2620-09-9

Usage

Chemical Properties

White Crystalline Solid

Upstream product

• 107-15-3 ethylenediamine 
• 79-04-9 chloroacetyl chloride 
• 4015-58-1 monochloroacetic acid anhydride 
• 96-34-4 methyl chloroacetate 

Downstream Products

• 134268-76-1 2-(2'-Hydroxy-biphenyl-2-yloxy)-N-{2-[2-(2'-hydroxy-biphenyl-2-yloxy)-acetylamino]-ethyl}-acetamide 
• 75948-92-4 N,N'-bis((S-benzylthio)acetamido)ethanediamine-1,2 
• 141944-98-1 N,N'-(ethane-1,2-diyl)bis(2-(2-formylphenoxy)acetamide) 
• 97848-26-5 N,N'-di(o-acetamidophenoxy)acetylethylenediamine 
• 132524-65-3 4,13-Dibenzyl-1,4,7,10,13,16-hexaaza-cyclooctadecane-2,6,11,15-tetraone 
• 97848-27-6 N,N'-diacetylethylenediamine 
• 97848-25-4 N,N'-di(o-nitrophenoxy)acetylethylenediamine 
• 97866-94-9 N,N'-di(m-acetamidophenoxy)acetylethylenediamine 
• 110663-50-8 4,7-ditoluenesulfonyl-1,4,7,10-tetraazacyclotridecane-2,9-dione 
• 121812-78-0 1,10-ditoluenesulfonyl-1,4,7,10-tetraazacyclotridecane-3,8-dione 
• 658053-81-7 1,2-bis(4-amino-5-phenyl-1,2,4-triazol-3-ylsulfanylacetamido)ethane 
• 658053-83-9 1,2-bis{4-amino-5-(p-methoxyphenyl)-1,2,4-triazol-3-ylsulfanylacetamido}ethane 

Relevant academic research and scientific papers

Preclinical evaluation of DO3P-AME-DO3P: A polyazamacrocyclic methylene phosphonate for diagnosis and therapy of skeletal metastases

A phosphonate derivative 10′-bis(acetamido)-ethane-bis[1,4,7- tri(methylene phosphonic acid)-1,4,7,10-tetraazacyclododecane] (DO3P-AME-DO3P), was synthesized with 90% yield in high purity. It was labeled with 99mTc in 97.5% efficiency and specific activity of 112-250 MBq/μmol. The binding affinity of 99mTc-DO3P-AME-DO3P towards bone minerals was tested in vitro by using hydroxy apatite as a bone model with absorption of 93% during the first hour of the experiment. Receptor binding assay on human bone cell line SAOS-2 demonstrated Kd value of 1.07 nM. Cell binding studies of DO3P-AME-DO3P on osteoblasts and osteoclasts cells performed in vitro displayed preferential affinity of the compound towards osteoclast (167.95 ± 3.56% dose/mg protein). The serum stability of 99mTc complex was found to be 96.8% after 24 h. Blood kinetics of 99mTc-DO3P-AME-DO3P performed on normal rabbits showed fast clearance with t1/2(F) = 15 min ± 0.014 min and t1/2(S) = 4 h 3 min ± 0.09 min. Biodistribution studies carried out in normal BALB/c mice showed bone-to-blood ratio of 20 and bone-to-muscle ratio of 33. The bone tissue demonstrated highest concentration of bound radioactivity with 10.73% ID/g at 1 h post injection. The protonation and stability constants were determined by pH-potentiometry titrations. The stability constants of DO3P-AME-DO3P with Lu(III), Sm(III), and Ho(III) were 19.7, 21.8, and 20.2 determined by "out of cell" method. The excellent bone seeking properties of DO3P-AME-DO3P make it a candidate of choice for SPECT imaging and preferential uptake of the compound in osteoclasts in comparison to osteoblasts; BMM and BMC can be used to understand the pathway of pathogenesis of osteoporosis and skeletal metastases.

Surface tension and aggregation properties of novel cationic gemini surfactants with diethylammonium headgroups and a diamido spacer

A series of novel cationic gemini surfactants with diethylammonium headgroups and a diamido spacer were synthesized, and their surface and bulk properties were investigated by surface tension, electrical conductivity, fluorescence, viscosity, dynamic light scattering (DLS), and transmission electron microscopy (TEM) measurements. An interesting phenomenon, that is, the obvious decline in surface tension upon increasing concentration above the critical micelle concentration (cmc), was found in these gemini surfactant solutions, and two explanations were proposed. This surface tension behavior could be explained by the rapid increase in the counterion activity in the bulk phase or the continued filling of the interface with increasing surfactant concentration above the cmc. More interestingly, not only vesicles but also the surfactant-concentration-induced vesicle to larger aggregate (spongelike aggregate) transition and the salt-induced vesicle and spongelike aggregate to micelle transition were found in the aqueous solutions of these gemini surfactants. The spongelike aggregate that is first reported in the cationic gemini surfactant-water binary system is probably caused by the adhesion and fusion of vesicles at high surfactant concentration.

A fluorescent sensor for thymine based on bis-BODIPY containing butanediamido bridges

The sensor for thymine detection has a great significance in the analysis of deoxyribonucleic acid in living organisms. In this work, a series of bis-BODIPY derivatives, namely, 3a-3c with diamido bridges were designed and prepared in yields of 74-77% through a simple procedure. The sensing abilities of compounds 3a-3c for adenine, guanine, cytosine, thymine, glucose, urea and haemoglobin were examined by UV-vis and fluorescence spectra. Sample 3b was demonstrated to be a good selective sensor for thymine among all the other tested species. The detection limit of sample 3b was as low as 1.53 × 10?6 M for thymine. The competitive experiments suggested that the selective sensor for thymine was influenced slightly by the other species. The proposed sensing mechanism was confirmed by FT-IR, 1H NMR and MS spectra. Sample 3b exhibited good bioimaging performance with bright green fluorescence in living cell imaging. The significant fluorescence quenching phenomenon after the addition of thymine implied the sensing ability of sample 3b for thymine in living cells.

A "turn-on" fluorescent sensor for cytosine in aqueous media based on diamino-bridged biphenyl acrylonitrile

The detection of cytosine is of significance for analyzing DNA bases, but no "turn-on"fluorescent sensor for cytosine in aqueous media has been reported so far. In this study, series of diamino-bridged biphenyl acrylonitriles 3a-3c were designed and synthesized with yields of 70-75%. The sensing experiments for 16 types of ions and biomolecules suggested that compound 3b with butanediamino bridges exhibited good selective sensing abilities towards cytosine based on "turn-on"fluorescence enhancement. The detection limit of compound 3b for cytosine attained 1.02 × 10-7 M. The selective sensing ability towards cytosine was little influenced by other species and remained stable between pH = 6-9. The sensing mechanism was proposed by the analysis of Job's plot, 1H NMR and MS binding spectra. The sensing ability for cytosine was successfully used for analysing urine samples with the recovery over 94%. Sample 3b also exhibited good bioimaging performance with bright blue-green fluorescence for sensing cytosine, implying the application prospect in complicated and living environment.

68Ga-Labeled bismacrocyclic methylene phosphonate as potential bone seeking PET radiopharmaceutical

Phosphonates-based agents are well-known bone-seeking radiopharmaceuticals with application in detection and therapy. With higher sensitivity and resolution offered by Positron Emission Tomography (PET), tracers based on this technique are gaining huge attention. 68Ga-based generator and radiotracers render independence from the on-site cyclotron. We report the development of 68Ga-labeled DOTA-based bismacrocyclic phosphonate derivative, for bone PET imaging. The synthesis and characterization of 68Ga- DO3P-AME-DO3P was carried out in > 95% purity. The radiotracer displayed high stability and low binding affinity (68Ga-DO3P-AME-DO3P to target and accumulate in bone, thus displaying its potential as a PET bone imaging agent.

In Situ Cyclization of Native Proteins: Structure-Based Design of a Bicyclic Enzyme

Increased tolerance of enzymes towards thermal and chemical stress is required for many applications and can be achieved by macrocyclization of the enzyme resulting in the stabilizing of its tertiary structure. Thus far, macrocyclization approaches utilize a very limited structural diversity, which complicates the design process. Herein, we report an approach that enables cyclization through the installation of modular crosslinks into native proteins composed entirely of proteinogenic amino acids. Our stabilization procedure involves the introduction of three surface-exposed cysteine residues, which are reacted with a triselectrophile, resulting in the in situ cyclization of the protein (INCYPRO). A bicyclic version of sortase A was designed that exhibits increased tolerance towards thermal as well as chemical denaturation, and proved to be efficient in protein labeling under denaturing conditions. In addition, we applied INCYPRO to the KIX domain, resulting in up to 24 °C increased thermal stability.

Quaternary ammonium salt type Gemini surface active agent and preparation, product and application thereof

The invention provides a quaternary ammonium salt type Gemini surface active agent and preparation, a product and application thereof. The surface active agent is shown as the formula (I), and please see the formula (I) in the description, wherein R1 is a saturated or unsaturated alkyl group with the main chain carbon atom number being 16-26, or a saturated or unsaturated alkyl group with the main chain carbon atom number being 16-26 and containing an amide group; R2 is methyl or ethyl or ethoxyl; R3 is selected from one of ethylidene; X is chlorine or bromine. According to the synthesized Gemini surface active agent, the highest temperature resisted by the surface active agent can reach 160 DEG C, and the temperature resistance is better than that of an existing conventional dimeric surface active agent.

Bispidine dioxotetraaza macrocycles: A new class of bispidines for 64Cu PET imaging

The three new dioxo-tetraazamacrocyclic ligands with a fused, very rigid bispidine (3,7-diazabicyclo[3.3.1]nonane) group connecting the two tertiary amine donors, and ethyl, propyl, or benzene groups connecting the two amide donors are highly preorganized and lead to very stable, uncharged Cu II complexes. Solution spectroscopy and solid state structures indicate that these are square pyramidal with a solvent molecule occupying the apical position. Cyclic voltammetry defines a reversible CuIII/II couple and a strongly negative irreversible CuII/I couple (ca. -2 V vs Fc/Fc+), indicating that the CuII complexes are very stable in solution. This is supported by superoxide dismutase (SOD) and human serum challenge experiments as well as the biodistribution, which all show that the benzene-based ligand has the highest in vitro and in vivo stability and that this was expected on the basis of the macrocycle ring size and shape and the highest degree of preorganization. This ligand is easy to functionalize for a possible coupling to biological vector molecules and/or fluorescence markers for PET (positron emission tomography) and multimodal imaging (i.e., PET and optical imaging).

Design, synthesis and biological evaluation of organophosphorous-homodimers as dual binding site acetylcholinesterase inhibitors

The cluster effect is an effective strategy to explore new lead compounds, and has been successfully applied in rational drug design and screening. A series of novel organophosphorous-homodimers were designed and synthesized based on the dual-site structure characteristics of acetylcholinesterase (AChE). The compounds were evaluated in vitro for their inhibitory activity to AChE extracted from Drosophila melanogaster and Musca domestic. Compound 4H showed an excellent inhibitor activity to both Drosophila melanogaster and Musca domestic with the corresponding IC50 values of 23 and 168 nM, respectively. Meanwhile, its activities against Drosophila melanogaster and Musca domestic AChE were more than 10,00,000 and 100,000-fold higher compared with the parent compound (MH), and was up to 245 and 107-fold higher than those of the positive control omethoate. The molecular docking study revealed that 4H possessed an optimal spacer length and can perfectly fit into the central pocket, active gorge, and peripheral site of DmAChE, and consequently exhibited highly improved inhibitor potency to DmAChE. The bioassay tests showed that 4 series compounds showed prominent insecticidal activities against both Lipaphser erysimi and Tetranychus cinnbarinus at a concentration of 200 mg/L. The insecticide activity of compound 4H was particularly significant that can cause 96% mortality to Tetranychus cinnbarinus after 24 h of treatment.

Bivalent organophosphorus compounds - Synthesis and acetylcholinesterase inhibitory activity

A series of novel symmetric S,S′-2,2′-(ethane-1,2- diylbis(azanediyl)) bis(2-oxoethane-2,1-diyl) O,O,O′,O′-tetraethyl diphosphorodithioate derivatives (12) was designed and synthesized based on the cluster effect and the multiple binding sites of acetylcholinesterase (AChE). The structures of all the newly synthesized title compounds were characterized by 1 H and 13 C NMR as well as elemental analyses. Their inhibitory activities against AChE were tested, and compound 12b exhibited the best activity (6.60-fold higher than ethion). The results suggested that the compound would bind to the catalytic center and the narrow gorge of the AChE simultaneously. Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional table.