21581-49-7Relevant academic research and scientific papers
Bioinspired underwater bonding and debonding on demand
Shafiq, Zahid,Cui, Jiaxi,Pastor-Perez, Lourdes,San Miguel, Veronica,Gropeanu, Radu A.,Serrano, Cristina,Del Campo, Aranzazu
, p. 4332 - 4335 (2012)
Mussel glue: Bioinspired underwater chemical bonding with the possibility of phototriggered debonding is reported. A four-arm star-poly(ethyleneglycol) end-functionalized by nitrodopamine was synthesized. The nitrodopamine offered the reactivity of catech
Catechol reactivity: Synthesis of dopamine derivatives substituted at the 6-position
Rote, Jennifer C.,Malkowski, Sarah N.,Cochrane, C. Skyler,Bailey, Gabrielle E.,Brown, Noah S.,Cafiero, Mauricio,Peterson, Larryn W.
, p. 435 - 441 (2017)
Dopamine is a ubiquitous neurotransmitter essential in the proper functioning of the human body. In addition to this critical role, the catecholamine core has shown utility as a scaffold for numerous drugs and in other applications, like metal detection and adhesive materials. Substituents at the 6-position of dopamine’s catechol core can modulate its stereoelectronic properties, the acidity of its phenolic hydroxyl groups, and the overall hydrophobicity of the molecule. Herein, we report the synthesis of a series of four novel dopamine analogues substituted at the 6-position of catechol core. The1H NMR chemical shift of the aromatic proton meta to the substituent correlated strongly with the Hammett σmconstant, confirming the electronic properties of substituents.
Erratum: Linking molecular behavior to macroscopic properties in ideal dynamic covalent networks (Journal of the American Chemical Society (2020) 142: 36 (15371-15385) DOI: 10.1021/jacs.0c06192)
Iten, Ramon,Marco-Dufort, Bruno,Tibbitt, Mark W.
, p. 18730 - 18731 (2020)
The "concentration of functional groups, c,"was defined incorrectly on page S18 of the Supporting Information. The (Table Presented) correct definition is as follows: c is the concentration of functional groups of one of the two network components, assuming that both components are present in equal amounts. Therefore, in a network formed from tetrafunctional macromers (f = 4) and where the total molar concentration of macromers is [PEG], c = f [PEG]/2 = 4[PEG]/2 = 2[PEG]. In the original Supporting Information, we took c as the total concentration of functional groups in the network, resulting in c = 4[PEG]. This formula was incorrect and resulted in erroneous values for select Keq or Gp data reported in Table 1 (page 15374) and Figure 8 (page 15381). The corrected Table 1 and Figure 8 are shown below, and the SI has been corrected accordingly. In addition, some of these data that are quoted in the article should be changed as follows (with the corrected values highlighted in bold). On page 15374: "Keq,c = 37.5 when c = 0.02 M,""Keq was determined to be 540 ± 65. [?] corresponding to Gp = 10.9 ± 2.0 kPa,"and "Keq was quantified as 277 ± 37 from NMR and 323 from DFT, corresponding to Gp = 8.0 ± 0.8 and 9.0 kPa, respectively."On page 15381: "The rheometric data exhibited a similar increase in Keq from 75 at pH 6 to 10750 at pH 9 (Figure 8c)"and "At pH 9, Keq = 1126 ± 108 and 565 (from spectroscopy and rheology, respectively) and then decreased sharply at pH 10 to Keq = 112 and 120 (Figure 8e,f)."On page 15373 (in the Figure 2 caption): "Keq = 540 ± 65."'Table Presented' These corrections do not affect any of the conclusions of the article but only the exact value of select parameters. We apologize for these errors and for any inconvenience caused to the readers. ? Associated Content: ? Supporting Information The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.0c10406. Synthesis, sample preparation, computational and experimental methods, and model descriptions (PDF). (Figure Presented).
Linking Molecular Behavior to Macroscopic Properties in Ideal Dynamic Covalent Networks
Marco-Dufort, Bruno,Iten, Ramon,Tibbitt, Mark W.
, p. 15371 - 15385 (2020)
Dynamic covalent networks (DCvNs) are increasingly used in advanced materials design with applications ranging from recyclable thermosets to self-healing hydrogels. However, the relationship between the underlying chemistry at the junctions of DCvNs and their macroscopic properties is still not fully understood. In this work, we constructed a robust framework to predict how complex network behavior in DCvNs emerges from the chemical landscape of the dynamic chemistry at the junction. Ideal dynamic covalent boronic ester-based hydrogels were used as model DCvNs. We developed physical models that describe how viscoelastic properties, as measured by shear rheometry, are linked to the molecular behavior of the dynamic junction, quantified via fluorescence and NMR spectroscopy and DFT calculations. Additionally, shear rheometry was combined with Transition State Theory to quantify the kinetics and thermodynamics of network rearrangements, enabling a mechanistic understanding including preferred reaction pathways for dynamic covalent chemistries. We applied this approach to corroborate the "loose-bolt"postulate for the reaction mechanism in Wulff-type boronic acids. These findings, grounded in molecular principles, advance our understanding and rational design of dynamic polymer networks, improving our ability to predict, design, and leverage their unique properties for future applications.
METAL NANOPARTICLE SURFACE LIGAND REPLACEMENT METHOD
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Page/Page column 18, (2018/06/06)
The invention relates to a method of producing inorganic nanoparticles with a polar surface, a) providing an inorganic nanoparticle with a coordinated organic ligand to the nanoparticles surface, b) providing a replacement salt comprising a replacement io
Radiofluorinated N-Octanoyl Dopamine ([18F]F-NOD) as a Tool to Study Tissue Distribution and Elimination of NOD in Vitro and in Vivo
Pretze, Marc,Pallavi, Prama,Roscher, Mareike,Klotz, Sarah,Caballero, Julio,Binzen, Uta,Greffrath, Wolfgang,Treede, Rolf-Detlef,Harmsen, Martin C.,Hafner, Mathias,Yard, Benito,W?ngler, Carmen,W?ngler, Bj?rn
, p. 9855 - 9865 (2016/11/19)
To mitigate pretransplantation injury in organs of potential donors, N-octanoyl dopamine (NOD) treatment might be considered as it does not affect hemodynamic parameters in braindead (BD) donors. To better assess optimal NOD concentrations for donor treat
Nitration of catecholamines with nitrogen oxides in mild conditions: A hypothesis for the reactivity of NO in physiological systems
De La Breteche, Marie-Laure
, p. 7231 - 7232 (2007/10/02)
Dopamine, norepinephrine and epinephrine react at room temperature, in acetate buffer (3pH6) with sodium nitrite or in non-deaerated phosphate buffer (pH 7.4) with NO. The corresponding 6-nitro derivatives are formed.
