{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T23:56:01Z","timestamp":1790726161419,"version":"4.1.0"},"reference-count":67,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2020,6,14]],"date-time":"2020-06-14T00:00:00Z","timestamp":1592092800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2020,9]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    A series of substituted quinolines was screened for their antiproliferative, cytotoxic, antibacterial activities, DNA\/protein binding affinity, and anticholinergic properties by using the 3\u2010(4,5\u2010dimethylthiazol\u20102\u2010yl)\u20102,5\u2010diphenyltetrazolium bromide cell proliferation, lactate dehydrogenase cytotoxicity, and microdilution assays, the Wolfe\u2013Shimmer equality method, the Ellman method, and the esterase assay, respectively. The results of the cytotoxic and anticancer activities of the compounds displayed that 6\u2010bromotetrahydroquinoline (\n                    <jats:bold>2<\/jats:bold>\n                    ), 6,8\u2010dibromotetrahydroquinoline (\n                    <jats:bold>3<\/jats:bold>\n                    ), 8\u2010bromo\u20106\u2010cyanoquinoline (\n                    <jats:bold>10<\/jats:bold>\n                    ), 5\u2010bromo\u20106,8\u2010dimethoxyquinoline (\n                    <jats:bold>12<\/jats:bold>\n                    ), the novel\n                    <jats:italic>N<\/jats:italic>\n                    \u2010nitrated 6,8\u2010dimethoxyquinoline (\n                    <jats:bold>13<\/jats:bold>\n                    ), and 5,7\u2010dibromo\u20108\u2010hydroxyquinoline (\n                    <jats:bold>17<\/jats:bold>\n                    ) showed a significant antiproliferative potency against the A549, HeLa, HT29, Hep3B, and MCF7 cancer cell lines (IC\n                    <jats:sub>50<\/jats:sub>\n                    \u2009=\u20092\u201350\u2009\u03bcg\/ml) and low cytotoxicity (\u223c7\u201335%) as the controls, 5\u2010fluorouracil and cisplatin. The compound\u2013DNA linkages are hyperchromic or hypochromic, causing variations in their spectra. This situation shows that they can be bound to DNA with the groove\u2010binding mode, with\n                    <jats:italic>K<\/jats:italic>\n                    <jats:sub>b<\/jats:sub>\n                    value in the range of 2.0\u2009\u00d7\u200910\n                    <jats:sup>3<\/jats:sup>\n                    \u20132.2\u2009\u00d7\u200910\n                    <jats:sup>5<\/jats:sup>\n                    \u2009M\n                    <jats:sup>\u20131<\/jats:sup>\n                    . Studies on human Gram(+) and Gram(\u2212) pathogenic bacteria showed that the substituted quinolines exhibited selective antimicrobial activities with MIC values of 62.50\u2013250\u2009\u03bcg\/ml. All tested quinoline derivatives were found to be effective inhibitors of acetylcholinesterase (AChE) and the human carbonic anhydrase I and II isoforms (hCA I and II), with\n                    <jats:italic>K<\/jats:italic>\n                    <jats:sub>i<\/jats:sub>\n                    values of 46.04\u2013956.82\u2009nM for hCA I, 54.95\u2013976.93\u2009nM for hCA II, and 5.51\u2013155.22\u2009nM for AChE. As a result, the preliminary data showed that substituted quinolines displayed effective pharmacological features. Molecular docking studies were performed to investigate the binding modes and interaction energies for compounds\n                    <jats:bold>2\u201317<\/jats:bold>\n                    with AChE (PDB ID: 4EY6), hCA I (PDB ID: 1BMZ), and hCA II (PDB ID: 2ABE).\n                  <\/jats:p>","DOI":"10.1002\/ardp.202000086","type":"journal-article","created":{"date-parts":[[2020,6,15]],"date-time":"2020-06-15T01:56:58Z","timestamp":1592186218000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":54,"title":["Quinoline\u2010based promising anticancer and antibacterial agents, and some metabolic enzyme inhibitors"],"prefix":"10.1002","volume":"353","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9656-1803","authenticated-orcid":false,"given":"Salih","family":"\u00d6kten","sequence":"first","affiliation":[{"name":"Department of Maths and Science Education K\u0131r\u0131kkale University Yah\u015fihan K\u0131r\u0131kkale Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9550-9111","authenticated-orcid":false,"given":"Ali","family":"Ayd\u0131n","sequence":"additional","affiliation":[{"name":"Department of Basic Medical Science, Faculty of Medicine Yozgat Bozok University Yozgat Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8710-2912","authenticated-orcid":false,"given":"\u00dcmit M.","family":"Ko\u00e7yi\u011fit","sequence":"additional","affiliation":[{"name":"Department of Basic Pharmacy Sciences, Faculty of Pharmacy Cumhuriyet University Sivas Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9293-5572","authenticated-orcid":false,"given":"Osman","family":"\u00c7akmak","sequence":"additional","affiliation":[{"name":"Department of Gastronomy, Faculty of Arts and Design \u0130stanbul Rumeli University Silivri \u0130stanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6744-929X","authenticated-orcid":false,"given":"Sultan","family":"Erkan","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Chemical Processing Technologies, Y\u0131ld\u0131zeli Vocational School Sivas Cumhuriyet University Sivas Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4545-3500","authenticated-orcid":false,"given":"Cenk A.","family":"Andac","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy Istanbul Istinye University Zeytinburnu Istanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3171-0633","authenticated-orcid":false,"given":"Parham","family":"Taslimi","sequence":"additional","affiliation":[{"name":"Department of Biotechnology, Faculty of Science Bart\u0131n University Bart\u0131n Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5993-1668","authenticated-orcid":false,"given":"\u0130lhami","family":"G\u00fcl\u00e7in","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Sciences Atat\u00fcrk University Erzurum Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,6,14]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2018.10.068"},{"key":"e_1_2_6_3_1","first-page":"1199","volume-title":"Foye's Principles of Medicinal Chemistry","author":"Roche V. F.","year":"2002"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.3906\/biy-1405-68"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo301652j"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2017.10.046"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.3906\/kim-1301-30"},{"key":"e_1_2_6_8_1","first-page":"152","volume":"8","author":"\u00d6kten S.","year":"2017","journal-title":"Turk. J. Clin. Lab."},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.2174\/1570180814666170504150050"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2011.02.063"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2016.11.025"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2011.06.032"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2014.07.044"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201603074"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2017.07.044"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.22260"},{"key":"e_1_2_6_17_1","doi-asserted-by":"crossref","first-page":"940","DOI":"10.17776\/csj.424045","volume":"39","author":"\u00d6kten S.","year":"2018","journal-title":"Cumhuriyet Sci. J."},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1177\/1747519819861389"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2012.04.029"},{"key":"e_1_2_6_20_1","first-page":"3250","volume":"53","author":"Nunoshiba T.","year":"1993","journal-title":"Cancer Res."},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.24820\/ark.5550190.p010.374"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(03)00684-X"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules21030340"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10787-017-0342-3"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2005.07.008"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(00)00652-1"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm970146h"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2005.12.017"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201300167"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.08.018"},{"key":"e_1_2_6_31_1","first-page":"8","volume":"33","author":"\u00d6kten S.","year":"2015","journal-title":"Sigma J. Eng. Nat. Sci."},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800128"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/ci400539q"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2008.09.009"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm100762r"},{"key":"e_1_2_6_36_1","first-page":"37","volume":"28","author":"Cheng C. C.","year":"1982","journal-title":"Org. React."},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2005.03.034"},{"key":"e_1_2_6_38_1","unstructured":"S. Martine K. Evelyne J.\u2010P. Macher B. Jean\u2010Jacques M. Abarghaz P. Wagner G. Ronsin US Patent 183909 A1 2006 Arlington VA."},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)00677-7"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2015.07.092"},{"key":"e_1_2_6_41_1","first-page":"82","volume":"9","author":"\u00d6kten S.","year":"2016","journal-title":"Org. Commun."},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.5530\/ijper.53.2.35"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201800167"},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2018.08.063"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1038\/nbt1284"},{"key":"e_1_2_6_46_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.gde.2004.12.001"},{"key":"e_1_2_6_47_1","doi-asserted-by":"publisher","DOI":"10.1186\/s12885-019-5949-x"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1158\/0008-5472.CAN-08-1181"},{"key":"e_1_2_6_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.advenzreg.2011.09.017"},{"key":"e_1_2_6_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/np990478k"},{"key":"e_1_2_6_51_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2014.10.020"},{"key":"e_1_2_6_52_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-017-13334-y"},{"key":"e_1_2_6_53_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.str.2012.09.005"},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcel.2015.11.010"},{"key":"e_1_2_6_55_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600536810045484"},{"key":"e_1_2_6_56_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2414314617006435"},{"key":"e_1_2_6_57_1","doi-asserted-by":"publisher","DOI":"10.3906\/biy-1402-60"},{"key":"e_1_2_6_58_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)95800-X"},{"key":"e_1_2_6_59_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.poly.2018.08.026"},{"key":"e_1_2_6_60_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2018.11.001"},{"key":"e_1_2_6_61_1","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(61)90145-9"},{"key":"e_1_2_6_62_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2018.11.038"},{"key":"e_1_2_6_63_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2018.12.012"},{"key":"e_1_2_6_64_1","volume-title":"GaussView 5.0","author":"Dennigton R. D.","year":"2009"},{"key":"e_1_2_6_65_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2017.11.091"},{"key":"e_1_2_6_66_1","unstructured":"PDB (Protein Data Bank);http:\/\/www.rcsb.org\/pdb\/; last accessed: 01 March 2020."},{"key":"e_1_2_6_67_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.21334"},{"key":"e_1_2_6_68_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.21256"}],"container-title":["Archiv der Pharmazie"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fardp.202000086","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ardp.202000086","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/ardp.202000086","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ardp.202000086","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,5]],"date-time":"2023-09-05T13:42:20Z","timestamp":1693921340000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/ardp.202000086"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,6,14]]},"references-count":67,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2020,9]]}},"alternative-id":["10.1002\/ardp.202000086"],"URL":"https:\/\/doi.org\/10.1002\/ardp.202000086","archive":["Portico"],"relation":{},"ISSN":["0365-6233","1521-4184"],"issn-type":[{"value":"0365-6233","type":"print"},{"value":"1521-4184","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,6,14]]},"assertion":[{"value":"2020-03-21","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-05-24","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-06-14","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"2000086"}}