Synthesis and characterization of novel naphthalene-derivatized tridentate ligands and their net neutral rhenium tricarbonyl complexes and cytotoxic effects on non-small cell lung cancer cells of interest

Darshani, Taniya; Fronczek, Frank R.; Priyadarshani, Varuni V.; Samarakoon, Sameera Ranganath; Perera, Inoka C.; Perera, Theshini

doi:10.1016/j.poly.2020.114652

Cited by 11 publications

(12 citation statements)

References 47 publications

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“…Darshani et al explored the in vitro cytotoxicity of diethylenetriamine sulfonamide ligands and their rhenium complexes (Figure 11) which shows that the metal complexes show higher cytotoxicity than their corresponding sulfonamide ligands (Darshani et al, 2020a). The complexes were found to be more potent than the reported values for cisplatin.…”

Section: Biological Applicationsmentioning

confidence: 99%

“…Figure1: The typical process for the synthesis of ethylenediamine sulfonamides Figure 2: The typical process for the synthesis of disubstituted ethylenediamine sulfonamides When it comes to monosubstituted ethylenediamine and diethylenetriamine ligands the amine is no longer the limiting reagent as excess ethylenediamine or diethylenetriamine is used to facilitate the monosubstitution (2020, Darshani et al, 2020a, Feng et al, 2017. Here the excess amine can serve as a base to abstract the proton released during sulfonylation.…”

Section: Synthesis Of N-sulfonamide Ligandsmentioning

confidence: 99%

“…Either of two different methods are employed for the synthesis of metal sulfonamide complexes. One is to react a solution of the ligand with a solution of the metal precursor and / or heat the mixture at reflux until the limiting reagent is fully consumed (Bodoki et al, 2009, Perera et al, 2013, Darshani et al, 2020b, Darshani et al, 2020a. The other is to utilize an electrochemical procedure to obtain the complex.…”

Section: Synthesis Of Metal-n(sulfonamido) Complexesmentioning

confidence: 99%

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Complexes of N, N- and N, N, N- Sulfonamide Ligands as Therapeutic and Diagnostic Agents

Theshini Perera,

Dilmi Witharana

2023

VJScience

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Ethylenediamine, diethylenetriamine and dipicolylamine have been used as the carrier ligands to synthesize bidentate (N,N) or tridentate (N,N,N) chelate systems that coordinate with metal centers. The terminal amine groups of ethylenediamine and diethylenetriamine and the central amine group of dipicolylamine can be easily substituted to give sulfonamide ligands having bulky aromatic fragments. In the formation of metal sulfonamides, the sulfonamide nitrogens of primary or secondary sulfonamidesdeprotonate and coordinate with metal centers forming M-N bonds while the free amines coordinate to metal centers through lone pairs. The reported synthetic approaches and the properties of these complexes and ligands are discussed in this review. The bulky sulfonamide moieties bring about unique biological features to the ligand system while enhancing the fluorescent properties of the ligand. The metal center itself incorporates interesting biological features to the complex. These properties of the metal center andthe ligand show a synergistic effect in the complexes that may come in handy when designing therapeutic or diagnostic agents. The increased lipophilicity of the ligands and thereby the complexes will ensure better uptake by target cells making them ideal candidates for biological applications. Keywords: Sulfonamide, ethylenediamine, diethylenetriamine, dipicolylamine

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Section: Biological Applicationsmentioning

confidence: 99%

Section: Synthesis Of N-sulfonamide Ligandsmentioning

confidence: 99%

Section: Synthesis Of Metal-n(sulfonamido) Complexesmentioning

confidence: 99%

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Complexes of N, N- and N, N, N- Sulfonamide Ligands as Therapeutic and Diagnostic Agents

Theshini Perera,

Dilmi Witharana

2023

VJScience

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“…This compound was around 5-fold less toxic against normal lung fibroblast cells. In contrast, a similar 2-naphtalenesulfonamide complex had no cytotoxic activity against the NCI-H292 cell line [ 112 ].…”

Section: D-elements Of Groupmentioning

confidence: 99%

Anticancer Metallocenes and Metal Complexes of Transition Elements from Groups 4 to 7

Kostova

2024

Molecules

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With the progression in the field of bioinorganic chemistry, the role of transition metal complexes as the most widely used therapeutics is becoming a more and more attractive research area. The complexes of transition metals possess a great variety of attractive pharmacological properties, including anticancer, anti-inflammatory, antioxidant, anti-infective, etc., activities. Transition metal complexes have proven to be potential alternatives to biologically active organic compounds, especially as antitumor agents. The performance of metal coordination compounds in living systems is anticipated to differ generally from the action of non-metal-containing drugs and may offer unique diagnostic and/or therapeutic opportunities. In this review, the rapid development and application of metallocenes and metal complexes of elements from Groups 4 to 7 in cancer diagnostics and therapy have been summarized. Most of the heavy metals discussed in the current review are newly discovered metals. That is why the use of their metal-based compounds has attracted a lot of attention concerning their organometallic and coordination chemistry. All of this imposes more systematic studies on their biological activity, biocompatibility, and toxicity and presupposes further investigations.

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“…Cancer treatment has greatly benefited from the extensive applications of platinum drugs . However, due to various harmful effects of this platinum-based drug in normal cells, it′s use has been restricted, prompting researchers to turn to nonplatinum anticancer metallodrugs. − After being tested on several cancer cell lines, researchers are increasingly interested in ruthenium, iridium, and rhenium-based metallodrugs. − The activity of ruthenium complex against cisplatin-resistant cells with a minimal toxic response all make delivery to cancer cells simpler and with fewer adverse effects . Some of Ru(II)-arene complexes have previously been reported as water-soluble in nature.…”

Section: Introductionmentioning

confidence: 99%

Luminescent 11-{Naphthalen-1-yl}dipyrido[3,2-a:2′,3′-c]phenazine-Based Ru(II)/Ir(III)/Re(I) Complexes for HCT-116 Colorectal Cancer Stem Cell Therapy

Das

Shanavas

Nagendra

et al. 2023

ACS Appl. Bio Mater.

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Due to a number of unpleasant considerations, marketed drugs have steadily lost their importance in the treatment of cancer. In order to find a viable cancer cell diagnostic agent, we therefore focused on metal complexes that displayed target adequacy, permeability to cancer cells, high standard water solubility, cytoselectivity, and luminescent behavior. In this aspect, luminescent 11-{naphthalen-1-yl} dipyrido [3,2-a:2′,3′-c] phenazine based Ru(II)/Ir(III)/Re(I) complexes have been prepared for HCT-116 colorectal cancer stem cell therapy. Our study successfully established the possible cytotoxicity of IrL complex at different doses on HCT-116 colorectal cancer stem cells (CRCSCs). Additionally, an immunochemistry analysis of the complex IrL showed that the molecule was subcellularly localized in the nucleus and other regions of the cytoplasm, where it caused nuclear DNA damage and mitochondrial dysfunction. The level of BAX and Bcl-2 was further quantified by qRT-PCR. The expression of proapoptotic BAX showed increased expression in the complex IrL-treated cell compared to the control, indicating the potential of complex IrL for apoptotic induction. Upon further validation, complex IrL was developed as an inhibitor of autophagy for the eradication of cancer stem cells.

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Synthesis and characterization of novel naphthalene-derivatized tridentate ligands and their net neutral rhenium tricarbonyl complexes and cytotoxic effects on non-small cell lung cancer cells of interest

Cited by 11 publications

References 47 publications

Complexes of N, N- and N, N, N- Sulfonamide Ligands as Therapeutic and Diagnostic Agents

Complexes of N, N- and N, N, N- Sulfonamide Ligands as Therapeutic and Diagnostic Agents

Anticancer Metallocenes and Metal Complexes of Transition Elements from Groups 4 to 7

Luminescent 11-{Naphthalen-1-yl}dipyrido[3,2-a:2′,3′-c]phenazine-Based Ru(II)/Ir(III)/Re(I) Complexes for HCT-116 Colorectal Cancer Stem Cell Therapy

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