Biological Properties of New Viologen-Phosphorus Dendrimers

Ciepluch, Karol; Katir, Nadia; Kadib, Abdelkrim El; Felczak, Aleksandra; Zawadzka, Katarzyna; Weber, Mathias; Klajnert, Barbara; Lisowska, Katarzyna; Caminade, Anne‐Marie; Bousmina, M.; Bryszewska, Maria; Majoral, Jean Pierre

doi:10.1021/mp200549c

Cited by 88 publications

(68 citation statements)

References 45 publications

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“…We focused on monitoring cell responses that reflect the cell condition, such as alterations in mitochondrial functions, ROS generation, and the induction of cell death processes. The MTT assay after VPD treatment was previously performed on B14 (Chinese hamster) and N2a cell lines [26]. The tested dendrimers were shown to be less toxic to B14 than to N2a cells, the viability of which was reduced to about 40-50% of the control at a concentration of 20 μM.…”

Section: Discussionmentioning

confidence: 99%

“…Cells were treated with five concentrations of a given dendrimer chosen based on previous results [26] (1, 2.5, 5, 10 and 20 μM) and incubated for 24 h in growing conditions prior to further experimentation.…”

Section: Dendrimer Treatmentmentioning

confidence: 99%

“…Several polycationic viologen-based dendrimers were tested for antiviral activity against human immunodeficiency virus (HIV-1), herpes simplex virus (HSV), vesicular stomatitis, Punta Toro virus, Sindbis virus, reovirus, and respiratory syncytial viruses and were shown to be good inhibitors of HIV-1 [25]. Ciepluch et al [26] studied eight novel dendrimers with both phosphorus groups and viologen units in their structure. These VPD differed in the core structure (tri-or hexafunctionalized), generation (G0 or G1), number of viologen units, and the number and type of surface groups, which are aldehydes, phosphonates or polyethyleneglycols (PEG).…”

Section: Introductionmentioning

confidence: 99%

“…Other than the results of simple cytotoxicity assays, there have been no reports on the influence of viologen-phosphorus structures on the cell condition and basic functions. This inclined us to continue studies on VPD cytotoxicity and examine the impact on murine neuroblastoma cells (N2a) of three of the eight studied by Ciepluch et al [26]. The tested compounds are water-soluble, zero generation dendrimers, which have either a trifunctionalized (VPD3) or hexafunctionalized (VPD1 and VPD2) core, three (VPD3) or six (VPD1 and VPD2) viologen units with Br¯ as a counteranion, and phosphonates (VPD1 and VPD3) or PEG (VPD2) as surface groups (Fig.…”

Section: Introductionmentioning

confidence: 99%

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Viologen-phosphorus dendrimers exhibit minor toxicity against a murine neuroblastoma cell line

Łaźniewska

Miłowska

Katir

et al. 2013

Cellular and Molecular Biology Letters

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Dendrimers containing viologen (derivatives of 4,4'-bipyridyl) units in their structure have been demonstrated to exhibit antiviral activity against human immunodeficiency virus (HIV-1). It has also recently been revealed that novel dendrimers with both viologen units and phosphorus groups in their structure show different antimicrobial, cytotoxic and hemotoxic properties, and have the ability to influence the activity of cholinesterases and to inhibit α-synuclein fibrillation. Since the influence of viologen-phosphorus structures on basic cellular processes had not been investigated, we examined the impact of such macromolecules on the murine neuroblastoma cell line (N2a). We selected three water-soluble viologen-phosphorus (VPD) dendrimers, which differ in their core structure, number of viologen units and number and type of surface groups, and analyzed several aspects of the cellular response. These included cell viability, generation of reactive oxygen species (ROS), alterations in mitochondrial activity, morphological modifications, and the induction of apoptosis and necrosis. The MTT assay results suggest that all of the tested dendrimers are only slightly cytotoxic. Although some changes in ROS formation and mitochondrial function were detected, the three compounds did not induce apoptosis or necrosis. In light of these results, we can assume that the tested VPD are relatively safe for mouse neuroblastoma cells. Although more research on their safety is needed, VPD seem to be promising nanoparticles for further biomedical investigation.

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Section: Discussionmentioning

confidence: 99%

Section: Dendrimer Treatmentmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Viologen-phosphorus dendrimers exhibit minor toxicity against a murine neuroblastoma cell line

Łaźniewska

Miłowska

Katir

et al. 2013

Cellular and Molecular Biology Letters

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“…Cytotoxicity, hemotoxicity, antimicrobial and antifungal activity of these dendrimers were also examined. Several conclusions could be inferred: (i) dendrimers bearing the highest number of viologen units cause more hemolysis; (ii) a few dendrimers, in particular the PEGylated one (V 6 -PEG 6 in Figure 11), are not toxic toward B14 (non-cancerous) cells but are very cytotoxic toward N2a cancerous cells; (iii) most tested dendrimers exhibited good antimicrobial properties toward the Gram-positive strain S. aureus; (iv) some dendrimers bearing the highest number of viologen units (such as V 18 -PO 12 in Figure 11) also limit the growth of Gram-negative strains E. coli and P. vulgaris [84].…”

Section: Functions As Constituents Of the Branches At One Or Several mentioning

confidence: 99%

Bifunctional Phosphorus Dendrimers and Their Properties

Caminade

Majoral

2016

Molecules

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Dendrimers are hyperbranched and monodisperse macromolecules, generally considered as a special class of polymers, but synthesized step-by-step. Most dendrimers have a uniform structure, with a single type of terminal function. However, it is often desirable to have at least two different functional groups. This review will discuss the case of bifunctional phosphorus-containing dendrimers, and the consequences for their properties. Besides the terminal functions, dendritic structures may have also a function at the core, or linked off-center to the core, or at the core of dendrons (dendritic wedges). Association of two dendrons having different terminal functions leads to Janus dendrimers (two faces). The internal structure can also possess functional groups on one layer, or linked to one layer, or on several layers. Finally, there are several ways to have two types of terminal functions, besides the case of Janus dendrimers: either each terminal function bears two functions sequentially, or two different functions are linked to each terminal branching point. Examples of each type of structure will be given in this review, as well as practical uses of such sophisticated structures in the fields of fluorescence, catalysis, nanomaterials and biology.

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Radical‐Cation Dimerization Overwhelms Inclusion in [n]Pseudorotaxanes

Nono

Dalvand

Wadhwa

et al. 2014

Chemistry A European J

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Suppression of the dimerization of the viologen radical cation by cucurbit[7]uril (CB7) in water is a well-known phenomenon. Herein, two counter-examples are presented. Two viologen-containing thread molecules were designed, synthesized, and thoroughly characterized by (1)H DOSY NMR spectrometry, UV/Vis absorption spectrophotometry, square-wave voltammetry, and chronocoulometry: BV(4+), which contains two viologen subunits, and HV(12+), which contains six. In both threads, the viologen subunits are covalently bonded to a hexavalent phosphazene core. The corresponding [3]- and [7]pseudorotaxanes that form on complexation with CB7, that is, BV(4+)⊂(CB7)2 and HV(12+)⊂(CB7)6, were also analyzed. The properties of two monomeric control threads, namely, methyl viologen (MV(2+)) and benzyl methyl viologen (BMV(2+)), as well as their [2]pseudorotaxane complexes with CB7 (MV(2+)⊂CB7 and BMV(2+)⊂CB7) were also investigated. As expected, the control pseudorotaxanes remained intact after one-electron reduction of their viologen-recognition stations. In contrast, analogous reduction of BV(4+)⊂(CB7)2 and HV(12+)⊂(CB7)6 led to host-guest decomplexation and release of the free threads BV(2(·+)) and HV(6(·+)), respectively. (1)H DOSY NMR spectrometric and chronocoulometric measurements showed that BV(2(·+)) and HV(6(·+)) have larger diffusion coefficients than the corresponding [3]- and [7]pseudorotaxanes, and UV/Vis absorption studies provided evidence for intramolecular radical-cation dimerization. These results demonstrate that radical-cation dimerization, a relatively weak interaction, can be used as a driving force in novel molecular switches.

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Biological Properties of New Viologen-Phosphorus Dendrimers

Cited by 88 publications

References 45 publications

Viologen-phosphorus dendrimers exhibit minor toxicity against a murine neuroblastoma cell line

Viologen-phosphorus dendrimers exhibit minor toxicity against a murine neuroblastoma cell line

Bifunctional Phosphorus Dendrimers and Their Properties

Radical‐Cation Dimerization Overwhelms Inclusion in [n]Pseudorotaxanes

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