5673-91-6Relevant academic research and scientific papers
Anatomy of a gel. Amino acid derivatives that rigidify water at submillimolar concentrations
Menger,Caran
, p. 11679 - 11691 (2000)
On the basis of suggestive X-ray data, 14 aroyl L-cystine derivatives were designed, synthesized, and examined for their ability to gelate water. Several members of this amino acid family are remarkably effective aqueous gelators (the best being one that can rigidify aqueous solutions at 0.25 mM, ca. 0.01%, in less than 30 s!). A few of the analogues separate from water as crystals, indicating a close relationship between gelation and crystallization. All effective gelators self-assemble into fibrous structures that entrain the solvent in the capillary spaces among them. Hydrogen-bonding sites on the compounds that might stabilize the fibers were identified from specific substitutions that replace a hydrogen donor with a methyl group, enhance the hydrogen-accepting ability of a carbonyl oxygen, or promote the hydrogen-donating ability of an amide proton. The structural variations were characterized via minimal gelation concentrations and times, X-ray crystallography, light and electron microscopy, rheology, and calorimetry. The multiple techniques, applied to the diverse compounds, allowed an extensive search into the basis of gelation. It was learned, for example, that the compound with the lowest minimum gelator concentration and time also has one of the weakest gels (i.e., it has a low elastic modulus). This is attributed to kinetic effects that perturb the length of the fibers. It was also argued that π/π stacking, the carboxyl carbonyl (but not the carboxyl proton), and solubility factors all contribute to the stability of a fiber. Polymorphism also plays a role. Rheological studies at different temperatures show that certain gels are stable to a 1-Hz, 3-Pa oscillating shear stress at temperatures as high as 90 °C. Other gels have a 'catastrophic' break at lower temperatures. Calorimetric data indicate a smooth transition from gel to sol as the temperature is increased. These and other issues are discussed in this 'anatomy' of a gel.
Dissipative self-assembly of a molecular gelator by using a chemical fuel
Boekhoven, Job,Brizard, Aurelie M.,Kowlgi, Krishna N. K.,Koper, Ger J. M.,Eelkema, Rienk,Van Esch, Jan H.
, p. 4825 - 4828 (2010)
(Figure Presented) Fueling the future: A fibrillar network (red fibers, see figure) is formed from an activated building block (red), which is obtained from a synthetic gelator (blue) in a dissipative self-assembly process that is fueled by an alkylating agent. When the available energy is depleted, the system reverts to its thermodynamic equilibrium, that is, an isotropic solution.
USE OF MEMBRANE INHIBITORS TO ENHANCE VACCINE DEVELOPMENT AGAINST ENVELOPED VIRUSES
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Paragraph 0015; 0084-0086; 0105, (2021/05/15)
The present application relates to method of vaccinating a subject against infection by an enveloped virus. The method includes providing a compound of the Formula (I) as described herein, and contacting the compound of Formula (I) with an isolated envelo
Dynamic covalent chemistry in aqueous solution by photoinduced radical disulfide metathesis
Klepel, Florian,Ravoo, Bart Jan
supporting information, p. 3840 - 3842 (2017/07/11)
Photoinduced radical disulfide metathesis (PRDM) is a dynamic covalent reaction that requires UV light to induce the homolytic cleavage of the disulfide bond, thus offering the opportunity to construct dynamic covalent systems that are dormant and can be photo-Activated on demand. In this work, we showcase how PRDM can be utilized in aqueous solution and demonstrate its potential by generating a UV responsive hydrogel from an asymmetrical disulfide precursor.
The Synthesis and Biological Evaluation of Anithiactin A/Thiasporine C and Analogues
Lamb, Richard A.,Badart, Michael P.,Swaney, Brooke E.,Gai, Sinan,Baird, Sarah K.,Hawkins, Bill C.
, p. 1829 - 1833 (2015/12/26)
The synthesis of anithiactin A has been achieved in four steps. Several closely related analogues were synthesised and their biological activity against colon and breast cancer cell lines evaluated. Anithiactin A was found not to be cytotoxic even at a hi
Controllable hydrogen sulfide donors and their activity against myocardial ischemia-reperfusion injury
Zhao, Yu,Bhushan, Shashi,Yang, Chuntao,Otsuka, Hiroyuki,Stein, Jason D.,Pacheco, Armando,Peng, Bo,Devarie-Baez, Nelmi O.,Aguilar, Hector C.,Lefer, David J.,Xian, Ming
, p. 1283 - 1290 (2013/07/26)
Hydrogen sulfide (H2S), known as an important cellular signaling molecule, plays critical roles in many physiological and/or pathological processes. Modulation of H2S levels could have tremendous therapeutic value. However, the study on H2S has been hindered due to the lack of controllable H2S releasing agents that could mimic the slow and moderate H2S release in vivo. In this work we report the design, synthesis, and biological evaluation of a new class of controllable H 2S donors. Twenty-five donors were prepared and tested. Their structures were based on a perthiol template, which was suggested to be involved in H2S biosynthesis. H2S release mechanism from these donors was studied and proved to be thiol-dependent. We also developed a series of cell-based assays to access their H2S-related activities. H9c2 cardiac myocytes were used in these experiments. We tested lead donors' cytotoxicity and confirmed their H2S production in cells. Finally we demonstrated that selected donors showed potent protective effects in an in vivo murine model of myocardial ischemia-reperfusion injury, through a H 2S-related mechanism.
Influence of chiral thiols on the diastereoselective synthesis of γ-lactams from cyclic anhydrides
Younai, Ashkaan,Fettinger, James C.,Shaw, Jared T.
scheme or table, p. 4320 - 4327 (2012/07/28)
The synthesis of γ-lactams from both four-component and imine-anhydride reactions is reported. The synthesis of 2-phenylcyclohexanethiol is described and this compound was evaluated along with an additional seven chiral thiols. A range of selectivity and yields was observed and comparisons to established reactions are made in order to account for the observed reactivity.
p-Hydroxyphenacyl bromide as photoremoveable thiol label: A potential phototrigger for thiol-containing biomolecules
Specht, Alexandre,Loudwig, Sandra,Peng, Ling,Goeldner, Maurice
, p. 8947 - 8950 (2007/10/03)
p-Hydroxyphenacyl bromide is described as a photoremovable thiol protecting group on three biomolecules containing a free thiol group. The protecting group is efficiently incorporated by chemical coupling to the biomolecule in an ethanol-buffer mixture. The photofragmentations (λ=312 nm) were analyzed by UV, HPLC and MS methods, yielding over 70% of the free biomolecules. The concomitant formation of p-hydroxyphenylacetic thioesters derived from the corresponding thiols, as a sulfur-containing side-product, should not hinder the use of this protecting group for the caging of thiol-containing biomolecules.
