Water Soluble Benzobisazole Rigid-Rod Copolymers

1993 ◽  
Vol 305 ◽  
Author(s):  
Thuy D. Dang ◽  
Fred E. Arnold
Keyword(s):  
Polyphosphoric Acid ◽  
Water Solubility ◽  
Water Soluble ◽  
Random Copolymers ◽  
Subsequent Reaction ◽  
Ionic Charge ◽  
Mole Percent ◽  
Repeat Units ◽  
Rigid Rod ◽  
Sulfonic Acid Groups

AbstractAlthough benzobisazole rigid-rod polymers are well recognized for their outstanding tensile and modulus properties as well as their excellent thermal and thermal-oxidative stabilities, they can only be fabricated from acidic solvents. Benzobisirnidazole polymers containing pendent benthiazole or sulfonic acid groups exhibit partial solubility in DMSO. Reaction of these systems with sodium methylsulfinylmethide in DMSO abstracts the acidic proton from the benzobisimidazo unit and forms the polyanion. Subsequent reaction of the polyanion with 1,3-propanesultone provides water soluble systems. Random copolymers containing benzobisimidazo and benzobisthiazole repeat units were prepared in polyphosphoric acid and subjected to the derivatization reaction. Benzobisimidazo content in the copolymers varied from 10–0 mole percent. Minimum ionic charge along the rigid-rod backbone to obtain water solubility was determined to be approximately 10 mole percent as reflected in the benzobisimidazole repeat units.

Synthesis of Aromatic Disulfonic Acids for Water-Soluble Dibenzo­thiophene Derivatives

Synthesis ◽  
2018 ◽  
Vol 50 (12) ◽  
pp. 2359-2366 ◽  
Author(s):  
Ryan McCulla ◽  
Sara Omlid ◽  
Ankita Isor ◽  
Kathryn Sulkowski ◽  
S. Chintala ◽  
...  
Keyword(s):  
High Performance ◽  
Atomic Oxygen ◽  
Water Solubility ◽  
Water Soluble ◽  
Flash Chromatography ◽  
Disulfonic Acid ◽  
Biological Applications ◽  
Purification Method ◽  
Highly Effective ◽  
Sulfonic Acid Groups

There is a need for efficient methods for the synthesis of water-soluble dibenzothiophene (DBT) and dibenzothiophene S-oxide (DBTO) derivatives to allow for the study of atomic oxygen in biological applications. Attaining water-solubility of aromatic compounds is effectively achieved through functionalization with sulfonic acid groups. Three approaches for the synthesis were considered. An indirect approach was unsuccessful. A modular approach was found to be highly effective for one DBTO disulfonic acid derivative (>99% pure). The direct approach was the most straightforward and highest-yielding route. Additionally, a highly effective, scalable, and improved purification method was identified for disulfonic acid DBT and DBTO derivatives, allowing for the isolation of positional isomers and other modifications by using reverse-phase high-performance flash chromatography.

scholarly journals Biodegradable polysarcosine with inserted alanine residues: Synthesis and enzymolysis

2021 ◽  
Author(s):  
Peng Zhou ◽  
Jun Ling
Keyword(s):  
Ring Opening ◽  
Water Solubility ◽  
Water Soluble ◽  
Random Copolymers ◽  
Biodegradation Rate ◽  
Pancreatic Elastase ◽  
Molecular Weights ◽  
Mild Conditions ◽  
Protective Shield ◽  
The One

Polysarcosine (PSar), a water-soluble polypeptoid, is gifted with biodegradability via random ring-opening copolymerization of sarcosine- and alanine-N-thiocarboxyanhydrides catalyzed by acetic acid in controlled manners. Kinetic investigation reveals the copolymerization behavior of the two monomers. The random copolymers, named PAS, with high molecular weights between 22.0 and 43.6 kg/mol and tunable Ala molar fractions varying from 6% to 43% are able to be degraded by porcine pancreatic elastase within 50 days in mild conditions (pH=8.0 at 37 °C). Both the biodegradation rate and water solubility of PAS depend on the content of Ala residues. PAS with Ala fractions below 43% are soluble in water while the one with 43% Ala self-assembles in water into nanoparticles. Moreover, PAS are non-cytotoxic at the concentration of 5 mg/mL. The biodegradability and biocompatibility endow the Ala-containing PSar with potential to replace PEG as protective shield in drug-delivery.

RAFT synthesis of poly(vinylpyrrolidone) amine and preparation of a water-soluble C60-PVP conjugate

2015 ◽  
Vol 6 (14) ◽  
pp. 2616-2619 ◽  
Author(s):  
Safwan Aroua ◽  
Elisha Gabrielle V. Tiu ◽  
Maxime Ayer ◽  
Takashi Ishikawa ◽  
Yoko Yamakoshi
Keyword(s):  
Water Solubility ◽  
Raft Polymerization ◽  
Acid Anhydride ◽  
Water Soluble ◽  
Subsequent Reaction ◽  
Anhydride Derivative

A well-defined C60-PVP conjugate with a sufficient water-solubility was successfully synthesized by RAFT polymerization of NVP and subsequent reaction with a C60 acid anhydride derivative.

BODIPY Fluorophores for Membrane Potential Imaging

2019 ◽  
Author(s):  
Jenna Franke ◽  
Benjamin Raliski ◽  
Steven Boggess ◽  
Divya Natesan ◽  
Evan Koretsky ◽  
...  
Keyword(s):  
Mammalian Cells ◽  
Water Solubility ◽  
Water Soluble ◽  
Voltage Sensitivity ◽  
Chemical Transformations ◽  
Direct Modification ◽  
Biological Compatibility ◽  
Meso Position ◽  
Ionizable Groups ◽  
Boron Center

Fluorophores based on the BODIPY scaffold are prized for their tunable excitation and emission profiles, mild syntheses, and biological compatibility. Improving the water-solubility of BODIPY dyes remains an outstanding challenge. The development of water-soluble BODIPY dyes usually involves direct modification of the BODIPY fluorophore core with ionizable groups or substitution at the boron center. While these strategies are effective for the generation of water-soluble fluorophores, they are challenging to implement when developing BODIPY-based indicators: direct modification of BODIPY core can disrupt the electronics of the dye, complicating the design of functional indicators; and substitution at the boron center often renders the resultant BODIPY incompatible with the chemical transformations required to generate fluorescent sensors. In this study, we show that BODIPYs bearing a sulfonated aromatic group at the meso position provide a general solution for water-soluble BODIPYs. We outline the route to a suite of 5 new sulfonated BODIPYs with 2,6-disubstitution patterns spanning a range of electron-donating and -withdrawing propensities. To highlight the utility of these new, sulfonated BODIPYs, we further functionalize them to access 13 new, BODIPY-based voltage-sensitive fluorophores. The most sensitive of these BODIPY VF dyes displays a 48% ΔF/F per 100 mV in mammalian cells. Two additional BODIPY VFs show good voltage sensitivity (≥24% ΔF/F) and excellent brightness in cells. These compounds can report on action potential dynamics in both mammalian neurons and human stem cell-derived cardiomyocytes. Accessing a range of substituents in the context of a water soluble BODIPY fluorophore provides opportunities to tune the electronic properties of water-soluble BODIPY dyes for functional indicators.

scholarly journals Synthesis, Characterization and Bactericidal Activity of a 4-Ammoniumbuthylstyrene-Based Random Copolymer

Polymers ◽  
2021 ◽  
Vol 13 (7) ◽  
pp. 1140
Author(s):  
Silvana Alfei ◽  
Gabriella Piatti ◽  
Debora Caviglia ◽  
Anna Maria Schito
Keyword(s):  
Antibacterial Activity ◽  
Bactericidal Activity ◽  
Antimicrobial Agents ◽  
Water Solubility ◽  
Physicochemical Characterization ◽  
Random Copolymer ◽  
Water Soluble ◽  
Cationic Polymers ◽  
Severe Infections

The growing resistance of bacteria to current chemotherapy is a global concern that urgently requires new and effective antimicrobial agents, aimed at curing untreatable infection, reducing unacceptable healthcare costs and human mortality. Cationic polymers, that mimic antimicrobial cationic peptides, represent promising broad-spectrum agents, being less susceptible to develop resistance than low molecular weight antibiotics. We, thus, designed, and herein report, the synthesis and physicochemical characterization of a water-soluble cationic copolymer (P5), obtained by copolymerizing the laboratory-made monomer 4-ammoniumbuthylstyrene hydrochloride with di-methyl-acrylamide as uncharged diluent. The antibacterial activity of P5 was assessed against several multi-drug-resistant clinical isolates of both Gram-positive and Gram-negative species. Except for strains characterized by modifications of the membrane charge, most of the tested isolates were sensible to the new molecule. P5 showed remarkable antibacterial activity against several isolates of genera Enterococcus, Staphylococcus, Pseudomonas, Klebsiella, and against Escherichia coli, Acinetobacter baumannii and Stenotrophomonas maltophilia, displaying a minimum MIC value of 3.15 µM. In time-killing and turbidimetric studies, P5 displayed a rapid non-lytic bactericidal activity. Due to its water-solubility and wide bactericidal spectrum, P5 could represent a promising novel agent capable of overcoming severe infections sustained by bacteria resistant the presently available antibiotics.

scholarly journals Effect of DMPA and Molecular Weight of Polyethylene Glycol on Water-Soluble Polyurethane

Polymers ◽  
2019 ◽  
Vol 11 (12) ◽  
pp. 1915 ◽  
Author(s):  
Eyob Wondu ◽  
Hyun Woo Oh ◽  
Jooheon Kim
Keyword(s):  
Molecular Weight ◽  
Contact Angle ◽  
Polyethylene Glycol ◽  
Photoelectron Spectroscopy ◽  
Water Solubility ◽  
Soft Segment ◽  
Water Soluble ◽  
Size Exclusion ◽  
Resonance Spectroscopy ◽  
Scanning Calorimetry

In this study water-soluble polyurethane (WSPU) was synthesized from isophorone diisocyanate (IPDI), and polyethylene glycol (PEG), 2-bis(hydroxymethyl) propionic acid or dimethylolpropionic acid (DMPA), butane-1,4-diol (BD), and triethylamine (TEA) using an acetone process. The water solubility was investigated by solubilizing the polymer in water and measuring the contact angle and the results indicated that water solubility and contact angle tendency were increased as the molecular weight of the soft segment decreased, the amount of emulsifier was increased, and soft segment to hard segment ratio was lower. The contact angle of samples without emulsifier was greater than 87°, while that of with emulsifier was less than 67°, indicating a shift from highly hydrophobic to hydrophilic. The WSPU was also analyzed using Fourier transform infrared spectroscopy (FT-IR) to identify the absorption of functional groups and further checked by X-ray photoelectron spectroscopy (XPS). The molecular weight of WSPU was measured using size-exclusion chromatography (SEC). The structure of the WSPU was confirmed by nuclear magnetic resonance spectroscopy (NMR). The thermal properties of WSPU were analyzed using thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC).

scholarly journals Enhanced Water Solubility and Oral Bioavailability of Paclitaxel Crystal Powders through an Innovative Antisolvent Precipitation Process: Antisolvent Crystallization Using Ionic Liquids as Solvent

Pharmaceutics ◽  
2020 ◽  
Vol 12 (11) ◽  
pp. 1008 ◽  
Author(s):  
Qilei Yang ◽  
Chang Zu ◽  
Wengang Li ◽  
Weiwei Wu ◽  
Yunlong Ge ◽  
...  
Keyword(s):  
Oral Bioavailability ◽  
High Performance ◽  
Water Solubility ◽  
Water Soluble ◽  
Precipitation Process ◽  
X Ray Diffraction ◽  
Scanning Calorimetry ◽  
Antisolvent Precipitation ◽  
Antisolvent Crystallization ◽  
Artificial Gastric Juice

Paclitaxel (PTX) is a poor water-soluble antineoplastic drug with significant antitumor activity. However, its low bioavailability is a major obstacle for its biomedical applications. Thus, this experiment is designed to prepare PTX crystal powders through an antisolvent precipitation process using 1-hexyl-3-methylimidazolium bromide (HMImBr) as solvent and water as an antisolvent. The factors influencing saturation solubility of PTX crystal powders in water in water were optimized using a single-factor design. The optimum conditions for the antisolvent precipitation process were as follows: 50 mg/mL concentration of the PTX solution, 25 °C temperature, and 1:7 solvent-to-antisolvent ratio. The PTX crystal powders were characterized via scanning electron microscopy, Fourier transform infrared spectroscopy, high-performance liquid chromatography–mass spectrometry, X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, Raman spectroscopy, solid-state nuclear magnetic resonance, and dissolution and oral bioavailability studies. Results showed that the chemical structure of PTX crystal powders were unchanged; however, precipitation of the crystalline structure changed. The dissolution test showed that the dissolution rate and solubility of PTX crystal powders were nearly 3.21-folds higher compared to raw PTX in water, and 1.27 times higher in artificial gastric juice. Meanwhile, the bioavailability of PTX crystal increased 10.88 times than raw PTX. These results suggested that PTX crystal powders might have potential value to become a new oral PTX formulation with high bioavailability.

scholarly journals Dietary Fiber, Atherosclerosis, and Cardiovascular Disease

Nutrients ◽  
2019 ◽  
Vol 11 (5) ◽  
pp. 1155 ◽  
Author(s):  
Ghada A. Soliman
Keyword(s):  
Cardiovascular Disease ◽  
Dietary Fiber ◽  
Water Solubility ◽  
Disease Risk ◽  
Current Knowledge ◽  
Digestive Enzyme ◽  
Water Soluble ◽  
Blood Cholesterol ◽  
Fiber Intake ◽  
Intestinal Transit Time

Observational studies have shown that dietary fiber intake is associated with decreased risk of cardiovascular disease. Dietary fiber is a non-digestible form of carbohydrates, due to the lack of the digestive enzyme in humans required to digest fiber. Dietary fibers and lignin are intrinsic to plants and are classified according to their water solubility properties as either soluble or insoluble fibers. Water-soluble fibers include pectin, gums, mucilage, fructans, and some resistant starches. They are present in some fruits, vegetables, oats, and barley. Soluble fibers have been shown to lower blood cholesterol by several mechanisms. On the other hand, water-insoluble fibers mainly include lignin, cellulose, and hemicellulose; whole-grain foods, bran, nuts, and seeds are rich in these fibers. Water-insoluble fibers have rapid gastric emptying, and as such may decrease the intestinal transit time and increase fecal bulk, thus promoting digestive regularity. In addition to dietary fiber, isolated and extracted fibers are known as functional fiber and have been shown to induce beneficial health effects when added to food during processing. The recommended daily allowances (RDAs) for total fiber intake for men and women aged 19–50 are 38 gram/day and 25 gram/day, respectively. It is worth noting that the RDA recommendations are for healthy people and do not apply to individuals with some chronic diseases. Studies have shown that most Americans do not consume the recommended intake of fiber. This review will summarize the current knowledge regarding dietary fiber, sources of food containing fiber, atherosclerosis, and heart disease risk reduction.

Nano-Sized [60]Fullerene-Cyclodextrin Molecules

2001 ◽  
Vol 675 ◽  
Author(s):  
Jeong-Seo Park ◽  
Han-Chang Kang ◽  
Kurt E. Geckeler
Keyword(s):  
Biomedical Applications ◽  
Addition Reaction ◽  
Water Soluble ◽  
Separation And Purification ◽  
Subsequent Reaction ◽  
Fullerene Derivatives ◽  
Covalently Bonded ◽  
Scattering Measurements ◽  
Ft Ir ◽  
Ft Ir Spectroscopy

ABSTRACTAs [60]fullerene is a very hydrophobic macromolecule, there have been a number of attempts to make it more hydrophilic for biomedical applications. By attaching hydrophilic moieties such as poly(oxyethylene)(POE) chains and cyclodextrin molecules to [60]fullerene, novel water-soluble and biocompatible materials have been successfully prepared [1,2].The synthesis of novel macrocyclic fullerene conjugates which are water-soluble is reported. The telechelic fullerene derivatives have been prepared via addition reaction of POE-based arms with covalently bonded β-cyclodextrin (CD) to [60]fullerene. To this end, a mono-tosylated CD derivative has been prepared in pyridine and then reacted with an amino-functional POE in the presence of triethylamine. The subsequent reaction of [60]fullerene with the hydrophilic POE-conjugated CD-derivative yielded the macrofullerene after separation and purification procedures.The macrocyclic [60]fullerene derivatives obtained were soluble in water and characterized by UV-VIS and FT-IR spectroscopy as well as light scattering measurements and thermogravimetric analysis.

The Emerging Role of Nanosuspensions for Drug Delivery and Stability

2021 ◽  
Vol 12 ◽  
Author(s):  
Hitesh Kumar Dewangan
Keyword(s):  
Water Solubility ◽  
Size Range ◽  
Aqueous Solubility ◽  
Active Surface ◽  
Water Soluble ◽  
Active Surface Area ◽  
Specific Interest ◽  
Advanced Therapies ◽  
Processing Techniques

: Poor solubility of some medicinal compounds is a serious challenge that can be addressed by using a nano-suspension for improved delivery. The nanoparticles enhance the bioavailability along with the aqueous solubility of the drug, which is accomplished by increasing the active surface area of the drug. The gained attention of the nanosuspension is due to its stabilization facility, which is achieved by polymers, such as polyethylene glycol (PEG), having a particular size range of 10 - 100 nm. Hence, these nanoparticles have the capacity of binding to the targeted with very low damage to the healthy tissues. These are prepared by various methods, such as milling, high-pressure homogenization, and emulsification, along with melt emulsification. Moreover, surface modification and solidification have been used to add specific properties to the advanced therapies as post-processing techniques. For many decades, it has been known that water solubility hampers the bioavailability and not all drugs are water-soluble. In order to combat this obstacle, nanotechnology has been found to be of specific interest. For elevating the bioavailability by increasing the dissolution rate, the methodology of reduction of the associated drug particles into their subsequent submicron range is incorporated. For oral and non-oral administration, these nanosuspension formulations are used for the delivery of drugs.

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