Transition metal complexes of pyridazine-based ligand: synthesis, characterization, biological activities, and molecular docking studies
A new class of pyridazine-based six Iron(II), Nickel(II) and Copper(II) metal complexes of (E) -2-(6-chloropyridazin-3-yl)-1-(1-(pyridin-2-yl)ethylidene)hydrazine ligand (L1)(1) derived from condensation of 2-(6-chloropyridazin-3-yl)hydrazine and pyridine-2-acetaldehyde were synthesized in 1:1 and 1...
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| Veröffentlicht in: | Journal of the Iranian Chemical Society 2023-12, Vol.20 (12), p.3103-3117 |
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| creator | Patil, Smita S. Tadavi, Samina K. Ghatole, Ajay M. Bendre, Ratnamala S. |
| description | A new class of pyridazine-based six Iron(II), Nickel(II) and Copper(II) metal complexes of
(E)
-2-(6-chloropyridazin-3-yl)-1-(1-(pyridin-2-yl)ethylidene)hydrazine ligand (L1)(1) derived from condensation of 2-(6-chloropyridazin-3-yl)hydrazine and pyridine-2-acetaldehyde were synthesized in 1:1 and 1:2 molar ratio with ligand and characterized by UV–visible,
1
H- and
13
C-NMR, FT-IR, mass and EPR spectroscopy, elemental analysis and molar conductance. The spectroscopic evidence specifies that the ligands behave as a tridentate ligand through the nitrogen atom of pyridine-2-acetaldehyde, nitrogen atoms of azomethine group and pyridazine ring. The mass spectra demonstrated that the complexes have prepared in 1:1 and 1:2 molar ratio with ligand and suitable metals salts. From the ESR spectroscopy, confirmed that the Cu(L1)(4) complex had the square planar geometry, whereas Cu(L1)
2
(7) complex had distorted octahedral geometry. The ligand and its six metal complexes were evaluated for their in vitro antibacterial activity against
Staphylococcus aureus
(MTCC 96),
Streptococcus pyogenes
(MTCC 442),
Escherichia coli
(MTCC 443),
Pseudomonas aeruginosa
(MTCC 1688) strains, and in vitro antifungal activity against
Candida albicans
(MTCC 227),
Aspergillus niger
(MTCC 282), and
Aspergillus clavatus
(MTCC 1323) strains by using micro-broth dilution method against standard antibiotics Gentamycin, Ampicillin, Chloramphenicol, Ciprofloxacin, Norfloxacin, and antifungal agents Nystatin and Griseofulvin. Cytotoxicity assays against human colon cancer MiaPaCa-2 and PanC-1 cell lines in vitro were completed for ligand (L1) by 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium by (MTT) method. Finally, the optimized structures of the ligand and its complexes have been used to accomplish molecular docking studies with receptors of DNA Gyrase (PDB ID-1aj6) enzyme to determine the most preferred mode of interaction.
Graphical abstract |
| doi_str_mv | 10.1007/s13738-023-02901-y |
| format | Article |
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(E)
-2-(6-chloropyridazin-3-yl)-1-(1-(pyridin-2-yl)ethylidene)hydrazine ligand (L1)(1) derived from condensation of 2-(6-chloropyridazin-3-yl)hydrazine and pyridine-2-acetaldehyde were synthesized in 1:1 and 1:2 molar ratio with ligand and characterized by UV–visible,
1
H- and
13
C-NMR, FT-IR, mass and EPR spectroscopy, elemental analysis and molar conductance. The spectroscopic evidence specifies that the ligands behave as a tridentate ligand through the nitrogen atom of pyridine-2-acetaldehyde, nitrogen atoms of azomethine group and pyridazine ring. The mass spectra demonstrated that the complexes have prepared in 1:1 and 1:2 molar ratio with ligand and suitable metals salts. From the ESR spectroscopy, confirmed that the Cu(L1)(4) complex had the square planar geometry, whereas Cu(L1)
2
(7) complex had distorted octahedral geometry. The ligand and its six metal complexes were evaluated for their in vitro antibacterial activity against
Staphylococcus aureus
(MTCC 96),
Streptococcus pyogenes
(MTCC 442),
Escherichia coli
(MTCC 443),
Pseudomonas aeruginosa
(MTCC 1688) strains, and in vitro antifungal activity against
Candida albicans
(MTCC 227),
Aspergillus niger
(MTCC 282), and
Aspergillus clavatus
(MTCC 1323) strains by using micro-broth dilution method against standard antibiotics Gentamycin, Ampicillin, Chloramphenicol, Ciprofloxacin, Norfloxacin, and antifungal agents Nystatin and Griseofulvin. Cytotoxicity assays against human colon cancer MiaPaCa-2 and PanC-1 cell lines in vitro were completed for ligand (L1) by 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium by (MTT) method. Finally, the optimized structures of the ligand and its complexes have been used to accomplish molecular docking studies with receptors of DNA Gyrase (PDB ID-1aj6) enzyme to determine the most preferred mode of interaction.
Graphical abstract</description><identifier>ISSN: 1735-207X</identifier><identifier>EISSN: 1735-2428</identifier><identifier>DOI: 10.1007/s13738-023-02901-y</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Acetaldehyde ; Ampicillin ; Analytical Chemistry ; Antibiotics ; Atomic properties ; Bacteria ; Biochemistry ; Chemical analysis ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Chloromycetin ; Coordination compounds ; Copper ; Dilution ; E coli ; Fungicides ; Gentamicin ; Hydrazines ; Inorganic Chemistry ; Ligands ; Mass spectra ; Molecular docking ; Nitrogen atoms ; NMR ; Norfloxacin ; Nuclear magnetic resonance ; Organic Chemistry ; Original Paper ; Physical Chemistry ; Pyridazines ; Pyridines ; Spectrum analysis ; Transition metal compounds</subject><ispartof>Journal of the Iranian Chemical Society, 2023-12, Vol.20 (12), p.3103-3117</ispartof><rights>Iranian Chemical Society 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c270t-b91864bfc998916c1df4ae7cb1f8d63ab7dd1a46a2aef2d525e1697cf5b7fd1b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s13738-023-02901-y$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s13738-023-02901-y$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Patil, Smita S.</creatorcontrib><creatorcontrib>Tadavi, Samina K.</creatorcontrib><creatorcontrib>Ghatole, Ajay M.</creatorcontrib><creatorcontrib>Bendre, Ratnamala S.</creatorcontrib><title>Transition metal complexes of pyridazine-based ligand: synthesis, characterization, biological activities, and molecular docking studies</title><title>Journal of the Iranian Chemical Society</title><addtitle>J IRAN CHEM SOC</addtitle><description>A new class of pyridazine-based six Iron(II), Nickel(II) and Copper(II) metal complexes of
(E)
-2-(6-chloropyridazin-3-yl)-1-(1-(pyridin-2-yl)ethylidene)hydrazine ligand (L1)(1) derived from condensation of 2-(6-chloropyridazin-3-yl)hydrazine and pyridine-2-acetaldehyde were synthesized in 1:1 and 1:2 molar ratio with ligand and characterized by UV–visible,
1
H- and
13
C-NMR, FT-IR, mass and EPR spectroscopy, elemental analysis and molar conductance. The spectroscopic evidence specifies that the ligands behave as a tridentate ligand through the nitrogen atom of pyridine-2-acetaldehyde, nitrogen atoms of azomethine group and pyridazine ring. The mass spectra demonstrated that the complexes have prepared in 1:1 and 1:2 molar ratio with ligand and suitable metals salts. From the ESR spectroscopy, confirmed that the Cu(L1)(4) complex had the square planar geometry, whereas Cu(L1)
2
(7) complex had distorted octahedral geometry. The ligand and its six metal complexes were evaluated for their in vitro antibacterial activity against
Staphylococcus aureus
(MTCC 96),
Streptococcus pyogenes
(MTCC 442),
Escherichia coli
(MTCC 443),
Pseudomonas aeruginosa
(MTCC 1688) strains, and in vitro antifungal activity against
Candida albicans
(MTCC 227),
Aspergillus niger
(MTCC 282), and
Aspergillus clavatus
(MTCC 1323) strains by using micro-broth dilution method against standard antibiotics Gentamycin, Ampicillin, Chloramphenicol, Ciprofloxacin, Norfloxacin, and antifungal agents Nystatin and Griseofulvin. Cytotoxicity assays against human colon cancer MiaPaCa-2 and PanC-1 cell lines in vitro were completed for ligand (L1) by 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium by (MTT) method. Finally, the optimized structures of the ligand and its complexes have been used to accomplish molecular docking studies with receptors of DNA Gyrase (PDB ID-1aj6) enzyme to determine the most preferred mode of interaction.
Graphical abstract</description><subject>Acetaldehyde</subject><subject>Ampicillin</subject><subject>Analytical Chemistry</subject><subject>Antibiotics</subject><subject>Atomic properties</subject><subject>Bacteria</subject><subject>Biochemistry</subject><subject>Chemical analysis</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chloromycetin</subject><subject>Coordination compounds</subject><subject>Copper</subject><subject>Dilution</subject><subject>E coli</subject><subject>Fungicides</subject><subject>Gentamicin</subject><subject>Hydrazines</subject><subject>Inorganic Chemistry</subject><subject>Ligands</subject><subject>Mass spectra</subject><subject>Molecular docking</subject><subject>Nitrogen atoms</subject><subject>NMR</subject><subject>Norfloxacin</subject><subject>Nuclear magnetic resonance</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Physical Chemistry</subject><subject>Pyridazines</subject><subject>Pyridines</subject><subject>Spectrum analysis</subject><subject>Transition metal compounds</subject><issn>1735-207X</issn><issn>1735-2428</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kMtKxDAUhoMoOI6-gKuA26km6SWtOxm8wYCbEdyFNJdOxrapSSt2nsDHNmMVdy4OOXD-_wt8AJxjdIkRolcexzTOI0TiMAXC0XgAZpjGaUQSkh_-7oi-HIMT77cIpRSlyQx8rh1vvemNbWGjel5DYZuuVh_KQ6thNzoj-c60Kiq5VxLWpuKtvIZ-bPuN8sYvoNhwx0WvnNnxPWcBS2NrWxkRaOFg3gNehWAowsbWSgw1d1Ba8WraCvp-kOF8Co40r706-3nn4Pnudr18iFZP94_Lm1UkCEV9VBY4z5JSi6LIC5wJLHXCFRUl1rnMYl5SKTFPMk640kSmJFU4K6jQaUm1xGU8BxcTt3P2bVC-Z1s7uDZ8yUhekBgFUSSkyJQSznrvlGadMw13I8OI7Y2zyTgLxtm3cTaGUjyVfAi3lXJ_6H9aX_HDiQ0</recordid><startdate>20231201</startdate><enddate>20231201</enddate><creator>Patil, Smita S.</creator><creator>Tadavi, Samina K.</creator><creator>Ghatole, Ajay M.</creator><creator>Bendre, Ratnamala S.</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20231201</creationdate><title>Transition metal complexes of pyridazine-based ligand: synthesis, characterization, biological activities, and molecular docking studies</title><author>Patil, Smita S. ; Tadavi, Samina K. ; Ghatole, Ajay M. ; Bendre, Ratnamala S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c270t-b91864bfc998916c1df4ae7cb1f8d63ab7dd1a46a2aef2d525e1697cf5b7fd1b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acetaldehyde</topic><topic>Ampicillin</topic><topic>Analytical Chemistry</topic><topic>Antibiotics</topic><topic>Atomic properties</topic><topic>Bacteria</topic><topic>Biochemistry</topic><topic>Chemical analysis</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chloromycetin</topic><topic>Coordination compounds</topic><topic>Copper</topic><topic>Dilution</topic><topic>E coli</topic><topic>Fungicides</topic><topic>Gentamicin</topic><topic>Hydrazines</topic><topic>Inorganic Chemistry</topic><topic>Ligands</topic><topic>Mass spectra</topic><topic>Molecular docking</topic><topic>Nitrogen atoms</topic><topic>NMR</topic><topic>Norfloxacin</topic><topic>Nuclear magnetic resonance</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Physical Chemistry</topic><topic>Pyridazines</topic><topic>Pyridines</topic><topic>Spectrum analysis</topic><topic>Transition metal compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Patil, Smita S.</creatorcontrib><creatorcontrib>Tadavi, Samina K.</creatorcontrib><creatorcontrib>Ghatole, Ajay M.</creatorcontrib><creatorcontrib>Bendre, Ratnamala S.</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of the Iranian Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Patil, Smita S.</au><au>Tadavi, Samina K.</au><au>Ghatole, Ajay M.</au><au>Bendre, Ratnamala S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Transition metal complexes of pyridazine-based ligand: synthesis, characterization, biological activities, and molecular docking studies</atitle><jtitle>Journal of the Iranian Chemical Society</jtitle><stitle>J IRAN CHEM SOC</stitle><date>2023-12-01</date><risdate>2023</risdate><volume>20</volume><issue>12</issue><spage>3103</spage><epage>3117</epage><pages>3103-3117</pages><issn>1735-207X</issn><eissn>1735-2428</eissn><abstract>A new class of pyridazine-based six Iron(II), Nickel(II) and Copper(II) metal complexes of
(E)
-2-(6-chloropyridazin-3-yl)-1-(1-(pyridin-2-yl)ethylidene)hydrazine ligand (L1)(1) derived from condensation of 2-(6-chloropyridazin-3-yl)hydrazine and pyridine-2-acetaldehyde were synthesized in 1:1 and 1:2 molar ratio with ligand and characterized by UV–visible,
1
H- and
13
C-NMR, FT-IR, mass and EPR spectroscopy, elemental analysis and molar conductance. The spectroscopic evidence specifies that the ligands behave as a tridentate ligand through the nitrogen atom of pyridine-2-acetaldehyde, nitrogen atoms of azomethine group and pyridazine ring. The mass spectra demonstrated that the complexes have prepared in 1:1 and 1:2 molar ratio with ligand and suitable metals salts. From the ESR spectroscopy, confirmed that the Cu(L1)(4) complex had the square planar geometry, whereas Cu(L1)
2
(7) complex had distorted octahedral geometry. The ligand and its six metal complexes were evaluated for their in vitro antibacterial activity against
Staphylococcus aureus
(MTCC 96),
Streptococcus pyogenes
(MTCC 442),
Escherichia coli
(MTCC 443),
Pseudomonas aeruginosa
(MTCC 1688) strains, and in vitro antifungal activity against
Candida albicans
(MTCC 227),
Aspergillus niger
(MTCC 282), and
Aspergillus clavatus
(MTCC 1323) strains by using micro-broth dilution method against standard antibiotics Gentamycin, Ampicillin, Chloramphenicol, Ciprofloxacin, Norfloxacin, and antifungal agents Nystatin and Griseofulvin. Cytotoxicity assays against human colon cancer MiaPaCa-2 and PanC-1 cell lines in vitro were completed for ligand (L1) by 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium by (MTT) method. Finally, the optimized structures of the ligand and its complexes have been used to accomplish molecular docking studies with receptors of DNA Gyrase (PDB ID-1aj6) enzyme to determine the most preferred mode of interaction.
Graphical abstract</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><doi>10.1007/s13738-023-02901-y</doi><tpages>15</tpages></addata></record> |
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| subjects | Acetaldehyde Ampicillin Analytical Chemistry Antibiotics Atomic properties Bacteria Biochemistry Chemical analysis Chemical synthesis Chemistry Chemistry and Materials Science Chloromycetin Coordination compounds Copper Dilution E coli Fungicides Gentamicin Hydrazines Inorganic Chemistry Ligands Mass spectra Molecular docking Nitrogen atoms NMR Norfloxacin Nuclear magnetic resonance Organic Chemistry Original Paper Physical Chemistry Pyridazines Pyridines Spectrum analysis Transition metal compounds |
| title | Transition metal complexes of pyridazine-based ligand: synthesis, characterization, biological activities, and molecular docking studies |
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