Biological Effects and Crystal X‐Ray Study of Novel Schiff Base Containing Pentafluorophenyl Hydrazine: In Vitro and in Silico Studies
A novel Schiff base namely 3,5‐di‐tert‐butyl‐6‐((2‐(perfluorophenyl)hydrazono)methyl)phenol was successfully synthesized and characterized using FT‐IR and 1H‐NMR, 13C‐NMR, and 19F‐NMR. The crystal structure analysis of the Schiff base compound was also characterized with single crystal X‐ray diffrac...
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| Veröffentlicht in: | Chemistry & biodiversity 2023-11, Vol.20 (11), p.e202301132-n/a |
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| creator | Hamurcu, Fatma Özmen, Ümmühan Özdemir Şentürk, Ozan Sanlı Kaya, Kerem Adem, Sevki Erden, Büşra Aksoy Celebioglu, Hasan Ufuk Erden, Yavuz Taslimi, Parham |
| description | A novel Schiff base namely 3,5‐di‐tert‐butyl‐6‐((2‐(perfluorophenyl)hydrazono)methyl)phenol was successfully synthesized and characterized using FT‐IR and 1H‐NMR, 13C‐NMR, and 19F‐NMR. The crystal structure analysis of the Schiff base compound was also characterized with single crystal X‐ray diffraction studies and supported the spectroscopic results. The cytotoxicity, anti‐bacterial properties, and enzyme inhibition of the compound were also investigated. The molecular docking studies were performed in order to explain the interactions of the synthesized compound with target enzymes. The newly synthesized hydrazone derivative Schiff base compound showed high cellular toxicity on MCF‐7 and PC‐3 cells. Also, this compound caused low antibacterial effect on E. coli and S. aureus. Besides, the compound exhibited the inhibitory effect against pancreatic cholesterol esterase and carbonic anhydrase isoenzyme I, II with IC50 values 63, 99, and 188 μM, respectively. Consequently, it has been determined that the prepared Schiff base is an active compound in terms of cytotoxicity, enzyme inhibition, and anti‐bacterial properties. These results provide preliminary information for some biological features of the compound and can play a major role in drug applications of the Schiff base compound. |
| doi_str_mv | 10.1002/cbdv.202301132 |
| format | Article |
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The crystal structure analysis of the Schiff base compound was also characterized with single crystal X‐ray diffraction studies and supported the spectroscopic results. The cytotoxicity, anti‐bacterial properties, and enzyme inhibition of the compound were also investigated. The molecular docking studies were performed in order to explain the interactions of the synthesized compound with target enzymes. The newly synthesized hydrazone derivative Schiff base compound showed high cellular toxicity on MCF‐7 and PC‐3 cells. Also, this compound caused low antibacterial effect on E. coli and S. aureus. Besides, the compound exhibited the inhibitory effect against pancreatic cholesterol esterase and carbonic anhydrase isoenzyme I, II with IC50 values 63, 99, and 188 μM, respectively. Consequently, it has been determined that the prepared Schiff base is an active compound in terms of cytotoxicity, enzyme inhibition, and anti‐bacterial properties. These results provide preliminary information for some biological features of the compound and can play a major role in drug applications of the Schiff base compound.</description><identifier>ISSN: 1612-1872</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.202301132</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Antibacterial activity ; antibacterial activity molecular docking ; anticancer ; Biological effects ; Carbonic anhydrase ; Carbonic anhydrase I ; Carbonic anhydrase II ; Cholesterol ; Crystal structure ; Cytotoxicity ; E coli ; enzyme inhibition ; Enzymes ; Hydrazine ; Hydrazines ; hydrazone ; Hydrazones ; Imines ; Molecular docking ; NMR ; Nuclear magnetic resonance ; Phenols ; Protons ; Schiff base ; Single crystals ; Structural analysis ; Synthesis ; Toxicity</subject><ispartof>Chemistry & biodiversity, 2023-11, Vol.20 (11), p.e202301132-n/a</ispartof><rights>2023 Wiley‐VHCA AG, Zurich, Switzerland</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3902-89cd4674a81070fa9a9b9436c7f9cae3d9ef0341930dd8e70fc89938d70234d43</citedby><cites>FETCH-LOGICAL-c3902-89cd4674a81070fa9a9b9436c7f9cae3d9ef0341930dd8e70fc89938d70234d43</cites><orcidid>0000-0002-3171-0633</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbdv.202301132$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.202301132$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Hamurcu, Fatma</creatorcontrib><creatorcontrib>Özmen, Ümmühan Özdemir</creatorcontrib><creatorcontrib>Şentürk, Ozan Sanlı</creatorcontrib><creatorcontrib>Kaya, Kerem</creatorcontrib><creatorcontrib>Adem, Sevki</creatorcontrib><creatorcontrib>Erden, Büşra Aksoy</creatorcontrib><creatorcontrib>Celebioglu, Hasan Ufuk</creatorcontrib><creatorcontrib>Erden, Yavuz</creatorcontrib><creatorcontrib>Taslimi, Parham</creatorcontrib><title>Biological Effects and Crystal X‐Ray Study of Novel Schiff Base Containing Pentafluorophenyl Hydrazine: In Vitro and in Silico Studies</title><title>Chemistry & biodiversity</title><description>A novel Schiff base namely 3,5‐di‐tert‐butyl‐6‐((2‐(perfluorophenyl)hydrazono)methyl)phenol was successfully synthesized and characterized using FT‐IR and 1H‐NMR, 13C‐NMR, and 19F‐NMR. The crystal structure analysis of the Schiff base compound was also characterized with single crystal X‐ray diffraction studies and supported the spectroscopic results. The cytotoxicity, anti‐bacterial properties, and enzyme inhibition of the compound were also investigated. The molecular docking studies were performed in order to explain the interactions of the synthesized compound with target enzymes. The newly synthesized hydrazone derivative Schiff base compound showed high cellular toxicity on MCF‐7 and PC‐3 cells. Also, this compound caused low antibacterial effect on E. coli and S. aureus. Besides, the compound exhibited the inhibitory effect against pancreatic cholesterol esterase and carbonic anhydrase isoenzyme I, II with IC50 values 63, 99, and 188 μM, respectively. Consequently, it has been determined that the prepared Schiff base is an active compound in terms of cytotoxicity, enzyme inhibition, and anti‐bacterial properties. These results provide preliminary information for some biological features of the compound and can play a major role in drug applications of the Schiff base compound.</description><subject>Antibacterial activity</subject><subject>antibacterial activity molecular docking</subject><subject>anticancer</subject><subject>Biological effects</subject><subject>Carbonic anhydrase</subject><subject>Carbonic anhydrase I</subject><subject>Carbonic anhydrase II</subject><subject>Cholesterol</subject><subject>Crystal structure</subject><subject>Cytotoxicity</subject><subject>E coli</subject><subject>enzyme inhibition</subject><subject>Enzymes</subject><subject>Hydrazine</subject><subject>Hydrazines</subject><subject>hydrazone</subject><subject>Hydrazones</subject><subject>Imines</subject><subject>Molecular docking</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Phenols</subject><subject>Protons</subject><subject>Schiff base</subject><subject>Single crystals</subject><subject>Structural analysis</subject><subject>Synthesis</subject><subject>Toxicity</subject><issn>1612-1872</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkT1PwzAQhiMEEqWwMltiYWmx4yix2Wj4KBICRAGxRa4_WlfGLnYCChMjI7-RX4JLUZFYmO50et73TvcmyS6CfQRhesDH4rmfwhRDhHC6lnRQjtIeIgSur_oi3Uy2QphFPs5JJ3kfaGfcRHNmwIlSktcBMCtA6dtQx9nD59vHDWvBqG5EC5wCl-5ZGjDiU60UGLAgQelszbTVdgKuZWyVaZx386m0rQHDVnj2qq08BOcW3Ovau29_bcFIG83dt7OWYTvZUMwEufNTu8nd6cltOexdXJ2dl0cXPY4pTHuEcpHlRcYIggVUjDI6phnOeaEoZxILKhXEGaIYCkFkRDihFBNRxMdkIsPdZH_pO_fuqZGhrh514NIYZqVrQpWSnOQ5QTSP6N4fdOYab-N1kaKYZnHxwrC_pLh3IXipqrnXj8y3FYLVIphqEUy1CiYK6FLwoo1s_6GrcnB8_6v9AkBaku0</recordid><startdate>202311</startdate><enddate>202311</enddate><creator>Hamurcu, Fatma</creator><creator>Özmen, Ümmühan Özdemir</creator><creator>Şentürk, Ozan Sanlı</creator><creator>Kaya, Kerem</creator><creator>Adem, Sevki</creator><creator>Erden, Büşra Aksoy</creator><creator>Celebioglu, Hasan Ufuk</creator><creator>Erden, Yavuz</creator><creator>Taslimi, Parham</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3171-0633</orcidid></search><sort><creationdate>202311</creationdate><title>Biological Effects and Crystal X‐Ray Study of Novel Schiff Base Containing Pentafluorophenyl Hydrazine: In Vitro and in Silico Studies</title><author>Hamurcu, Fatma ; Özmen, Ümmühan Özdemir ; Şentürk, Ozan Sanlı ; Kaya, Kerem ; Adem, Sevki ; Erden, Büşra Aksoy ; Celebioglu, Hasan Ufuk ; Erden, Yavuz ; Taslimi, Parham</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3902-89cd4674a81070fa9a9b9436c7f9cae3d9ef0341930dd8e70fc89938d70234d43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Antibacterial activity</topic><topic>antibacterial activity molecular docking</topic><topic>anticancer</topic><topic>Biological effects</topic><topic>Carbonic anhydrase</topic><topic>Carbonic anhydrase I</topic><topic>Carbonic anhydrase II</topic><topic>Cholesterol</topic><topic>Crystal structure</topic><topic>Cytotoxicity</topic><topic>E coli</topic><topic>enzyme inhibition</topic><topic>Enzymes</topic><topic>Hydrazine</topic><topic>Hydrazines</topic><topic>hydrazone</topic><topic>Hydrazones</topic><topic>Imines</topic><topic>Molecular docking</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Phenols</topic><topic>Protons</topic><topic>Schiff base</topic><topic>Single crystals</topic><topic>Structural analysis</topic><topic>Synthesis</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hamurcu, Fatma</creatorcontrib><creatorcontrib>Özmen, Ümmühan Özdemir</creatorcontrib><creatorcontrib>Şentürk, Ozan Sanlı</creatorcontrib><creatorcontrib>Kaya, Kerem</creatorcontrib><creatorcontrib>Adem, Sevki</creatorcontrib><creatorcontrib>Erden, Büşra Aksoy</creatorcontrib><creatorcontrib>Celebioglu, Hasan Ufuk</creatorcontrib><creatorcontrib>Erden, Yavuz</creatorcontrib><creatorcontrib>Taslimi, Parham</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry & biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hamurcu, Fatma</au><au>Özmen, Ümmühan Özdemir</au><au>Şentürk, Ozan Sanlı</au><au>Kaya, Kerem</au><au>Adem, Sevki</au><au>Erden, Büşra Aksoy</au><au>Celebioglu, Hasan Ufuk</au><au>Erden, Yavuz</au><au>Taslimi, Parham</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Biological Effects and Crystal X‐Ray Study of Novel Schiff Base Containing Pentafluorophenyl Hydrazine: In Vitro and in Silico Studies</atitle><jtitle>Chemistry & biodiversity</jtitle><date>2023-11</date><risdate>2023</risdate><volume>20</volume><issue>11</issue><spage>e202301132</spage><epage>n/a</epage><pages>e202301132-n/a</pages><issn>1612-1872</issn><eissn>1612-1880</eissn><abstract>A novel Schiff base namely 3,5‐di‐tert‐butyl‐6‐((2‐(perfluorophenyl)hydrazono)methyl)phenol was successfully synthesized and characterized using FT‐IR and 1H‐NMR, 13C‐NMR, and 19F‐NMR. The crystal structure analysis of the Schiff base compound was also characterized with single crystal X‐ray diffraction studies and supported the spectroscopic results. The cytotoxicity, anti‐bacterial properties, and enzyme inhibition of the compound were also investigated. The molecular docking studies were performed in order to explain the interactions of the synthesized compound with target enzymes. The newly synthesized hydrazone derivative Schiff base compound showed high cellular toxicity on MCF‐7 and PC‐3 cells. Also, this compound caused low antibacterial effect on E. coli and S. aureus. Besides, the compound exhibited the inhibitory effect against pancreatic cholesterol esterase and carbonic anhydrase isoenzyme I, II with IC50 values 63, 99, and 188 μM, respectively. Consequently, it has been determined that the prepared Schiff base is an active compound in terms of cytotoxicity, enzyme inhibition, and anti‐bacterial properties. These results provide preliminary information for some biological features of the compound and can play a major role in drug applications of the Schiff base compound.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/cbdv.202301132</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0002-3171-0633</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Antibacterial activity antibacterial activity molecular docking anticancer Biological effects Carbonic anhydrase Carbonic anhydrase I Carbonic anhydrase II Cholesterol Crystal structure Cytotoxicity E coli enzyme inhibition Enzymes Hydrazine Hydrazines hydrazone Hydrazones Imines Molecular docking NMR Nuclear magnetic resonance Phenols Protons Schiff base Single crystals Structural analysis Synthesis Toxicity |
| title | Biological Effects and Crystal X‐Ray Study of Novel Schiff Base Containing Pentafluorophenyl Hydrazine: In Vitro and in Silico Studies |
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