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
Hauptverfasser: Kakoulidou, Chrisoula, Chasapis, Christos T., Hatzidimitriou, Antonios G., Fylaktakidou, Konstantina C., Psomas, George
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container_issue 43
container_start_page 16688
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] (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
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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 . 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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 . 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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 . 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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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