volume":"1615","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8282-457X","authenticated-orcid":false,"given":"Istv\u00e1n","family":"Ilisz","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Attila","family":"Bajtai","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Istv\u00e1n","family":"Szatm\u00e1ri","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ferenc","family":"F\u00fcl\u00f6p","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7473-7596","authenticated-orcid":false,"given":"Wolfgang","family":"Lindner","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Antal","family":"P\u00e9ter","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.chroma.2019.460771_bib0001","series-title":"Alkaloids: Nature\u2019s Curse or Blessing, First ed., Verlag Helvetica Chimica Acta","author":"Hesse","year":"2002"},{"key":"10.1016\/j.chroma.2019.460771_bib0002","first-page":"103","article-title":"The Sarpagine Group of Indole Alkaloids","author":"Lounasmaa","year":"1999"},{"key":"10.1016\/j.chroma.2019.460771_bib0003","doi-asserted-by":"crossref","first-page":"3378","DOI":"10.1016\/j.tet.2009.02.051","article-title":"Novel chemistry of \u00df-carbolines. Expedient synthesis of polycyclic scaffolds","volume":"65","author":"Gonz\u00e1lez-G\u00f3mez","year":"2009","journal-title":"Tetrahedron"},{"key":"10.1016\/j.chroma.2019.460771_bib0004","doi-asserted-by":"crossref","first-page":"3306","DOI":"10.1016\/j.bmcl.2008.04.030","article-title":"Synthesis of 2-[3-(7-chloro-quinolin-4-ylamino)-alkyl]-1-(substituted phenyl)-2,3,4,9-tetrahydro-1H-\u03b2-carbolines as a new class of antimalarial agents","volume":"14","author":"Gupta","year":"2008","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.chroma.2019.460771_bib0005","doi-asserted-by":"crossref","first-page":"3104","DOI":"10.1021\/jm701066a","article-title":"Lavendamycin antitumor agents: structure-based design, synthesis, and NAD(P)H: quinone oxidoreductase 1 (NQO1) model validation with molecular docking and biological studies","volume":"51","author":"Hassani","year":"2008","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.chroma.2019.460771_bib0006","series-title":"Isoquinolines, Part Two","author":"Kathawala","year":"1990"},{"key":"10.1016\/j.chroma.2019.460771_bib0007","doi-asserted-by":"crossref","first-page":"208","DOI":"10.1111\/j.0953-8194.2004.01156.x","article-title":"Stress-, as well as suckling-induced prolactin release is blocked by a structural analog of the putative hypophyseotrofic prolactin-releasing factor, salsolinol","volume":"16","author":"Bodn\u00e1r","year":"2004","journal-title":"J. Neuroendocrinol."},{"key":"10.1016\/j.chroma.2019.460771_bib0008","doi-asserted-by":"crossref","first-page":"170","DOI":"10.2174\/1573407211666150910202200","article-title":"Pharmacological and biological activities of benzazepines: an overview","volume":"11","author":"Shah","year":"2015","journal-title":"Curr. Bioactive. Comp."},{"key":"10.1016\/j.chroma.2019.460771_bib0009","doi-asserted-by":"crossref","first-page":"3858","DOI":"10.1016\/j.ejmech.2011.05.054","article-title":"Design, synthesis and bioevaluation of novel candidate selective estrogen receptor modulators","volume":"46","author":"Yadav","year":"2011","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.chroma.2019.460771_bib0010","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1016\/j.ejmech.2013.04.061","article-title":"Synthesis and antimosquito properties of 2,6-substituted benzo[d]thiazole and 2,4-substituted benzo[d]thiazole analogues against Anopheles arabiensis","volume":"65","author":"Venugopala","year":"2013","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.chroma.2019.460771_bib0011","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1016\/S0021-9673(97)00938-2","article-title":"High-performance liquid chromatographic separation of enantiomers of unusual amino acids on a teicoplanin chiral stationary phase","volume":"793","author":"P\u00e9ter","year":"1998","journal-title":"J. Chromatogr. A"},{"key":"10.1016\/j.chroma.2019.460771_bib0012","doi-asserted-by":"crossref","first-page":"337","DOI":"10.1007\/s10337-012-2194-8","article-title":"Analytical and preparative chiral separation of \u00df\u2013carboline derivatives, LDL oxidation inhibitors, using HPLC and CE methodologies: determination of enantiomeric purity","volume":"75","author":"Lipka","year":"2012","journal-title":"Chromatographia"},{"key":"10.1016\/j.chroma.2019.460771_bib0013","doi-asserted-by":"crossref","first-page":"313","DOI":"10.1016\/S0378-4347(96)00359-3","article-title":"Assay for the (R)- and (S)-enantiomers of salsolinols in biological samples and foods with ion-pair high-performance liquid chromatography using \u03b2-cyclodextrin as a chiral mobile phase additive","volume":"689","author":"Deng","year":"1997","journal-title":"J. Chromatogr. B"},{"key":"10.1016\/j.chroma.2019.460771_bib0014","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1016\/0378-4347(95)00136-7","article-title":"Determination of the (R)-enantiomers and (S)-enantiomers of salsolinol and N-methylsalsolinol by use of a chiral high-performance liquid-chromatographic column","volume":"670","author":"Deng","year":"1995","journal-title":"J. Chromatogr. B"},{"key":"10.1016\/j.chroma.2019.460771_bib0015","doi-asserted-by":"crossref","first-page":"S123","DOI":"10.1007\/s10337-011-1991-9","article-title":"Enantioseparation of 1-phenyl-1,2,3,4-tetrahydroisoqunoline on polysaccharide-based chiral stationary phases","volume":"73","author":"Kazoka","year":"2011","journal-title":"Chromatographia"},{"key":"10.1016\/j.chroma.2019.460771_bib0016","doi-asserted-by":"crossref","first-page":"142","DOI":"10.1002\/bmc.3002","article-title":"High-performance liquid chromatographic enantioseparation of naphthol-substituted tetrahydroisoquinolines on polysaccharide-based chiral stationary phases","volume":"28","author":"Ilisz","year":"2014","journal-title":"Biomed. Chromatogr."},{"key":"10.1016\/j.chroma.2019.460771_bib0017","doi-asserted-by":"crossref","first-page":"4071","DOI":"10.1016\/j.chroma.2011.04.088","article-title":"Liquid chromatographic resolution of 1-aryl-1,2,3,4-tetrahydroisoquinolines on a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid","volume":"1218","author":"Lee","year":"2011","journal-title":"J. Chromatogr. A"},{"key":"10.1016\/j.chroma.2019.460771_bib0018","doi-asserted-by":"crossref","first-page":"961","DOI":"10.1007\/s00216-014-8247-0","article-title":"High-performance liquid chromatographic enantioseparation of cationic 1,2,3,4-tetrahydroisoquinoline analogs on Cinchona alkaloid-based zwitterionic chiral stationary phases","volume":"407","author":"Ilisz","year":"2015","journal-title":"Anal. Bioanal. Chem."},{"key":"10.1016\/j.chroma.2019.460771_bib0019","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1016\/j.chroma.2012.10.033","article-title":"Recent developments on polysaccharide-based chiral stationary phases for liquid-phase separation of enantiomers","volume":"1269","author":"Chankvetadze","year":"2012","journal-title":"J. Chromatogr. A"},{"key":"10.1016\/j.chroma.2019.460771_bib0020","doi-asserted-by":"crossref","first-page":"56","DOI":"10.1016\/j.chroma.2016.05.061","article-title":"Chiral recognition in separation science \u2013 an update","volume":"1467","author":"Scriba","year":"2016","journal-title":"J. Chromatogr. A"},{"key":"10.1016\/j.chroma.2019.460771_bib0021","doi-asserted-by":"crossref","first-page":"44","DOI":"10.1016\/j.chroma.2014.01.075","article-title":"Enantioseparation of \u03b2;2-amino acids on cinchona alkaloid-based zwitterionic chiral stationary phases. Structural and temperature effects","volume":"1334","author":"Ilisz","year":"2014","journal-title":"J. Chromatogr. A"},{"key":"10.1016\/j.chroma.2019.460771_bib0022","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1016\/j.chroma.2014.06.087","article-title":"Direct high-performance liquid chromatographic enantioseparation of secondary amino acids on Cinchona alkaloid-based chiral zwitterionic stationary phases. Unusual temperature behavior","volume":"1363","author":"Ilisz","year":"2014","journal-title":"J. Chromatogr. A"},{"key":"10.1016\/j.chroma.2019.460771_bib0023","doi-asserted-by":"crossref","first-page":"8780","DOI":"10.1021\/ac801384f","article-title":"Synergistic effects on enantioselectivity of zwitterionic chiral stationary phases for separations of chiral acids, bases, and amino acids by HPLC","volume":"80","author":"Hoffmann","year":"2008","journal-title":"Anal. Chem."},{"key":"10.1016\/j.chroma.2019.460771_bib0024","doi-asserted-by":"crossref","first-page":"1560","DOI":"10.1002\/jssc.201200103","article-title":"Increments to chiral recognition facilitating enantiomer separations of chiral acids, bases, and ampholytes using Cinchona-based zwitterion exchanger chiral stationary phases","volume":"35","author":"Wernisch","year":"2012","journal-title":"J. Sep. Sci."},{"key":"10.1016\/j.chroma.2019.460771_bib0025","doi-asserted-by":"crossref","first-page":"611","DOI":"10.2174\/1570179413666151218201331","article-title":"One-pot \u03b1-arylation of \u03b2-carboline with indole and naphthol derivatives","volume":"13","author":"Sas","year":"2014","journal-title":"Curr. Org. Synth."},{"key":"10.1016\/j.chroma.2019.460771_bib0026","doi-asserted-by":"crossref","first-page":"7216","DOI":"10.1016\/j.tet.2015.03.011","article-title":"Selective N-alkylation of isoquinolines, benzazepines and thienopyridines with aromatic aldehydes and naphthols","volume":"71","author":"Sas","year":"2015","journal-title":"Tetrahedron"},{"key":"10.1016\/j.chroma.2019.460771_bib0027","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S0021-9673(02)01444-9","article-title":"Influence of mobile phase acid-base equilibria on the chromatographic behaviour of protolytic compounds","volume":"982","author":"Roses","year":"2002","journal-title":"J. Chromatogr. A"},{"key":"10.1016\/j.chroma.2019.460771_bib0028","doi-asserted-by":"crossref","first-page":"180","DOI":"10.1016\/j.chroma.2018.05.064","article-title":"Dedicated comparisons of diverse polysaccharide- and zwitterionic Cinchona alkaloid-based chiral stationary phases probed with basic and ampholitic indole analogs in liquid and subcritical fluid chromatography mode","volume":"1563","author":"Bajtai","year":"2018","journal-title":"J. Chromatogr. A"},{"key":"10.1016\/j.chroma.2019.460771_bib0029","doi-asserted-by":"crossref","first-page":"2779","DOI":"10.1002\/jssc.201900228","article-title":"High-performance liquid chromatographic and subcritical fluid chromatographic separation of \u03b1;-arylated \u00df-carboline, N-alkylated tetrahydroisoquinolines and their bioisosteres on polysaccharide-based chiral stationary phases","volume":"42","author":"Bajtai","year":"2019","journal-title":"J. Sep. Sci."},{"key":"10.1016\/j.chroma.2019.460771_bib0030","doi-asserted-by":"crossref","first-page":"1266","DOI":"10.1002\/jssc.201701293","article-title":"Chiral separation of helical chromenes with chloromethyl phenylcarbamate polysaccharide-based stationary phases","volume":"41","author":"Ianni","year":"2018","journal-title":"J. Sep. Sci."},{"key":"10.1016\/j.chroma.2019.460771_bib0031","doi-asserted-by":"crossref","first-page":"140","DOI":"10.1002\/jssc.201200885","article-title":"HPLC separation of enantiomers of chiral arylpropionic acid derivatives using polysaccharide based chiral columns and normal phase eluents with emphasis on elution order","volume":"36","author":"Matarshvili","year":"2013","journal-title":"J. Sep. Sci."},{"key":"10.1016\/j.chroma.2019.460771_bib0032","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1002\/bmc.3015","article-title":"The effect of mobile phase composition in the enantioseparation of pharmaceutically relevant compounds with polysaccharide-based stationary phases","volume":"28","author":"Sardella","year":"2014","journal-title":"Biomed. Chromatogr."},{"key":"10.1016\/j.chroma.2019.460771_bib0033","doi-asserted-by":"crossref","first-page":"4886","DOI":"10.1016\/j.chroma.2010.12.031","article-title":"Study of the enantiomeric separation of an acetamide intermediate by using supercritical fluid chromatography and several polysaccharide based chiral stationary phase","volume":"1218","author":"Toribio","year":"2011","journal-title":"J. Chromatogr. A"},{"key":"10.1016\/j.chroma.2019.460771_bib0034","doi-asserted-by":"crossref","first-page":"197","DOI":"10.1016\/j.chroma.2014.11.033","article-title":"Insights into chiral recognition mechanisms in supercritical fluid chromatography V. Effect of the nature and proportion of alcohol mobile phase modifier with amylose and cellulose tris-(3,5-dimethylphenylcarbamate) stationary phases","volume":"1373","author":"Khater","year":"2014","journal-title":"J. Chromatogr. A"},{"key":"10.1016\/j.chroma.2019.460771_bib0035","doi-asserted-by":"crossref","first-page":"1471","DOI":"10.1002\/jssc.201701341","article-title":"Cellulose tris-(3,5-dimethylphenylcarbamate)-based chiral stationary phase for the enantioseparation of drugs in supercritical fluid chromatography: comparison with HPLC","volume":"41","author":"Kal\u00edkov\u00e1","year":"2018","journal-title":"J. Sep. Sci."},{"key":"10.1016\/j.chroma.2019.460771_bib0036","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1016\/j.chroma.2019.03.028","article-title":"Fast enantioseparation of indole phytoalexins in additive free supercritical fluid chromatography","volume":"1596","author":"Kozlov","year":"2019","journal-title":"J. Chromatogr. A"},{"key":"10.1016\/j.chroma.2019.460771_bib0037","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/S0021-9673(03)01262-7","article-title":"Effects of alcohol mobile-phase modifiers on the structure and chiral selectivity of amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase","volume":"1015","author":"Wang","year":"2003","journal-title":"J. Chromatogr. A"},{"key":"10.1016\/j.chroma.2019.460771_bib0038","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1002\/chir.22690","article-title":"Evaluation of the chiral recognition properties and the column performances of three chiral stationary phases based on cellulose for the enantioseparation of six dihydropyridines by high-performance liquid chromatography","volume":"29","author":"Yu","year":"2017","journal-title":"Chirality"},{"key":"10.1016\/j.chroma.2019.460771_bib0039","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1016\/j.chroma.2017.03.077","article-title":"Chemometric evaluation of the combined effect of temperature, pressure, and co-solvent fractions on the chiral separation of basic pharmaceuticals using actual vs set operational conditions","volume":"1499","author":"Foss","year":"2017","journal-title":"J. Chromatogr. A"},{"key":"10.1016\/j.chroma.2019.460771_bib0040","doi-asserted-by":"crossref","first-page":"4190","DOI":"10.1021\/ac0103672","article-title":"Solid-state NMR characterization of amylose tris(3,5-dimethylphenylcarbamate) chiral stationary-phase structure as a function of mobile-phase composition","volume":"73","author":"Wenslow","year":"2001","journal-title":"Anal. Chem."},{"key":"10.1016\/j.chroma.2019.460771_bib0041","doi-asserted-by":"crossref","first-page":"479","DOI":"10.1023\/A:1007923124523","article-title":"The orientation of N-H..O=C and NH...N hydrogen bonds in biological systems: how good is a point charge as a model for a hydrogen bonding","volume":"11","author":"Apaya","year":"1997","journal-title":"J. Comput. Aided Mol. Des."},{"key":"10.1016\/j.chroma.2019.460771_bib0042","first-page":"1955","article-title":"Chromatography on chiral stationary phases","volume":"7","author":"Allenmark","year":"1997","journal-title":"J. Mater. Sci."},{"key":"10.1016\/j.chroma.2019.460771_bib0043","doi-asserted-by":"crossref","first-page":"1254","DOI":"10.1021\/ja9631458","article-title":"Thermodynamic study of an unusual chiral separation - propranolol enantiomers on an immobilized cellulose","volume":"119","author":"Fornstedt","year":"1997","journal-title":"J. Amer. Chem. Soc."},{"key":"10.1016\/j.chroma.2019.460771_bib0044","doi-asserted-by":"crossref","first-page":"1319","DOI":"10.1002\/jssc.201701264","article-title":"Van\u2019t Hoff analysis in chiral chromatography","volume":"41","author":"Asnin","year":"2018","journal-title":"J. Sep. Sci."}],"container-title":["Journal of Chromatography A"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S002196731931218X?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S002196731931218X?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,11,3]],"date-time":"2025-11-03T17:54:40Z","timestamp":1762192480000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S002196731931218X"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,3]]},"references-count":44,"alternative-id":["S002196731931218X"],"URL":"https:\/\/doi.org\/10.1016\/j.chroma.2019.460771","relation":{},"ISSN":["0021-9673"],"issn-type":[{"value":"0021-9673","type":"print"}],"subject":[],"published":{"date-parts":[[2020,3]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Enantioseparation of \u00df-carboline, tetrahydroisoquinoline and benzazepine analogues of pharmaceutical importance: Utilization of chiral stationary phases based on polysaccharides and sulfonic acid modified Cinchonaalkaloids in high-performance liquid and subcritical fluid chromatography","name":"articletitle","label":"Article Title"},{"value":"Journal of Chromatography A","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.chroma.2019.460771","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2020 The Authors. Published by Elsevier B.V.","name":"copyright","label":"Copyright"}],"article-number":"460771"}}