Nucleic acid binding study of surfactant copper(<scp>ii</scp>) complex containing dipyrido[3,2-a:2′-3′-c]phenazine ligand as an intercalator: in vitro antitumor activity of complex in human liver carcinoma (HepG2) cancer cells

Nagaraj, Karuppiah; Murugan, Krishnan Senthil; Thangamuniyandi, Pilavadi; Sakthinathan, Subramanian

doi:10.1039/c4ra08049a

Cited by 18 publications

(9 citation statements)

References 57 publications

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“…At the same time, 3 and 6 gave rise to more complex binding interactions which could not be elucidated using the classic Bard et al binding model. These results suggest that additional hydrophobic interaction could also occur and contribute to the DNA binding event of such complexes as it was previously discussed in the literature for cationic surfactants. ,− …”

Section: Resultssupporting

confidence: 73%

“…They have been extensively used in recent years in imaging and drug delivery applications. − The presence of metals in the headgroup of these amphiphilic structures confers them with advantageous properties . In this context, Ru(II)-based metallosurfactants have shown great potential in several biological applications such as in the imaging of physiological hypoxia, phospholipid membranes labeling, gene therapy, or anticancer agents. ,− …”

Section: Introductionmentioning

confidence: 99%

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Effect of Alkyl Chain Length on the Photophysical, Photochemical, and Photobiological Properties of Ruthenium(II) Polypyridyl Complexes for Their Application as DNA-Targeting, Cellular-Imaging, and Light-Activated Therapeutic Agents

Estalayo-Adrián

Blasco

Bright

et al. 2021

ACS Appl. Bio Mater.

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A family of six Ru(II) polypyridyl complexes (1–6) which contain phenanthroline-based ligands functionalized with alkyl chains of different lengths (one methyl group, 10 and 21 carbon alkyl chains) and either 1,10-phenanthroline (phen) or 1,4,5,8-tetraazaphenanthrene (TAP) as ancillary ligands have been synthesized and characterized. The influence of the alkyl chain length on their photophysical and photochemical properties as well as in their photobiological applications has been elucidated by monitoring the changes in their MLCT-centered absorption and emission bands. The presence of one methyl group or 10 carbon alkyl chains does not seem to significantly affect the photophysical and photochemical properties of the resulting Ru(II) complexes when compared to the well-known [Ru(phen)3]2+ and [Ru(TAP)2phen]2+. However, an effect on their emission properties and in their ability to photosensitize singlet oxygen is observed for the Ru(II) complexes containing 21 carbon alkyl chains. The binding of these complexes to salmon testes DNA (stDNA) was investigated by observing the changes in the photophysical properties. Complexes 1, 2, 4, and 5 all showed changes in their MLCT bands that could be analyzed using conventional fitting methods, such as the Bard equation. In contrast, complexes 3 and 6, possessing long aliphatic chains, gave rise to nonclassic behavior. In addition to these analyses, both thermal denaturation and circular dichroism studies of 1–6 were carried out in the presence of stDNA which confirmed that these complexes bind to DNA. Confocal microscopy and viability studies in HeLa cervical cancer cells reveal an alkyl chain-length dependence on the cellular uptake and cytotoxicity of the resulting Ru(II) complexes due to an enhancement of their lipophilicity with increasing alkyl chain length. Thus, complexes containing 10 and 21 carbon alkyl chains are rapidly taken up into HeLa cells and, in particular, those with 21 carbon alkyl chains show a significant phototoxicity against the same cell line. Therefore, this study provides further insight into the possible modulation of the photophysical, photochemical, and photobiological properties of Ru(II) polypyridyl complexes by varying the length of the alkyl chains attached to the polypyridyl ligands coordinated to the Ru(II) center and the nature of the auxiliary groups, which we show has a significant effect on photophysical and biological properties.

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Section: Resultssupporting

confidence: 73%

Section: Introductionmentioning

confidence: 99%

Effect of Alkyl Chain Length on the Photophysical, Photochemical, and Photobiological Properties of Ruthenium(II) Polypyridyl Complexes for Their Application as DNA-Targeting, Cellular-Imaging, and Light-Activated Therapeutic Agents

Estalayo-Adrián

Blasco

Bright

et al. 2021

ACS Appl. Bio Mater.

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“…This binding was considered principally due to hydrophobic interactions. 59 The separation between E 0 0 b and E 0 0 f can be used to estimate the ratio of binding constants of the reduced and oxidized forms to DNA using the following equation: 54…”

Section: Redox Behaviormentioning

confidence: 99%

Two new mixed copper(ii)–dipeptide complexes of N,N-donor heterocycle ligands: studies on their non-covalent DNA binding, chemical nuclease, antioxidant and anticancer activities

et al. 2016

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“…In a Tris-HCl buffer solution with a pH of 7.4, all substances were incubated with CT-DNA in a 1 : 1 ratio. Temperature increases of two degrees Celsius per minute were applied to test substances in the range of 25 to 100°C, and the changes in absorbance at 260 nm were carefully scrutinized [ 33 – 35 ].…”

Section: Methodsmentioning

confidence: 99%

Comprehensive Assessment of Biomolecular Interactions of Morpholine‐Based Mixed Ligand Cu(II) and Zn(II) Complexes of 2,2′‐Bipyridine as Potential Anticancer and SARS‐CoV‐2 Agents: A Synergistic Experimental and Structure‐Based Virtual Screening

Sakthikumar

Krause

Isamura

2022

Bioinorganic Chemistry and Applications

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A new class of pharmacologically active mixed-ligand complexes (1a-2a) [MII(L)2 (bpy)], where L = 2-(4-morpholinobenzylideneamino)phenol), bpy = 2,2′-bipyridine, MII = Cu (1a), and Zn (2a), were assigned an octahedral geometry by analytical and spectral measurements. Gel electrophoresis showed that complex (1a) demonstrated the complete DNA cleavage mediated by H2O2. The overall DNA-binding constants observed from UV-vis, fluorometric, hydrodynamic, and electrochemical titrations were in the following sequence: (1a) > (2a) > (HL), which suggests that the complexes might intercalate DNA, a possibility that is further supported by the biothermodynamic characteristics. The binding constant results of BSA by electronic absorption and fluorometric titration demonstrate that complex (1a) exhibits the highest binding effectiveness among others, which means that all compounds could interact with BSA through a static approach, additionally supported by FRET measurements. Density FunctionalTheory (DFT) and molecular docking calculations were relied on to unveil the electronic structure, reactivity, and interacting capability of all substances with DNA, BSA, and SARS-CoV-2 main protease (Mpro). These observed binding energies fell within the following ranges: −7.7 to −8.6, −7.2 to −10.2, and −6.7 to −8.2 kcal/mol, respectively. The higher reactivity of the complexes compared to free ligand is supported by the Frontier MolecularOrbital (FMO) theory. The in vitro antibacterial, cytotoxic, and radical scavenging characteristics revealed that complex (1a) has the best biological efficacy compared to others. This is encouraged because all experimental findings are closely correlated with the theoretical measurements.

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Nucleic acid binding study of surfactant copper(ii) complex containing dipyrido[3,2-a:2′-3′-c]phenazine ligand as an intercalator: in vitro antitumor activity of complex in human liver carcinoma (HepG2) cancer cells

Abstract: A new surfactant copper(ii) complex, [Cu(dppz)2DA](ClO4)2, where dppz = dipyrido[3,2-a:2′-3′-c]phenazine and DA-dodecylamine, has been synthesized and characterized by physico-chemical and spectroscopic methods.

Cited by 18 publications

References 57 publications

Effect of Alkyl Chain Length on the Photophysical, Photochemical, and Photobiological Properties of Ruthenium(II) Polypyridyl Complexes for Their Application as DNA-Targeting, Cellular-Imaging, and Light-Activated Therapeutic Agents

Effect of Alkyl Chain Length on the Photophysical, Photochemical, and Photobiological Properties of Ruthenium(II) Polypyridyl Complexes for Their Application as DNA-Targeting, Cellular-Imaging, and Light-Activated Therapeutic Agents

Two new mixed copper(ii)–dipeptide complexes of N,N-donor heterocycle ligands: studies on their non-covalent DNA binding, chemical nuclease, antioxidant and anticancer activities

Comprehensive Assessment of Biomolecular Interactions of Morpholine‐Based Mixed Ligand Cu(II) and Zn(II) Complexes of 2,2′‐Bipyridine as Potential Anticancer and SARS‐CoV‐2 Agents: A Synergistic Experimental and Structure‐Based Virtual Screening

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