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Chemical Structure| 1892-57-5 Chemical Structure| 1892-57-5
Chemical Structure| 1892-57-5

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Collins, Coby S ; Zhang, Mengxue ; Sturgill, CJ ; Ruff, Christian X ; Melton, Bryce ; Stefik, Morgan

Abstract: The controlled preparation of porous nanomaterials from block polymer templates is important for diverse applications from energy devices to optical coatings and sorbents. The architectural dimensions determine the overall performance for many of these applications, however the independent control of these dimensions has remained limited to a narrow range of solvent conditions for kinetically trapped ("persistent") micelle templates. Polymers with a photo-reactive chemistry are shown to enable crosslinked micelle templates that universally remain persistent under diverse solvent conditions. Specifically, poly(poly(ethylene glycol methacrylate))-b-poly(butyl methacrylate-co-coumarin methacrylate) (OBC) was prepared by RAFT polymerization and the resulting micelles were crosslinked with UV light (X-OBC). TEM images revealed that crosslinking in MeOH-only led to a mixture of micelles and unimers whereas crosslinking in MeOH–H2O led to pure micelles. Absorbance measurements indicated 50% dimerization (crosslinking) occurred after 180 min of UV exposure. The near universal solvent compatibility of X-OBC persistent micelles is demonstrated with DLS measurements in toluene, DCM, DMF, THF, EtOH, and MeOH, whereas OBC is shown to release unimers in DCM, DMF, THF, and toluene, or precipitate from EtOH due to a morphology change. Spectroscopic testing of micelle crosslinking occurred at each templating step. Micelle entrapment was also validated with SAXS and SEM measurements after nanomaterial templating where X-OBC enabled sample series with constant pore size whereas OBC did not. Furthermore, the results uniquely show X-OBC micelle persistence when processed from non-selective solvents. These results highlight how molecular engineering and tailored processing can enable the generalized synthesis of controlled porous nanomaterials.

Purchased from AmBeed: ;

Saccomano, Samuel C ; Knudson, Luke D ; Reynolds, Brandon ; Samo, Ty J ; Nuccio, Erin E ; Mendonsa, Adrian A , et al.

Abstract: Typical oxygen-sensitive dyes have lifetimes in the μs-ms regime for sensitive oxygen detection based on molecular quenching. Due to the long triplet-state lifetimes and poor quenching efficiency of these probes, it has been difficult to develop short lifetime probes. We have developed oxygen sensors using a short-lifetime dye (~30–60 ns) that forms an anthracene-aniline exciplex, which is quenched by molecular oxygen through an excited-state charge transfer mechanism. To achieve measurements in aqueous systems, we have tethered the dyes together via a C3 alkyl linker to facilitate greater exciplex formation at low dye concentration (20 μg mL-1) and encapsulated the resulting compound into polymeric nanoparticles to form an aqueous-dispersible short-lifetime oxygen nanosensor. The sensors emit at 420 nm (unfolded dye) and 500 nm (exciplex), and the ratiometric Stern-Volmer Constant is 1.52 ± 0.02 L mol-1, showing good sensitivity from 0% to 40% dissolved oxygen without the tradeoff of a long lifetime needed for direct molecular quenching. In this paper, we characterize this sensor for both lifetime-based measurements using time-correlated single-photon counting and ratiometric intensity-based measurements using the unfolded dye emission as an internal reference peak.

Keywords: Excited state complex ; oxygen sensing ; polymeric nanosensors ; short lifetime ; fluorescence

Purchased from AmBeed:

Aryal, Pramod ; Bietsch, Jonathan ; Grandhi, Gowri Sankar ; Chen, Richard ; Adhikari, Surya B ; Sarabamoun, Ephraiem S , et al.

Abstract: Diarylethenes (DAEs) are an important class ofphotoswitchable compounds that typically undergo reversiblephotochemical conversions between the open and closed cyclizedforms upon treatment with UV light or visible light. In this study,we introduced thioacid functional groups to several photochromicdithienylethene (DTE) derivatives and established a method thatcan be used to prepare these photoswitchable thioacids. Fourthioacid-functionalized diarylethene derivatives were synthesizedthrough the activation of carboxylic acids with N-hydroxysuccini-mide, followed by reactions with sodium hydrosulfide with yields over 90%. These derivatives exhibited reversible photoswitchingand photochromic properties upon treatment with ultraviolet (UV) and visible lights. The thioacid groups on these compounds canact as reaction sites for attaching other desirable functionalities. The photochromic properties of these new derivatives werecharacterized by using ultraviolet−visible (UV−vis) spectroscopy. The photocyclizations of one of the derivatives and its potassiumsalt were also characterized by using nuclear magnetic resonance (NMR) spectroscopy. The anions of the thioacid formed water-soluble photochromic systems, and their applications as colorimetric sensors in agarose hydrogels were demonstrated.

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Adrian O. Dukes ; Pathum M. Weerawarna ; Allison N. Devitt ; Richard B. Silverman ;

Abstract: Inhibition of human ornithine aminotransferase interferes with and metabolism in hepatocellular carcinoma, depriving tumors of essential nutrients. A proposed mechanism-based inhibitor containing a bicyclo[3.1.1]heptanol warhead is reported herein. The proposed inactivation mechanism involves a novel α-iminol rearrangement. The synthesis of the proposed inhibitor features an asymmetric intramolecular , utilizing a chiral sulfinamide. This study presents a novel approach toward the synthesis of functionalized bicyclo[3.1.1]heptanes and highlights an underutilized method to access enantiopure exocyclic amines.

Purchased from AmBeed: ; ;

Vlasenko, Yulia A ; To, Avery J ; Fortier, Tess ; Evans, Natasha M ; Lindsay, Cole J ; Palermo, Peter J , et al.

Abstract: Herein, the successful syntheses of D3- and 13C-N-methyl and D9-tert-butyl Hoechst dyes are presented. This includes the preparation of the labelled D3- and 13C-N-methyl piperazines and D9-tert-butylated hydroxytoluene precursors. The tert-butyl Hoechst dye is known to bind a specific RNA aptamer. Spectroscopic NMR studies of the labelled Hoechst dye-aptamer complexes allowed for the unambiguous assignment of chemical shifts, as well as the dynamics of the bound dye.

Keywords: 13C- ; D- ; Hoechst dye ; NMR spectroscopy

Purchased from AmBeed: ;

Giménez-Warren, Javier ; Peña, Álvaro ; Heredero, Juan ; Mata, Elena ; Blandín, Beatriz ; de Miguel, Diego , et al.

Abstract: Ionizable lipids are an essential component of lipid nanoparticles (LNPs) for an efficient mRNA delivery. However, optimizing their chemical structures for high protein expression, efficient endosomal escape, and selective organ targeting remains challenging due to complex structure-activity relationships and multistep synthesis. In this study, we introduce a rapid, high-throughput platform for screening ionizable lipids using a two-step, scalable synthesis involving a one-pot 3-component click-like reaction. This method, herein known as the STAAR approach, standing for Sequential Thiolactone Amine Acrylate Reaction, allowed for the combinatorial synthesis and in vivo screening of 91 novel lipids, followed by a structure-activity study. This led to the development of CP-LC-0729, an ionizable lipid that significantly surpasses the benchmark in protein expression while showing no in vivo toxicity. Additionally, the STAAR lipid platform was further validated by incorporating a one-step strategy to yield a permanently cationic lipid which was tested following a fifth-lipid formulation strategy. The in vivo results showed a highly selective lung delivery with a 32-fold increase in protein expression, outperforming current endogenous targeting strategies. All these findings underscore the potential of lipid CP-LC-0729 and the STAAR lipid platform in advancing the efficiency and specificity of mRNA delivery systems, while also advancing the development of new ionizable lipids.

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Product Details of EDC

CAS No. :1892-57-5
Formula : C8H17N3
M.W : 155.24
SMILES Code : CN(C)CCCN=C=NCC
MDL No. :MFCD00044916
InChI Key :LMDZBCPBFSXMTL-UHFFFAOYSA-N
Pubchem ID :15908

Safety of EDC

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H311-H314-H373-H410
Precautionary Statements:P260-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352+P312-P314-P333+P313-P391-P405-P501
Class:8(6.1)
UN#:2922
Packing Group:

Application In Synthesis of EDC

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1892-57-5 ]

[ 1892-57-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 2886-33-1 ]
  • [ 88950-64-5 ]
  • [ 1892-57-5 ]
  • [ 1415763-45-9 ]
YieldReaction ConditionsOperation in experiment
94% With hydrogenchloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In dichloromethane; Step 1. Synthesis of 1-[(tert-butoxycarbonyl)amino]cyclopropanecarbonyl-L-aspartic acid dibenzyl ester To a solution of 1-(tert-butoxycarbonyl)aminocyclopropanecarboxylic acid (257 mg, 1.28 mmol), L-aspartic acid dibenzyl ester tosylate (806 mg, 1.66 mmol), WSC hydrochloride (367 mg, 1.92 mmol), and 1-hydroxybenzotriazole (291 mg, 1.92 mmol) in dichloromethane (4.0 ml) was added N,N-diisopropylethylamine (1.30 mL, 7.66 mmol), and the mixture was stirred at room temperature for 7 hours. 1N Hydrochloric acid was added to the reaction mixture, the mixture was extracted 3 times with dichloromethane, and the obtained dichloromethane layer was washed with saturated brine. After drying over anhydrous magnesium sulfate, the desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (598 mg, 1.20 mmol, 94%). 1H NMR (400 MHz, CDCl3) delta 7.41-7.23 (10H, m), 5.14 (2H, s), 5.11-4.96 (2H, m), 4.93-4.82 (1H, m), 3.08 (1H, dd, J=17.1, 4.3 Hz), 2.92 (1H, dd, J=17.1, 3.8 Hz), 1.60-1.49 (2H, m), 1.44 (9H, s), 1.09-0.96 (2H, m). MS (ESI) m/z 497 (M+H)+
 

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