88192-19-2

Usage

Uses

Used in Chemical Synthesis Industry:
1-Propanamine, 3-azidois used as a reagent for the preparation of perylenedimides derivatives by reacting with 1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxyanhydride. This reaction is part of click chemistry, a set of bioorthogonal reactions that can occur within biological systems without interfering with native biochemical processes.
Used in Polymer and Material Science:
1-Propanamine, 3-azidois used as a functionalizing agent for bismethylolpropionic acid (bis-MPA) monomers, incorporating azide functional groups to generate high-generation dendrimers. Dendrimers are highly branched macromolecules with a well-defined structure, and their functionalization with azide groups can lead to new properties and applications.
Used in Photodynamic Therapy:
1-Propanamine, 3-azidois used as a functionalizing agent for clickable zinc tetraphenylporphyrin scaffolds through click chemistry. This allows for the development of new photodynamic therapy agents, which can be used to treat various diseases, including cancer, by generating reactive oxygen species upon light activation.

InChI:InChI=1/C3H8N4/c4-2-1-3-6-7-5/h1-4H2

Upstream product

• 861535-91-3 (3-azido-propyl)-carbamic acid ethyl ester 
• 100910-72-3 1,3-diazido-propane 
• 5003-71-4 3-bromopropylamine hydrochloride 
• 14753-26-5 3-chloropropan-1-amine 
• 18370-81-5 (3-bromopropyl)amine 
• 41236-20-8 3-bromopropan-1-amine hydrochloride 
• 156-87-6 propan-1-ol-3-amine 
• 129392-84-3 tert-butyl N-(3-azidopropyl)carbamate 
• 58503-62-1 1-azido-3-iodopropane 
• 603-35-0 triphenylphosphine 
• 67-56-1 methanol 
• 177489-73-5 1-azido-3-isocyanatopropane 
• 6276-54-6 3-chloropropylamine hydrochloride 

Downstream Products

• 109-76-2 Trimethylenediamine 
• 83708-45-6 N-phenyl-1,3-propanediamine dihydrochloride 
• 10517-44-9 1,3-diaminopropane dihydrochloride 
• 177489-83-7 benzyl (3-azidopropyl)carbamate 

Relevant academic research and scientific papers

Fit to be tied: Conformation-directed macrocyclization of peptoid foldamers

Covalent macrocyclic constraints can be readily installed on N-substituted glycine "peptoid" oligomer substrates. Cu(I)-catalyzed [3+2] cycloaddition reactions were conducted on solid support to ligate peptoid side chain azide and alkyne functionalities. Intramolecular macrocycle formation is facilitated by preorganizing the reactive groups across one turn of the helical secondary structure. These results confirm that conformational ordering can be exploited to assist the macrocyclization of folded oligomers.

Amphiphilic peptoid transporters-synthesis and evaluation

Cell-penetrating peptoids are an important class of peptidomimetics, which can replace highly biodegradable cell penetrating peptides for enhanced drug delivery. Typically, they contain positively charged amino side chains which are synthesized via their protected analogues. To avoid the use of amine protecting groups a Click-chemistry based modular synthesis of novel hydrophilic as well as amphiphilic cell penetrating peptoids was developed to generate novel structures for drug delivery in cells.

Multivalent peptidomimetic conjugates: A versatile platform for modulating androgen receptor activity

We introduce a family of multivalent peptidomimetic conjugates that modulate the activity of the androgen receptor (AR). Bioactive ethisterone ligands were conjugated to a set of sequence-specific peptoid oligomers. Certain multivalent peptoid conjugates enhance AR-mediated transcriptional activation. We identify a linear and a cyclic conjugate that exhibit potent anti-proliferative activity in LNCaP-abl cells, a model of therapy-resistant prostate cancer. The linear conjugate blocks AR action by competing for ligand binding. In contrast, the cyclic conjugate is active despite its inability to compete against endogenous ligand for binding to AR in vitro, suggesting a non-competitive mode of action. These results establish a versatile platform to design competitive and non-competitive AR modulators with potential therapeutic significance.

Synthesis and PI3 kinase inhibition activity of a Wortmannin-Leucine derivative

Wortmannin is a potent covalent inhibitor of PI3K that shows substantial in vivo toxicity and thus is unsuitable for systemic therapeutic applications. One possible approach to minimize systemic toxicity is to generate a latent wortmannin pro-drug that will be selectively activated in target tissues. To test this approach, a wortmannin derivative with a leucine linker attached to C20 has been synthesized and tested for inhibition of PI3K activity in prostate cancer cells. Analysis of PI3K pathway inhibition by Wormannin-Leu (Wn-L) and intact Wortmannin (Wn) showed that attachment of Leu at C-20 decreased potency of PI3K pathway inhibition 10-fold compared to intact wortmannin, yet exceeded the potency of a competitive PI3K inhibitor LY294002.

Synthesis and single enzyme activity of a clicked lipase-BSA hetero-dimer

Click chemistry is used to construct a novel lipase-BSA hetero-dimer, in which the latter protein acts as a foot enabling the anchoring of the enzyme onto the surface for single enzyme studies. The Royal Society of Chemistry 2006.

Versatile synthesis of asymmetrical dendron-like/dendron-like poly(ε-caprolactone)-b-poly(γ-benzyl- L -glutamate) block copolymers

Dendron-like/dendron-like poly(ε-caprolactone)-b-poly(γ-benzyl- L-glutamate) block copolymers with asymmetrical topology (PCL 208-b-PBLG n, both the subscript and the superscript denote the degree of polymerization and the branch number, respectively; n = 1, 2, and 4) were synthesized by combining ring-opening polymerization (ROP) and click chemistry. The dendron-like propargyl focal point PCL 208 precursor with eight branches was synthesized from the controlled ROP of ε-caprolactone, and then click conjugated with azido focal point poly(amido amine) dendrons to generate the PCL 208-dendrons with multiple primary amine groups. The PCL 208-dendrons were further used as macroinitiators for the ROP of γ-benzyl-L-glutamate N-carboxyanhydride to produce the targeted asymmetrical block copolymers. Their molecular structures and physicochemical properties were thoroughly characterized by means of FT-IR, 1H NMR, gel permeation chromatography, differential scanning calorimetry, and wide angle X-ray diffraction. Both the maximal melting temperature and the degree of crystallinity of PCL block within copolymers decreased with increasing the PBLG branches and/or the chain length, demonstrating that the crystallinity of PCL block was progressively suppressed by PBLG block. Meanwhile, the PBLG block within copolymers progressively transformed from β-sheet to α-helical conformation with increasing the PBLG chain length. Consequently, this provides a versatile strategy for the synthesis of biodegradable and biomimetic block copolymers with asymmetrical dendritic topology.

Hypoxia-Activated and Indomethacin-Mediated Theranostic Prodrug Releasing Drug On-Demand for Tumor Imaging and Therapy

A smart theranostic prodrug IMC-FDU-TZBC-NO2, releasing active drug on-demand based on hypoxia-activated and indomethacin-mediated, for solid tumor imaging and efficient therapy was designed. This prodrug was constructed by conjugating chemotherapy drug 5-fluoro-2-deoxyuridine (FDU), targeting moiety indomethacin (IMC), and the hypoxic trigger 4-nitrobenzyl group to a fluorescent dye precursor, which was mediated by IMC and activated by NTR under hypoxic conditions. The fluorescent dye IMC-TZBCM was generated and FDU was released at the same time in tumor cells. The rates and amounts of FDU release and IMC-TZBCM generation were regulated by hypoxia status, and increased with increasing degree of hypoxia. Nevertheless, it is "locked" in normal cells. It combined the advantages of tumor targeting, diagnosis, and chemotherapy functions, showed excellent targeting ability to cancer cells, excellent stability in physiological conditions, high cellular uptake efficiency, and on-demand drug release behavior. The in vitro and in vivo assays demonstrated that IMC-FDU-TZBC-NO2 exhibits enhanced anticancer potency and low side effects. The novel targeted theranostic prodrug activated by hypoxia shows a great potential in cancer therapy.

Synthesis of a naphthalene-diimide cyclophane for tuning supramolecular interactions by metal ions

A new supramolecular species of naphthalene-diimide cyclophane containing triazole units was synthesized, and its fluorescent responses to metal ions were investigated in dichloromethane (DCM). The fluorescence emission of NDI was quenched by intramolecular electron transfer, whereas the appearance of dimer emission of the naphthalene-diimide in the presence of Mg2+, Ba 2+, Hg2+, Ca2+, Zn2+ and Pb 2+ was observed. A new naphthalene-diimide cyclophane was synthesized, and the tuning of photoinduced electronic transfer in this cyclophane by metal ions was investigated. Monomer or dimer emission of naphthalenetetracarboxdiimide (NDI) was observed in the presence of different divalent metal ions. Copyright

Cyclodextrin-/photoisomerization-modulated assembly and disassembly of an azobenzene-grafted polyoxometalate cluster

Herein, a mono-lacunary Keggin-type polyoxometalate (POM), [SiW11O39]8?, grafted with an azobenzene group through Sn ion bridging was prepared, and the formed organic-inorganic hybrid cluster was characterized via elemental analysis, NMR, TGA, and IR techniques. A vesicular structure of the hybrid cluster assembly in aqueous media was observed in the TEM image, and it dissociated in the presence of α-/β-, γ-cyclodextrins (α-/β-, γ-CDs); this dissociation was driven by the host-guest interactions. The monodispersed inclusion complex further reassembled into smaller micelles under irradiation with 365 nm light, and this transformation was reversibly controlled by alternating the irradiation with 450 nm light. Moreover, in the case of the POM-Azo/β-CD system, reassembly from the monodispersed state to the vesicular state was achieved by the addition of a competitive guest molecule. Thus, the reversible host-guest interactions combining reversible photoisomerization of the azobenzene group provided multiple ways to modulate the assembly and disassembly of the POM hybrid as well as the changes between different assemblies. The present study inspires the potential use of these kind of hybrid POMs in enhanced catalytic reactions and recycling.

Dendron conjugation to graphene oxide using click chemistry for efficient gene delivery

Owing to its large surface area and rapid cellular uptake, graphene oxide (GO) is emerging as an attractive candidate material for delivery of drugs and genes. The inherent sp2 π-π interaction of GO helps to carry drugs and single stranded RNA (ssRNA) but there is no such interaction with double stranded DNA (dsDNA). In this work, a polyamidoamine (PAMAM) dendron was conjugated with nano GO (nGO) through "click" chemistry to improve the DNA complexation capability of GO as well as its transfection efficiency. The DNA complexation capability of GO was significantly enhanced after dendronization of GO yielding spherical nanosized (250-350 nm) particles of the dendronized GO (DGO)/pDNA complex with a positive zeta potential. The transfection efficiency of GO dramatically increased after conjugation of the PAMAM dendron. Transfection efficiency of 51% in HeLa cells with cell viability of 80% was observed. The transfection efficiency was significantly higher than that of polyethyleneimine 25 kDa (27% efficiency) and also surpassed that of lipofectamine 2000 (47% efficiency). The uptake of the DGO/pDNA complex by the caveolae mediated endocytosis pathway may significantly contribute to the high transfection efficiency. Thus, dendronized GO is shown to be an efficient gene carrier with minimal toxicity and is a promising candidate for use as a nonviral carrier for gene therapy.