2715-36-8

Usage

Uses

Used in Pharmaceutical Industry:
6-O-Methacryloyl-1,2:3,4-di-O-isopropylidine-D-galactopyranose is used as a building block for the synthesis of glycopolymers, which have potential applications in drug delivery systems. These glycopolymers can be tailored to target specific cells or tissues, improving the efficacy and reducing the side effects of certain medications.
Used in Biomedical Research:
In the field of biomedical research, 6-O-Methacryloyl-1,2:3,4-di-O-isopropylidine-D-galactopyranose is used as a key component in the development of biocompatible materials. These materials can be utilized in tissue engineering, where they serve as scaffolds for cell growth and tissue regeneration.
Used in Material Science:
6-O-Methacryloyl-1,2:3,4-di-O-isopropylidine-D-galactopyranose is used as a monomer in the creation of advanced polymer materials with unique properties. These materials can be employed in various applications, such as sensors, coatings, and adhesives, where their carbohydrate moieties provide specific interactions with biological systems.
Used in Cosmetics Industry:
In the cosmetics industry, 6-O-Methacryloyl-1,2:3,4-di-O-isopropylidine-D-galactopyranose is used as an ingredient in the formulation of skincare products. The glycopolymers derived from this monomer can enhance the delivery of active ingredients, providing improved skin hydration and protection.
Used in Food Industry:
6-O-Methacryloyl-1,2:3,4-di-O-isopropylidine-D-galactopyranose can be used in the development of edible coatings and films for the food industry. These coatings can help extend the shelf life of perishable products, maintain their freshness, and provide a barrier against environmental factors.
Used in Environmental Applications:
6-O-Methacryloyl-1,2:3,4-di-O-isopropylidine-D-galactopyranose is used in the creation of biodegradable polymers for environmental applications. These polymers can be employed in the production of eco-friendly packaging materials, reducing the environmental impact of plastic waste.

Upstream product

• 3646-73-9 α-D-galactopyranose 
• 67-64-1 acetone 
• 920-46-7 Methacryloyl chloride 
• 106-91-2 2,3-Epoxypropyl methacrylate 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 79-41-4 poly(methacrylic acid) 

Downstream Products

• 19179-68-1 6-O-methacryloyl-D-galactose 

Relevant academic research and scientific papers

D-galactose-based organogelator for phase-selective solvent removal and sequestration of cationic dyes

Naturally occurring sugar-based monomers are attractive substrates in the design of functional glycopolymers. In this study, we report on the development of D-galactose based organogels of varying crosslink density capable of selective adsorption of dyes and solvents. Free radical polymerization of 6-O-methacryloyl-1,2;3,4-di-O-isopropylidene-D-galactose in the presence of nonamethylene glycoldimethacrylate generated novel crosslinked polymers OG10, OG15 and OG20 with 10, 15 and 20 wt% crosslinker, respectively. Depending on the nature of the solvent, OG10 undergoes swelling upto 935%. The negative zeta potential, as determined from DLS measurements, and the gelation ability suggested the potential utility of the polymer for dye removal from water. OG10 displayed significant adsorption of rhodamine B (RhB) (>95%), crystal violet (>93%), and methylene blue (>70%) dyes as well as the selective adsorption of >90% RhB from a solution containing both RhB and methyl orange. These porous organogels are also found to be suitable for phase-selective removal of organic solvents.

Double-targeting and pH/oxidation reduction double-sensitive core cross-linking nanoparticle as well as preparation method and application

The invention discloses double-targeting and pH/oxidation reduction double-sensitive core cross-linking nanoparticles as well as a preparation method and application. Hydrophilic layers with folic acid targeting ligand and poly 6O-methyl acryloyl chloride-D-galactopyranose (PMApGP) are arranged on the surfaces of nanoparticles, hydrophobic cores with pH/oxidation reduction double-sensitive polymerunits are arranged inside the nanoparticles, and the hydrophobic cores are cross-linked under the action of dithiothreitol, therefore, stable and reversible double-targeting and pH/oxidation reduction double-sensitive core cross-linking nanoparticles are prepared. Medicine-carrying nanoparticles are prepared from adriamycin as a model medicine, and the stability and the pH/reduction double-sensitivity of medicine-carrying cross-linking nanoparticles can be observed through in-vitro medicine release experiments. Results show that the double-targeting and double-sensitive core cross-linking nanoparticles are simple and convenient in preparation method and high in medicine carrying rate, and the nanoparticles have the properties that the nanoparticles are stable in vitro and low in pH valueinside tumor cells and have hydrophilic-hydrophobic transfer with pH/oxidation reduction sensitive polymer units, and medicines can be rapidly released from a cross-linking structure.

Amphiphilic diblock terpolymer PMAgala-b-P(MAA-co-MAChol)s with attached galactose and cholesterol grafts and their intracellular pH-responsive doxorubicin delivery

In this work, a series of diblock terpolymer poly(6-O-methacryloyl-d-galactopyranose)-b-poly(methacrylic acid-co-6-cholesteryloxy hexyl methacrylate) amphiphiles bearing attached galactose and cholesterol grafts denoted as the PMAgala-b-P(MAA-co-MAChol)s were designed and prepared, and these terpolymer amphiphiles were further exploited as a platform for intracellular doxorubicin (DOX) delivery. First, employing a sequential RAFT strategy with preliminarily synthesized poly(6-O-methacryloyl-1,2:3,4-di-O-isopropylidene-d-galactopyranose) (PMAIpGP) macro-RAFT initiator and a successive trifluoroacetic acid (TFA)-mediated deprotection, a series of amphiphilic diblock terpolymer PMAgala-b-P(MAA-co-MAChol)s were prepared, and were further characterized by NMR, Fourier transform infrared spectrometer (FTIR), gel permeation chromatography (GPC), differential scanning calorimetry (DSC), and a dynamic contact angle testing instrument (DCAT). In aqueous media, spontaneous micellization of the synthesized diblock terpolymer amphiphiles were continuously examined by critical micellization concentration assay, dynamic light scattering (DLS), and transmission electron microscopy (TEM), and the efficacies of DOX loading by these copolymer micelles were investigated along with the complexed nanoparticle stability. Furthermore, in vitro DOX release of the drug-loaded terpolymer micelles were studied at 37 °C in buffer under various pH conditions, and cell toxicities of as-synthesized diblock amphiphiles were examined by MTT assay. Finally, with H1299 cells, intracellular DOX delivery and localization by the block amphiphile vectors were investigated by invert fluorescence microscopy. As a result, it was revealed that the random copolymerization of MAA and MAChol comonomers in the second block limited the formation of cholesterol liquid-crystal phase and enhanced DOX loading efficiency and complex nanoparticle stability, that ionic interactions between the DOX and MAA comonomer could be exploited to trigger efficient DOX release under acidic condition, and that the diblock terpolymer micellular vector could alter the DOX trafficking in cells. Hence, these suggest the pH-sensitive PMAgala-b-P(MAA-co-MAChol)s might be further exploited as a smart nanoplatform toward efficient antitumor drug delivery.

Synthesis of three different galactose-based methacrylate monomers for the production of sugar-based polymers

Glycopolymers, synthetic sugar-containing macromolecules, are attracting ever-increasing interest from the chemistry community. Glycidyl methacrylate (GMA) is an important building block for the synthesis of sugar based methacrylate monomers and polymers. Normally, glycidyl methacrylate shows some advantages such as reactivity against nucleophiles or milder synthetic conditions such as other reactive methacrylate monomers. However, condensation reactions of glycidyl methacrylate with for instance protected galactose monomer leads to a mixture of two products due to a strong competition between the two possible pathways: epoxide ring opening or transesterification. In this paper, we propose two alternative routes to synthesize regiospecific galactose-based methacrylate monomers using the epoxy-ring opening reaction. In the first alternative route, the protected galactose is first oxidized to the acid in order to make it more reactive against the epoxide of GMA. In the second route, the protected sugar was first treated with epichlorohydrin followed by the epoxy ring opening reaction with methacrylic acid, to create an identical analogue of the ring-opening product of GMA. These two monomers were polymerized using conventional radical polymerization and were compared to the previously known galactose-methacrylate one. The new polymers show similar thermal stability but lower glass transition temperature (Tg) with respect to the known galactose methacrylate polymer.

Water soluble and fluorescent copolymers as highly sensitive and selective fluorescent chemosensors for the detection of cyanide anions in biological media

We report a simple colorimetric method based on a water soluble polymer (WSP) for the sensitive and selective detection of cyanide in a biological solution. The WSPs were prepared from a radical polymerization of a methacrylate with a cyanide chemosensor moiety based on a coumarin-dicyano-vinyl derivative motif, and the polymer was then rendered water soluble by copolymerizing this hydrophobic monomer with other glyco-conjugated methacrylate derivatives. The lowest concentration for the quantification of cyanide ions was 0.05 μM, and the polymer exhibited nearly no calorimetric response to the presence of other common anions. Therefore, the chemical incorporation of some carbohydrates, as lactose or its usual monosaccharide moieties (glucose, lactose), represents a new method for the implementation of polymers for the detection of cyanide anions in water, exhibiting both good selectivity and efficiency. The Royal Society of Chemistry 2013.

One-pot synthesis of hyperbranched glycopolymers by RAFT polymerization

Soluble hyperbranched glycopolymers were prepared by copolymerization of glycan monomers with reversible addition-fragmentation chain transfer polymerization (RAFT) inimers in a simple one-pot reaction. Two novel RAFT inimers, 2-(methacryloyloxy)ethyl 4-c

Synthesis of water-soluble polymeric prodrugs possessing 4-methylcatechol derivatives by mechanochemical solid-state copolymerization and nature of drug release.

In this study we synthesized the water-soluble polymeric prodrugs possessing a 4-methylcatechol (4MC) derivative as a side chain by mechanochemical solid-state copolymerization. 1-benzoyl-4-methylcatechol (Bz4MC) was selected as a model compound of 4MC, and its methacryloyl derivative (1) was synthesized. 6-O-methacryloyl-D-galactose (2) was also prepared as a water-soluble monomer. The mechanochemical solid-state copolymerization of 1 and 2 was carried out to obtain the water-soluble polymeric prodrug possessing the Bz4MC as a side chain. The mechanochemical copolymerization of 1 and 2 proceeded to completion, and the polymeric prodrug produced possessed a narrow molecular weight distribution. Three kinds of polymeric prodrugs, whose compositions were different from one another, were hydrolyzed in vitro. The hydrolysis of these polymeric prodrugs proceeded to completion. The rate constants of hydrolysis decreased with increasing the mole fraction of 1 in polymeric prodrug. It was suggested that the rate constant of hydrolysis could be controlled by the composition, the mole fraction of 1 in the polymeric prodrug.