Synthesis, structural, DNA/protein binding and cytotoxic studies of copper(I) ∝-diimine hydrazone complexes

[Display omitted] •Cu(I) complexes with α-diimine hydrazone ligands were designed, synthesized and characterized.•DNA/BSA binding and cytotoxic studies of the new Cu(I) complexes were evaluated.•The complex 4 shows better activity. A series of copper(I) complexes with α-diimine hydrazone ligands of...

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Veröffentlicht in:Inorganica Chimica Acta 2022-04, Vol.533, p.120780, Article 120780
Hauptverfasser: Gayathri, S., Viswanathamurthi, P., Thuslim, V., Sathya, M., Ranjani, M., Prabhakaran, R., Haribabu, J., Echeverria, Cesar
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container_start_page 120780
container_title Inorganica Chimica Acta
container_volume 533
creator Gayathri, S.
Viswanathamurthi, P.
Thuslim, V.
Sathya, M.
Ranjani, M.
Prabhakaran, R.
Haribabu, J.
Echeverria, Cesar
description [Display omitted] •Cu(I) complexes with α-diimine hydrazone ligands were designed, synthesized and characterized.•DNA/BSA binding and cytotoxic studies of the new Cu(I) complexes were evaluated.•The complex 4 shows better activity. A series of copper(I) complexes with α-diimine hydrazone ligands of the type [Cu(PPh3)2(L1-4)] (1–4) were synthesized by the reacting [Cu(CH3COO)(PPh3)2] with α-diimine ligands (L1-4) [L1 = 1, 2-bis(2-(benzothiazole-2-yl)hydrazineylidene)-1, 2-dihydro acenaphthylene (AQBH), L2 = 1, 2-bis(2-(quinolin-2-yl)hydrazineylidene)-1, 2-dihydro acenaphthylene (AQQH), L3 = 9, 10-bis(2-(benzothiazol-2-yl)dihydrazano)phenanthren-9,10-one (PQBH), L4 = 9,10-bis(2-(quinolin-2-yl)dihydrazano)phenanthren-9(10H)-one (PQQH)]. The new complexes were characterized by elemental analysis, UV–vis, FT-IR, 1H 13C NMR spectra and electrospray ionization-mass spectrometry (ESI-MS). Especially, the solid state structure of L1 (AQBH) was established using single crystal X-ray analysis. The interaction of complexes with CT-DNA was explored in detail using absorption and emission spectral methods to gain some insight into the structure–activity relationship. The obtained results revealed that complexes could interact with CT-DNA via intercalation. The interaction of these synthesized Cu (I) complexes with bovine serum albumin (BSA) was also evaluated using absorption and fluorescence techniques, which provided a static quenching mechanism between them. In addition, the cytotoxicity of compounds against HepG-2 (hepatic carcinoma) cancer and Vero normal (kidney epithelial cells extracted from an African green monkey) cells was evaluated by MTT assay. It was found that complex 4 (19.54 µM) exhibited potential activity towards HepG-2 cells which was more efficient than cisplatin (48.50 µM).
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A series of copper(I) complexes with α-diimine hydrazone ligands of the type [Cu(PPh3)2(L1-4)] (1–4) were synthesized by the reacting [Cu(CH3COO)(PPh3)2] with α-diimine ligands (L1-4) [L1 = 1, 2-bis(2-(benzothiazole-2-yl)hydrazineylidene)-1, 2-dihydro acenaphthylene (AQBH), L2 = 1, 2-bis(2-(quinolin-2-yl)hydrazineylidene)-1, 2-dihydro acenaphthylene (AQQH), L3 = 9, 10-bis(2-(benzothiazol-2-yl)dihydrazano)phenanthren-9,10-one (PQBH), L4 = 9,10-bis(2-(quinolin-2-yl)dihydrazano)phenanthren-9(10H)-one (PQQH)]. The new complexes were characterized by elemental analysis, UV–vis, FT-IR, 1H 13C NMR spectra and electrospray ionization-mass spectrometry (ESI-MS). Especially, the solid state structure of L1 (AQBH) was established using single crystal X-ray analysis. The interaction of complexes with CT-DNA was explored in detail using absorption and emission spectral methods to gain some insight into the structure–activity relationship. The obtained results revealed that complexes could interact with CT-DNA via intercalation. The interaction of these synthesized Cu (I) complexes with bovine serum albumin (BSA) was also evaluated using absorption and fluorescence techniques, which provided a static quenching mechanism between them. In addition, the cytotoxicity of compounds against HepG-2 (hepatic carcinoma) cancer and Vero normal (kidney epithelial cells extracted from an African green monkey) cells was evaluated by MTT assay. 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A series of copper(I) complexes with α-diimine hydrazone ligands of the type [Cu(PPh3)2(L1-4)] (1–4) were synthesized by the reacting [Cu(CH3COO)(PPh3)2] with α-diimine ligands (L1-4) [L1 = 1, 2-bis(2-(benzothiazole-2-yl)hydrazineylidene)-1, 2-dihydro acenaphthylene (AQBH), L2 = 1, 2-bis(2-(quinolin-2-yl)hydrazineylidene)-1, 2-dihydro acenaphthylene (AQQH), L3 = 9, 10-bis(2-(benzothiazol-2-yl)dihydrazano)phenanthren-9,10-one (PQBH), L4 = 9,10-bis(2-(quinolin-2-yl)dihydrazano)phenanthren-9(10H)-one (PQQH)]. The new complexes were characterized by elemental analysis, UV–vis, FT-IR, 1H 13C NMR spectra and electrospray ionization-mass spectrometry (ESI-MS). Especially, the solid state structure of L1 (AQBH) was established using single crystal X-ray analysis. The interaction of complexes with CT-DNA was explored in detail using absorption and emission spectral methods to gain some insight into the structure–activity relationship. The obtained results revealed that complexes could interact with CT-DNA via intercalation. The interaction of these synthesized Cu (I) complexes with bovine serum albumin (BSA) was also evaluated using absorption and fluorescence techniques, which provided a static quenching mechanism between them. In addition, the cytotoxicity of compounds against HepG-2 (hepatic carcinoma) cancer and Vero normal (kidney epithelial cells extracted from an African green monkey) cells was evaluated by MTT assay. It was found that complex 4 (19.54 µM) exhibited potential activity towards HepG-2 cells which was more efficient than cisplatin (48.50 µM).</description><subject>Absorption</subject><subject>BSA binding</subject><subject>Cancer</subject><subject>Chemical analysis</subject><subject>Coordination compounds</subject><subject>Copper</subject><subject>Copper(I) complexes</subject><subject>Crystal structure</subject><subject>CT-DNA binding</subject><subject>Cytotoxicity</subject><subject>Diimide</subject><subject>Epithelium</subject><subject>Hydrazones</subject><subject>Ligands</subject><subject>Mass spectrometry</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Serum albumin</subject><subject>Single crystals</subject><subject>Spectral methods</subject><subject>Synthesis</subject><subject>Toxicity</subject><subject>X ray analysis</subject><subject>α-Diimine hydrazone ligands</subject><issn>0020-1693</issn><issn>1873-3255</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9kEtKBDEQhoMoOD4O4C7gRsEe8-ikp3ElvkF0oa5DJqlohplOm6TF8QRewst5EiPj2lUV1P9X_fUhtEfJmBIqj2djb_SYEUbHlJFmQtbQiE4aXnEmxDoaEcJIRWXLN9FWSjNCOJFcjNDiYdnlF0g-HeGU42DyEPX8CJ_fnR73MWTwHZ76zvruGevOYrPMIYd3b4p6sB4SDg6b0PcQD24O8ffnV2W9X_gO8MvSRv0RSmfCop_DO6QdtOH0PMHuX91GT5cXj2fX1e391c3Z6W1lWE1yRafOuZrxaSOl0EI6KSaN4bwG3dZSO90SKwS1rQDWcsKpNbVrW9qWmTUC-DbaX-0tL7wOkLKahSF25aRiUjYTwYWsi4quVCaGlCI41Ue_0HGpKFG_VNVMFarql6paUS2ek5UHSvw3D1El46EzYH0Ek5UN_h_3Dy5egQo</recordid><startdate>20220401</startdate><enddate>20220401</enddate><creator>Gayathri, S.</creator><creator>Viswanathamurthi, P.</creator><creator>Thuslim, V.</creator><creator>Sathya, M.</creator><creator>Ranjani, M.</creator><creator>Prabhakaran, R.</creator><creator>Haribabu, J.</creator><creator>Echeverria, Cesar</creator><general>Elsevier B.V</general><general>Elsevier Science Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20220401</creationdate><title>Synthesis, structural, DNA/protein binding and cytotoxic studies of copper(I) ∝-diimine hydrazone complexes</title><author>Gayathri, S. ; Viswanathamurthi, P. ; Thuslim, V. ; Sathya, M. ; Ranjani, M. ; Prabhakaran, R. ; Haribabu, J. ; Echeverria, Cesar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c240t-1bfff423b7665a56f6587c334ea946afa90d551d95e293031dc4f99196afdc5e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Absorption</topic><topic>BSA binding</topic><topic>Cancer</topic><topic>Chemical analysis</topic><topic>Coordination compounds</topic><topic>Copper</topic><topic>Copper(I) complexes</topic><topic>Crystal structure</topic><topic>CT-DNA binding</topic><topic>Cytotoxicity</topic><topic>Diimide</topic><topic>Epithelium</topic><topic>Hydrazones</topic><topic>Ligands</topic><topic>Mass spectrometry</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Serum albumin</topic><topic>Single crystals</topic><topic>Spectral methods</topic><topic>Synthesis</topic><topic>Toxicity</topic><topic>X ray analysis</topic><topic>α-Diimine hydrazone ligands</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gayathri, S.</creatorcontrib><creatorcontrib>Viswanathamurthi, P.</creatorcontrib><creatorcontrib>Thuslim, V.</creatorcontrib><creatorcontrib>Sathya, M.</creatorcontrib><creatorcontrib>Ranjani, M.</creatorcontrib><creatorcontrib>Prabhakaran, R.</creatorcontrib><creatorcontrib>Haribabu, J.</creatorcontrib><creatorcontrib>Echeverria, Cesar</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Inorganica Chimica Acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gayathri, S.</au><au>Viswanathamurthi, P.</au><au>Thuslim, V.</au><au>Sathya, M.</au><au>Ranjani, M.</au><au>Prabhakaran, R.</au><au>Haribabu, J.</au><au>Echeverria, Cesar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, structural, DNA/protein binding and cytotoxic studies of copper(I) ∝-diimine hydrazone complexes</atitle><jtitle>Inorganica Chimica Acta</jtitle><date>2022-04-01</date><risdate>2022</risdate><volume>533</volume><spage>120780</spage><pages>120780-</pages><artnum>120780</artnum><issn>0020-1693</issn><eissn>1873-3255</eissn><abstract>[Display omitted] •Cu(I) complexes with α-diimine hydrazone ligands were designed, synthesized and characterized.•DNA/BSA binding and cytotoxic studies of the new Cu(I) complexes were evaluated.•The complex 4 shows better activity. A series of copper(I) complexes with α-diimine hydrazone ligands of the type [Cu(PPh3)2(L1-4)] (1–4) were synthesized by the reacting [Cu(CH3COO)(PPh3)2] with α-diimine ligands (L1-4) [L1 = 1, 2-bis(2-(benzothiazole-2-yl)hydrazineylidene)-1, 2-dihydro acenaphthylene (AQBH), L2 = 1, 2-bis(2-(quinolin-2-yl)hydrazineylidene)-1, 2-dihydro acenaphthylene (AQQH), L3 = 9, 10-bis(2-(benzothiazol-2-yl)dihydrazano)phenanthren-9,10-one (PQBH), L4 = 9,10-bis(2-(quinolin-2-yl)dihydrazano)phenanthren-9(10H)-one (PQQH)]. The new complexes were characterized by elemental analysis, UV–vis, FT-IR, 1H 13C NMR spectra and electrospray ionization-mass spectrometry (ESI-MS). Especially, the solid state structure of L1 (AQBH) was established using single crystal X-ray analysis. The interaction of complexes with CT-DNA was explored in detail using absorption and emission spectral methods to gain some insight into the structure–activity relationship. The obtained results revealed that complexes could interact with CT-DNA via intercalation. The interaction of these synthesized Cu (I) complexes with bovine serum albumin (BSA) was also evaluated using absorption and fluorescence techniques, which provided a static quenching mechanism between them. In addition, the cytotoxicity of compounds against HepG-2 (hepatic carcinoma) cancer and Vero normal (kidney epithelial cells extracted from an African green monkey) cells was evaluated by MTT assay. It was found that complex 4 (19.54 µM) exhibited potential activity towards HepG-2 cells which was more efficient than cisplatin (48.50 µM).</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><doi>10.1016/j.ica.2021.120780</doi></addata></record>
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subjects Absorption
BSA binding
Cancer
Chemical analysis
Coordination compounds
Copper
Copper(I) complexes
Crystal structure
CT-DNA binding
Cytotoxicity
Diimide
Epithelium
Hydrazones
Ligands
Mass spectrometry
NMR
Nuclear magnetic resonance
Serum albumin
Single crystals
Spectral methods
Synthesis
Toxicity
X ray analysis
α-Diimine hydrazone ligands
title Synthesis, structural, DNA/protein binding and cytotoxic studies of copper(I) ∝-diimine hydrazone complexes
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