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Synthesis, Cytotoxicity, and Photophysical Investigations of 2-Amino-4,6-diphenylnicotinonitriles: An Experimental and Theoretical Study
In this study, we present a comprehensive investigation of 2-amino-4,6-diphenylnicotinonitriles (APNs, - ), including their synthesis, cytotoxicity against breast cancer cell lines, and photophysical properties. Compound demonstrates exceptional cytotoxicity, surpassing the potency of Doxorubicin. T...
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| Published in: | Molecules (Basel, Switzerland) Switzerland), 2024-04, Vol.29 (8), p.1808 |
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| Main Authors: | , , , , |
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| container_issue | 8 |
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| container_title | Molecules (Basel, Switzerland) |
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| creator | Al-Ghamdi, Alwah R Rahman, Shofiur Al-Wabli, Reem I Al-Mutairi, Maha S Rahman, A F M Motiur |
| description | In this study, we present a comprehensive investigation of 2-amino-4,6-diphenylnicotinonitriles (APNs,
-
), including their synthesis, cytotoxicity against breast cancer cell lines, and photophysical properties. Compound
demonstrates exceptional cytotoxicity, surpassing the potency of Doxorubicin. The fluorescence spectra of the synthesized
-
in different solvents reveal solvent-dependent shifts in the emission maximum values, highlighting the influence of the solvent environment on their fluorescence properties. A quantum chemical TD-DFT analysis provides insights into the electronic structure and fluorescence behavior of
-
, elucidating HOMO-LUMO energy gaps, electronegativity values, and dipole moments, contributing to a deeper understanding of their electronic properties and potential reactivity. These findings provide valuable knowledge for the development of APNs (
-
) as fluorescent sensors and potential anticancer agents. |
| doi_str_mv | 10.3390/molecules29081808 |
| format | article |
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-
), including their synthesis, cytotoxicity against breast cancer cell lines, and photophysical properties. Compound
demonstrates exceptional cytotoxicity, surpassing the potency of Doxorubicin. The fluorescence spectra of the synthesized
-
in different solvents reveal solvent-dependent shifts in the emission maximum values, highlighting the influence of the solvent environment on their fluorescence properties. A quantum chemical TD-DFT analysis provides insights into the electronic structure and fluorescence behavior of
-
, elucidating HOMO-LUMO energy gaps, electronegativity values, and dipole moments, contributing to a deeper understanding of their electronic properties and potential reactivity. These findings provide valuable knowledge for the development of APNs (
-
) as fluorescent sensors and potential anticancer agents.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules29081808</identifier><identifier>PMID: 38675628</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>2-amino-4,6-diphenylnicotinonitrile ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Breast cancer ; Cell Line, Tumor ; Cell Survival - drug effects ; Cytotoxicity ; DFT ; Expected values ; Fluorescence ; Humans ; Hydrogen bonds ; MCF-7 Cells ; Molecular Structure ; Nanoparticles ; Nitriles - chemical synthesis ; Nitriles - chemistry ; Nitriles - pharmacology ; Nitrogen ; NMR ; Nuclear magnetic resonance ; photophysical properties ; Quantum Theory ; Registered nurses ; Solvents ; Spectrometry, Fluorescence ; TD-DFT</subject><ispartof>Molecules (Basel, Switzerland), 2024-04, Vol.29 (8), p.1808</ispartof><rights>COPYRIGHT 2024 MDPI AG</rights><rights>2024 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c457t-6dfb4e1844918b5b5ba420b8dd420985a22871d0f3e756300210e527d6a4c5a03</cites><orcidid>0000-0003-4219-4758 ; 0000-0002-5807-5625 ; 0000-0002-7061-7765 ; 0009-0006-5331-8540 ; 0000-0002-7836-2496</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/3047000370/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/3047000370?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,25753,27924,27925,37012,37013,44590,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38675628$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Al-Ghamdi, Alwah R</creatorcontrib><creatorcontrib>Rahman, Shofiur</creatorcontrib><creatorcontrib>Al-Wabli, Reem I</creatorcontrib><creatorcontrib>Al-Mutairi, Maha S</creatorcontrib><creatorcontrib>Rahman, A F M Motiur</creatorcontrib><title>Synthesis, Cytotoxicity, and Photophysical Investigations of 2-Amino-4,6-diphenylnicotinonitriles: An Experimental and Theoretical Study</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>In this study, we present a comprehensive investigation of 2-amino-4,6-diphenylnicotinonitriles (APNs,
-
), including their synthesis, cytotoxicity against breast cancer cell lines, and photophysical properties. Compound
demonstrates exceptional cytotoxicity, surpassing the potency of Doxorubicin. The fluorescence spectra of the synthesized
-
in different solvents reveal solvent-dependent shifts in the emission maximum values, highlighting the influence of the solvent environment on their fluorescence properties. A quantum chemical TD-DFT analysis provides insights into the electronic structure and fluorescence behavior of
-
, elucidating HOMO-LUMO energy gaps, electronegativity values, and dipole moments, contributing to a deeper understanding of their electronic properties and potential reactivity. These findings provide valuable knowledge for the development of APNs (
-
) as fluorescent sensors and potential anticancer agents.</description><subject>2-amino-4,6-diphenylnicotinonitrile</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Breast cancer</subject><subject>Cell Line, Tumor</subject><subject>Cell Survival - drug effects</subject><subject>Cytotoxicity</subject><subject>DFT</subject><subject>Expected values</subject><subject>Fluorescence</subject><subject>Humans</subject><subject>Hydrogen bonds</subject><subject>MCF-7 Cells</subject><subject>Molecular Structure</subject><subject>Nanoparticles</subject><subject>Nitriles - chemical synthesis</subject><subject>Nitriles - chemistry</subject><subject>Nitriles - pharmacology</subject><subject>Nitrogen</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>photophysical properties</subject><subject>Quantum Theory</subject><subject>Registered nurses</subject><subject>Solvents</subject><subject>Spectrometry, Fluorescence</subject><subject>TD-DFT</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNptUk1v1DAQjRCIlsIP4IIiceGwKXbsxA631arASpVAajlHTjzZeJXYwXZQ8w_42czulvKpOYw1eu_5vdEkyUtKLhmryNvRDdDOA4S8IpJKIh8l55TnJGOEV49_e58lz0LYE5JTTounyRmTpSjKXJ4n328WG3sIJqzSzRJddHemNXFZpcrq9HOPg6lfgmnVkG7tNwjR7FQ0zobUdWmerUdjXcZXZabN1INdBmtaF3FoTfQGvb1L1za9upvAmxFsRJ2D8m0PzkM86t7EWS_PkyedGgK8uO8XyZf3V7ebj9n1pw_bzfo6a3khYlbqruFAJecVlU2BpTBkI7XGVslC5bkUVJOOASZkh8gEilzoUvG2UIRdJNuTrnZqX09oSvmldsrUx4Hzu1p59DVATXF1ZdMJyVXOW5AVa0SnpWqwupICar05aU3efZ1xN_VoQgvDoCy4OdTIFxUXOa8Q-vov6N7N3mLSI4oQwgT5hdop_N_YzkWv2oNovRYVKwopSo6oy_-gsDSMuHwLHe79TwI9EVrvQvDQPeSmpD5cUv3PJSHn1b3huRlBPzB-ng77AbJfxfQ</recordid><startdate>20240401</startdate><enddate>20240401</enddate><creator>Al-Ghamdi, Alwah R</creator><creator>Rahman, Shofiur</creator><creator>Al-Wabli, Reem I</creator><creator>Al-Mutairi, Maha S</creator><creator>Rahman, A F M Motiur</creator><general>MDPI AG</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0003-4219-4758</orcidid><orcidid>https://orcid.org/0000-0002-5807-5625</orcidid><orcidid>https://orcid.org/0000-0002-7061-7765</orcidid><orcidid>https://orcid.org/0009-0006-5331-8540</orcidid><orcidid>https://orcid.org/0000-0002-7836-2496</orcidid></search><sort><creationdate>20240401</creationdate><title>Synthesis, Cytotoxicity, and Photophysical Investigations of 2-Amino-4,6-diphenylnicotinonitriles: An Experimental and Theoretical Study</title><author>Al-Ghamdi, Alwah R ; Rahman, Shofiur ; Al-Wabli, Reem I ; Al-Mutairi, Maha S ; Rahman, A F M Motiur</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c457t-6dfb4e1844918b5b5ba420b8dd420985a22871d0f3e756300210e527d6a4c5a03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>2-amino-4,6-diphenylnicotinonitrile</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Breast cancer</topic><topic>Cell Line, Tumor</topic><topic>Cell Survival - drug effects</topic><topic>Cytotoxicity</topic><topic>DFT</topic><topic>Expected values</topic><topic>Fluorescence</topic><topic>Humans</topic><topic>Hydrogen bonds</topic><topic>MCF-7 Cells</topic><topic>Molecular Structure</topic><topic>Nanoparticles</topic><topic>Nitriles - chemical synthesis</topic><topic>Nitriles - chemistry</topic><topic>Nitriles - pharmacology</topic><topic>Nitrogen</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>photophysical properties</topic><topic>Quantum Theory</topic><topic>Registered nurses</topic><topic>Solvents</topic><topic>Spectrometry, Fluorescence</topic><topic>TD-DFT</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Al-Ghamdi, Alwah R</creatorcontrib><creatorcontrib>Rahman, Shofiur</creatorcontrib><creatorcontrib>Al-Wabli, Reem I</creatorcontrib><creatorcontrib>Al-Mutairi, Maha S</creatorcontrib><creatorcontrib>Rahman, A F M Motiur</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Al-Ghamdi, Alwah R</au><au>Rahman, Shofiur</au><au>Al-Wabli, Reem I</au><au>Al-Mutairi, Maha S</au><au>Rahman, A F M Motiur</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, Cytotoxicity, and Photophysical Investigations of 2-Amino-4,6-diphenylnicotinonitriles: An Experimental and Theoretical Study</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2024-04-01</date><risdate>2024</risdate><volume>29</volume><issue>8</issue><spage>1808</spage><pages>1808-</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>In this study, we present a comprehensive investigation of 2-amino-4,6-diphenylnicotinonitriles (APNs,
-
), including their synthesis, cytotoxicity against breast cancer cell lines, and photophysical properties. Compound
demonstrates exceptional cytotoxicity, surpassing the potency of Doxorubicin. The fluorescence spectra of the synthesized
-
in different solvents reveal solvent-dependent shifts in the emission maximum values, highlighting the influence of the solvent environment on their fluorescence properties. A quantum chemical TD-DFT analysis provides insights into the electronic structure and fluorescence behavior of
-
, elucidating HOMO-LUMO energy gaps, electronegativity values, and dipole moments, contributing to a deeper understanding of their electronic properties and potential reactivity. These findings provide valuable knowledge for the development of APNs (
-
) as fluorescent sensors and potential anticancer agents.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>38675628</pmid><doi>10.3390/molecules29081808</doi><orcidid>https://orcid.org/0000-0003-4219-4758</orcidid><orcidid>https://orcid.org/0000-0002-5807-5625</orcidid><orcidid>https://orcid.org/0000-0002-7061-7765</orcidid><orcidid>https://orcid.org/0009-0006-5331-8540</orcidid><orcidid>https://orcid.org/0000-0002-7836-2496</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | Molecules (Basel, Switzerland), 2024-04, Vol.29 (8), p.1808 |
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| language | eng |
| recordid | cdi_doaj_primary_oai_doaj_org_article_13046bf784a24ce893b7fd8ababaf61e |
| source | Publicly Available Content Database; PubMed Central |
| subjects | 2-amino-4,6-diphenylnicotinonitrile Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Breast cancer Cell Line, Tumor Cell Survival - drug effects Cytotoxicity DFT Expected values Fluorescence Humans Hydrogen bonds MCF-7 Cells Molecular Structure Nanoparticles Nitriles - chemical synthesis Nitriles - chemistry Nitriles - pharmacology Nitrogen NMR Nuclear magnetic resonance photophysical properties Quantum Theory Registered nurses Solvents Spectrometry, Fluorescence TD-DFT |
| title | Synthesis, Cytotoxicity, and Photophysical Investigations of 2-Amino-4,6-diphenylnicotinonitriles: An Experimental and Theoretical Study |
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