77544-68-4

Usage

Uses

Used in Pharmaceutical Industry:
Ethanol, 2-[2-(2-hydroxyethoxy)ethoxy]-, 1-(4-methylbenzenesulfonate) is used as a building block for the synthesis of pharmaceutical compounds. The hydrophilic PEG spacer improves the solubility and bioavailability of the final product, while the hydroxyl group allows for the attachment of various functional groups or drug molecules.
Used in Chemical Synthesis:
Ethanol, 2-[2-(2-hydroxyethoxy)ethoxy]-, 1-(4-methylbenzenesulfonate) is used as an intermediate in the synthesis of various organic compounds. The tosyl group acts as a good leaving group, facilitating nucleophilic substitution reactions, which are essential in the formation of a wide range of chemical products.
Used in Bioconjugation:
Ethanol, 2-[2-(2-hydroxyethoxy)ethoxy]-, 1-(4-methylbenzenesulfonate) is used as a linker in bioconjugation processes. The hydroxyl group can be used to attach biomolecules, such as proteins, peptides, or nucleic acids, to other molecules or surfaces, enabling the development of biosensors, drug delivery systems, and other bioanalytical tools.

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 104-15-4 toluene-4-sulfonic acid 
• 112-35-6 triethylene glucol monomethyl ether 

Downstream Products

• 152523-72-3 3-<2-<2-(2-hydroxyethoxy)ethoxy>ethoxy>-2-(2-propenyloxy)benzaldehyde 
• 135643-72-0 N-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethyl}-4-methyl-benzenesulfonamide 
• 135643-71-9 9-[(4-methylphenyl)sulfonyl]-3,6,12,15-tetraoxa-9-aza-1,17-heptadecanediol 
• 17455-13-9 18-crown-6 ether 
• 2615-15-8 pentaethylene glycol 
• 86520-52-7 2-[2-(2-azidoethoxy)ethoxy]ethanol 
• 133699-10-2 10,10,10-Triphenyl-3,6,9-trioxadecyl-p-toluenesulfonate 
• 69502-33-6 2-(2-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate 
• 89203-08-7 2-<2-<2-(4-tert-butylphenoxy)ethoxy>ethoxy>ethanol 
• 333382-86-8 2-(2-(2-(4-bromophenoxy)ethoxy)ethoxy)ethan-1-ol 
• 359014-85-0 2-(2-{2-[4-(2-Methoxyethoxy)phenoxy]ethoxy}ethoxy)ethanol 
• 88037-68-7 1,2-bis{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}benzene 
• 462628-58-6 4,5-bis-{2'-[2''-(2'''-hydroxyethoxy)ethoxy]ethoxy}-1,2-dibromobenzene 
• 764687-71-0 3-[4-(2-{2-[2-(4-cyclohepta-2,4,6-trienyl-phenoxy)-ethoxy]-ethoxy}-ethoxy)-phenyl]-propan-1-ol 

Relevant academic research and scientific papers

Phthalimide–Oxy Derivatives for 3′- or 5′-Conjugation of Oligonucleotides by Oxime Ligation and Circularization of DNA by “Bis- or Tris-Click” Oxime Ligation

A solid support and two phosphoramidites exhibiting a phthalimide–oxy group were synthesized. First, after treatment with hydrazine, the resulting 5′- and 3′-oxyamine oligonucleotides were conjugated with aldehyde derivatives by oxime ligation. Second, ol

Therapeutic effects of isothiocyanate prodrugs on rheumatoid arthritis

Isothiocyanates 7a and 7b have poor stability and aqueous solubility. To address these problems, prodrugs 8a and 8b were synthesized. Prodrugs 8a and 8b were stable in HEPES buffer at pH 4.4, but released the active compounds 7a and 7b in HEPES buffer at

In Vitro Photodynamic Studies of a BODIPY-Based Photosensitizer

A new halogenated 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivative was designed as a singlet-oxygen photosensitizer (PS) for use as a photodynamic therapy (PDT) agent, and its photophysical properties were characterized. The PS, having two i

Synthesis and in vitro anticancer activity of zinc(II) phthalocyanines conjugated with coumarin derivatives for dual photodynamic and chemotherapy

The combination of photodynamic therapy and chemotherapy is a promising strategy to overcome growing problems in contemporary medicine, such as low therapeutic efficacy and drug resistance. Four zinc(II) phthalocyanine-coumarin conjugates were synthesized and characterized. In these complexes, zinc(II) phthalocyanine was used as the photosensitizing unit, and a coumarin derivative was selected as the cytostatic moiety; the two components were linked via a tri(ethylene glycol) chain. These conjugates exhibit high photocytotoxicity against HepG2 human hepatocarcinoma cells, with low IC50 values in the range of 0.014-0.044 μm. The high photodynamic activities of these conjugates are in accordance with their low aggregation tendency and high cellular uptake. One of these conjugates exhibits high photocytotoxicity and significantly higher chemocytotoxicity. The results clearly show that the two antitumor components in these conjugates work in a cooperative fashion. As shown by confocal microscopy, the conjugates can localize in the mitochondria and lysosomes, and one of the conjugates can also localize in the cell nuclei.

The dynamic covalent reaction based on diselenide-containing crown ether irradiated by visible light

A novel diselenide-containing crown ether (BC7Se2) was fabricated, which can polymerize to form cyclic oligomers through intermolecular dynamic covalent reaction by irradiation of visible light. The size and distribution of oligomers are relate

Persistent room-temperature phosphorescence or high-contrast phosphorescent mechanochromism: polymorphism-dependent different emission characteristics from a single gold(i) complex

Luminophores with persistent room-temperature phosphorescence (p-RTP) or effective phosphorescent mechanochromism features have significant potential applications in the field of optoelectronic materials. Until now, p-RTP and remarkable phosphorescent mechanochromism phenomena have been observed in some luminescent molecules with different molecular structures. However, separately realizing p-RTP and high-contrast phosphorescent mechanochromism in different polymorphs from a single luminophore is still a valuable and challenging topic. In this work, two polymorphs1Band1YGof a new gold(i) complex with blue and yellow-green luminescence, respectively, are reported. Interestingly,1Bexhibits high-contrast phosphorescent mechanochromic behavior, while1YGexhibits a persistent room-temperature phosphorescence effect. This is the first example of simultaneously obtaining double-purpose crystalline materials with a high-contrast phosphorescent mechanochromism or persistent room-temperature phosphorescence feature from a single luminophore.

Mitochondrion-targeting PEGylated BODIPY dyes for near-infrared cell imaging and photodynamic therapy

A series of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-based photosensitizers (AmBXI, X = H, M, Br) featuring a cationic mitochondrion-targeting group and near-infrared (NIR) absorption was synthesized. After extending the photosensitizers' π conjugation via Knoevenagel reaction, both the absorbance and emission maxima of AmBXI shifted to the phototherapeutic wavelength range (650-900 nm). Theoretical computations indicate that the introduction of bromine atoms promotes spin-orbit coupling, so that for each additional bromine atom in AmBXI an increase in singlet oxygen quantum yield would be expected (0.3%, 2.2%, and 4.1%, for AmBHI, AmBMI, and AmBBrI, respectively). Moreover, AmBXI photosensitizers exhibited low cytotoxicity in the dark and high phototoxicity, with the half maximal inhibitory concentrations of AmBBrI found to be 46.93 nM and 22.84 nM, while those of AmBMI were 129.7 nM and 58.34 nM in HeLa and MCF-7 cancer cells, respectively. Notably, introduction of a single bromine atom was enough to produce a cytotoxic effect. Furthermore, the presence of a quaternary ammonium group in AmBXI enabled the dyes to localize and stain the negatively charged mitochondria. The results presented herein indicate the straightforward and facile synthesis of NIR-light triggered mitochondrion-targeting photosensitizers. This journal is

Discovery of novel potent covalent inhibitor-based EGFR degrader with excellent in vivo efficacy

Although several Epidermal growth factor receptor (EGFR) inhibitors have been approved for the treatment of non-small-cell lung cancers (NSCLC), acquired drug resistance and side effects largely encumbered their application in clinic. The emerging technology Proteolysis targeting chimera (PROTAC) could be an alternative strategy to overcome these problems. Here, we reported the discovery of Dacomitinib-based EGFR degraders. Promising compound 13 can effectively induce degradation of EGFRdel19 with DC50 value of 3.57 nM in HCC-827 cells, but not to other EGFR mutant, wild-type EGFR protein and the same family receptors (HER2 and HER4). Of note, 13 is the first EGFR-PROTAC to evaluate antitumor effect in vivo, and exhibited excellent antitumor efficacy (TGI = 90%) at a dose of 30 mg/kg without causing observable toxic effects. The preliminary mechanism study demonstrated that 13 can efficiently induce EGFR protein degradation through ubiquitin proteasome pathway and inhibit phosphorylation of downstream pathways in vitro and in vivo, which indicated that 13 exerted antitumor effect by degradation of EGFR protein in tumor tissue. Overall, our study provided further evidence to validate EGFR-PROTACs as a promising strategy for lung cancer therapy.

MODULAR CHEMICAL PROBE FOR DETECTION OF AMINO ACID CITRULLINE IN PHYSIOLOGICAL SAMPLES

An improved chemical probe for the detection of the amino acid citrulline combines: 1) a reactive head formed of 1,3-dicarbonyl moiety that reacts with a citrulline side chain in an improved manner compared to currently used 1,2-dicarbonyl moieties; and 2) a modular action of the probe where citrulline side chains are labeled first using reactive heads described above, and attachment of a read-out subunit or tag, be it a fluorophore, a nanoparticle, or an antigen is performed separately. The modular nature of the chemical probe increases the sensitivity of the probes due to their smaller size. Additionally, the chemical probes of the present disclosure allow the same sample to be analyzed using a variety of read-out methods.

Selenacrown Macrocycle in Aqueous Medium: Synthesis, Redox-Responsive Self-Assembly, and Enhanced Disulfide Formation Reaction

Organic selenides are famous for their coordination and catalytic functions in the organic phase, albeit challenging for aqueous medium. Herein, the combination of a hydrophilic body of crown ether and substitution of one oxygen atom with a selenium one provides a new type of design route for organic selenide entities with charming functions in aqueous solution. The selenacrown ether C9Se presented here intrinsically shows an amphiphile-like property. Its nanosphere structure in water readily expands the catalysis of organic selenide to aqueous substrates in thiol/disulfide conversion.