85030-56-4

Usage

Uses

Used in Pharmaceutical Industry:
3,6,9,12-tetraoxatridecylamine is used as a PEGylation agent for improving the solubility, stability, and bioavailability of therapeutic proteins and peptides. PEGylation can enhance the pharmacokinetic properties and reduce the immunogenicity of these biomolecules, leading to better therapeutic efficacy and safety.
Used in Drug Delivery Systems:
3,6,9,12-tetraoxatridecylamine is used as a component in the design and synthesis of drug delivery systems, such as nanoparticles, liposomes, and hydrogels. The PEGylation of these systems can improve their stability, circulation time, and targeting capabilities, allowing for more effective and controlled drug release.
Used in Bioconjugation:
3,6,9,12-tetraoxatridecylamine is used as a crosslinking agent for the conjugation of biomolecules, such as antibodies, enzymes, and aptamers, to various surfaces or carriers. The reactive NH2 group allows for the formation of stable covalent bonds, enabling the development of novel biosensors, diagnostic tools, and therapeutic agents.
Used in Cosmetics and Personal Care Industry:
3,6,9,12-tetraoxatridecylamine is used as a PEGylated ingredient in cosmetics and personal care products, such as creams, lotions, and shampoos. The PEGylation can improve the texture, spreadability, and skin feel of these products, as well as provide enhanced hydration and moisturization benefits.

InChI:InChI=1/C9H21NO4/c1-11-4-5-13-8-9-14-7-6-12-3-2-10/h2-10H2,1H3

Upstream product

• 62921-76-0 2,5,8,11-tetraoxatridecan-13-ol tosylate 
• 23783-42-8 tetraethylene glycol monomethyl ether 
• 199445-54-0 2-(2,5,8,11-tetraoxatridecan-13-yl)isoindoline-1,3-dione 
• 155887-96-0 2,5,8,11,14,17-hexaoxanonadecan-19-yl 4-methylbenzenesulfonate 
• 1043884-49-6 1-azido-2-[2-(2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethane 
• 130955-37-2 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethyl) methanesulfonate 
• 23601-40-3 hexaethylene glycol monomethyl ether 
• 136918-14-4 phthalimide 
• 112-35-6 triethylene glucol monomethyl ether 
• 606130-90-9 1-{2-[2-(2-azidoethoxy)ethoxy]ethoxy}-2-methoxyethane 

Downstream Products

• 222036-72-8 N-[4-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethylsulfamoyl)-phenyl]-acetamide 
• 1020857-34-4 6-N-benzyloxycarbonyl-2-N-(2H,2H,4H,4H-3,6,9,12,-tetraoxaperfluorotridecanoyl)-L-lysine (2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}ethyl)amide 
• 1067915-47-2 N-(2-{2-[2-(2-methoxyethoxy)-ethoxy]-ethoxy}-ethyl)-N',N''-di((R)-3,7-dimethyloctyl)benzene-1,3,5-tricarboxamide 
• 1113050-39-7 N-((R)-3,7-dimethyloctyl)-N',N''-di(2-{2-[2-(2-methoxyethoxy)-ethoxy]-ethoxy}-ethyl)benzene-1,3,5-tricarboxamide 
• 1113050-40-0 N,N',N''-tri(2-{2-[2-(2-methoxyethoxy)-ethoxy]-ethoxy}-ethyl)benzene-1,3,5-tricarboxamide 
• 1187212-69-6 1-(4-(2-(5-5,8,11,14-tetraoxa-2-azapentadecylpyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-cyclopropylurea 
• 498-23-7 citraconic acid 
• 222036-74-0 4-(N-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethyl)sulfonamido)aniline 

Relevant academic research and scientific papers

Self-Assembly Can Direct Dynamic Covalent Bond Formation toward Diversity or Specificity

With the advent of reversible covalent chemistry the study of the interplay between covalent bond formation and noncovalent interactions has become increasingly relevant. Here we report that the interplay between reversible disulfide chemistry and self-assembly can give rise either to molecular diversity, i.e., the emergence of a unprecedentedly large range of macrocycles or to molecular specificity, i.e., the autocatalytic emergence of a single species. The two phenomena are the result of two different modes of self-assembly, demonstrating that control over self-assembly pathways can enable control over covalent bond formation.

Tuneable Transient Thermogels Mediated by a pH- and Redox-Regulated Supramolecular Polymerization

A multistimuli-responsive transient supramolecular polymerization of β-sheet-encoded dendritic peptide monomers in water is presented. The amphiphiles, which contain glutamic acid and methionine, undergo a glucose oxidase catalyzed, glucose-fueled transient hydrogelation in response to an interplay of pH and oxidation stimuli, promoted by the production of reactive oxygen species (ROS). Adjusting the enzyme and glucose concentration allows tuning of the assembly and the disassembly rates of the supramolecular polymers, which dictate the stiffness and transient stability of the hydrogels. The incorporation of triethylene glycol chains introduces thermoresponsive properties to the materials. We further show that repair enzymes are able to reverse the oxidative damage in the methionine-based thioether side chains. Since ROS play an important role in signal transduction cascades, our strategy offers great potential for applications of these dynamic biomaterials in redox microenvironments.

Synthesis and pH-dependent hydrolysis profiles of mono- and dialkyl substituted maleamic acids

Maleamic acid derivatives as weakly acid-sensitive linkers or caging groups have been used widely in smart delivery systems. Here we report on the controlled synthetic methods to mono- and dialkyl substituted maleamic acids and their pH-dependent hydrolysis behaviors. Firstly, we studied the reaction between n-butylamine and citraconic anhydride, and found that the ratio of the two n-butyl citraconamic acid isomers (α and β) could be finely tuned by controlling the reaction temperature and time. Secondly, we investigated the effects of solvent, basic catalyst, and temperature on the reaction of n-butylamine with 2,3-dimethylmaleic anhydride, and optimized the reaction conditions to efficiently synthesize the dimethylmaleamic acids. Finally, we compared the pH-dependent hydrolysis profiles of four OEG-NH2 derived water-soluble maleamic acid derivatives. The results reveal that the number, structure, and position of the substituents on the cis-double bond exhibit a significant effect on the pH-related hydrolysis kinetics and selectivity of the maleamic acid derivatives. Interestingly, for the mono-substituted citraconamic acids (α-/β-isomer), we found that their hydrolyses are accompanied by the isomerization between the two isomers.

ALKYNYL INDAZOLE DERIVATIVE AND USE THEREOF

The main object of the present invention is to provide a novel compound which has a VEGF receptor tyrosine kinase inhibitory activity and is useful as an active ingredient for the treatment of diseases accompanying angiogenesis or edema, for example, age-related macular degeneration or the like. The present invention includes, for example, an alkynyl indazole derivative represented by the following general formula (I), a pharmaceutical acceptable salt thereof, and a medicine containing thereof.

N-monosubstituted methoxy-oligo(ethylene glycol) carbamate ester prodrugs of resveratrol

Resveratrol is a natural polyphenol with many interesting biological activities. Its pharmacological exploitation in vivo is, however, hindered by its rapid elimination via phase II conjugative metabolism at the intestinal and, most importantly, hepatic levels. One approach to bypass this problem relies on prodrugs. We report here the synthesis, characterization, hydrolysis, and in vivo pharmacokinetic behavior of resveratrol prodrugs in which the OH groups are engaged in an N-monosubstituted carbamate ester linkage. As promoiety, methoxy-oligo(ethylene glycol) groups (m-OEG) (CH3-[OCH2CH2]n-) of defined chain length (n = 3, 4, 6) were used. These are expected to modulate the chemico-physical properties of the resulting derivatives, much like longer poly(ethylene glycol) (PEG) chains, while retaining a relatively low MW and, thus, a favorable drug loading capacity. Intragastric administration to rats resulted in the appearance in the bloodstream of the prodrug and of the products of its partial hydrolysis, confirming protection from first-pass metabolism during absorption.

Rapid preparation of multifunctional surfaces for orthogonal ligation by microcontact chemistry

Microcontact chemistry has been applied to patterned glass and silicon substrates by successive reaction of unprotected and monoprotected heterobifunctional linkers with alkene-terminated self-assembled monolayers (SAMs) to produce bi-, tri-, and tetrafunctional surfaces. Photochemical microcontact printing of an azide thiol linker followed by immobilization of an acid thiol linker on an undecenyl-terminated SAM results in a well-defined, micropatterned surface with terminal azide, acid, and alkene groups. Biologically relevant molecules (biotin, carbohydrates) have been selectively attached to the surface by means of orthogonal ligation chemistry, and the resulting microarrays display selective binding to fluorescently labeled proteins. An orthogonally addressable, tetrafunctional surface (azide, acid, alkene, and amine) can be prepared by an additional printing step of a tert-butyloxycarbonyl (Boc)-protected alkyne amine linker on the azide structures by using the copper(I)-catalyzed azide-alkyne Huisgen cycloaddition and subsequent removal of the protective group. Copyright

Simple and efficient: Ethylene glycol isonitrile gold(I) chlorides for the formation and stabilization of gold nanoparticles

Ethylene glycol isonitriles C≡N(CH2CH2O) nCH3 (5a, n = 1; 5b, n = 3; 5c, n = 4) with different chain lengths were prepared by using straightforward synthesis methodologies including the Gabriel synthesis and an Appel-type reaction protocol. Upon treatment with [AuCl(SMe)2], compounds 5a-c gave the corresponding isocyanide gold(I) chlorides [AuCl{C≡N(CH2CH2O) nCH3}] (7a, n = 1; 7b, n = 3; 7c, n = 4). Single-crystal X-ray diffraction studies reveal a polymeric (7a) or dimeric (7c) structure with aurophilic interactions. Gold(I) complexes 7a-c were applied in the formation and stabilization of gold nanoparticles (AuNPs). The isonitriles with their ethylene glycol functionalities, which provide multiple donating capabilities, are able to stabilize the encapsulated gold colloids. The reduction of 7a-c by the addition of Na[BH4] in tetrahydrofuran or methanol produces AuNPs without the further addition of any stabilizer, since metal-organic 7a-c combine the stabilizing component and gold source in one molecule. The dependency of different solvents, concentrations, and varying ethylene glycol chain lengths on the NP size and size distribution is reported. Characterization by TEM, UV/Vis spectroscopy, and XRPD revealed that AuNPs are formed with a size between 6.4(±1.4) to 9.5(±2.3) nm in methanol and 18.2(±2.3) to 27.2(±3.5) nm in tetrahydrofuran. Copyright

INHIBITORS OF PROTEIN TYROSINE KINASE ACTIVITY

This invention relates to compounds that inhibit protein tyrosine kinase activity. In particular the invention relates to compounds that inhibit the protein tyrosine kinase activity of growth factor receptors, resulting in the inhibition of receptor signaling, for example, the inhibition of VEGF receptor signaling. The invention also provides compounds, compositions and methods for treating cell proliferative diseases and conditions and opthalmological diseases, disorders and conditions.

Nanowells on silica particles in water containing long-distance porphyrin heterodimers

Smooth and nonswelling spherical silica particles with a diameter of 100 nm and an aminopropyl coating are soluble in water at pH 11, coagulate quickly at pH 3, and redissolve at pH 9. Electron microscopy as well as visible spectra of covalently attached porphyrins indicate the aggregation state of the particles. Long-chain α,ω-dicarboxylic acids with a terminal oligoethyleneglycol (=OEG)-amide group were attached in a second self-assembly step to the remaining amine groups around the porphyrins. Form-stable 2-nm wells were thus obtained and were characterized by fluorescence quenching experiments using the bottom porphyrin as a target. The one-dimensional diffusion of fitting quencher molecules along the 2-nm pathway took several minutes. Porphyrins with a diameter above 2 nm could not enter the form-stable gaps at all. Added tyrosine stuck irreversibly to the walls of the nanowells and prevented the entrance of quencher molecules, the OEG-headgroups fixated 2,6-diaminoanthraquinone. A ring of methylammonium groups was then fixed at the walls of the wells at a distance of 5 or 10 A with respect to the bottom porphyrin. 2,6-Disulfonatoanthraquinone was attached only loosely to this ring, but the exactly fitting manganese(III) meso-(tetraphenyl-4-sulfonato)porphyrinate (Mn(III) TPPS) was tightly bound. Transient fluorescence experiments showed a fast decay time of 0.2 ns for the bottom porphyrin, when the Mn(III) TPPS was fixated at a distance of 5 A. Two different dyes have thus been immobilized at a defined subnanometer distance in an aqueous medium.

Oxindole-based inhibitors of cyclin-dependent kinase 2 (CDK2): Design, synthesis, enzymatic activities, and X-ray crystallographic analysis

Two closely related classes of oxindole-based compounds, 1H-indole-2,3-dione 3-phenylhydrazones and 3-(anilinomethylene)-1,3-dihydro-2H-indol-2-ones, were shown to potently inhibit cyclin-dependent kinase 2 (CDK2). The initial lead compound was prepared as a homologue of the 3-benzylidene-1,3-dihydro-2H-indol-2-one class of kinase inhibitor. Crystallographic analysis of the lead compound bound to CDK2 provided the basis for analogue design. A semiautomated method of ligand docking was used to select compounds for synthesis, and a number of compounds with low nanomolar inhibitory activity versus CDK2 were identified. Enzyme binding determinants for several analogues were evaluated by X-ray crystallography. Compounds in this series inhibited CDK2 with a potency ～10-fold greater than that for CDK1. Members of this class of inhibitor cause an arrest of the cell cycle and have shown potential utility in the prevention of chemotherapy-induced alopecia.