Coordination-Driven Self-Assembly of Ionic Irregular Hexagonal Metallamacrocycles via an Organometallic Clip and Their Cytotoxicity Potency

Bhowmick, Sourav; Jana, Achintya; Singh, Khushwant; Gupta, Prerak; Gangrade, Ankit; Mandal, Biman B.; Das, Neeladri

doi:10.1021/acs.inorgchem.7b01561

Cited by 26 publications

(27 citation statements)

References 98 publications

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“…Commercially available 2,6-dichloropyrazine is the synthetic precursor for both donor and acceptor tectons employed herein for the self-assembly reaction. In the first step, 2,6-diiodopyrazine ( 1 ) was obtained from 2,6-dichloropyrazine, which was further reacted in two steps to yield 2,6-bis((3-iodophenyl)ethynyl)pyrazine ( 3 ) via the formation of 2,6-diethynylpyrazine ( 2 ) (Scheme 1 ) (Bhowmick et al, 2017 ).…”

Section: Resultsmentioning

confidence: 99%

Self-Assembly of a [1 + 1] Ionic Hexagonal Macrocycle and Its Antiproliferative Activity

et al. 2018

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A unique irregular hexagon was self-assembled using an organic donor clip (bearing terminal pyridyl units) and a complementary organometallic acceptor clip. The resulting metallamacrocycle was characterized by multinuclear NMR, mass spectrometry, and elemental analyses. Molecular modeling confirmed hexagonal shaped cavity for this metallamacrocycle which is a unique example of a discrete hexagonal framework self-assembled from only two building blocks. Cytotoxicity of the Pt-based acceptor tecton and the self-assembled PtII-based macrocycle was evaluated using three cancer cell lines and results were compared with cisplatin. Results confirmed a positive effect of the metallamacrocycle formation on cell growth inhibition.

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Section: Resultsmentioning

confidence: 99%

Self-Assembly of a [1 + 1] Ionic Hexagonal Macrocycle and Its Antiproliferative Activity

et al. 2018

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“…At predefined time points, scaffolds were treated with MTT [3-(4,5-dimethylthiazol-2-yl)-2,5diphenyltetrazolium bromide] for 4 h following the previously described protocol. [45] The resulting blue formazan crystals indicated the boundaries of cell growth. The macroscopic images were captured and processed using ImageJ software to calculate the % area coverage over time.…”

Section: Assessment Of Viability and Functionality Of Dwj Treated Vascular Cells -Expression Of Functional Genes (Qrt-pcr)mentioning

confidence: 99%

Functionalized Silk Vascular Grafts with Decellularized Human Wharton's Jelly Improves Remodeling via Immunomodulation in Rabbit Jugular Vein

Gupta

Chaudhuri

Janani

et al. 2021

Adv Healthcare Materials

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Cell-free polymeric tissue-engineered vascular grafts (TEVGs) have shown great promise towards clinical translation; however, their limited bioactivity and remodeling ability challenge this cause. Here, a novel cell-free bioresorbable small diameter silk TEVG system functionalized with decellularized human Wharton's jelly (dWJ) matrix is developed and successfully implanted as interposition grafts into rabbit jugular vein. Implanted TEVGs remain patent for two months and integrate with host tissue, demonstrating neo-tissue formation and constructive remodeling. Mechanistic analysis reveals that dWJ matrix is a reservoir of various immunomodulatory cytokines (Interleukin-8, 6, 10, 4 and tumor necrosis factor alpha (TNF-)), which aids in upregulating M2 macrophage-associated genes facilitating pro-remodeling behavior. Besides, dWJ treatment to human endothelial cells upregulates the expression of functional genes (cluster of differentiation 31 (CD31), endothelial nitric oxide synthase (eNOS), and vascular endothelial (VE)-cadherin), enables faster cell migration, and elevates nitric oxide (NO) production leading to the in situ development of endothelium. The dWJ functionalized silk TEVGs support increased host cell recruitment than control, including macrophages and vascular cells. It endows superior graft remodeling in terms of a dense medial layer comprising smooth muscle cells and elevates the production of extracellular matrix proteins (collagen and elastin). Altogether, these findings suggest that dWJ functionalization imitates the usefulness of cell seeding and enables graft remodeling.

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“…Hexagonal metallamacrocycles have been obtained by self-assembly of an organometallic platinum(II) clip A4 with linear dipodal ligands, 4,4′-bipyridine or pyrazine, depicted in Figure 2 (Bhowmick et al, 2018). Both macrocycles ( 6a and 7 ) exhibited cytotoxicity higher than cisplatin against the human breast cancer cell line MCF7.…”

Section: Metallacyclesmentioning

confidence: 99%

Biomedical Applications of Metallosupramolecular Assemblies—Structural Aspects of the Anticancer Activity

Ahmedova

2018

Front. Chem.

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The design and development of metallosupramolecular systems has resulted in construction of a myriad of fascinating structures with highly diverse properties and potential applications. Assessment of the biomedical applications of metallosupramolecular assemblies is an emerging field of research that stems from the recently demonstrated promising results on such systems. After the pioneering works of Therrien and coworkers on organometallic Ru-cages with promising anticancer properties, this topic has evolved to the more recent studies on bioactivity of supramolecular coordination complexes built from different metal ions and various multidentate ligands. Sufficient amount of data on the anticancer activity of metallosupramolecules has already been reported and allows outlining some general tendencies in the structural aspects of the biological activity. The main structural properties of the complexes that can be readily modified to enhance their activity are the size, the shape and charge of the formed complexes. Moreover, the intrinsic properties of the building components could predetermine some of the main characteristics of the overall supramolecular complex, such as its optical properties, chemical reactivity, solubility, etc., and could, thereby, define the areas of its biomedical applications. The unique structural property of most of the metallosupramolecular assemblies, however, is the presence of a discrete cavity that renders a whole range of additional applications resulting from specific host-guest interactions. The encapsulations of small bioactive or fluorescent molecules have been employed for delivery or recognition purposes in many examples. On the other hand, metallosupramolecules have been imbedded into target-specific polymeric nanoparticles that resulted in a successful combination of their therapeutic and diagnostic properties, making them promising for theranostic application in cancer treatment. The aim of this review paper is to mark out some key tendencies in the reported metallosupramolecular structures in relation with their biological activity and potential areas of biomedical application. In this way, a useful set of guidelines can be delineated to help synthetic chemists broaden the application areas of their supramolecular systems by few structural changes.

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Coordination-Driven Self-Assembly of Ionic Irregular Hexagonal Metallamacrocycles via an Organometallic Clip and Their Cytotoxicity Potency

Cited by 26 publications

References 98 publications

Self-Assembly of a [1 + 1] Ionic Hexagonal Macrocycle and Its Antiproliferative Activity

Self-Assembly of a [1 + 1] Ionic Hexagonal Macrocycle and Its Antiproliferative Activity

Functionalized Silk Vascular Grafts with Decellularized Human Wharton's Jelly Improves Remodeling via Immunomodulation in Rabbit Jugular Vein

Biomedical Applications of Metallosupramolecular Assemblies—Structural Aspects of the Anticancer Activity

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