Transition metal() complexes of halogenated derivatives of ()-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline: structure, antioxidant activity, DNA-binding DNA photocleavage, interaction with albumin and studies
Two novel halogenated (Br- and F-) quinazoline derivatives, namely [( E )-4-(2-((6-bromopyridin-2-yl)methylene)hydrazinyl)quinazoline] ( L 1 ) and [( E )-4-(2-((3-fluoropyridin-2-yl)methylene)hydrazinyl) quinazoline] ( L 2 ), were synthesized and characterized. Their interaction with a series of met...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2022-11, Vol.51 (43), p.16688-1675 |
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| container_title | Dalton transactions : an international journal of inorganic chemistry |
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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] (
L
1
) and [(
E
)-4-(2-((3-fluoropyridin-2-yl)methylene)hydrazinyl) quinazoline] (
L
2
), 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.
Six transition metal(
ii
) complexes with halogenated quinazoline derivatives as ligands were characterized and evaluated for interaction with calf-thymus DNA, photocleavage of plasmid-DNA, affinity for bovine serum albumin, and antioxidant activity. |
| doi_str_mv | 10.1039/d2dt02622h |
| format | Article |
| fullrecord | <record><control><sourceid>rsc</sourceid><recordid>TN_cdi_rsc_primary_d2dt02622h</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>d2dt02622h</sourcerecordid><originalsourceid>FETCH-rsc_primary_d2dt02622h3</originalsourceid><addsrcrecordid>eNqFkD9PwzAQxS0EEuXPwo7kMZFqSJzSqmyIgpiYulfX-JoccuxgO6XuB-Xz4AoEI9N70rv73dMxdlUWN2VRzW-VVKGQUynbIzYqJ7OZmMtqcvzr5fSUnXn_VhRSFndyxD6XDoynQNbwDgPoLOe17XqNO_TcbngL2jZoIKDiCh1tIdD2O8pyMRGZFFkfHSkyQoqoE6SNGg3mbVQO9mSizt8HMrC3mgzecx_cUIfB4ZiDSYd3pJJyqBOYQhzzxeuDWJNJxObged_aYGuNsIUmLZEJ6A7TqfIHhZaDXg8dmURTCT4oQn_BTjagPV7-6Dm7fn5aPr4I5-tV76gDF1d_z6r-y78AAe9yaA</addsrcrecordid><sourcetype>Publisher</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Transition metal() complexes of halogenated derivatives of ()-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline: structure, antioxidant activity, DNA-binding DNA photocleavage, interaction with albumin and 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] (
L
1
) and [(
E
)-4-(2-((3-fluoropyridin-2-yl)methylene)hydrazinyl) quinazoline] (
L
2
), 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.
Six transition metal(
ii
) complexes with halogenated quinazoline derivatives as ligands were characterized and evaluated for interaction with calf-thymus DNA, photocleavage of plasmid-DNA, affinity for bovine serum albumin, and antioxidant activity.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/d2dt02622h</identifier><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2022-11, Vol.51 (43), p.16688-1675</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</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() complexes of halogenated derivatives of ()-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline: structure, antioxidant activity, DNA-binding DNA photocleavage, interaction with albumin and 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] (
L
1
) and [(
E
)-4-(2-((3-fluoropyridin-2-yl)methylene)hydrazinyl) quinazoline] (
L
2
), 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.
Six transition metal(
ii
) complexes with halogenated quinazoline derivatives as ligands were characterized and evaluated for interaction with calf-thymus DNA, photocleavage of plasmid-DNA, affinity for bovine serum albumin, and antioxidant activity.</description><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFkD9PwzAQxS0EEuXPwo7kMZFqSJzSqmyIgpiYulfX-JoccuxgO6XuB-Xz4AoEI9N70rv73dMxdlUWN2VRzW-VVKGQUynbIzYqJ7OZmMtqcvzr5fSUnXn_VhRSFndyxD6XDoynQNbwDgPoLOe17XqNO_TcbngL2jZoIKDiCh1tIdD2O8pyMRGZFFkfHSkyQoqoE6SNGg3mbVQO9mSizt8HMrC3mgzecx_cUIfB4ZiDSYd3pJJyqBOYQhzzxeuDWJNJxObged_aYGuNsIUmLZEJ6A7TqfIHhZaDXg8dmURTCT4oQn_BTjagPV7-6Dm7fn5aPr4I5-tV76gDF1d_z6r-y78AAe9yaA</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><scope/></search><sort><creationdate>20221108</creationdate><title>Transition metal() complexes of halogenated derivatives of ()-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline: structure, antioxidant activity, DNA-binding DNA photocleavage, interaction with albumin and 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-rsc_primary_d2dt02622h3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><creationdate>2022</creationdate><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><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() complexes of halogenated derivatives of ()-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline: structure, antioxidant activity, DNA-binding DNA photocleavage, interaction with albumin and 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>1675</epage><pages>16688-1675</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] (
L
1
) and [(
E
)-4-(2-((3-fluoropyridin-2-yl)methylene)hydrazinyl) quinazoline] (
L
2
), 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.
Six transition metal(
ii
) complexes with halogenated quinazoline derivatives as ligands were characterized and evaluated for interaction with calf-thymus DNA, photocleavage of plasmid-DNA, affinity for bovine serum albumin, and antioxidant activity.</abstract><doi>10.1039/d2dt02622h</doi><tpages>18</tpages></addata></record> |
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| identifier | ISSN: 1477-9226 |
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| recordid | cdi_rsc_primary_d2dt02622h |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | Transition metal() complexes of halogenated derivatives of ()-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline: structure, antioxidant activity, DNA-binding DNA photocleavage, interaction with albumin and studies |
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