New organometallic ruthenium(ii) complexes containing chelidonic acid (4-oxo-4H-pyran-2,6-dicarboxylic acid)

synthesis, structure and in vitro biological activity

Thangavel Sathiya Kamatchi, Palaniappan Kalaivani, Paramasivan Poornima, Viswanadha Vijaya Padma, Frank R. Fronczek, Karuppannan Natarajan*

*Corresponding author for this work

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Two new bivalent organometallic ruthenium complexes [Ru(HL)(CH 3CN)(CO)(PPh3)2] (3) and [Ru(HL)(CH 3CN)(CO)(AsPh3)2] (4), (HL = 4-oxo-4H-pyran-2,6-dicarboxylic acid) were synthesized, structurally characterized and their biological activities (anti-microbial, DNA-protein interactions, antioxidant and cytotoxic activity studies (MTT, LDH release and NO release)) have been investigated and compared with that of appropriate precursor complexes [RuHCl(CO)(PPh3)3] (1), [RuHCl(CO)(AsPh3)3] (2) and the ligand H2L. The crystal structure of the complex 3 was solved by a single crystal X-ray diffraction technique, which revealed that it is a distorted octahedral with HL as a dibasic bidentate donor and the chelator was observed to undergo C-H activation at one of the ortho positions, leading to the formation of a five membered metallacycle. The in vitro antimicrobial activity was carried out using the well diffusion method against different species of pathogenic bacteria and fungi and complex 4 exhibited a better activity in inhibiting the growth of the tested organisms. DNA-protein interactions of the complexes have been examined by photophysical studies, which revealed that the complexes can bind with DNA through non-intercalation and the complexes strongly quench the intrinsic fluorescence of bovine serum albumin, through a static quenching process. The free radical scavenging ability, assessed by a series of in vitro antioxidant assays involving the DPPH radical, hydroxyl radical, nitric oxide radical, superoxide anion radical, hydrogen peroxide and a metal chelating assay showed that the new complexes 3 and 4 possess excellent radical scavenging properties over 1, 2, H2L, and the standard drugs, vitamin C and BHT. The in vitro cytotoxic activities of the compounds have been validated against A549 cells via an MTT assay, LDH release, NO release and the values were compared with that of the standard drug cisplatin. The results indicated that the new complexes, specifically the complex 3, displayed a higher cytotoxic activity in inhibiting the growth of A549 cells, outperforming by five fold, the standard drug cisplatin.

Original languageEnglish
Pages (from-to)2004-2022
Number of pages19
JournalRSC Advances
Volume4
Issue number4
Early online date15 Oct 2013
DOIs
Publication statusPublished - 2014
Externally publishedYes

Fingerprint

Pyrans
Dicarboxylic Acids
Ruthenium
Organometallics
Carbon Monoxide
Bioactivity
Assays
DNA
Scavenging
Antioxidants
Acids
Cisplatin
Proteins
Vitamins
Nitric oxide
Pharmaceutical Preparations
Chelation
Fungi
Free radicals
Hydrogen peroxide

Cite this

Kamatchi, Thangavel Sathiya ; Kalaivani, Palaniappan ; Poornima, Paramasivan ; Padma, Viswanadha Vijaya ; Fronczek, Frank R. ; Natarajan, Karuppannan. / New organometallic ruthenium(ii) complexes containing chelidonic acid (4-oxo-4H-pyran-2,6-dicarboxylic acid) : synthesis, structure and in vitro biological activity. In: RSC Advances. 2014 ; Vol. 4, No. 4. pp. 2004-2022.
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abstract = "Two new bivalent organometallic ruthenium complexes [Ru(HL)(CH 3CN)(CO)(PPh3)2] (3) and [Ru(HL)(CH 3CN)(CO)(AsPh3)2] (4), (HL = 4-oxo-4H-pyran-2,6-dicarboxylic acid) were synthesized, structurally characterized and their biological activities (anti-microbial, DNA-protein interactions, antioxidant and cytotoxic activity studies (MTT, LDH release and NO release)) have been investigated and compared with that of appropriate precursor complexes [RuHCl(CO)(PPh3)3] (1), [RuHCl(CO)(AsPh3)3] (2) and the ligand H2L. The crystal structure of the complex 3 was solved by a single crystal X-ray diffraction technique, which revealed that it is a distorted octahedral with HL as a dibasic bidentate donor and the chelator was observed to undergo C-H activation at one of the ortho positions, leading to the formation of a five membered metallacycle. The in vitro antimicrobial activity was carried out using the well diffusion method against different species of pathogenic bacteria and fungi and complex 4 exhibited a better activity in inhibiting the growth of the tested organisms. DNA-protein interactions of the complexes have been examined by photophysical studies, which revealed that the complexes can bind with DNA through non-intercalation and the complexes strongly quench the intrinsic fluorescence of bovine serum albumin, through a static quenching process. The free radical scavenging ability, assessed by a series of in vitro antioxidant assays involving the DPPH radical, hydroxyl radical, nitric oxide radical, superoxide anion radical, hydrogen peroxide and a metal chelating assay showed that the new complexes 3 and 4 possess excellent radical scavenging properties over 1, 2, H2L, and the standard drugs, vitamin C and BHT. The in vitro cytotoxic activities of the compounds have been validated against A549 cells via an MTT assay, LDH release, NO release and the values were compared with that of the standard drug cisplatin. The results indicated that the new complexes, specifically the complex 3, displayed a higher cytotoxic activity in inhibiting the growth of A549 cells, outperforming by five fold, the standard drug cisplatin.",
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New organometallic ruthenium(ii) complexes containing chelidonic acid (4-oxo-4H-pyran-2,6-dicarboxylic acid) : synthesis, structure and in vitro biological activity. / Kamatchi, Thangavel Sathiya; Kalaivani, Palaniappan; Poornima, Paramasivan; Padma, Viswanadha Vijaya; Fronczek, Frank R.; Natarajan, Karuppannan.

In: RSC Advances, Vol. 4, No. 4, 2014, p. 2004-2022.

Research output: Contribution to journalArticle

TY - JOUR

T1 - New organometallic ruthenium(ii) complexes containing chelidonic acid (4-oxo-4H-pyran-2,6-dicarboxylic acid)

T2 - synthesis, structure and in vitro biological activity

AU - Kamatchi, Thangavel Sathiya

AU - Kalaivani, Palaniappan

AU - Poornima, Paramasivan

AU - Padma, Viswanadha Vijaya

AU - Fronczek, Frank R.

AU - Natarajan, Karuppannan

PY - 2014

Y1 - 2014

N2 - Two new bivalent organometallic ruthenium complexes [Ru(HL)(CH 3CN)(CO)(PPh3)2] (3) and [Ru(HL)(CH 3CN)(CO)(AsPh3)2] (4), (HL = 4-oxo-4H-pyran-2,6-dicarboxylic acid) were synthesized, structurally characterized and their biological activities (anti-microbial, DNA-protein interactions, antioxidant and cytotoxic activity studies (MTT, LDH release and NO release)) have been investigated and compared with that of appropriate precursor complexes [RuHCl(CO)(PPh3)3] (1), [RuHCl(CO)(AsPh3)3] (2) and the ligand H2L. The crystal structure of the complex 3 was solved by a single crystal X-ray diffraction technique, which revealed that it is a distorted octahedral with HL as a dibasic bidentate donor and the chelator was observed to undergo C-H activation at one of the ortho positions, leading to the formation of a five membered metallacycle. The in vitro antimicrobial activity was carried out using the well diffusion method against different species of pathogenic bacteria and fungi and complex 4 exhibited a better activity in inhibiting the growth of the tested organisms. DNA-protein interactions of the complexes have been examined by photophysical studies, which revealed that the complexes can bind with DNA through non-intercalation and the complexes strongly quench the intrinsic fluorescence of bovine serum albumin, through a static quenching process. The free radical scavenging ability, assessed by a series of in vitro antioxidant assays involving the DPPH radical, hydroxyl radical, nitric oxide radical, superoxide anion radical, hydrogen peroxide and a metal chelating assay showed that the new complexes 3 and 4 possess excellent radical scavenging properties over 1, 2, H2L, and the standard drugs, vitamin C and BHT. The in vitro cytotoxic activities of the compounds have been validated against A549 cells via an MTT assay, LDH release, NO release and the values were compared with that of the standard drug cisplatin. The results indicated that the new complexes, specifically the complex 3, displayed a higher cytotoxic activity in inhibiting the growth of A549 cells, outperforming by five fold, the standard drug cisplatin.

AB - Two new bivalent organometallic ruthenium complexes [Ru(HL)(CH 3CN)(CO)(PPh3)2] (3) and [Ru(HL)(CH 3CN)(CO)(AsPh3)2] (4), (HL = 4-oxo-4H-pyran-2,6-dicarboxylic acid) were synthesized, structurally characterized and their biological activities (anti-microbial, DNA-protein interactions, antioxidant and cytotoxic activity studies (MTT, LDH release and NO release)) have been investigated and compared with that of appropriate precursor complexes [RuHCl(CO)(PPh3)3] (1), [RuHCl(CO)(AsPh3)3] (2) and the ligand H2L. The crystal structure of the complex 3 was solved by a single crystal X-ray diffraction technique, which revealed that it is a distorted octahedral with HL as a dibasic bidentate donor and the chelator was observed to undergo C-H activation at one of the ortho positions, leading to the formation of a five membered metallacycle. The in vitro antimicrobial activity was carried out using the well diffusion method against different species of pathogenic bacteria and fungi and complex 4 exhibited a better activity in inhibiting the growth of the tested organisms. DNA-protein interactions of the complexes have been examined by photophysical studies, which revealed that the complexes can bind with DNA through non-intercalation and the complexes strongly quench the intrinsic fluorescence of bovine serum albumin, through a static quenching process. The free radical scavenging ability, assessed by a series of in vitro antioxidant assays involving the DPPH radical, hydroxyl radical, nitric oxide radical, superoxide anion radical, hydrogen peroxide and a metal chelating assay showed that the new complexes 3 and 4 possess excellent radical scavenging properties over 1, 2, H2L, and the standard drugs, vitamin C and BHT. The in vitro cytotoxic activities of the compounds have been validated against A549 cells via an MTT assay, LDH release, NO release and the values were compared with that of the standard drug cisplatin. The results indicated that the new complexes, specifically the complex 3, displayed a higher cytotoxic activity in inhibiting the growth of A549 cells, outperforming by five fold, the standard drug cisplatin.

U2 - 10.1039/c3ra43865a

DO - 10.1039/c3ra43865a

M3 - Article

VL - 4

SP - 2004

EP - 2022

JO - RSC Advances

JF - RSC Advances

SN - 2046-2069

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ER -