464190-91-8

Usage

Uses

Used in Bioconjugation:
N3-PEG1-CH2CH2NH2 is used as a linker for bioconjugation, allowing the selective and stable attachment of biomolecules, such as proteins, peptides, and nucleic acids, to other molecules or surfaces. The amino group provides reactivity with carboxylic acids and activated NHS esters, while the azide group enables Click Chemistry reactions with alkyne, BCN, and DBCO to form a stable triazole linkage.
Used in Drug Delivery Systems:
In the pharmaceutical industry, N3-PEG1-CH2CH2NH2 is used as a component in drug delivery systems to improve the solubility, stability, and bioavailability of therapeutic agents. The PEGylation of drugs using this linker can enhance their pharmacokinetic properties, reduce immunogenicity, and extend circulation time in the body.
Used in Materials Science:
N3-PEG1-CH2CH2NH2 is employed as a building block in the development of novel materials with tailored properties, such as self-assembling structures, hydrogels, and stimuli-responsive materials. The ability to form stable covalent bonds with a wide range of molecules allows for the creation of complex and functional materials for various applications, including tissue engineering, diagnostics, and sensors.
Used in Chemical Synthesis:
In the field of chemical synthesis, N3-PEG1-CH2CH2NH2 serves as a versatile intermediate for the synthesis of more complex molecules and macromolecules. The dual functional groups enable the stepwise assembly of molecular structures through well-defined chemical reactions, facilitating the development of new compounds with specific properties and applications.

Upstream product

• 176220-30-7 1-(2-(tert-Butoxycarbonylamino)ethoxy)-2-azidoethane 
• 76-05-1 trifluoroacetic acid 
• 24345-74-2 1,5-diazido-3-oxapentane 
• 1441062-11-8 C₁₂H₁₂N₄O₃ 

Downstream Products

• 1267640-53-8 C₂₇H₃₃N₅O₄ 

Relevant academic research and scientific papers

AGENTS AND METHODS FOR TREATING TAUOPATHIES

Disclosed are agents that include a flavanol (e.g., epigallocatechm-3-gailate) or a flavanol analog, a linker coupled to the flavanol or the flavanol analog, and a earner (e.g., iron oxide nanoparticle) coupled to the linker. The disclosed agents can be u

Catalytic Synthesis of PEGylated EGCG Conjugates that Disaggregate Alzheimer's Tau

The naturally occurring flavonoid ( )-epigallocatechin gallate (EGCG) is a potent disaggregant of tau fibrils. Guided by the recent cryo-electron microscopy (cryoEM) structure of EGCG bound to fibrils of tau derived from an Alzheimer s brain donor, methods to site-specifically modify the EGCG D-ring with aminoPEGylated linkers are reported. The resultant molecules inhibit tau fibril seeding by Alzheimer s brain extracts. Formulations of aminoPEGylated EGCG conjugated to the (quasi)-brain-penetrant nanoparticle Ferumoxytol inhibit seeding by AD-tau with linker length affecting activity. The protecting groupfree catalytic cycloaddition of amino azides to mono-propargylated EGCG described here provides a blueprint for access to stable nanoparticulate forms of EGCG potentially useful as therapeutics to eliminate Alzheimer s-related tau tangles.

Visible light-activatable cyclodextrin-conjugates for the efficient delivery of nitric oxide with fluorescent reporter and their inclusion complexes with betaxolol

This contribution reports the design, synthesis, photochemical properties and drug inclusion capability of two novel β-cyclodextrin (βCD) conjugates, βCD-NBFNO1 and βCD-NBFNO2, covalently integrating an N-nitroso amino-nitro-benzofurazan in the primary and secondary hydroxyl rims of the βCD scaffold, respectively through flexible spacers of different length. Both βCD conjugates are water-soluble and release nitric oxide (NO) under the input of either blue or green light, with quantum yields ΦNO (blue) = 0.13, 0.31 and ΦNO (green) = 0.007, 0.013 respectively, the former representing the largest values ever reported for nonmetal-containing NO donors activatable by visible light. The good contrast between the fluorescence green emission of the chromogenic moiety after and before the NO release permits the easy and in real-time quantification of the amount of NO generated, without the addition of external fluorescent agents. Despite the presence of the appendages, these βCD derivatives are also able to complex betaxolol, a β-blocker drug widely used for the reduction of the intraocular pressure, with binding constants Kb = 500 ± 50 and 1100 ± 100 M-1, respectively, without affecting the photochemical performances. In view of the well-known vasodilator properties of NO, the present βCD derivatives represent intriguing candidates for biopharmaceutical research studies addressed to combined therapeutic ocular applications.

Design and Synthesis of Oleanolic Acid Trimers to Enhance Inhibition of Influenza Virus Entry

Influenza is a major threat to millions of people worldwide. Entry inhibitors are of particular interest for the development of novel therapeutic strategies for influenza. We have previously discovered oleanolic acid (OA) to be a mild influenza hemagglutinin (HA) inhibitor. In this work, inspired by the 3D structure of HA as a homotrimeric receptor, we designed and synthesized 15 OA trimers with different linkers and central region via the copper-catalyzed azide-alkyne cycloaddition reaction. All of the OA trimers were evaluated for their antiviral activities in vitro, and 12c, 12e, 13c, and 13d were observed to exhibit robust potency (IC50 in the submicromolar range) against influenza A/WSN/33 (H1N1) virus that was stronger than that observed with oseltamivir. In addition, these compounds also displayed strong biological activity against A/Hong Kong/4801/2014 and B/Sichuan/531/2018 (BV). The results of hemagglutination inhibition assays and surface plasmon resonance binding assays suggest that these OA trimers may interrupt the interaction between the HA protein of influenza virus and the host cell sialic acid receptor, thus blocking viral entry. These findings highlight the utility of multivalent OA conjugates to enhance the ligand-target interactions in anti-influenza virus drug design and are also helpful for studying antiviral drugs derived from natural products.

Small-molecular probe for glaucocalyxin A (GLA), and preparation method and application thereof

The invention relates to a small-molecular probe for GLA, and a preparation method and application thereof, belonging to the field of medicinal chemistry. The small-molecular probe structurally comprises three parts, namely GLA, a linker and a reporter (b

Glaucocalyxin A (GLA)-biotin small-molecular probe, and preparation method and application thereof

The invention relates to a GLA small-molecular probe, and a preparation method and application thereof, belonging to the field of medicinal chemistry. The GLA small-molecular probe structurally comprises three parts, namely GLA, a linker and a reporter (b

Tri-Orthogonal Scaffolds for the Solid-Phase Synthesis of Peptides

Multi-orthogonal scaffolds can be useful for the attachment of several different compounds to the same central skeleton. Such compounds can find applications in the development of protein mimics because of their potential to mimic several distant epitopes

Clickable prodrugs bearing potent and hydrolytically cleavable nicotinamide phosphoribosyltransferase inhibitors

Purpose: Our previous study indicated that carborane containing small-molecule 1-(hydroxymethyl)-7-(4′-(trans-3″-(3′″-pyridyl)acrylamido)butyl)-1,7-dicarbadodecaborane (hm-MC4-PPEA), was a potent inhibitor of nicotinamide phosphoribosyltransferase (Nampt)

Thermal response of a PVCL-HA conjugate

The synthesis and self-assembling of a thermoresponsive conjugate of hyaluronic acid (HA) and poly(N-vinylcaprolactam) (PVCL) is reported. Both polymers were end functionalized: HA via reductive amination, thereby introducing an azide endgroup to the chain end, and PVCL via thioetherification to introduce a propargyl group. The two were coupled with a copper assisted "click" reaction into a bioconjugate composed of HA blocks with the molar mass 3,600 g mol-1 (1618 saccharide units) and PVCL blocks of 3,500 g mol-1 (μ25 repeating units). The cloud point temperature measured by transmittance was 50-51 °C in water. The calorimetrically observed phase transition temperature of PVCL in the conjugate increased by 2 °C to 47.7 °C, whereas the enthalpy of the phase transition was unaffected by the conjugation. HA-PVCL conjugate self-assembles in water upon heating into monodisperse, colloidally stable, hollow spherical particles whose size may be tuned with the heating rate of the solution. Slow and fast heating resulted in vesicles with the hydrodynamic radii of 443 or 275 nm, respectively. The heating rate did not, however, affect the cloud point. Salt did not noticeably affect the size of the polymer particles, presumably because of interactions between the HA and PVCL blocks.

A Fluorescent and Switchable Rotaxane Dual Organocatalyst

Rotaxane organocatalysis presents a new direction toward controlled one-pot catalytic reactions. By combining molecular switches and catalysts, fluorescence and pH-responsive switching along with the exclusive selectivity of dual catalytic reactions are d