945841-51-0

Usage

Uses

Used in Polymer Synthesis:
Propargyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate is used as a monomer for the synthesis of alkyne-functionalized polycarbonates. The incorporation of alkynes allows for post-polymerization modification through CuAAC or thiol-yne click reactions, enabling the attachment of various functional groups to the polymer backbone.
Used in Post-Polymerization Modification:
Propargyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate is used as a precursor for post-polymerization modification of alkyne-functionalized polycarbonates. The alkyne groups can be rapidly modified through CuAAC or thiol-yne click reactions, allowing for the installation of azides or thiols onto the polymer backbone for further functionalization or conjugation to biomolecules or small molecules of interest.
Used in Drug Delivery Systems:
Propargyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate can be used in the development of drug delivery systems, where the alkyne-functionalized polycarbonates can be modified to incorporate drug molecules or targeting ligands. The high efficiency of CuAAC or thiol-yne click reactions allows for precise and efficient drug loading and release from the polymeric carrier.
Used in Bioconjugation:
Propargyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate can be used in bioconjugation applications, where the alkyne-functionalized polycarbonates can be modified to attach biomolecules or small molecules of interest. The CuAAC or thiol-yne click reactions provide a highly efficient and specific method for attaching these molecules to the polymer backbone, enabling the development of novel bioconjugates for various applications.

Upstream product

• 1252553-69-7 pentafluorophenyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate 
• 107-19-7 propargyl alcohol 
• 873849-85-5 prop-2-yn-1-yl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate 
• 541-41-3 chloroformic acid ethyl ester 
• 1006903-28-1 5-methyl-2-oxo-[1,3]dioxane-5-carboxylic acid chloride 
• 507471-78-5 5-methyl-2-oxo-[1,3]dioxane-5-carboxylic acid 

Relevant academic research and scientific papers

Reversibly light-responsive biodegradable poly(carbonate) micelles constructed via CuAAC reaction

Light-responsive poly(carbonate)s PEG113-b-PMPCn-SP were synthesized via copper catalyzed azide-alkyne cycloaddition reaction between azide-modified spiropyran (SP-N3) and amphiphilic copolymer PEG113-b-PMPCn. PEG113-b-PMPC25-SP can self-assemble to biocompatible micelles with an average diameter of ～96 nm and a critical aggregation concentration of 0.0148 mg mL-1. Under 365 nm UV light irradiation, the characteristic absorption intensity of merocyanine (MC) progressively increased and most of the micellar aggregations were disrupted within 10 min, suggesting the completion of the transformation of hydrophobic SP to hydrophilic MC. Subsequent exposuring the micelles to 620 nm visible light, spherical micelles aggregated again. The light-controlled release and re-encapsulation behaviors of coumarin 102-loaded micelles were further investigated by fluorescence spectroscopy. This study provides a convenient way to construct smart poly(carbonate)s nanocarriers for controlled release and reencapsulation of hydrophobic drugs.

Cinnamyl modified polymer micelles as efficient carriers of caffeic acid phenethyl ester

A synthetic strategy towards modular polymer platform capable of further tunable degree of modification is presented. Initially, a well-defined amphiphilic block copolymer with alkyne side groups distributed along the biodegradable hydrophobic block was successfully prepared applying controlled ring-opening copolymerization of D,L-lactide and an acetylene-functional cyclic carbonate initiated by polyoxyethylene macroinitiator. In the second synthetic step a desired number of cinnamyl pendant groups was introduced into the hydrophobic block via “click” reaction. The functional block copolymers self-associated in aqueous media into stable micelles with narrow size distribution and average diameters of around 50 nm. The micelles' functional hydrophobic cores were loaded with caffeic acid phenethyl ester (CAPE) as bioactive compound with great potential for therapeutic application. It was demonstrated that the initial drug-release profiles, hence the stability of the loaded nanocarriers during circulation, can be modulated via the number of cinnamyl groups into the micelles core. Initial in-vitro evaluations were preformed on empty and drug-loaded functional polymer micelles indicating their potential for application in nanomedicine as safe and biocompatible drug-delivery nanovehicles with enhanced stability.

Degradable pH-responsive polymer prodrug micelles with aggregation-induced emission for cellular imaging and cancer therapy

Polymeric micelles with simultaneous bioimaging, drug delivery monitoring, and effective delivery of therapeutic agents to target sites have attracted increasing attention in cancer therapy. In this study, a new biodegradable, pH-responsive, aggregation-induced emission (AIE)-active polycarbonate brush-like polymer was developed by combining ring-opening polymerization with click reaction. The anticancer drug, doxorubicin (DOX), was covalently conjugated to the polymer backbone via acid-sensitive Schiff base linkage, resulting in the pH-sensitive controlled release of DOX. The prodrug polymer self-assembled into nanomicelles in an aqueous solution, as confirmed using dynamic light scattering and transmission electron microscopy. Fluorescence imaging results demonstrated that prodrug micelles could be traced owing to the AIE features of micelles. In vitro drug release studies showed that DOX release was faster in acidic conditions (pH 5.0), whereas only a minimal amount of DOX was released in a physiological environment (pH 7.4). In summary, these smart prodrug micelles could be promising candidates for simultaneous intracellular imaging and cancer therapy.

Visual Biopsy by Hydrogen Peroxide-Induced Signal Amplification

Visual biopsy has attracted special interest by surgeons due to its simplicity and practicality; however, the limited sensitivity of the technology makes it difficult to achieve an early diagnosis. To circumvent this problem, herein, we report a visual si

Synthesis, characterization and applications of selenocysteine-responsive nanoprobe based on dinitrobenzene sulfonyl-modified poly(carbonate) micelles

In trace amounts, selenium (Se) participates in different physiological functions of the human body. Its biological significance is manifested in its presence as selenocysteine (Sec) in genetically encoded selenoproteins that are important in redox regulation, anti-inflammation, and cancer treatment. Recently, stimuli-responsive micelles were developed as biosensors, but there are no nanomicelle probes for the selective imaging of Sec under biological conditions (pH = 7.4). Herein, we report the design and preparation of a 2,4-dinitrobenzenesulfonyl-decorated block poly(carbonate) copolymer, viz. PMPC-Dns, for Sec imaging. We found that PMPC-Dns trapped with the fluorescent drug doxorubicin (DOX) selectively responds to Sec, while getting little interference from biological thiols, amines or alcohols. We applied the PMPC-Dns probe successfully to image endogenous Sec in cervical cancer tissues as well as in HeLa cells. In the course of these studies, we observed simultaneous release of the trapped DOX. Hence, besides Sec imaging, the probe can be used for controlled delivery of hydrophobic molecules for biomedical applications.

Photo-responsive reversible micelles based on azobenzene-modified poly(carbonate)s via azide-alkyne click chemistry

Photo-induced reversible amphipathic copolymer PMPC-azo was click conjugated by connecting amphiphilic poly(ethylene glycol)-modified poly(carbonate)s (PEG-b-poly(MPC)) and azide-functional trifluoromethoxy-azobenzene (azo-N3). The resulting copolymer self-assembled into spherical micelles with a hydrophobic azo core stabilized by a hydrophilic PEG corona in aqueous solution. As characterized by time-resolved UV-vis spectroscopy, dynamic light scattering (DLS) and transmission electron microscopy (TEM), these micelles showed reversible self-assembly and disassembly in aqueous solution under alternating UV and visible light irradiation. The model drug Nile Red (NR) was then successfully encapsulated into the micelles. Light-controlled release and re-encapsulation behaviors were demonstrated by fluorescence spectroscopy. The cell cytotoxicity of PMPC-azo micelles was also evidenced by MTT assay. This study provides a convenient method to construct smart nanocarriers for controlled release and re-encapsulation of hydrophobic drugs. This journal is

POLYMERS BEARING PENDANT PENTAFLUOROPHENYL ESTER GROUPS, AND METHODS OF SYNTHESIS AND FUNCTIONALIZATION THEREOF

A one pot method of preparing cyclic carbonyl compounds comprising an active pendant pentafluorophenyl ester group is disclosed. The cyclic carbonyl compounds can be polymerized by ring opening methods to form ROP polymers comprising repeat units comprising a side chain pentafluorophenyl ester group. Using a suitable nucleophile, the pendant pentafluorophenyl ester group can be selectively transformed into a variety of other functional groups before or after the ring opening polymerization.

A simple and efficient synthesis of functionalized cyclic carbonate monomers using a versatile pentafluorophenyl ester intermediate

An improved two-step synthetic route to functionalized cyclic carbonate monomers that features a novel cyclic carbonate intermediate with an active pentafluorophenyl ester group (MTC-OPhF5) has been developed. The versatile pentafluorophenyl ester intermediate can be synthesized on the gram to kilogram scale in one high-yielding step and is easy to store and handle on the benchtop. The active pentafluorophenyl ester of MTC-OPhF5 is amenable to further substitution with suitable nucleophiles such as alcohols and amines to generate functionalized cyclic carbonates in high yields. The substitution reaction is tolerant of a wide variety of functionalities, including various hydrophobic and hydrophilic groups, reactive functionalities (via thiol-ene click chemistry or alkyl halides), and protected acids, alcohols, thiols, and amines. In view of the ever-increasing need for biodegradable and biocompatible polymers, this new methodology provides a simple and versatile platform for the synthesis of new and innovative materials.

Tagging alcohols with cyclic carbonate: A versatile equivalent of (meth)acrylate for ring-opening polymerization

Cyclic carbonate monomers based on a single biocompatible scaffold allow for incorporation of a wide range of functional groups into macromolecules via ring-opening polymerization. The Royal Society of Chemistry.