185378-83-0

Basic information

• Product Name: Bis-propargyl-PEG6
• Synonyms: Bis-propargyl-PEG6;Alkyne-PEG6-Alkyne
• CAS NO: 185378-83-0
• Molecular Formula: C₁₆H₂₆O₆
• Molecular Weight: 314.37404
• Mol File: 185378-83-0.mol

Chemical Properties

• Appearance: /
• Solubility: Soluble in DMSO, DCM, DMF
• CAS DataBase Reference: Bis-propargyl-PEG6(CAS DataBase Reference)
• NIST Chemistry Reference: Bis-propargyl-PEG6(185378-83-0)
• EPA Substance Registry System: Bis-propargyl-PEG6(185378-83-0)

Safety Data

• Hazardous Substances Data: 185378-83-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Bis-propargyl-PEG6 is used as a molecular building block for the development of novel drug conjugates and targeted therapies. The Click Chemistry reactions facilitated by its propargyl groups allow for the efficient and specific attachment of various therapeutic agents, such as drugs, peptides, or antibodies, to the PEG backbone. This enhances the solubility, stability, and bioavailability of the conjugated drugs, potentially improving their therapeutic efficacy.
Used in Bioconjugation and Labeling:
In the field of molecular biology and biochemistry, Bis-propargyl-PEG6 is used as a versatile linker for bioconjugation and labeling applications. The stable triazole linkage formed through Click Chemistry reactions enables the covalent attachment of biomolecules, such as proteins, nucleic acids, or other macromolecules, to the PEGylated scaffold. This can be useful for studying molecular interactions, developing biosensors, or creating targeted drug delivery systems.
Used in Material Science:
Bis-propargyl-PEG6 can be utilized as a key component in the synthesis of advanced materials with tailored properties. The hydrophilic nature of the PEG units, combined with the versatility of the propargyl groups for Click Chemistry reactions, allows for the creation of novel polymers, hydrogels, or surface coatings with applications in drug delivery, tissue engineering, or as components of medical devices.
Used in Diagnostics:
In the diagnostics industry, Bis-propargyl-PEG6 can be employed as a component in the development of imaging agents or contrast agents. The PEGylation of these agents can improve their pharmacokinetics, reducing clearance rates and increasing circulation times in the body. Additionally, the propargyl groups can be used to attach specific targeting moieties, such as antibodies or peptides, to enhance the specificity of the imaging agent for particular tissues or cells.

Upstream product

• 4792-15-8 Pentaethylene glycol 
• 106-96-7 propargyl bromide 

Downstream Products

• 1119249-29-4 bis-1,18-[1-(3-(2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol-N-yl)-propyl)triazol-4-yl]-2,5,8,11,14,17-hexaoxaoctadecane 

Relevant articles and documents

Synthesis and metal ion binding studies of enediyne-containing crown ethers

The 3-ene-1,5-diyne crown ether 5 is a novel enediyne-containing crown ether that was designed as a model system for a class of enediynes that might undergo alkali metal ion-triggered Bergman cyclization. We report the preparation of 5 by two different routes. In the shorter and preferable route, a carbenoid coupling reaction is employed to simultaneously construct the enediyne moiety and effect a macrocyclization of an acyclic bis(propargyl)bromide 15 to the 24-membered crown ether 5. Under standard reaction conditions, this carbenoid coupling produces as the major product the isomeric 5-ene-1,3-diyne-crown ethers (Z)-16 and (E)-16. The formation of 5-ene-1,3-diynes from the carbenoid coupling of propargyl bromides is unprecedented. We present evidence that it is the polyether nature of dibromide 15 that leads to the formation of the 5-ene-1,3-diyne-crown ether products. Judicious control of the reaction conditions can be used to produce either 5 or (Z)-16 from 15 in synthetically useful yields. Both enediyne-crown ethers 5 and (Z)-16 bind alkali metal ions, as evidenced by their ability to extract alkali metal picrates into organic solvents. Enediyne-crown ether 5 undergoes Bergman cyclization at 135°C in DMSO/1,4-cyclohexadiene to produce the known o-xylyl crown ether 4. Crown ether 5 represents an enediyne in which molecular recognition of alkali metals might serve as a trigger for Bergman cyclization.

Synthesis of Metallopolymers and Direct Visualization of the Single Polymer Chain

During the past few decades, the study of the single polymer chain has attracted considerable attention with the goal of exploring the structure-property relationship of polymers. It still, however, remains challenging due to the variability and low atomic resolution of the amorphous single polymer chain. Here, we demonstrated a new strategy to visualize the single metallopolymer chain with a hexameric or trimeric supramolecule as a repeat unit, in which Ru(II) with strong coordination and Fe(II) with weak coordination were combined together in a stepwise manner. With the help of ultrahigh-vacuum, low-temperature scanning tunneling microscopy (UHV-LT-STM) and scanning tunneling spectroscopy (STS), we were able to directly visualize both Ru(II) and Fe(II), which act as staining reagents on the repeat units, thus providing detailed structural information for the single polymer chain. As such, the direct visualization of the single random polymer chain is realized to enhance the characterization of polymers at the single-molecule level.

Limits of the inversion phenomenon in triazolyl-substituted β-cyclodextrin dimers

Six different β-cyclodextrin (β-CD) dimers have been synthesized by copper-catalyzed azide alkyne cycloaddition. The nature of the spacer connecting the two β-CDs has been varied in length and hydrophilicity. For each dimer, a detailed NMR study was carried out in D2O. It was found that, whereas β-CD dimers having short spacer exhibited only one conformation, β-CD dimers having long and/or hydrophobic spacers showed two different conformations. Indeed, the latter underwent an inversion process leading to self-inclusion of the spacer in one of the two CD cavities. The behavior of the six β-CD dimers in water has thus been rationalized and this allowed the proportion of "free" cavities actually available for molecular recognition to be determined. Six β-cyclodextrin (β-CD) dimers have been synthesized by CuAAC. Depending on the nature of the spacer connecting the CDs, one or two conformations could be detected by NMR spectroscopic analysis. An inversion process was observed for dimers with a long and/or hydrophilic spacer. The proportion of "free" β-CD cavities actually available for molecular recognition could be determined. Copyright

Limits of the Inversion Phenomenon in Triazolyl-Substituted β-Cyclodextrin Dimers

Six different β-cyclodextrin (β-CD) dimers have been synthesized by copper-catalyzed azide alkyne cycloaddition. The nature of the spacer connecting the two β-CDs has been varied in length and hydrophilicity. For each dimer, a detailed NMR study was carried out in D2O. It was found that, whereas β-CD dimers having short spacer exhibited only one conformation, β-CD dimers having long and/or hydrophobic spacers showed two different conformations. Indeed, the latter underwent an inversion process leading to self-inclusion of the spacer in one of the two CD cavities. The behavior of the six β-CD dimers in water has thus been rationalized and this allowed the proportion of "free" cavities actually available for molecular recognition to be determined. Six β-cyclodextrin (β-CD) dimers have been synthesized by CuAAC. Depending on the nature of the spacer connecting the CDs, one or two conformations could be detected by NMR spectroscopic analysis. An inversion process was observed for dimers with a long and/or hydrophilic spacer. The proportion of "free" β-CD cavities actually available for molecular recognition could be determined.

Towards multivalent CD1d ligands: Synthesis and biological activity of homodimeric α-galactosyl ceramide analogues

A library of dimeric CD1d ligands, containing two α-galactosyl ceramide (α-GalCer) units linked by spacers of varying lengths has been synthesised. The key dimerisation reactions were carried out via copper-catalysed click reactions between a 6″-azido-6″-deoxy- α-galactosyl ceramide derivative and various diynes. Each α-GalCer dimer was tested for its ability to stimulate iNKT cells.