Dipicolinate Complexes of Oxovanadium(IV) and Dioxovanadium(V) with 2-Phenylpyridine and 4,4′-Dimethoxy-2,2′-bipyridyl as New Precatalysts for Olefin Oligomerization
Abstract:Polyolefins are used in everyday life, including in the production of many types of plastic. In addition, polyolefins account for over 50% of the polymers produced in the world. After conducting the oligomerization reactions of 2-propen-1-ol, 2-chloro-2-propen-1-ol, and norborene, polyolefins are obtained. In this report, two complexes of oxovanadium(IV) and dioxovanadium(V) with dipicolinate, 2-phenylyridine, and 4,4′-dimethoxy-2,2′-bipyridyl as precatalysts for 2-propen-1-ol, 2-chloro-2-propen-1-ol, and norb… Show more
“…The dipicolinate oxovanadium(IV) and dioxovanadium(V) complex compounds with 4,4′-dimethoxy-2,2′-bipyridyl and 2-phenylpyridine ( Figure 1 ) were synthesized in the same way as described in the publications: 31 for [VO(dipic)(dmbipy)] · 2 H 2 O and 32 for [VOO(dipic)](2-phepyH) · H 2 O. Figure 1 Simplified structural formulas of ( 1 ) [VO(dipic)(dmbipy)] · 2 H 2 O and ( 2 ) [VOO(dipic)](2-phepyH) · H 2 O (2D above, 3D below).…”
Section: Methodsmentioning
confidence: 99%
“…The results of elemental analysis of oxovanadium(IV) for [VO(dipic)(dmbipy)] · 2 H 2 O are 47.46% C, 3.69% H, and 8.77% N, where analysis calculations are the following: 47.10% C, 3.93% H, and 8.68% N. All the results concerning the analysis of the physicochemical properties of this complex are described in the literature. 31 However, the second compound complex, ie, [VOO(dipic)](2-phepyH) · H 2 O was synthesized as crystals and for this reason it was subjected to XRD analysis. The complete crystallographic characterization of the obtained dipicolinate complex of dioxovanadium(V) with 2-phenylpyridine has been described in the publication.…”
Introduction
Solid lipid nanoparticles (SLN) have been considered lately as promising drug delivery system in treatment of many human diseases including cancers. We previously studied potential drug compounds that were effective inhibitors of PTP1B phosphatase – possible target for breast cancer treatment. Based on our studies, two complexes were selected for encapsulation into the SLNs, the compound 1 ([VO(dipic)(dmbipy)] · 2 H
2
O) and compound
2
([VOO(dipic)](2-phepyH) · H
2
O). Here, we investigate the effect of encapsulation of those compounds on cell cytotoxicity against MDA-MB-231 breast cancer cell line. The study also included the stability evaluation of the obtained nanocarriers with incorporated active substances and characterization of their lipid matrix. Moreover, the cell cytotoxicity studies against the MDA-MB-231 breast cancer cell line in comparison and in combination with vincristine have been performed. Wound healing assay was carried out to observe cell migration rate.
Methods
The properties of the SLNs such as particle size, zeta potential (ZP), and polydispersity index (PDI) were investigated. The morphology of SLNs was observed by scanning electron microscopy (SEM), while the crystallinity of the lipid particles was analyzed by differential scanning calorimetry (DSC) and X-ray diffraction (XRD). The cell cytotoxicity of complexes and their encapsulated forms was carried out against MDA-MB-231 breast cancer cell line using standard MTT protocols. The wound healing assay was performed using live imaging microscopy.
Results
SLNs with a mean size of 160 ± 25 nm, a ZP of −34.00 ± 0.5, and a polydispersity index of 30 ± 5% were obtained. Encapsulated forms of compounds showed significantly higher cytotoxicity also in co-incubation with vincristine. Moreover, our research shows that the best compound was complex 2 encapsulated into lipid nanoparticles.
Conclusion
We observed that encapsulation of studied complexes into SLNs increases their cell cytotoxicity against MDA-MB-231 cell line and enhanced the effect of vincristine.
“…The dipicolinate oxovanadium(IV) and dioxovanadium(V) complex compounds with 4,4′-dimethoxy-2,2′-bipyridyl and 2-phenylpyridine ( Figure 1 ) were synthesized in the same way as described in the publications: 31 for [VO(dipic)(dmbipy)] · 2 H 2 O and 32 for [VOO(dipic)](2-phepyH) · H 2 O. Figure 1 Simplified structural formulas of ( 1 ) [VO(dipic)(dmbipy)] · 2 H 2 O and ( 2 ) [VOO(dipic)](2-phepyH) · H 2 O (2D above, 3D below).…”
Section: Methodsmentioning
confidence: 99%
“…The results of elemental analysis of oxovanadium(IV) for [VO(dipic)(dmbipy)] · 2 H 2 O are 47.46% C, 3.69% H, and 8.77% N, where analysis calculations are the following: 47.10% C, 3.93% H, and 8.68% N. All the results concerning the analysis of the physicochemical properties of this complex are described in the literature. 31 However, the second compound complex, ie, [VOO(dipic)](2-phepyH) · H 2 O was synthesized as crystals and for this reason it was subjected to XRD analysis. The complete crystallographic characterization of the obtained dipicolinate complex of dioxovanadium(V) with 2-phenylpyridine has been described in the publication.…”
Introduction
Solid lipid nanoparticles (SLN) have been considered lately as promising drug delivery system in treatment of many human diseases including cancers. We previously studied potential drug compounds that were effective inhibitors of PTP1B phosphatase – possible target for breast cancer treatment. Based on our studies, two complexes were selected for encapsulation into the SLNs, the compound 1 ([VO(dipic)(dmbipy)] · 2 H
2
O) and compound
2
([VOO(dipic)](2-phepyH) · H
2
O). Here, we investigate the effect of encapsulation of those compounds on cell cytotoxicity against MDA-MB-231 breast cancer cell line. The study also included the stability evaluation of the obtained nanocarriers with incorporated active substances and characterization of their lipid matrix. Moreover, the cell cytotoxicity studies against the MDA-MB-231 breast cancer cell line in comparison and in combination with vincristine have been performed. Wound healing assay was carried out to observe cell migration rate.
Methods
The properties of the SLNs such as particle size, zeta potential (ZP), and polydispersity index (PDI) were investigated. The morphology of SLNs was observed by scanning electron microscopy (SEM), while the crystallinity of the lipid particles was analyzed by differential scanning calorimetry (DSC) and X-ray diffraction (XRD). The cell cytotoxicity of complexes and their encapsulated forms was carried out against MDA-MB-231 breast cancer cell line using standard MTT protocols. The wound healing assay was performed using live imaging microscopy.
Results
SLNs with a mean size of 160 ± 25 nm, a ZP of −34.00 ± 0.5, and a polydispersity index of 30 ± 5% were obtained. Encapsulated forms of compounds showed significantly higher cytotoxicity also in co-incubation with vincristine. Moreover, our research shows that the best compound was complex 2 encapsulated into lipid nanoparticles.
Conclusion
We observed that encapsulation of studied complexes into SLNs increases their cell cytotoxicity against MDA-MB-231 cell line and enhanced the effect of vincristine.
“…The polycarboxylate oxovanadium(IV) and dioxovanadium(V) complex compounds (Figure 1) were synthesized according to the procedures described in the literature: [22,23] for [24] for [VO(ida)(bipy)]•2 H 2 O (Com-pound 3), [25] [VO(dipic)(dmbipy)]•2 H 2 O (Compound 4). The complex compound [VOO(dipic)](2-phepyH)•H 2 O was synthesized in crystalline form and all data specifying the XRD analysis of this complex have been described in the publication [22].…”
One of the main goals of recent bioinorganic chemistry studies has been to design and synthesize novel substances to treat human diseases. The promising compounds are metal-based and metal ion binding components such as vanadium-based compounds. The potential anticancer action of vanadium-based compounds is one of area of investigation in this field. In this study, we present five oxovanadium(IV) and dioxovanadium(V) complexes as potential PTP1B inhibitors with anticancer activity against the MCF-7 breast cancer cell line, the triple negative MDA-MB-231 breast cancer cell line, and the human keratinocyte HaCaT cell line. We observed that all tested compounds were effective inhibitors of PTP1B, which correlates with anticancer activity. [VO(dipic)(dmbipy)]·2 H2O (Compound 4) and [VOO(dipic)](2-phepyH)·H2O (Compound 5) possessed the greatest inhibitory effect, with IC50 185.4 ± 9.8 and 167.2 ± 8.0 nM, respectively. To obtain a better understanding of the relationship between the structure of the examined compounds and their activity, we performed a computer simulation of their binding inside the active site of PTP1B. We observed a stronger binding of complexes containing dipicolinic acid with PTP1B. Based on our simulations, we suggested that the studied complexes exert their activity by stabilizing the WPD-loop in an open position and limiting access to the P-loop.
“…The results showed that these complexes after activation by MMAO-12 have very high catalytic activity of more than 1000 kg/(mol V • h). [24,25,26] The synthesis of the transition metal complex with welldefined structural features (selection of the appropriate ligand that shape steric hinge and electron density) and its skillful integration with the appropriate activator is an attractive strategy that allows to obtain the effective catalytic system for a specific oligomerization or polymerization process. In view of this, herein we investigated the ethylene polymerization and polar monomers oligomerization in the presence of dipicolinate oxovanadium(IV) complexes.…”
Section: Introductionmentioning
confidence: 99%
“…Our research group studied oxovanadium(IV) and dioxovanadium(V) complexes with polycarboxylate anions such as thiodiacetate, oxydiacetate, dipicolinate and ligands: 1,10‐phenanthroline, 2‐phenylpyridine, 4,4′‐dimethoxy‐2,2′‐dipyridyl and 2,2′‐bipyridine as precatalysts for 3‐buten‐2‐ol, 2‐propen‐1‐ol, 2‐chloro‐2‐propen‐1‐ol and 2,3‐dibromo‐2‐propen‐1‐ol oligomerizations. The results showed that these complexes after activation by MMAO‐12 have very high catalytic activity of more than 1000 kg/(mol V ⋅ h) [24,25,26] …”
In the field of polymers and organometallic chemistry, a significant gap is apparent in the area of research on well‐defined metal complexes targeted for using in catalysis leading to olefinic oligomers and polymers. Here, we report on the use in these processes the dipicolinate oxovanadium(IV) complexes, without and with auxiliary ligands, i. e. 1,10‐phenanthroline and 2,2’‐bipyridine. The investigated complexes turned out to be versatile precatalysts. After reaction with appropriate activator, they exhibited 11 times higher a catalytic activity than reference vanadium(IV) complexes with salen ligands – so far, precatalysts from a group of vanadium(IV) complexes with the highest known catalytic activity for polymerization of ethylene. In the case of the oligomerization of polar monomers (2‐chloro‐2‐propen‐1‐ol and 3‐buten‐2‐ol) the complexes described in this report have a catalytic activity (very high) similar to vanadium(IV) complexes known in the literature.
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