{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,6]],"date-time":"2026-07-06T15:34:10Z","timestamp":1783352050997,"version":"3.54.6"},"reference-count":38,"publisher":"Oxford University Press (OUP)","issue":"7","license":[{"start":{"date-parts":[[2021,9,11]],"date-time":"2021-09-11T00:00:00Z","timestamp":1631318400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/academic.oup.com\/journals\/pages\/open_access\/funder_policies\/chorus\/standard_publication_model"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2022,9,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Thirteen pairs of I3P enantiomers were screened using nine polysaccharide chiral stationary phases and three different mobile phases. The purification strategy for 13 pairs of I3P enantiomers were designed and optimized considering enantiomeric purity and enrichment of isomers. Out of 13 I3P derivatives which were screened using supercritical fluid chromatography, 10 derivatives displayed excellent baseline separation using a Lux Cellulose\u20144 column and their resolution from higher to lower order of I3P-11, 13, 4, 12, 2, 1, 9, 3, 7 and 8 derivatives whereas in case of Lux Cellulose\u20142 column, the moderate separation was achieved as compared to Cellulose\u20144 in the order I3P-5, 6 and 10 derivatives. Excellent enantiomeric separations and retentions for all 13 I3P enantiomer derivatives were obtained in Cellulose\u20144 and Cellulose\u20142 columns in presences of methanol as organic modifier without any additives except in the case of I3P 12 enantiomer. The absolute stereochemical assignment of the purified isomers was determined through an optical rotation study. Among the series of I3P derivatives, I3P-5 showed potent antioxidant activity against catalase with an IC50 value of 13.78\u00a0\u03bcM. Further molecular docking, MM\/GBSA and molecular dynamics studies revealed that the I3P-5 derivatives effectively bind to catalase with a docking score of \u22125.41\u00a0kcal\/mol. Which validated chiral docking and indicated great potential for enantiomeric separation in drug discovery and present studies (R)\u2014enantiomer preferentially depicts good binding capacity with catalase.<\/jats:p>","DOI":"10.1093\/chromsci\/bmab102","type":"journal-article","created":{"date-parts":[[2021,8,11]],"date-time":"2021-08-11T19:11:56Z","timestamp":1628709116000},"page":"692-704","source":"Crossref","is-referenced-by-count":10,"title":["Enantiomeric Separation of Indole-3-Propanamide Derivatives by Using Supercritical Fluid Chromatography on a Polysaccharide-Based Chiral Stationary Phase"],"prefix":"10.1093","volume":"60","author":[{"given":"Kaveesha Srinivasa","family":"Suryakoppa","sequence":"first","affiliation":[{"name":"Discovery Chemistry\u2014Analytical Research and Development , , Biocon Park, SEZ, Bommasandra Industrial Estate - Phase-IV, Bommasandra\u2014Jigani Link Road, Bengaluru 560 099, Karnataka , India"},{"name":"Syngene International Ltd , , Biocon Park, SEZ, Bommasandra Industrial Estate - Phase-IV, Bommasandra\u2014Jigani Link Road, Bengaluru 560 099, Karnataka , India"},{"name":"Department of Chemistry , Jawaharlal Nehru National College of Engineering, , Shimoga 577204, Karnataka , India"},{"name":"Visvesvaraya Technological University , Jawaharlal Nehru National College of Engineering, , Shimoga 577204, Karnataka , India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vivek Hamse","family":"Kameshwar","sequence":"additional","affiliation":[{"name":"School of Natural Science , , BGSIT campus, Adichunchanagiri University, B. G Nagara, 571448 Mandya, Karnataka , India"},{"name":"Adichunchanagiri University-Center for Research and Innovation , , BGSIT campus, Adichunchanagiri University, B. G Nagara, 571448 Mandya, Karnataka , India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ramesh","family":"Appadurai","sequence":"additional","affiliation":[{"name":"Discovery Chemistry\u2014Analytical Research and Development , , Biocon Park, SEZ, Bommasandra Industrial Estate - Phase-IV, Bommasandra\u2014Jigani Link Road, Bengaluru 560 099, Karnataka , India"},{"name":"Syngene International Ltd , , Biocon Park, SEZ, Bommasandra Industrial Estate - Phase-IV, Bommasandra\u2014Jigani Link Road, Bengaluru 560 099, Karnataka , India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Siddalingamurthy","family":"Eranna","sequence":"additional","affiliation":[{"name":"Research and Development , , R23, Bommasandra industrial area, Jigani Link Road, Bengaluru 560099, Karnataka , India"},{"name":"Synus lab LLP , , R23, Bommasandra industrial area, Jigani Link Road, Bengaluru 560099, Karnataka , India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"M H Moinuddin","family":"Khan","sequence":"additional","affiliation":[{"name":"Department of Chemistry , Jawaharlal Nehru National College of Engineering, , Shimoga 577204, Karnataka , India"},{"name":"Visvesvaraya Technological University , Jawaharlal Nehru National College of Engineering, , Shimoga 577204, Karnataka , India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"286","published-online":{"date-parts":[[2021,9,11]]},"reference":[{"issue":"9","key":"2022090302181696300_ref1","doi-asserted-by":"crossref","first-page":"1233","DOI":"10.1016\/S0960-894X(01)00182-2","article-title":"2-aryl indole NK1 receptor antagonists: Optimisation of indole substitution","volume":"11","author":"Cooper","year":"2001","journal-title":"Bioorganic & Medicinal Chemistry Letters"},{"issue":"5","key":"2022090302181696300_ref2","doi-asserted-by":"crossref","first-page":"598","DOI":"10.1021\/jm00031a009","article-title":"Tyrosine kinase inhibitors. 2. Synthesis of 2,2\u2032-dithiobis(1H-indole-3-alkanamides) and investigation of their inhibitory activity against epidermal growth factor receptor and pp60v-src protein tyrosine kinases","volume":"37","author":"Thompson","year":"1994","journal-title":"Journal of Medicinal Chemistry"},{"issue":"17","key":"2022090302181696300_ref3","doi-asserted-by":"crossref","first-page":"5203","DOI":"10.1016\/j.bmcl.2010.07.001","article-title":"Synthesis of N-aryl-3-(indol-3-yl)propanamides and their immunosuppressive activities","volume":"20","author":"Giraud","year":"2010","journal-title":"Bioorganic & Medicinal Chemistry Letters"},{"issue":"3","key":"2022090302181696300_ref4","doi-asserted-by":"crossref","first-page":"394","DOI":"10.1021\/jm00055a011","article-title":"Substituted 3-(phenylmethyl)-1H-indole-5-carboxamides and 1-(phenylmethyl)indole-6-carboxamides as potent, selective, orally active antagonists of the peptidoleukotrienes","volume":"36","author":"Jacobs","year":"1993","journal-title":"Journal of Medicinal Chemistry"},{"issue":"2","key":"2022090302181696300_ref5","doi-asserted-by":"crossref","first-page":"268","DOI":"10.1016\/j.chroma.2006.04.008","article-title":"Study of the enantiomeric separation of oxfendazole and cetirizine using subcritical fluid chromatography on an amylose-based column","volume":"1121","author":"Toribio","year":"2006","journal-title":"Journal of Chromatography A"},{"issue":"12","key":"2022090302181696300_ref6","doi-asserted-by":"crossref","first-page":"4712","DOI":"10.1021\/ac1010926","article-title":"Chiral separations: Fundamental review 2010","volume":"82","author":"Ward","year":"2010","journal-title":"Analytical Chemistry"},{"issue":"1\u20132","key":"2022090302181696300_ref7","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1016\/j.chroma.2005.03.073","article-title":"Integration of supercritical fluid chromatography into drug discovery as a routine support tool","volume":"1074","author":"White","year":"2005","journal-title":"Journal of Chromatography A"},{"issue":"1\u20132","key":"2022090302181696300_ref8","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1016\/S0021-9673(03)00725-8","article-title":"Rapid method development for chiral separation in drug discovery using sample pooling and supercritical fluid chromatography\u2013mass spectrometry","volume":"1003","author":"Zhao","year":"2003","journal-title":"Journal of Chromatography A"},{"issue":"3","key":"2022090302181696300_ref9","doi-asserted-by":"crossref","first-page":"799","DOI":"10.1016\/j.jpba.2005.06.032","article-title":"Supercritical fluid chromatography\/tandem mass spectrometric method for analysis of pharmaceutical compounds in metabolic stability samples","volume":"40","author":"Hsieh","year":"2006","journal-title":"Journal of Pharmaceutical and Biomedical Analysis"},{"issue":"26","key":"2022090302181696300_ref10","doi-asserted-by":"crossref","first-page":"5140","DOI":"10.1016\/j.chroma.2009.04.069","article-title":"Enantioseparation of paroxetine intermediate on an amylose-derived chiral stationary phase by supercritical fluid chromatography","volume":"1216","author":"Su","year":"2009","journal-title":"Journal of Chromatography A"},{"key":"2022090302181696300_ref11","doi-asserted-by":"crossref","first-page":"242","DOI":"10.1002\/chir.20735","article-title":"Chiral separation of phospine-containing \u03b1-amino acid derivatives using two complementary cellulosic stationary phases in supercritical fluid chromatography","volume":"22","author":"West","year":"2009","journal-title":"Chirality"},{"issue":"12","key":"2022090302181696300_ref12","doi-asserted-by":"crossref","first-page":"4925","DOI":"10.1021\/ac101194x","article-title":"Supercritical fluid chromatography","volume":"82","author":"Taylor","year":"2010","journal-title":"Analytical Chemistry"},{"issue":"1","key":"2022090302181696300_ref13","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1016\/j.jchromb.2008.06.051","article-title":"Common approaches for efficient method development with immobilised polysaccharide-derived chiral stationary phases\u2605","volume":"875","author":"Franco","year":"2008","journal-title":"Journal of Chromatography B"},{"issue":"1\u20132","key":"2022090302181696300_ref14","doi-asserted-by":"crossref","first-page":"214","DOI":"10.1016\/j.chroma.2007.12.026","article-title":"Enantiomer resolution screening strategy using multiple immobilised polysaccharide-based chiral stationary phases","volume":"1191","author":"Zhang","year":"2008","journal-title":"Journal of Chromatography A"},{"issue":"10","key":"2022090302181696300_ref15","doi-asserted-by":"crossref","first-page":"871","DOI":"10.1002\/chir.20680","article-title":"Comparative studies between covalently immobilized and coated chiral stationary phases based on polysaccharide derivatives for enantiomer separation ofN-protected \u03b1-amino acids and their ester derivatives","volume":"21","author":"Jin","year":"2009","journal-title":"Chirality"},{"issue":"2","key":"2022090302181696300_ref16","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1002\/chir.20513","article-title":"Enantioseparation of 2-aryl-1,3-dicarbonyl analogues by high performance liquid chromatography using polysaccharide type chiral stationary phase","volume":"20","author":"Xu","year":"2007","journal-title":"Chirality"},{"issue":"18","key":"2022090302181696300_ref17","doi-asserted-by":"crossref","first-page":"2879","DOI":"10.1080\/10826070802388615","article-title":"Enantiomeric separation of several Oxirane derivatives by high performance liquid chromatography on polysaccharide-based chiral stationary phases","volume":"31","author":"Zhou","year":"2008","journal-title":"Journal of Liquid Chromatography & Related Technologies"},{"issue":"1\u20132","key":"2022090302181696300_ref18","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/S0021-9673(97)00648-1","article-title":"3-Fluoro-, 3-chloro- and 3-bromo-5-methylphenylcarbamates of cellulose and amylose as chiral stationary phases for high-performance liquid chromatographic enantioseparation","volume":"787","author":"Chankvetadze","year":"1997","journal-title":"Journal of Chromatography A"},{"issue":"11","key":"2022090302181696300_ref19","doi-asserted-by":"crossref","first-page":"6077","DOI":"10.1021\/cr8005558","article-title":"Structure control of polysaccharide derivatives for efficient separation of enantiomers by chromatography","volume":"109","author":"Ikai","year":"2009","journal-title":"Chemical Reviews"},{"key":"2022090302181696300_ref20","doi-asserted-by":"crossref","first-page":"523","DOI":"10.1016\/j.envint.2018.09.041","article-title":"Chiral pharmaceuticals: environment sources, potential human health impacts, remediation technologies and future perspective","volume":"121","author":"Zhou","year":"2018","journal-title":"Environment International"},{"issue":"12","key":"2022090302181696300_ref21","doi-asserted-by":"crossref","first-page":"4017","DOI":"10.1039\/C8DT00089A","article-title":"Chirality in metal-based anticancer agents","volume":"47","author":"Wang","year":"2018","journal-title":"Dalton Transactions"},{"issue":"7","key":"2022090302181696300_ref22","doi-asserted-by":"crossref","first-page":"760","DOI":"10.2174\/156802611795165098","article-title":"The significance of chirality in drug design and development","volume":"11","author":"Brooks","year":"2011","journal-title":"Current Topics in Medicinal Chemistry"},{"key":"2022090302181696300_ref23","first-page":"391(6)","article-title":"Multiple protective functions of catalase against intercellular apoptosis-inducing ROS signaling of human tumor cells","author":"Heinzelmann","year":"2010","journal-title":"Biological Chemistry"},{"key":"2022090302181696300_ref24","doi-asserted-by":"crossref","first-page":"1258","DOI":"10.1016\/j.ijbiomac.2018.03.053","article-title":"The inhibitory effect of farnesiferol C against catalase; kinetics, interaction mechanism and molecular docking simulation","volume":"113","author":"Yekta","year":"2018","journal-title":"International Journal of Biological Macromolecules"},{"issue":"1","key":"2022090302181696300_ref25","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/S1570-0232(03)00420-3","article-title":"Determination of the enantiomers of ketamine and norketamine in human plasma by enantioselective liquid chromatography-mass spectrometry","volume":"794","author":"Rodriguez Rosas","year":"2003","journal-title":"J Chromatogr B Analyt Technol Biomed Life Sci"},{"issue":"23","key":"2022090302181696300_ref26","doi-asserted-by":"crossref","first-page":"3153","DOI":"10.1080\/00397911.2013.769601","article-title":"Choline chloride\/urea ionic liquid catalyzed a convenient one-pot synthesis of Indole-3-propanamide derivatives","volume":"43","author":"Siddalingamurthy","year":"2013","journal-title":"Synthetic Communications"},{"key":"2022090302181696300_ref27","doi-asserted-by":"crossref","first-page":"673","DOI":"10.1016\/B978-0-12-091302-2.50032-3","volume-title":"In: Methods of enzymatic analysis","author":"Aebi","year":"1974"},{"issue":"1\u20132","key":"2022090302181696300_ref28","first-page":"161","article-title":"Synthesis, characterization and bioactivity studies of novel 1,3,4-oxadiazole small molecule that targets basic phospholipase A2 from Vipera russelli","volume":"426","author":"Kameshwar","year":"2016","journal-title":"Molecular and Cellular Biochemistry"},{"issue":"14","key":"2022090302181696300_ref29","doi-asserted-by":"crossref","first-page":"3048","DOI":"10.1016\/j.bmcl.2017.05.059","article-title":"Design, synthesis of novel furan appended benzothiazepine derivatives and in vitro biological evaluation as potent VRV-PL-8a and H+\/K+ ATPase inhibitors","volume":"27","author":"Lokeshwari","year":"2017","journal-title":"Bioorganic & Medicinal Chemistry Letters"},{"issue":"2","key":"2022090302181696300_ref30","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1002\/prot.10613","article-title":"A hierarchical approach to all-atom protein loop prediction","volume":"55","author":"Jacobson","year":"2004","journal-title":"Proteins: Structure, Function, and Bioinformatics"},{"issue":"12","key":"2022090302181696300_ref31","doi-asserted-by":"crossref","first-page":"3218","DOI":"10.1080\/07391102.2017.1384401","article-title":"Pharmacophore generation, atom-based 3D-QSAR, molecular docking and molecular dynamics simulation studies on benzamide analogues as FtsZ inhibitors","volume":"36","author":"Tripathy","year":"2017","journal-title":"Journal of Biomolecular Structure and Dynamics"},{"key":"2022090302181696300_ref32","doi-asserted-by":"crossref","first-page":"1038","DOI":"10.3389\/fphar.2018.01038","article-title":"In silico prediction, characterization, molecular docking, and dynamic studies on fungal SDRs as novel targets for searching potential fungicides against Fusarium wilt in tomato","volume":"9","author":"Aamir","year":"2018","journal-title":"Front Pharmacol"},{"issue":"12","key":"2022090302181696300_ref33","doi-asserted-by":"crossref","first-page":"3289","DOI":"10.1246\/bcsj.68.3289","article-title":"Chiral discrimination on polysaccharides derivatives","volume":"68","author":"Yashima","year":"1995","journal-title":"Bulletin of the Chemical Society of Japan"},{"issue":"2","key":"2022090302181696300_ref34","doi-asserted-by":"crossref","first-page":"253","DOI":"10.2174\/1871530320666200719020709","article-title":"Prostate carcinogenesis: Insights in relation to epigenetics and inflammation","volume":"21","author":"Pandareesh","year":"2021","journal-title":"Endocrine, Metabolic & Immune Disorders - Drug Targets"},{"issue":"1","key":"2022090302181696300_ref35","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s11523-016-0452-7","article-title":"Targeting multiple oncogenic pathways for the treatment of hepatocellular carcinoma","volume":"12","author":"Swamy","year":"2016","journal-title":"Targeted Oncology"},{"issue":"22","key":"2022090302181696300_ref36","doi-asserted-by":"crossref","first-page":"12069","DOI":"10.1039\/C7RA13321A","article-title":"Recent advances in the application of indoles in multicomponent reactions","volume":"8","author":"Mohammadi Ziarani","year":"2018","journal-title":"RSC Advances"},{"issue":"16","key":"2022090302181696300_ref37","doi-asserted-by":"crossref","first-page":"4805","DOI":"10.1021\/jm060522a","article-title":"Accurate prediction of the relative potencies of members of a series of kinase inhibitors using molecular docking and MM-GBSA scoring","volume":"49","author":"Lyne","year":"2006","journal-title":"Journal of Medicinal Chemistry"},{"issue":"4","key":"2022090302181696300_ref38","doi-asserted-by":"crossref","first-page":"623","DOI":"10.1134\/S0026893308040195","article-title":"Radius of gyration as an indicator of protein structure compactness","volume":"42","author":"Lobanov","year":"2008","journal-title":"Molecular Biology"}],"container-title":["Journal of Chromatographic Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/academic.oup.com\/chromsci\/article-pdf\/60\/7\/692\/45670146\/bmab102.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/academic.oup.com\/chromsci\/article-pdf\/60\/7\/692\/45670146\/bmab102.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,9,6]],"date-time":"2024-09-06T08:27:43Z","timestamp":1725611263000},"score":1,"resource":{"primary":{"URL":"https:\/\/academic.oup.com\/chromsci\/article\/60\/7\/692\/6369009"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,9,11]]},"references-count":38,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2021,9,11]]},"published-print":{"date-parts":[[2022,9,3]]}},"URL":"https:\/\/doi.org\/10.1093\/chromsci\/bmab102","relation":{},"ISSN":["0021-9665","1945-239X"],"issn-type":[{"value":"0021-9665","type":"print"},{"value":"1945-239X","type":"electronic"}],"subject":[],"published-other":{"date-parts":[[2022,8]]},"published":{"date-parts":[[2021,9,11]]}}}