Antioxidant activity of novel nitrogen scaffold with docking investigation and correlation of DFT stimulation
Heterocyclic scaffolds are frequently employed in drug development to treat a variety of conditions, including cancers. These substances have the ability to engage covalently or non-covalently with particular residues in the target proteins, inhibiting them. In this study, the formation of N-, S-, a...
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description | Heterocyclic scaffolds are frequently employed in drug development to treat a variety of conditions, including cancers. These substances have the ability to engage covalently or non-covalently with particular residues in the target proteins, inhibiting them. In this study, the formation of N-, S-, and O-containing heterocycles by the interaction of chalcone with nitrogen-containing nucleophiles such as hydrazine, hydroxyl amine, guanidine, urea, and aminothiourea was explored. FT-IR, UV-visible, NMR, and mass spectrometric studies were used to confirm the heterocyclic compounds that were produced. These substances were tested for their antioxidant activity by their capacity to scavenge the artificial radicals 2,2-diphenyl-1-picrylhydrazyl (DPPH). The strongest antioxidant activity was demonstrated by compound
3
(IC
50
= 93.4 μM), whereas compound 8 (IC
50
= 448.70 μM) had the lowest activity when compared to vitamin C (IC
50
141.9 μM). Also, the experimental findings and the docking estimation of these heterocyclic compounds with
PDBID:3RP8
were in agreement. Additionally, the compounds' global reactivity characteristics, such as HOMO-LUMO gaps, electronic hardness, chemical potential, electrophilicity index, and Mulliken charges, were identified using DFT/B3LYP/6-31G(d,p) basis sets. The two chemicals that displayed the best antioxidant activity also had their molecular electrostatic potential (MEP) ascertained using DFT simulations.
Heterocyclic scaffolds are frequently employed in drug development to treat a variety of conditions, including cancers. |
doi_str_mv | 10.1039/d3ra02393a |
format | Article |
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3
(IC
50
= 93.4 μM), whereas compound 8 (IC
50
= 448.70 μM) had the lowest activity when compared to vitamin C (IC
50
141.9 μM). Also, the experimental findings and the docking estimation of these heterocyclic compounds with
PDBID:3RP8
were in agreement. Additionally, the compounds' global reactivity characteristics, such as HOMO-LUMO gaps, electronic hardness, chemical potential, electrophilicity index, and Mulliken charges, were identified using DFT/B3LYP/6-31G(d,p) basis sets. The two chemicals that displayed the best antioxidant activity also had their molecular electrostatic potential (MEP) ascertained using DFT simulations.
Heterocyclic scaffolds are frequently employed in drug development to treat a variety of conditions, including cancers.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d3ra02393a</identifier><identifier>PMID: 37197676</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Antioxidants ; Chemical potential ; Chemistry ; Docking ; Heterocyclic compounds ; Hydrazines ; Molecular orbitals ; Nitrogen ; NMR ; Nuclear magnetic resonance ; Nucleophiles ; Scaffolds ; Spectrometry</subject><ispartof>RSC advances, 2023-05, Vol.13 (21), p.1458-14593</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2023</rights><rights>This journal is © The Royal Society of Chemistry 2023 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c429t-80f034e20f1ddd1b57c5ce93977d6bbe0a6ead7515d154f367cd41451fcc280a3</citedby><cites>FETCH-LOGICAL-c429t-80f034e20f1ddd1b57c5ce93977d6bbe0a6ead7515d154f367cd41451fcc280a3</cites><orcidid>0000-0002-0293-3491</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10183801/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10183801/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37197676$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shalaby, Mona A</creatorcontrib><creatorcontrib>Fahim, Asmaa M</creatorcontrib><creatorcontrib>Rizk, Sameh A</creatorcontrib><title>Antioxidant activity of novel nitrogen scaffold with docking investigation and correlation of DFT stimulation</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>Heterocyclic scaffolds are frequently employed in drug development to treat a variety of conditions, including cancers. These substances have the ability to engage covalently or non-covalently with particular residues in the target proteins, inhibiting them. In this study, the formation of N-, S-, and O-containing heterocycles by the interaction of chalcone with nitrogen-containing nucleophiles such as hydrazine, hydroxyl amine, guanidine, urea, and aminothiourea was explored. FT-IR, UV-visible, NMR, and mass spectrometric studies were used to confirm the heterocyclic compounds that were produced. These substances were tested for their antioxidant activity by their capacity to scavenge the artificial radicals 2,2-diphenyl-1-picrylhydrazyl (DPPH). The strongest antioxidant activity was demonstrated by compound
3
(IC
50
= 93.4 μM), whereas compound 8 (IC
50
= 448.70 μM) had the lowest activity when compared to vitamin C (IC
50
141.9 μM). Also, the experimental findings and the docking estimation of these heterocyclic compounds with
PDBID:3RP8
were in agreement. Additionally, the compounds' global reactivity characteristics, such as HOMO-LUMO gaps, electronic hardness, chemical potential, electrophilicity index, and Mulliken charges, were identified using DFT/B3LYP/6-31G(d,p) basis sets. The two chemicals that displayed the best antioxidant activity also had their molecular electrostatic potential (MEP) ascertained using DFT simulations.
Heterocyclic scaffolds are frequently employed in drug development to treat a variety of conditions, including cancers.</description><subject>Antioxidants</subject><subject>Chemical potential</subject><subject>Chemistry</subject><subject>Docking</subject><subject>Heterocyclic compounds</subject><subject>Hydrazines</subject><subject>Molecular orbitals</subject><subject>Nitrogen</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Nucleophiles</subject><subject>Scaffolds</subject><subject>Spectrometry</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdkstrVDEUh4NY2tJ2414JuBFhNI-b5GYlQ2tVKAhS1yGTxzT13qQmuWP73zftnY7VbPI4Hx_n8AsArzD6gBGVHy3NGhEqqX4BDgnq-IIgLl8-Ox-Ak1KuUVucYcLxPjigAkvBBT8E4zLWkG6D1bFCbWrYhHoHk4cxbdwAY6g5rV2ExWjv02Dhn1CvoE3mV4hrGOLGlRrWujki1NFCk3J2w3xvlrPzS9iAcZqfjsGe10NxJ9v9CPw8_3x5-nVx8f3Lt9PlxcJ0RNZFjzyinSPIY2stXjFhmHGSSiEsX60c0txpKxhmFrPOUy6M7XDHsDeG9EjTI_Bp9t5Mq9FZ42LNelA3OYw636mkg_q3EsOVWqeNwgj3tEe4Gd5tDTn9ntqQagzFuGHQ0aWpKNJjRjrJhGzo2__Q6zTl2ObbUh2lpFHvZ8rkVEp2ftcNRuohSXVGfywfk1w2-M3z_nfoU24NeD0DuZhd9e9XoPc6UqUp</recordid><startdate>20230509</startdate><enddate>20230509</enddate><creator>Shalaby, Mona A</creator><creator>Fahim, Asmaa M</creator><creator>Rizk, Sameh A</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-0293-3491</orcidid></search><sort><creationdate>20230509</creationdate><title>Antioxidant activity of novel nitrogen scaffold with docking investigation and correlation of DFT stimulation</title><author>Shalaby, Mona A ; Fahim, Asmaa M ; Rizk, Sameh A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c429t-80f034e20f1ddd1b57c5ce93977d6bbe0a6ead7515d154f367cd41451fcc280a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Antioxidants</topic><topic>Chemical potential</topic><topic>Chemistry</topic><topic>Docking</topic><topic>Heterocyclic compounds</topic><topic>Hydrazines</topic><topic>Molecular orbitals</topic><topic>Nitrogen</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Nucleophiles</topic><topic>Scaffolds</topic><topic>Spectrometry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shalaby, Mona A</creatorcontrib><creatorcontrib>Fahim, Asmaa M</creatorcontrib><creatorcontrib>Rizk, Sameh A</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shalaby, Mona A</au><au>Fahim, Asmaa M</au><au>Rizk, Sameh A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antioxidant activity of novel nitrogen scaffold with docking investigation and correlation of DFT stimulation</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2023-05-09</date><risdate>2023</risdate><volume>13</volume><issue>21</issue><spage>1458</spage><epage>14593</epage><pages>1458-14593</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>Heterocyclic scaffolds are frequently employed in drug development to treat a variety of conditions, including cancers. These substances have the ability to engage covalently or non-covalently with particular residues in the target proteins, inhibiting them. In this study, the formation of N-, S-, and O-containing heterocycles by the interaction of chalcone with nitrogen-containing nucleophiles such as hydrazine, hydroxyl amine, guanidine, urea, and aminothiourea was explored. FT-IR, UV-visible, NMR, and mass spectrometric studies were used to confirm the heterocyclic compounds that were produced. These substances were tested for their antioxidant activity by their capacity to scavenge the artificial radicals 2,2-diphenyl-1-picrylhydrazyl (DPPH). The strongest antioxidant activity was demonstrated by compound
3
(IC
50
= 93.4 μM), whereas compound 8 (IC
50
= 448.70 μM) had the lowest activity when compared to vitamin C (IC
50
141.9 μM). Also, the experimental findings and the docking estimation of these heterocyclic compounds with
PDBID:3RP8
were in agreement. Additionally, the compounds' global reactivity characteristics, such as HOMO-LUMO gaps, electronic hardness, chemical potential, electrophilicity index, and Mulliken charges, were identified using DFT/B3LYP/6-31G(d,p) basis sets. The two chemicals that displayed the best antioxidant activity also had their molecular electrostatic potential (MEP) ascertained using DFT simulations.
Heterocyclic scaffolds are frequently employed in drug development to treat a variety of conditions, including cancers.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>37197676</pmid><doi>10.1039/d3ra02393a</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0002-0293-3491</orcidid><oa>free_for_read</oa></addata></record> |
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source | DOAJ Directory of Open Access Journals; PubMed Central Open Access; EZB-FREE-00999 freely available EZB journals; PubMed Central |
subjects | Antioxidants Chemical potential Chemistry Docking Heterocyclic compounds Hydrazines Molecular orbitals Nitrogen NMR Nuclear magnetic resonance Nucleophiles Scaffolds Spectrometry |
title | Antioxidant activity of novel nitrogen scaffold with docking investigation and correlation of DFT stimulation |
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