2210-03-9

Usage

Uses

Used in Personal Care Products:
Bronopol is used as a preservative in personal care products to inhibit the growth of bacteria, mold, and fungi, thereby extending the shelf life and maintaining the quality of these products.
Used in Pharmaceuticals:
In the pharmaceutical industry, Bronopol is utilized as a preservative to prevent microbial contamination in medications, ensuring their safety and efficacy.
Used in Household Cleaning Agents:
Bronopol is employed as a preservative in household cleaning agents to prevent the growth of microorganisms that could degrade the product's effectiveness or pose health risks.
Despite its widespread use, Bronopol has been the subject of controversy due to its potential as a skin irritant and its association with allergic reactions in some individuals. However, it continues to be an effective preservative in various industries.

InChI:InChI=1/C5H11BrO2/c1-5(2-6,3-7)4-8/h7-8H,2-4H2,1H3

Upstream product

• 77-85-0 2-(hydroxymethyl)-2-methylpropane-1,3-diol 
• 123-91-1 1,4-dioxane 
• 3143-02-0 3-hydroxymethyl-3-methyloxethane 
• 10035-10-6 hydrogen bromide 

Downstream Products

• 500345-09-5 5-bromomethyl-5-methyl-2,2-di-p-tolyl-[1,3]dioxane 
• 7468-34-0 5-bromomethyl-2-cyclohexyl-5-methyl-2-phenyl-[1,3]dioxane 
• 500564-30-7 5-bromomethyl-5-methyl-2,2-diphenyl-[1,3]dioxane 
• 500345-08-4 2,2-dibenzyl-5-bromomethyl-5-methyl-[1,3]dioxane 
• 3143-02-0 3-hydroxymethyl-3-methyloxethane 
• 145282-86-6 1-Benzyl-2-(5-bromomethyl-5-methyl-[1,3]dioxan-2-yl)-4,5-diphenyl-1H-imidazole 
• 117901-62-9 2-methyl-2-(phenylselenyl)methylpropane-1,3-diol 
• 412344-67-3 1-(5-methyl-2,2-diphenyl-[1,3]dioxan-5-ylmethyl)-piperidine 

Relevant academic research and scientific papers

Unprecedented access to functional biodegradable polymers and coatings

The ever-growing biomedical technology such as tissue engineering, regenerative medicine, and controlled drug release intimately relies on the development of advanced functional biomaterials. Here, we report on versatile and robust synthesis of novel vinyl sulfone (VS)-functionalized biodegradable polymers that offer unprecedented access to advanced functional biodegradable polymers and coatings through selective Michael-type conjugate reaction with thiol-containing molecules. VS-functionalized biodegradable polymers including poly(ε-caprolactone) (PCL), poly(l-lactide) (PLA), and poly(trimethylene carbonate) (PTMC) were conveniently prepared with controlled molecular weights and functionalities through ring-opening copolymerization of ε-caprolactone (ε-CL), l-lactide (LA), or trimethylene carbonate (TMC) with a new cyclic carbonate monomer, vinyl sulfone carbonate (VSC), in toluene at 110 °C using isopropanol as an initiator and stannous octoate as a catalyst. Interestingly, these VS-functionalized biodegradable polymers allowed quantitative modification, without aid of a catalyst, with various thiol-containing molecules including 2-mercaptoethanol, cystamine, cysteine, GRGDC peptide, and thiolated poly(ethylene glycol) (PEG-SH) at a ligand-SH/VS molar ratio of 2/1 in DMF at room temperature, confirming that the Michael-type conjugate addition to VS is highly selective and tolerant to most other functional groups including hydroxyl, carboxyl, and amine. Remarkably, results of contact angle measurements, X-ray photoelectron spectroscopy (XPS), and fluorescence studies showed that biodegradable coatings based on these VS-functionalized polymers allowed direct, efficient, and clean (without catalyst and byproduct) surface functionalization with thiol-containing molecules in aqueous conditions, which is unprecedented and opens a new avenue to surface functionalization of medical implants as well as cell and tissue scaffolds. The preliminary cell culture studies using MG6 cells showed that unmodified VS-functionalized PCL films, similar to tissue culture plate, could well support cell attachment and growth, indicating that VS-functionalized PCL film is nontoxic and biocompatible. The surface of VS-functionalized PCL films could be elegantly engineered with thiolated nonfouling polymers (e.g., PEG and glycol chitosan) or cell adhesive motif (GRGDC peptide) to control cell attachment and growth. We are convinced that these vinyl sulfone-functionalized biodegradable polymers have a tremendous potential in biomedical engineering.

Synthesis and properties of tunable thermoresponsive aliphatic polycarbonate copolymers with oligo ethylene glycol containing thioether and/or sulphone groups

A series of novel thermoresponsive copolycarbonates were constructed by cyclic trimethylene carbonate (MTC) monomers bearing oligo ethylene glycol (OEG) and with thioether or/and sulphone linkages. They were initiated by 1,4-benzenedimethanol with N-(3,5-trifluoromethyl)phenyl-N′-cyclohexylthiourea (TU)/1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) as the organic catalyst. The lower critical solution temperature (LCST) properties of the polycarbonates with thioether or sulphone linkage were studied and discussed with regard to molecular weight, salt concentration and polymer concentration. By using monomers of different OEG chain lengths and thioether and/or sulphone linkages, the LCSTs of biodegradable and thermoresponsive polycarbonate copolymers can be easily tuned within a wide temperature window from 0 °C to 46°C (3 g L-1 in aqueous solution). In addition, block polycarbonates with two tunable LCSTs were further synthesized and investigated. Results showed that LCST1 was constructed by polycarbonate with a hydrophobic thioether linkage, while the LCST2 was achieved by a polycarbonate containing hydrophilic sulphone linkage.

Synthesis and polymerization of alkyl halide-functional cyclic carbonates

To increase the diversity in functional aliphatic polycarbonates, a series of novel chloro- and bromo-functional six-membered cyclic carbonate monomers were synthesized. Despite asymmetry in the monomer functionalities, homopolymerization of the monomers afforded semicrystalline polycarbonates with a high tendency to crystallize from the melt and/or on precipitation from a THF solution. Melting points were found in the 90-105 °C or 120-155 °C range for polymers comprising methyl or ethyl moieties, respectively, in the backbone. The monomers were further copolymerized with trimethylene carbonate to form random copolymers. Even among some of these random copolymers elements of semicrystallinity were found as confirmed by melting endotherms in DSC. The results clearly show that the incorporation of alkyl halide functionalities in aliphatic polycarbonates may lead to materials with a high ability to form crystallites, even in random copolymers, likely driven by polar interactions due to the presence of the halide functionalities.

Synthesis and character of novel polycarbonate for constructing biodegradable multi-stimuli responsive delivery system

Here, we design a novel triple-stimuli-sensitive graft copolymer assembly which responds to the changes in temperature, reducing agent, and light. The graft copolymer consists of thermo-responsive tetraethylene glycolyl poly(trimethylene carbonate) (P(MTC-4EG)) as backbone and light-sensitive poly(2-nitrobenzyl methacrylate) (PNBM) as side chain linked by an intervening disulfide bond. In aqueous solution, the polymer can self-assemble into micelle with thermo-sensitive shell (P(MTC-4EG)), light-sensitive core (PNBM), and disulfide linker. The assemblies in response to stimuli were revealed by dynamic light scatting (DLS) and transmission electron microscopy (TEM). The drug release behaviors of Nile Red (NR)-loaded carriers were also valued with stimuli from temperature, reducing agent, and light.

Reversible core-crosslinked nanocarriers with pH-modulated targeting and redox-controlled drug release for overcoming drug resistance

Herein, a pH and redox dual-sensitive core-crosslinked targeting nanocarrier was prepared and used for co-delivery of doxorubicin (DOX) and tariquidar (TQR). The nanocarrier not only had excellent stability but also prevented the leakage of the drug in the normal physiological environment efficiently. Meanwhile, the targeting function of nanocarriers could also be suppressed in the normal physiological environment, protecting nanocarriers from being captured by RAW264.7 cells. Under mild acidic conditions, the targeting function was regained, leading to an effective tumor cell uptake of the nanocarrier. Furthermore, reduction-responsive drug release would occur in the cytoplasm due to the collapse of the reduction-sensitive crosslinked structure in the nanocarrier. By means of ligand-receptor mediated endocytosis and TQR-mediated glycoprotein (P-gp) inhibition, the IC50 value of DOX to MCF-7/ADR cells reduced from more than 100 μg mL-1 to 8.55 μg mL-1, exhibiting great potential in overcoming drug resistance.

How Do Ring Size and π-Donating Thiolate Ligands Affect Redox-Active, α-Imino-N-heterocycle Ligand Activation?

Considerable effort has been devoted to the development of first-row transition-metal catalysts containing redox-active imino-pyridine ligands that are capable of storing multiple reducing equivalents. This property allows abundant and inexpensive first-row transition metals, which favor sequential one-electron redox processes, to function as competent catalysts in the concerted two-electron reduction of substrates. Herein we report the syntheses and characterization of a series of iron complexes that contain both π-donating thiolate and π-accepting (α-imino)-N-heterocycle redox-active ligands, with progressively larger N-heterocycle rings (imidazole, pyridine, and quinoline). A cooperative interaction between these complementary redox-active ligands is shown to dictate the properties of these complexes. Unusually intense charge-transfer (CT) bands, and intraligand metrical parameters, reminiscent of a reduced (α-imino)-N-heterocycle ligand (L?-), initially suggested that the electron-donating thiolate had reduced the N-heterocycle. Sulfur K-edge X-ray absorption spectroscopic (XAS) data, however, provides evidence for direct communication, via backbonding, between the thiolate sulfur and the formally orthogonal (α-imino)-N-heterocycle ligand π?-orbitals. DFT calculations provide evidence for extensive delocalization of bonds over the sulfur, iron, and (α-imino)-N-heterocycle, and TD-DFT shows that the intense optical CT bands involve transitions between a mixed Fe/S donor, and (α-imino)-N-heterocycle π?-acceptor orbital. The energies and intensities of the optical and S K-edge pre-edge XAS transitions are shown to correlate with N-heterocycle ring size, as do the redox potentials. When the thiolate is replaced with a thioether, or when the low-spin S = 0 Fe(II) is replaced with a high-spin S = 3/2 Co(II), the N-heterocycle ligand metrical parameters and electronic structure do not change relative to the neutral L0 ligand. With respect to the development of future catalysts containing redox-active ligands, the energy cost of storing reducing equivalents is shown to be lowest when a quinoline, as opposed to imidazole or pyridine, is incorporated into the ligand backbone of the corresponding Fe complex.

ROS-Responsive Chalcogen-Containing Polycarbonates for Photodynamic Therapy

Reactive oxygen species (ROS)-responsive polymers have attracted attention for their potential in photodynamic therapy. Herein, we report the ROS-responsive aliphatic polycarbonates prepared by the ring-opening polymerization (ROP) of three six-membered cyclic carbonate monomers with ethyl selenide, phenyl selenide or ethyl telluride groups. Under catalysis of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), all three monomers underwent the controlled anionic ROP, showing a feature of equilibrium polymerization due to the bulky effect of 5,5-disubstituents. With PEG macroinitiator, three series amphiphilic block copolymers were prepared. They could form spherical nanoparticles of ～100 nm, which were stable in neutral phosphate buffer but dissociated rapidly under triggering of H2O2. We studied the H2O2-induced oxidation profiles of selenide- or telluride-containing small molecules by 1H NMR and revealed the factors that affect the oxidation kinetics and products. On this basis, the oxidative degradation mechanism of the copolymer nanoparticles has been clarified. Under the same oxidative condition, the telluride-containing nanoparticle degraded with the fastest rate while the phenyl selenide-based one degraded most slowly. These ROS-responsive nanoparticles could load photosensitizer chlorin e6 (Ce6) and anticancer drug doxorubicin (DOX). Under red light irradiation, Ce6-sensitized production of 1O2 that triggered the degradation of nanoparticles, resulting in an accelerated payload release. In vitro cytotoxicity assays demonstrate that the nanoparticles coloaded with DOX and Ce6 exhibited a synergistic cell-killing effect to MCF-7 cells, representing a novel responsive nanoplatform for PDT and/or chemotherapy.

ISOINDOLINONE INHIBITORS OF THE MDM2-P53 INTERACTION HAVING ANTICANCER ACTIVITY

The invention provides a compound of formula (I): (I) or tautomer or a solvate or a pharmaceutically acceptable salt thereof, wherein the various substituents are as defined in the claims. Also provided are pharmaceutical compositions containing the compounds of formula (I), processes for making the compounds and the medical uses of the compounds.

Triphos derivatives and diphosphines as ligands in the ruthenium-catalysed alcohol amination with NH3

The ruthenium-triphos and diphosphine-catalysed amination of alcohols with ammonia is reported. Various types of triphos derivatives with electron-donating functional group were synthesized and used as ligands in the Ru-catalysed alcohol amination with NH3. The triphos derivatives are effective for the formation of primary amines. On the other hand, if hemilabile diphosphines as tridentate ligands are used, mixtures of secondary-along with primary amines are obtained. It was found that even simple diphosphines can be used as ligands for the selective formation of the secondary amines. The diphosphine system allows a new entry to the Ru-catalysed formation of secondary amines.

RAFAMYCIN ANALOGS AND METHODS FOR MAKING SAME

A semi-synthetic rapamycin analog with a triazole moiety or a pharmaceutically acceptable salt or prodrug thereof, is a broad-spectrum cytostatic agent and a mTOR inhibitor, and is useful in the treatment of various cancers, or tumors in organs such as kidney, liver, breast, head and neck, lung, prostate, and restenosis in coronary arteries, peripheral arteries, and arteries in the brain, immune and autoimmune diseases. Also disclosed are fungal growth-, restenosis-, post-transplant tissue rejection- and immune- and autoimmune disease-inhibiting compositions and a method of inhibiting cancer, fungal growth, restenosois, post-transplant tissue rejection, and immune and autoimmune disease in a mammal. One particular preferred application of such triazole-moiety containing rapamycin analog is in treating renal carcinoma, lung cancer, colon cancer, and breast cancers wherein potency of the drug, its half-life, tissue distribution properties, and its pharmacokinetic properties including bioavailability through oral and intravenous routes are essential to the clinical outcomes.