Ligand role on insulin-mimetic properties of vanadium complexes. Structural and biological studies

Szklarzewicz, Janusz; Jurowska, Anna; Hodorowicz, Maciej; Kazek, Grzegorz; Głuch‐Lutwin, Monika; Sapa, Jacek

doi:10.1016/j.ica.2020.120135

Cited by 19 publications

(6 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Vanadium compounds have been widely investigated due to a broad application in catalysis − and a wide range of pharmacological properties. − In the area of medicinal applications, the exploration of vanadium-based compounds has been focused on their insulin-mimetic properties, − ,− anticancer activities, − ,− antibacterial action, ,,,− and effects on enzymes. ,,, In particular, bis(ethylmaltolato)oxidovanadium(IV) (BEOV) entered the phase IIa clinical trials as an antidiabetic agent and its improved pharmacokinetics relative to vanadyl sulfate was evidenced. − Vanadocene dichloride, (η 5 -C 5 H 5 ) 2 VCl 2 (C 5 H 5 = cyclopentadienyl), was demonstrated to have antitumor effects on a wide spectrum of cancer cells, including testicular cancer, leukemia, breast cancer, glioblastoma, and colon cancer. − ,− Among oxidovanadium(IV) derivatives, special attention has been devoted to bis(4,7-dimethyl-1,10-phenanthroline)-sulfatooxidovanadium(IV) (Metvan), which was found to induce apoptosis in leukemia, multiple myeloma, and solid tumors such as breast, prostate, testis, and glioblasto...…”

Section: Introductionmentioning

confidence: 99%

“…Vanadium compounds have been widely investigated due to a broad application in catalysis 1 − 9 and a wide range of pharmacological properties. 10 − 19 In the area of medicinal applications, the exploration of vanadium-based compounds has been focused on their insulin-mimetic properties, 11 − 15 , 20 − 25 anticancer activities, 11 − 19 , 26 − 40 antibacterial action, 12 , 14 , 15 , 41 − 43 and effects on enzymes. 12 , 14 , 15 , 44 In particular, bis(ethylmaltolato)oxidovanadium(IV) (BEOV) entered the phase IIa clinical trials as an antidiabetic agent and its improved pharmacokinetics relative to vanadyl sulfate was evidenced.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

In Vitro and In Vivo Biological Activities of Dipicolinate Oxovanadium(IV) Complexes

et al. 2023

View full text Add to dashboard Cite

The work is focused on anticancer properties of dipicolinate (dipic)-based vanadium(IV) complexes [VO(dipic)(N∩N)] bearing different diimines (2-(1H-imidazol-2-yl)pyridine, 2-(2-pyridyl)benzimidazole, 1,10-phenanthroline-5,6-dione, 1,10-phenanthroline, and 2,2′-bipyridine), as well as differently 4,7-substituted 1,10-phenanthrolines. The antiproliferative effect of V(IV) systems was analyzed in different tumors (A2780, HCT116, and HCT116-DoxR) and normal (primary human dermal fibroblasts) cell lines, revealing a high cytotoxic effect of [VO(dipic)(N∩N)] with 4,7-dimethoxy-phen (5), 4,7-diphenyl-phen (6), and 1,10-phenanthroline (8) against HCT116-DoxR cells. The cytotoxicity differences between these complexes can be correlated with their different internalization by HCT116-DoxR cells. Worthy of note, these three complexes were found to (i) induce cell death through apoptosis and autophagy pathways, namely, through ROS production; (ii) not to be cytostatic; (iii) to interact with the BSA protein; (iv) do not promote tumor cell migration or a pro-angiogenic capability; (v) show a slight in vivo anti-angiogenic capability, and (vi) do not show in vivo toxicity in a chicken embryo.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

In Vitro and In Vivo Biological Activities of Dipicolinate Oxovanadium(IV) Complexes

et al. 2023

View full text Add to dashboard Cite

show abstract

“…Since these compounds were soluble in water, we had the opportunity to determine for the first time their stability in water. By using a DMSO/H 2 O mixture, the complexes were shown to be stable at pH = 7, but were unstable at pH = 2 [ 16 , 17 , 18 , 19 , 20 ]. In Figure 7 and Figure 8 a similar behavior can be observed: at pH = 7 the band at 400 nm does not change with time ( Figure 7 ).…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, it is worth searching for new organic vanadium compounds in order to optimize their pharmaceutical activity. So far, we have tested plenty of vanadium(III, IV and V) complexes with Schiff bases, controlling both the starting compound for the synthesis of complexes, such as [VO(acac) 2 ], VOSO 4 , [V(acac) 3 ], and V 2 O 5 , as well as changing the substituents in the aromatic ring of aldehyde and hydrazide—Schiff-base components [ 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. The obtained compounds were highly soluble in organic solvents, but insoluble in water.…”

Section: Introductionmentioning

confidence: 99%

Ionic Dioxidovanadium(V) Complexes with Schiff-Base Ligands as Potential Insulin-Mimetic Agents—Substituent Effect on Structure and Stability

et al. 2022

View full text Add to dashboard Cite

Four dioxidovanadium(V) complexes with Schiff-base ligands based on 2-hydroxybenzhydrazide with four different substituted salicylaldehydes (5-chlorosalicylaldehyde, 3,5-dichlorosalicylaldehyde, 5-nitrosalicylaldehyde, 3-bromo-5-chlorosalicylaldehyde) were synthesized and described, by using V2O5 and triethylamine. The single crystal X-ray structure measurements as well as elemental analyses and IR spectra confirmed the formulas of the ionic complexes with a protonated triethylamine acting as counterion, HTEA[VO2(L)] (HL = Schiff-base ligand). The kinetic stability of the complexes at pH = 2 and 7 was discussed with respect to the neutral vanadium(V) complexes previously studied as potential insulin-mimetic agents. A correlation between the substituents in an aromatic ring of the Schiff-base ligands with crystal packing, and also with the stability of the compounds, was presented.

show abstract

“…Previous research by our team on vanadium complexes with potential application in metabolic disorders involved the synthesis of one hundred dozen new vanadium complexes from different structural groups, described in publications [e.g. [42][43][44][45][46][47][48][49][50][51][52] and patented in part [52,53]. For mentioned 110 vanadium complexes screening tests for antidiabetic activity in in vitro and three cell-based models were conducted making our research unique and outstanding [54].…”

Section: Introductionmentioning

confidence: 99%

Vanadium Complexes with Thioanilidine Derivatives of Aminoacids: Inhibition of Human Phosphatases and Cell-Type Specificity in Various Models of Metabolic Disturbances

Kazek¹,

Głuch‐Lutwin²,

Mordyl³

et al. 2023

Preprint

View full text Add to dashboard Cite

The synthesis and characteristics of the novel ONS-type vanadium(V) complexes with thioanilidine derivatives of aminoacids have been described. They showed inhibition of human protein tyrosine phosphatases (PTP1B, LAR, SHP1 and SHP2) in the submicromolar range and as well as inhibition of non-tyrosine phosphatases (CDC25A and PPA2) similar to bis(maltolato)oxovanadium(IV)(BMOV). The ONS complexes increased [14C]-deoxy-D-glucose transport into C2C12 myocytes, and one of them, VC070 also enhanced this transport in 3T3-L1 adipocytes. These complexes inhibited gluconeogenesis in hepatocytes HepG2, but none of them decreased lipid accumulation in the non-alcoholic fatty liver disease model using the same cells. Compared to the tested ONO-type vanadium complexes with 5-bromosalicylaldehyde and substituted benzhydrazides as components of Schiff base ligand, the ONS complexes revealed stronger inhibition of protein tyrosine phosphatases, but the ONO complexes showed greater activity in the cell models, in general. Moreover, the most of the active complexes from both groups showed better effects than VOSO4 and BMOV. Complexes from both groups activated AKT and ERK signaling pathway in hepatocytes to a comparable extent. One of the ONO complexes, VC068, showed activity in all above models, including also glucose utilization in the myocytes and glucose transport in insulin-resistant hepatocytes. The discussion has put forward explications for the results within the wider scope of the knowledge about vanadium complexes.

show abstract

Ligand role on insulin-mimetic properties of vanadium complexes. Structural and biological studies

Cited by 19 publications

References 35 publications

In Vitro and In Vivo Biological Activities of Dipicolinate Oxovanadium(IV) Complexes

In Vitro and In Vivo Biological Activities of Dipicolinate Oxovanadium(IV) Complexes

Ionic Dioxidovanadium(V) Complexes with Schiff-Base Ligands as Potential Insulin-Mimetic Agents—Substituent Effect on Structure and Stability

Vanadium Complexes with Thioanilidine Derivatives of Aminoacids: Inhibition of Human Phosphatases and Cell-Type Specificity in Various Models of Metabolic Disturbances

Contact Info

Product

Resources

About