225523-86-4

Usage

Uses

Used in Bioconjugation:
Azido-PEG7-azide is used as a bioconjugation agent for the formation of stable covalent bonds between biomolecules and other chemical entities. The application reason is its ability to react with alkyne groups through Click Chemistry, allowing for the creation of well-defined and stable bioconjugates with minimal disruption to the native structure and function of the biomolecules.
Used in Drug Delivery Systems:
In the pharmaceutical industry, Azido-PEG7-azide is used as a component in the design of drug delivery systems. The application reason is its solubility-enhancing PEG spacer and reactive azide groups, which facilitate the attachment of drug molecules to the delivery system through Click Chemistry. This can improve the pharmacokinetics, biodistribution, and overall efficacy of the drug.
Used in Materials Science:
Azido-PEG7-azide is employed as a building block in the synthesis of functional materials, such as hydrogels and polymeric scaffolds. The application reason is its ability to form stable triazole linkages through Click Chemistry, which can be used to create well-defined and mechanically robust materials with tailored properties for various applications, including tissue engineering and sensor development.
Used in Chemical Synthesis:
In the field of chemical synthesis, Azido-PEG7-azide is used as a versatile reagent for the modification of various chemical compounds. The application reason is its reactive azide groups, which can be used to introduce PEGylated moieties into a wide range of molecules, thereby improving their solubility, stability, and biocompatibility.

Upstream product

• 57436-38-1 3,6,9,12,15,18,21-heptaoxatricosane-1,23-diyl bis(4-methylbenzenesulfonate) 
• 37860-51-8 tetraethylene glycol di(p-toluenesulfonate) 
• 139115-90-5 2-(2-azidoethoxy)ethanol 
• 112-60-7 Tetraethylene glycol 
• 106481-21-4 3,6,9,12,15,18,21-heptaoxatricosane-1,23-diyl dimethanesulfonate 
• 5117-19-1 octaethylene glycol 
• 54797-77-2 1,23-dichloro-3,6,9,12,15,18,21-heptaoxatricosane 

Downstream Products

• 1333154-77-0 α-amino,ω-azido,α,ω-dideoxy-octaethyleneglycol 
• 332941-25-0 1,23-diamino-3,6,9,12,15,18,21-heptaoxatricosane 

Relevant academic research and scientific papers

BIS(2-HALOACETAMIDO)-COMPOUNDS FOR USE AS LINKING AGENTS AND RESULTANT PRODUCTS WHICH COMPRISE ANTIBODIES, HALF-ANTIBODIES AND ANTIBODY FRAGMENTS

Bis(2-haloacetamido)- compounds for use as linkers to chemically cross-linking multiple thiol groups, and particularly, although not exclusively, the thiol groups of cysteine amino acids in peptide chains are described, along with their use as linking age

Bivalent HIV-1 fusion inhibitors based on peptidomimetics

Membrane fusion is a valid target for inhibition of HIV-1 replication. A 34-mer fragment peptide (C34), which is contained in the HIV-1 envelope protein gp41, has significant anti-HIV activity. Previously, a dimeric derivative of C34 linked by a disulfide bridge at its C-terminus was found to have more potent anti-HIV activity than the C34 peptide monomer. To date, several peptidomimetic small inhibitors have been reported, but most have lower potency than peptide derivatives related to C34. In the present study we applied this dimerization concept to these peptidomimetic small inhibitors and designed several bivalent peptidomimetic HIV-1 fusion inhibitors. The importance of the length of linkers crosslinking two peptidomimetic compounds was demonstrated and several potent bivalent inhibitors containing tethered peptidomimetics were produced.

SMALL MOLECULE BASED ANTIBODY-RECRUITING COMPOUNDS FOR CANCER TREATMENT

The present invention relates to chimeric (including bifunctional) compounds, compositions comprising those compounds and methods of treating cancer in a patient or subject, especially including metastatic cancer where cancer cells exhibit overexpression (heightened expression) of cell surface urokinase-type plasminogen activator receptor (urokinase receptor) compared to normal (non-cancerous) cells. The compounds bind to the urokinase-type plasminogen activator receptor (uPAR) on the surface of a cancer cell, including a metastatic cancer cell, and consequently recruit native antibodies of the patient or subject where the antibodies can selectively degrade and/or deactivate targeted cancer cells through antibody-dependent cellular phagocytosis and antibody-dependent cellular cytotoxicity (ADCC) and/or complement dependent cytotoxicity (CDC) against a large number and variety of cancers, thus providing cancer cell death and an inhibition of growth, elaboration and/or metastasis of the cancer, including remission and cure of the patient's cancer.

Re-engineering the Immune Response to Metastatic Cancer: Antibody-Recruiting Small Molecules Targeting the Urokinase Receptor

Developing selective strategies to treat metastatic cancers remains a significant challenge. Herein, we report the first antibody-recruiting small molecule (ARM) that is capable of recognizing the urokinase-type plasminogen activator receptor (uPAR), a uniquely overexpressed cancer cell-surface marker, and facilitating the immune-mediated destruction of cancer cells. A co-crystal structure of the ARM-U2/uPAR complex was obtained, representing the first crystal structure of uPAR complexed with a non-peptide ligand. Finally, we demonstrated that ARM-U2 substantially suppresses tumor growth in vivo with no evidence of weight loss, unlike the standard-of-care agent doxorubicin. This work underscores the promise of antibody-recruiting molecules as immunotherapeutics for treating cancer.

Efficient synthesis of diverse heterobifunctionalized clickable oligo(ethylene glycol) linkers: Potential applications in bioconjugation and targeted drug delivery

Herein we describe the sequential synthesis of a variety of azide-alkyne click chemistry-compatible heterobifunctional oligo(ethylene glycol) (OEG) linkers for bioconjugation chemistry applications. Synthesis of these bioorthogonal linkers was accomplished through desymmetrization of OEGs by conversion of one of the hydroxyl groups to either an alkyne or azido functionality. The remaining distal hydroxyl group on the OEGs was activated by either a 4-nitrophenyl carbonate or a mesylate (-OMs) group. The -OMs functional group served as a useful precursor to form a variety of heterobifunctionalized OEG linkers containing different highly reactive end groups, e.g., iodo, -NH2, -SH and maleimido, that were orthogonal to the alkyne or azido functional group. Also, the alkyne- and azide-terminated OEGs are useful for generating larger discrete poly(ethylene glycol) (PEG) linkers (e.g., PEG 16 and PEG24) by employing a Cu(i)-catalyzed 1,3-dipolar cycloaddition click reaction. The utility of these clickable heterobifunctional OEGs in bioconjugation chemistry was demonstrated by attachment of the integrin (αvβ3) receptor targeting peptide, cyclo-(Arg-Gly-Asp-d-Phe-Lys) (cRGfKD) and to the fluorescent probe sulfo-rhodamine B. The synthetic methodology presented herein is suitable for the large scale production of several novel heterobifunctionalized OEGs from readily available and inexpensive starting materials.

A "Clickable" MTX Reagent as a Practical Tool for Profiling Small-Molecule-Intracellular Target Interactions via MASPIT

We present a scalable synthesis of a versatile MTX reagent with an azide ligation handle that allows rapid γ-selective conjugation to yield MTX fusion compounds (MFCs) appropriate for MASPIT, a three-hybrid system that enables the identification of mammalian cytosolic proteins that interact with a small molecule of interest. We selected three structurally diverse pharmacologically active compounds (tamoxifen, reversine, and FK506) as model baits. After acetylene functionalization of these baits, MFCs were synthesized via a CuAAC reaction, demonstrating the general applicability of the MTX reagent. In analytical mode, MASPIT was able to give concentration-dependent reporter signals for the established target proteins. Furthermore, we demonstrate that the sensitivity obtained with the new MTX reagent was significantly stronger than that of a previously used non-regiomeric conjugate mixture. Finally, the FK506 MFC was explored in a cellular array screen for targets of FK506. Out of a pilot collection of nearly 2000 full-length human ORF preys, FKBP12, the established target of FK506, emerged as the prey protein that gave the highest increase in luciferase activity. This indicates that our newly developed synthetic strategy for the straightforward generation of MFCs is a promising asset to uncover new intracellular targets using MASPIT cellular array screening.

Selective inhibition of human brain tumor cells through multifunctional quantum-dot-based siRNA delivery

(Figure Presented) More than one Job: Quantum dots (QDs) conjugated with thiol-modified small Interfering RNA (siRNA) were functlonalized with thiol-modlfied RGD and HIV-Tat peptides. These multifunctional QDs were used for the targeted delivery and track

Efficient synthesis of Hsp90 inhibitor dimers as potential antitumor agents

The PU-H58-dimers 13a-15b were efficiently synthesized and their biological properties were evaluated. The copper-catalyzed alkyne azide coupling was effective in simultaneously linking three components via a triazole formation to afford the target dimers