{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T17:33:07Z","timestamp":1790875987522,"version":"4.1.0"},"reference-count":48,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2026,8,26]],"date-time":"2026-08-26T00:00:00Z","timestamp":1787702400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"},{"start":{"date-parts":[[2026,8,26]],"date-time":"2026-08-26T00:00:00Z","timestamp":1787702400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100006560","name":"Yildiz Teknik \u00dcniversitesi","doi-asserted-by":"publisher","award":["FDK\u20102024\u20106554"],"award-info":[{"award-number":["FDK\u20102024\u20106554"]}],"id":[{"id":"10.13039\/501100006560","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["J Biochem &amp;amp; Molecular Tox"],"published-print":{"date-parts":[[2026,9]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Two novel axially substituted silicon phthalocyanines bearing 5,7\u2010dichloro\u20108\u2010hydroxy\u20102\u2010methylquinoline (\n                    <jats:bold>1a<\/jats:bold>\n                    ) and N\u2010(hydroxymethyl)phthalimide (\n                    <jats:bold>2a<\/jats:bold>\n                    ) moieties were synthesized and characterized by UV\u2010Vis, FT\u2010IR,\n                    <jats:sup>1<\/jats:sup>\n                    H NMR, and mass spectrometry techniques. The biological potential of the synthesized compounds was evaluated through in vitro inhibition studies against acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human carbonic anhydrase isoenzymes I and II (hCA I and hCA II). IC\n                    <jats:sub>50<\/jats:sub>\n                    values were determined as 91.28\u2009\u00b1\u200925.21, 43.31\u2009\u00b1\u200920.35, 8.50\u2009\u00b1\u20092.80 and 23.35\u2009\u00b1\u200912.98\u2009\u00b5M, for compound\n                    <jats:bold>1a<\/jats:bold>\n                    , and 2.78\u2009\u00b1\u20091.05, 4.88\u2009\u00b1\u20091.50, 0.94\u2009\u00b1\u20091.06 and 4.15\u2009\u00b1\u20093.01\u2009\u00b5M for compound\n                    <jats:bold>2a<\/jats:bold>\n                    against AChE, BChE, hCA I, and hCA II enzymes respectively. Compound\n                    <jats:bold>2a<\/jats:bold>\n                    exhibited remarkable inhibitory activity. Molecular docking results supported the experimental findings, indicating that compound\n                    <jats:bold>2a<\/jats:bold>\n                    exhibited significantly higher inhibitory potency than compound\n                    <jats:bold>1a<\/jats:bold>\n                    . Structure\u2010activity relationship analysis demonstrated that compound\n                    <jats:bold>2a<\/jats:bold>\n                    exhibits improved enzyme inhibition. The combined experimental and computational findings showed that compound\n                    <jats:bold>2a<\/jats:bold>\n                    is a promising multifunctional enzyme inhibitor. Compound\n                    <jats:bold>2a<\/jats:bold>\n                    exhibited remarkable inhibitory activity across all targets. Molecular docking supported the experimental findings, with compound\n                    <jats:bold>2a<\/jats:bold>\n                    showing more favorable Vinardo binding affinities (\u22128.11, \u22123.94, \u22127.39, and \u22127.15\u2009kcal\/mol against AChE, BChE, hCA I, and hCA II, respectively) than compound\n                    <jats:bold>1a<\/jats:bold>\n                    , primarily through additional hydrogen\u2010bonding interactions provided by its phthalimide groups. The docking protocol was validated by redocking the co\u2010crystallized ligands, which reproduced the crystallographic poses with RMSD values below 2.0\u2009\u00c5 for all targets. DFT calculations revealed narrow HOMO\u2010LUMO energy gaps (0.666\u2009eV for\n                    <jats:bold>1a<\/jats:bold>\n                    and 0.881\u2009eV for\n                    <jats:bold>2a<\/jats:bold>\n                    ), consistent with the high reactivity of the phthalocyanine core, while in silico ADMET analysis indicated favorable toxicity profiles for both compounds. The combined experimental and computational findings identify compound\n                    <jats:bold>2a<\/jats:bold>\n                    as a promising multifunctional enzyme inhibitor.\n                  <\/jats:p>","DOI":"10.1002\/jbt.71090","type":"journal-article","created":{"date-parts":[[2026,8,26]],"date-time":"2026-08-26T16:06:00Z","timestamp":1787760360000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Quinoline and Phthalimide Substituted Silicon Phthalocyanines as Multi\u2010Target Inhibitors of Cholinesterases and Carbonic Anhydrases"],"prefix":"10.1002","volume":"40","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7860-2998","authenticated-orcid":false,"given":"Seda","family":"\u00dcnl\u00fc","sequence":"first","affiliation":[{"name":"Department of Chemistry Yildiz Technical University Esenler Istanbul Turkey"},{"name":"Department of Chemistry Istanbul Medeniyet University Istanbul Turkey"},{"name":"Science and Advanced Technologies Research Center (BILTAM) Istanbul Medeniyet University Istanbul T\u00fcrkiye"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0869-8517","authenticated-orcid":false,"given":"Zeynep","family":"K\u00f6ksal","sequence":"additional","affiliation":[{"name":"Department of Chemistry Istanbul Medeniyet University Istanbul Turkey"},{"name":"Science and Advanced Technologies Research Center (BILTAM) Istanbul Medeniyet University Istanbul T\u00fcrkiye"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2917-8860","authenticated-orcid":false,"given":"Kevser K\u00fcbra","family":"K\u0131rbo\u011fa","sequence":"additional","affiliation":[{"name":"Bioengineering Department Bilecik Seyh Edebali University Bilecik Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4965-8116","authenticated-orcid":false,"given":"Fikriye","family":"Tuncel Elmal\u0131","sequence":"additional","affiliation":[{"name":"Department of Chemistry Yildiz Technical University Esenler Istanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,8,26]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cej.2025.168911"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.snb.2023.134733"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/J.OPTMAT.2025.117709"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/J.SNA.2021.112828"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/J.MOLLIQ.2019.111012"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/J.MOLLIQ.2022.119821"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c01677"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1111\/php.13782"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1080\/10406638.2021.1893194"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/J.MOLSTRUC.2025.144615"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0OB02299C"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2017.06.004"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pdpdt.2023.103734"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/J.MOLSTRUC.2026.145314"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/ARDP.201800167"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/J.BIOORG.2019.103310"},{"key":"e_1_2_9_18_1","doi-asserted-by":"crossref","unstructured":"E.G\u00fczel B. 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