Novel tetrazole PtII and PdII complexes with enhanced water solubility: synthesis, structural characterization and evaluation of antiproliferative activity

2020 ◽  
Vol 0 (0) ◽  
Author(s):  
Tatiyana V. Serebryanskaya ◽  
Alexander S. Lyakhov ◽  
Ludmila S. Ivashkevich ◽  
Yuri V. Grigoriev ◽  
Andreii S. Kritchenkov ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
High Performance ◽  
Water Solubility ◽  
Thermal Analyses ◽  
High Water ◽  
Acetonitrile Solution ◽  
X Ray ◽  
Molecular And Crystal Structures ◽  
Tetrazole Derivatives ◽  
High Water Solubility

AbstractNovel platinum(II) and palladium(II) chlorido complexes with tetrazole derivatives 1-(2-hydroxyethyl)tetrazole (het) and 1-[tris(hydroxymethyl)methyl]tetrazole (thm), viz. cis-[Pt(het)2Cl2], trans-[Pt(het)2Cl2], trans-[Pt(thm)2Cl2], trans-[Pd(het)2Cl2], and trans-[Pd(thm)2Cl2], were synthesized. The compounds were characterized by elemental and high-resolution electrospray ionization (HRESI) mass spectrometry, high-performance liquid chromatography (HPLC), 1H, 13C and 195Pt nuclear magnetic resonance (NMR) spectroscopy, thermal analyses, and Infrared (IR) spectroscopy. Molecular and crystal structures of trans-[PdL2Cl2] and trans-[PtL2Cl2] (L = het, thm) were established by single-crystal X-ray analysis. The complex cis-[Pt(het)2Cl2] was found to undergo cis–to–trans isomerization upon heating in acetonitrile solution and in the solid state. The synthesized complexes show rather high water solubility lying in the range of 2–10 mg/L.

Water-soluble Au nanoclusters for multiplexed mass spectrometry imaging

2017 ◽  
Vol 53 (94) ◽  
pp. 12688-12691 ◽  
Author(s):  
Jinan Li ◽  
Jing Liu ◽  
Zheyi Liu ◽  
Yuan Tan ◽  
Xiaoyan Liu ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Mass Spectrometry Imaging ◽  
Water Solubility ◽  
High Water ◽  
Water Soluble ◽  
Detection Sensitivity ◽  
Lateral Resolution ◽  
Au Nanoclusters ◽  
High Water Solubility

Homogeneous Au nanoclusters were utilized for enhancing the detection sensitivity and lateral resolution of multiplexed mass spectrometry imaging due to their high ultraviolet adsorption, high water solubility, and high biocompatibility.

scholarly journals Reversible switching of arylazopyrazole within a metal–organic cage

2019 ◽  
Vol 15 ◽  
pp. 2398-2407 ◽  
Author(s):  
Anton I Hanopolskyi ◽  
Soumen De ◽  
Michał J Białek ◽  
Yael Diskin-Posner ◽  
Liat Avram ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Water Solubility ◽  
Green Light ◽  
High Water ◽  
Isomerization Reaction ◽  
X Ray ◽  
X Ray Crystallography ◽  
New Family ◽  
Metal Organic ◽  
High Water Solubility

Arylazopyrazoles represent a new family of molecular photoswitches characterized by a near-quantitative conversion between two states and long thermal half-lives of the metastable state. Here, we investigated the behavior of a model arylazopyrazole in the presence of a self-assembled cage based on Pd–imidazole coordination. Owing to its high water solubility, the cage can solubilize the E isomer of arylazopyrazole, which, by itself, is not soluble in water. NMR spectroscopy and X-ray crystallography have independently demonstrated that each cage can encapsulate two molecules of E-arylazopyrazole. UV-induced switching to the Z isomer was accompanied by the release of one of the two guests from the cage and the formation of a 1:1 cage/Z-arylazopyrazole inclusion complex. DFT calculations suggest that this process involves a dramatic change in the conformation of the cage. Back-isomerization was induced with green light and resulted in the initial 1:2 cage/E-arylazopyrazole complex. This back-isomerization reaction also proceeded in the dark, with a rate significantly higher than in the absence of the cage.

Tri(3-pyridyl)phosphine as Amphiphilic Ligand in the Rhodium-catalysed Hydroformylation of 1-Hexene

2007 ◽  
Vol 62 (3) ◽  
pp. 339-345 ◽  
Author(s):  
Wolfgang H. Meyer ◽  
Richard J. Bowen ◽  
David G. Billing
Keyword(s):  
Model Compound ◽  
Water Solubility ◽  
High Water ◽  
Rhodium Complex ◽  
Rhodium Complexes ◽  
X Ray Diffraction ◽  
Catalyst Recycling ◽  
X Ray ◽  
Distribution Behavior ◽  
High Water Solubility

The molecular structure of carbonylchlorobis(tri(3-pyridyl)phosphine)rhodium, 1, has been determined by X-ray diffraction methods. The N-protonated trifluoromethanesulfonate (triflate) complex 3 was synthesised as a model compound for the extraction of a rhodium complex bearing amphiphilic ligands which can allow catalyst recycling in the hydroformylation of alkenes by using their distribution behavior in organic and aqueous solvents of different pH. The high water-solubility of the employed ligand renders the recycling method as only partly successful due to insufficient extraction from the water phase into the organic phase. In the hydroformylation of 1-hexene the production of n-heptanal is slightly disfavoured when using the ligand tri(3-pyridyl)phosphine as compared to triphenylphosphine which can be ascribed to a higher amount of ligand-deficient active rhodium complexes of the less basic pyridyl phosphine ligand under CO pressure.

A Fluorescence Quenching Analysis of the Binding of Fluoroquinolones to Humic Acid

2017 ◽  
Vol 71 (11) ◽  
pp. 2512-2518 ◽  
Author(s):  
Ryan P. Ferrie ◽  
Gregory E. Hewitt ◽  
Bruce D. Anderson
Keyword(s):  
Humic Acid ◽  
Fluorescence Quenching ◽  
Water Solubility ◽  
Binding Constants ◽  
High Water ◽  
Static Quenching ◽  
Temperature Range ◽  
Equilibrium Binding ◽  
Quenching Analysis ◽  
High Water Solubility

Fluorescence quenching was used to investigate the interaction of six fluoroquinolones with humic acid. Static quenching was observed for the binding of ciprofloxacin, enoxacin, fleroxacin, levofloxacin, norfloxacin, and ofloxacin to humic acid. The equilibrium binding constants were found from Stern–Volmer plots of the data. The quenching experiments were repeated over a temperature range of 25–45 ℃ and van’t Hoff plots were generated. From these linear plots, thermodynamic values were calculated for Δ H, Δ G, and Δ S for each of the fluoroquinolones. The equilibrium binding constants were found to be <1 for all the antibiotics studied. The calculated ΔH values were all negative and ranged from −9.5 to −27.6 kJ/mol. The high water solubility of the antibiotics and low ΔH of binding suggests that the antibiotics will be transported easily through the environment. Finally, whether the fluoroquinolones are in a protonated, deprotonated, or partially protonated state is found to correlate to the strength of binding to humic acid.

scholarly journals New Active Pharmaceutical Ingredient-Ionic Liquids (API-ILs) Derived from Indomethacin and Mebendazole

Proceedings ◽  
2018 ◽  
Vol 9 (1) ◽  
pp. 48 ◽  
Author(s):  
◽  
Emilia Tojo
Keyword(s):  
Ionic Liquids ◽  
Water Solubility ◽  
Methanesulfonic Acid ◽  
Active Pharmaceutical Ingredient ◽  
High Water ◽  
Solubility In Water ◽  
Pharmaceutical Ingredients ◽  
Low Toxicity ◽  
Low Solubility ◽  
High Water Solubility

The transformation of two solid Active Pharmaceutical Ingredients (APIs) into new ionic liquids (IL)s that incorporate APIs (API-ILs) is reported. The structures of the APIs (indomethacin and mebendazole) were selected by their susceptibility to being transformed into API-ILs (either to form the cation or the anion) and their limited bioavailability due to their low solubility in water. The counterions, such as those derived from 2-dimethylaminoethanol (DMEA), tetramethylguanidine (TMG), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,4-diazabicyclo[2.2.2] (TED), <i>p</i>-toluensulfonic acid, glycolic acid, methanesulfonic acid, and saccharin, were carefully chosen, aiming for high biocompatibility, low toxicity, and high water solubility. The synthesis was carried out by direct treatment of the API with the corresponding selected acid or base. Finally, the solubility in water of all the synthesized salts was determined.

scholarly journals Comparison of Chemotherapeutic Activities of Rhodamine-Based GUMBOS and NanoGUMBOS

Molecules ◽  
2020 ◽  
Vol 25 (14) ◽  
pp. 3272
Author(s):  
Nimisha Bhattarai ◽  
Mi Chen ◽  
Rocío L. Pérez ◽  
Sudhir Ravula ◽  
Robert M. Strongin ◽  
...  
Keyword(s):  
Cellular Uptake ◽  
Water Solubility ◽  
High Water ◽  
Acid Group ◽  
Ester Group ◽  
Mitochondrial Targeting ◽  
Organic Salts ◽  
Nanoparticle Formation ◽  
Rhodamine Derivatives ◽  
High Water Solubility

Rhodamine derivatives have been widely investigated for their mitochondrial targeting and chemotherapeutic properties that result from their lipophilic cationic structures. In previous research, we have found that conversion of Rhodamine 6G into nanoGUMBOS, i.e., nanomaterials derived from a group of uniform materials based on organic salts (GUMBOS), led to selective chemotherapeutic toxicity for cancer cells over normal cells. Herein, we investigate the chemotherapeutic activity of GUMBOS derived from four different rhodamine derivatives, two bearing an ester group, i.e., Rhodamine 123 (R123) and SNAFR-5, and two bearing a carboxylic acid group, i.e., rhodamine 110 (R110) and rhodamine B (RB). In this study, we evaluate (1) relative hydrophobicity via octanol–water partition coefficients, (2) cytotoxicity, and (3) cellular uptake in order to evaluate possible structure–activity relationships between these different compounds. Intriguingly, we found that while GUMBOS derived from R123 and SNAFR-5 formed nanoGUMBOS in aqueous medium, no distinct nanoparticles are observed for RB and R110 GUMBOS. Further investigation revealed that the relatively high water solubility of R110 and RB GUMBOS hinders nanoparticle formation. Subsequently, while R123 and SNAFR-5 displayed selective chemotherapeutic toxicity similar to that of previously investigated R6G nanoGUMBOS, the R110 and RB GUMBOS were lacking in this property. Additionally, the chemotherapeutic toxicities of R123 and SNAFR-5 nanoGUMBOS were also significantly greater than R110 and RB GUMBOS. Observed results were consistent with decreased cellular uptake of R110 and RB as compared to R123 and SNAFR-5 compounds. Moreover, these results are also consistent with previous observations that suggest that nanoparticle formation is critical to the observed selective chemotherapeutic properties as well as the chemotherapeutic efficacy of rhodamine nanoGUMBOS.

A facile, green, and solvent-free route to nitrogen–sulfur-codoped fluorescent carbon nanoparticles for cellular imaging

RSC Advances ◽  
2014 ◽  
Vol 4 (23) ◽  
pp. 11872-11875 ◽  
Author(s):  
Hong Huang ◽  
Ya-Chun Lu ◽  
Ai-Jun Wang ◽  
Jin-Hua Liu ◽  
Jian-Rong Chen ◽  
...  
Keyword(s):  
Water Solubility ◽  
High Water ◽  
Cellular Imaging ◽  
Solvent Free ◽  
High Quantum Yield ◽  
Long Lifetime ◽  
Low Cytotoxicity ◽  
Fluorescent Carbon Nanoparticles ◽  
Excellent Stability ◽  
High Water Solubility

A simple, solvent-free method was developed for preparation of fluorescent NSCPs by direct pyrolysis of gentamycin sulfate. The NSCPs showed high water-solubility, long lifetime, high quantum yield, excellent stability and low cytotoxicity, and thus can be used for cellular imaging.

Effect of Soil Organic Matter on the Phytotoxicity of Thirteens-Triazine Herbicides

Weed Science ◽  
1979 ◽  
Vol 27 (2) ◽  
pp. 158-161 ◽  
Author(s):  
A. Rahman ◽  
L. J. Matthews
Keyword(s):  
Organic Matter ◽  
Soil Organic Matter ◽  
Avena Sativa ◽  
Water Solubility ◽  
Sandy Loam ◽  
High Water ◽  
Triazine Herbicides ◽  
Greenhouse Experiments ◽  
High Water Solubility

The influence of soil organic matter on the initial and residual phytotoxicity of thirteens-triazine herbicides was investigated in greenhouse experiments using three Horotiu sandy loam soils with organic matter levels of 9.8, 15.5, and 20.6%. The amount of herbicide required to reduce the growth of oats (Avena sativaL. ‘Mapua’) by 50% (GR50) when compared with the control was determined for each herbicide and each organic matter level. Results showed that the GR50values for all herbicides were highly and positively correlated with the soil organic matter. In general, the phytotoxicity of compounds of high water solubility was less influenced by soil organic matter than those having low water solubility. The chloro-triazines persisted longer in soil than did the methoxy- or methylthio-triazines. Simazine [2-chloro-4,6-bis(ethylamino)-s-triazine] and atrazine [2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine] were the most persistent of the chloro-triazines.

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