945841-51-0

Basic information

• Product Name: propargyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate
• Synonyms: propargyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate
• CAS NO: 945841-51-0
• Molecular Weight: 198.175
• Mol File: 945841-51-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: propargyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: propargyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate(945841-51-0)
• EPA Substance Registry System: propargyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate(945841-51-0)

Safety Data

• Hazardous Substances Data: 945841-51-0(Hazardous Substances Data)

Usage

General Description

5-Methyl-5-propargyloxycarbonyl-1,3-dioxane-2-one is an alkyne-functionalized, cyclic carbonate monomer that can be polymerized or copolymerized to yield alkyne-functionalized polycarbonates. The incorporation of alkynes allows for rapid post-polymerization modification through reactions, such as copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) or thiol-yne click reactions. These reactions are highly preferable for functionalization due their high efficiency and the ability to easily install the corresponding functionality (e.g., azides or thiols) onto the biomolecule or small molecule of interest.

Upstream product

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

Relevant articles and documents

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.

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.

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.