Transition metal( ii ) complexes of halogenated derivatives of ( E )-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline: structure, antioxidant activity, DNA-binding DNA photocleavage, interaction with albumin and in silico studies
Two novel halogenated (Br- and F-) quinazoline derivatives, namely [( E )-4-(2-((6-bromopyridin-2-yl)methylene)hydrazinyl)quinazoline] (L1) and [( E )-4-(2-((3-fluoropyridin-2-yl)methylene)hydrazinyl) quinazoline] (L2), were synthesized and characterized. Their interaction with a series of metal( ii...
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Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2022-11, Vol.51 (43), p.16688-16705 |
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creator | Kakoulidou, Chrisoula Chasapis, Christos T. Hatzidimitriou, Antonios G. Fylaktakidou, Konstantina C. Psomas, George |
description | Two novel halogenated (Br- and F-) quinazoline derivatives, namely [(
E
)-4-(2-((6-bromopyridin-2-yl)methylene)hydrazinyl)quinazoline] (L1) and [(
E
)-4-(2-((3-fluoropyridin-2-yl)methylene)hydrazinyl) quinazoline] (L2), were synthesized and characterized. Their interaction with a series of metal(
ii
) ions (= Mn(
ii
), Ni(
ii
), Cu(
ii
), Zn(
ii
) and Cd(
ii
)) resulted in the formation of six mononuclear complexes characterized by spectroscopic techniques and single-crystal X-ray crystallography. The complexes bear the formulae [Ni(L
1
)
2
](NO
3
)
2
(1), [Zn(L
2
)
2
](NO
3
)(PF
6
) (2), [Cd(L
2
)(H
2
O)(CH
3
OH)(NO
3
)](NO
3
) (3), [Cu(L
2
)Cl
2
] (4), [Ni(L
2
)
2
](NO
3
)
2
(5) and [Mn(L
2
)(CH
3
OH)(Cl)
2
] (6). The biological activity of the compounds was further evaluated
in vitro
regarding their interaction with calf-thymus DNA, their cleavage ability towards supercoiled circular pBR322 plasmid DNA in the absence or presence of irradiation at various wavelengths (UVA, UVB and visible light), their affinity to bovine serum albumin and their ability to scavenge 1,1-diphenyl-picrylhydrazyl and 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) radicals and to reduce H
2
O
2
.
In silico
molecular docking calculations were employed to study the behavior of the complexes towards calf-thymus DNA and bovine serum albumin. |
doi_str_mv | 10.1039/d2dt02622h |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2728467621</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2732961536</sourcerecordid><originalsourceid>FETCH-LOGICAL-c292t-81d2071dd107ac72b0c1c439e82fb0786f6221ae2b37eb20def22dd8ee950e893</originalsourceid><addsrcrecordid>eNpdkc1u1DAQgCMEEqVw4QkscdlFDdiTbH64Vd3SIlVwWc6RY082U3ntre0sTV-Y18DbRRw4zUjzzTejmSx7L_gnwYv2swYdOVQA44vsTJR1nbdQlC__5VC9zt6EcM85AF_BWfZ746UNFMlZtsMozYIRsSVTbrc3-IiBuYGN0rgtWhlRM42eDjLS4VRasGu2zMt8AfliP3vSZHPIZ5Nc42zQ4nKctZdPZGezfJjIyidnyOIXFqKfVJw8XjBp0_xH0ikyqZKb4nzB1t8v855sMm6POduPLjplUB7kNjWRjeiPdNr8F8WRSdNPO7LJplORBTKkXBozacLwNns1SBPw3d94nv38er25us3vftx8u7q8yxW0EPNGaOC10FrwWqoaeq6EKosWGxh6XjfVkG4rJEJf1NgD1zgAaN0gtiuOTVucZ4uTd-_dw4QhdjsKCo2RFt0UOqihKau6ApHQD_-h927yNm2XqALaSqyKKlEfT5TyLgSPQ7f3tJN-7gTvjj_v1rDePP_8tvgD34migQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2732961536</pqid></control><display><type>article</type><title>Transition metal( ii ) complexes of halogenated derivatives of ( E )-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline: structure, antioxidant activity, DNA-binding DNA photocleavage, interaction with albumin and in silico studies</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Kakoulidou, Chrisoula ; Chasapis, Christos T. ; Hatzidimitriou, Antonios G. ; Fylaktakidou, Konstantina C. ; Psomas, George</creator><creatorcontrib>Kakoulidou, Chrisoula ; Chasapis, Christos T. ; Hatzidimitriou, Antonios G. ; Fylaktakidou, Konstantina C. ; Psomas, George</creatorcontrib><description>Two novel halogenated (Br- and F-) quinazoline derivatives, namely [(
E
)-4-(2-((6-bromopyridin-2-yl)methylene)hydrazinyl)quinazoline] (L1) and [(
E
)-4-(2-((3-fluoropyridin-2-yl)methylene)hydrazinyl) quinazoline] (L2), were synthesized and characterized. Their interaction with a series of metal(
ii
) ions (= Mn(
ii
), Ni(
ii
), Cu(
ii
), Zn(
ii
) and Cd(
ii
)) resulted in the formation of six mononuclear complexes characterized by spectroscopic techniques and single-crystal X-ray crystallography. The complexes bear the formulae [Ni(L
1
)
2
](NO
3
)
2
(1), [Zn(L
2
)
2
](NO
3
)(PF
6
) (2), [Cd(L
2
)(H
2
O)(CH
3
OH)(NO
3
)](NO
3
) (3), [Cu(L
2
)Cl
2
] (4), [Ni(L
2
)
2
](NO
3
)
2
(5) and [Mn(L
2
)(CH
3
OH)(Cl)
2
] (6). The biological activity of the compounds was further evaluated
in vitro
regarding their interaction with calf-thymus DNA, their cleavage ability towards supercoiled circular pBR322 plasmid DNA in the absence or presence of irradiation at various wavelengths (UVA, UVB and visible light), their affinity to bovine serum albumin and their ability to scavenge 1,1-diphenyl-picrylhydrazyl and 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) radicals and to reduce H
2
O
2
.
In silico
molecular docking calculations were employed to study the behavior of the complexes towards calf-thymus DNA and bovine serum albumin.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/d2dt02622h</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Biological activity ; Cadmium ; Cattle ; Copper ; Crystallography ; Hydrogen peroxide ; Manganese ; Methylene ; Molecular docking ; Nickel ; Plasmids ; Serum albumin ; Single crystals ; Sulfonic acid ; Transition metals ; Zinc</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2022-11, Vol.51 (43), p.16688-16705</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c292t-81d2071dd107ac72b0c1c439e82fb0786f6221ae2b37eb20def22dd8ee950e893</citedby><cites>FETCH-LOGICAL-c292t-81d2071dd107ac72b0c1c439e82fb0786f6221ae2b37eb20def22dd8ee950e893</cites><orcidid>0000-0002-8728-6245 ; 0000-0002-5879-7265 ; 0000-0002-2186-2617</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Kakoulidou, Chrisoula</creatorcontrib><creatorcontrib>Chasapis, Christos T.</creatorcontrib><creatorcontrib>Hatzidimitriou, Antonios G.</creatorcontrib><creatorcontrib>Fylaktakidou, Konstantina C.</creatorcontrib><creatorcontrib>Psomas, George</creatorcontrib><title>Transition metal( ii ) complexes of halogenated derivatives of ( E )-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline: structure, antioxidant activity, DNA-binding DNA photocleavage, interaction with albumin and in silico studies</title><title>Dalton transactions : an international journal of inorganic chemistry</title><description>Two novel halogenated (Br- and F-) quinazoline derivatives, namely [(
E
)-4-(2-((6-bromopyridin-2-yl)methylene)hydrazinyl)quinazoline] (L1) and [(
E
)-4-(2-((3-fluoropyridin-2-yl)methylene)hydrazinyl) quinazoline] (L2), were synthesized and characterized. Their interaction with a series of metal(
ii
) ions (= Mn(
ii
), Ni(
ii
), Cu(
ii
), Zn(
ii
) and Cd(
ii
)) resulted in the formation of six mononuclear complexes characterized by spectroscopic techniques and single-crystal X-ray crystallography. The complexes bear the formulae [Ni(L
1
)
2
](NO
3
)
2
(1), [Zn(L
2
)
2
](NO
3
)(PF
6
) (2), [Cd(L
2
)(H
2
O)(CH
3
OH)(NO
3
)](NO
3
) (3), [Cu(L
2
)Cl
2
] (4), [Ni(L
2
)
2
](NO
3
)
2
(5) and [Mn(L
2
)(CH
3
OH)(Cl)
2
] (6). The biological activity of the compounds was further evaluated
in vitro
regarding their interaction with calf-thymus DNA, their cleavage ability towards supercoiled circular pBR322 plasmid DNA in the absence or presence of irradiation at various wavelengths (UVA, UVB and visible light), their affinity to bovine serum albumin and their ability to scavenge 1,1-diphenyl-picrylhydrazyl and 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) radicals and to reduce H
2
O
2
.
In silico
molecular docking calculations were employed to study the behavior of the complexes towards calf-thymus DNA and bovine serum albumin.</description><subject>Biological activity</subject><subject>Cadmium</subject><subject>Cattle</subject><subject>Copper</subject><subject>Crystallography</subject><subject>Hydrogen peroxide</subject><subject>Manganese</subject><subject>Methylene</subject><subject>Molecular docking</subject><subject>Nickel</subject><subject>Plasmids</subject><subject>Serum albumin</subject><subject>Single crystals</subject><subject>Sulfonic acid</subject><subject>Transition metals</subject><subject>Zinc</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpdkc1u1DAQgCMEEqVw4QkscdlFDdiTbH64Vd3SIlVwWc6RY082U3ntre0sTV-Y18DbRRw4zUjzzTejmSx7L_gnwYv2swYdOVQA44vsTJR1nbdQlC__5VC9zt6EcM85AF_BWfZ746UNFMlZtsMozYIRsSVTbrc3-IiBuYGN0rgtWhlRM42eDjLS4VRasGu2zMt8AfliP3vSZHPIZ5Nc42zQ4nKctZdPZGezfJjIyidnyOIXFqKfVJw8XjBp0_xH0ikyqZKb4nzB1t8v855sMm6POduPLjplUB7kNjWRjeiPdNr8F8WRSdNPO7LJplORBTKkXBozacLwNns1SBPw3d94nv38er25us3vftx8u7q8yxW0EPNGaOC10FrwWqoaeq6EKosWGxh6XjfVkG4rJEJf1NgD1zgAaN0gtiuOTVucZ4uTd-_dw4QhdjsKCo2RFt0UOqihKau6ApHQD_-h927yNm2XqALaSqyKKlEfT5TyLgSPQ7f3tJN-7gTvjj_v1rDePP_8tvgD34migQ</recordid><startdate>20221108</startdate><enddate>20221108</enddate><creator>Kakoulidou, Chrisoula</creator><creator>Chasapis, Christos T.</creator><creator>Hatzidimitriou, Antonios G.</creator><creator>Fylaktakidou, Konstantina C.</creator><creator>Psomas, George</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8728-6245</orcidid><orcidid>https://orcid.org/0000-0002-5879-7265</orcidid><orcidid>https://orcid.org/0000-0002-2186-2617</orcidid></search><sort><creationdate>20221108</creationdate><title>Transition metal( ii ) complexes of halogenated derivatives of ( E )-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline: structure, antioxidant activity, DNA-binding DNA photocleavage, interaction with albumin and in silico studies</title><author>Kakoulidou, Chrisoula ; Chasapis, Christos T. ; Hatzidimitriou, Antonios G. ; Fylaktakidou, Konstantina C. ; Psomas, George</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c292t-81d2071dd107ac72b0c1c439e82fb0786f6221ae2b37eb20def22dd8ee950e893</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Biological activity</topic><topic>Cadmium</topic><topic>Cattle</topic><topic>Copper</topic><topic>Crystallography</topic><topic>Hydrogen peroxide</topic><topic>Manganese</topic><topic>Methylene</topic><topic>Molecular docking</topic><topic>Nickel</topic><topic>Plasmids</topic><topic>Serum albumin</topic><topic>Single crystals</topic><topic>Sulfonic acid</topic><topic>Transition metals</topic><topic>Zinc</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kakoulidou, Chrisoula</creatorcontrib><creatorcontrib>Chasapis, Christos T.</creatorcontrib><creatorcontrib>Hatzidimitriou, Antonios G.</creatorcontrib><creatorcontrib>Fylaktakidou, Konstantina C.</creatorcontrib><creatorcontrib>Psomas, George</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kakoulidou, Chrisoula</au><au>Chasapis, Christos T.</au><au>Hatzidimitriou, Antonios G.</au><au>Fylaktakidou, Konstantina C.</au><au>Psomas, George</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Transition metal( ii ) complexes of halogenated derivatives of ( E )-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline: structure, antioxidant activity, DNA-binding DNA photocleavage, interaction with albumin and in silico studies</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><date>2022-11-08</date><risdate>2022</risdate><volume>51</volume><issue>43</issue><spage>16688</spage><epage>16705</epage><pages>16688-16705</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>Two novel halogenated (Br- and F-) quinazoline derivatives, namely [(
E
)-4-(2-((6-bromopyridin-2-yl)methylene)hydrazinyl)quinazoline] (L1) and [(
E
)-4-(2-((3-fluoropyridin-2-yl)methylene)hydrazinyl) quinazoline] (L2), were synthesized and characterized. Their interaction with a series of metal(
ii
) ions (= Mn(
ii
), Ni(
ii
), Cu(
ii
), Zn(
ii
) and Cd(
ii
)) resulted in the formation of six mononuclear complexes characterized by spectroscopic techniques and single-crystal X-ray crystallography. The complexes bear the formulae [Ni(L
1
)
2
](NO
3
)
2
(1), [Zn(L
2
)
2
](NO
3
)(PF
6
) (2), [Cd(L
2
)(H
2
O)(CH
3
OH)(NO
3
)](NO
3
) (3), [Cu(L
2
)Cl
2
] (4), [Ni(L
2
)
2
](NO
3
)
2
(5) and [Mn(L
2
)(CH
3
OH)(Cl)
2
] (6). The biological activity of the compounds was further evaluated
in vitro
regarding their interaction with calf-thymus DNA, their cleavage ability towards supercoiled circular pBR322 plasmid DNA in the absence or presence of irradiation at various wavelengths (UVA, UVB and visible light), their affinity to bovine serum albumin and their ability to scavenge 1,1-diphenyl-picrylhydrazyl and 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) radicals and to reduce H
2
O
2
.
In silico
molecular docking calculations were employed to study the behavior of the complexes towards calf-thymus DNA and bovine serum albumin.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d2dt02622h</doi><tpages>18</tpages><orcidid>https://orcid.org/0000-0002-8728-6245</orcidid><orcidid>https://orcid.org/0000-0002-5879-7265</orcidid><orcidid>https://orcid.org/0000-0002-2186-2617</orcidid><oa>free_for_read</oa></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1477-9226 |
ispartof | Dalton transactions : an international journal of inorganic chemistry, 2022-11, Vol.51 (43), p.16688-16705 |
issn | 1477-9226 1477-9234 |
language | eng |
recordid | cdi_proquest_miscellaneous_2728467621 |
source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Biological activity Cadmium Cattle Copper Crystallography Hydrogen peroxide Manganese Methylene Molecular docking Nickel Plasmids Serum albumin Single crystals Sulfonic acid Transition metals Zinc |
title | Transition metal( ii ) complexes of halogenated derivatives of ( E )-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline: structure, antioxidant activity, DNA-binding DNA photocleavage, interaction with albumin and in silico studies |
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