- Mechanochemical Preparation of Protein : hydantoin Hybrids and Their Release Properties
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Mechanochemistry is a versatile methodology that can be employed both for covalent bond formation in organic synthesis as well as a mediator to allow preparation novel colloidal dispersions for drug delivery. Herein, ball-milling was employed for the solid-state preparation of fluorescent hydrophobic hydantoins, followed by the unprecedented mechanochemically-mediated complexation of hydrophobic hydantoins within hydrophilic protein β-lactoglobulin (BLG) and BLG nanofibrils (BLGNFs). These hydantoin:protein materials were in turn incorporated into hydrogels. The effect of incorporation of hydantoins into proteins, as well as the effect of protein structure, on the release properties were then investigated. The conversion of BLG to BLGNFs led to a more sustained release demonstrating that heat treatment of BLG into BLGNFs could be employed to modify release properties. To the best of our knowledge, this is the first example where protein : hydantoin complexes were prepared by mechanochemical methodology and mechanochemistry was combined with self-assembly in order to prepare protein nanomaterials for drug-delivery applications. In addition, the use of the developed protein materials is not limited to delivery of drugs but can for example be employed as components of smart food (delivery of nutrients) or release systems of pesticides.
- Colacino, Evelina,Porcheddu, Andrea,Solin, Niclas,Wang, Lei,Yuan, Yusheng
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- Direct (Hetero)arylation of Heteroarenes Catalyzed by Unsymmetrical Pd-PEPPSI-NHC Complexes under Mild Conditions
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With the aim of developing a facile and efficient method to access structurally intriguing and valuable functionalized (hetero)aryls, two unsymmetrical Pd-PEPPSI-type NHC complexes (PEPPSI, pyridine-enhanced precatalyst preparation, stabilization, and initiation; NHC, N-heterocyclic carbene) were designed and synthesized to catalyze the direct arylation of heteroarenes with (hetero)aryl bromides. The results demonstrated that the utilization of this "unsymmetrical"strategy led to much higher efficiency in comparison to the commonly used C2-symmetric Pd-PEPPSI-type NHC complexes. Furthermore, a broad range of heteroaromatics and (hetero)aryl bromide partners with a wide variety of functional groups were all amenable to the developed protocol even at as low as 0.05 mol % catalyst loading and under aerobic conditions. More importantly, along with our study, we also found that the present protocol could provide expedient access to the gram-scale synthesis of the muscle relaxant drug dantrolene and conjugated mesopolymers.
- Song, A-Xiang,Zeng, Xiao-Xiao,Ma, Bei-Bei,Xu, Chang,Liu, Feng-Shou
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p. 3524 - 3534
(2020/10/09)
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- Dantrolene prodrug and method for using same
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The disclosure is directed to a dantrolene prodrug, a composition thereof, and a method of using the dantrolene prodrug in the treatment of disease.
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Paragraph 0308-0310; 0313-0315
(2020/07/15)
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- Continuous Visible-Light Photoflow Approach for a Manganese-Catalyzed (Het)Arene C?H Arylation
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Manganese photocatalysts enabled versatile room-temperature C?H arylation reactions by means of continuous visible-light photoflow, thus allowing for efficient C?H arylations in 30 minutes with ample scope. The robustness of the manganese-catalyzed photoflow strategy was shown by visible light-induced gram-scale synthesis, clearly outperforming the batch performance.
- Liang, Yu-Feng,Steinbock, Ralf,Yang, Long,Ackermann, Lutz
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supporting information
p. 10625 - 10629
(2018/08/01)
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- Blue light mediated C-H arylation of heteroarenes using TiO2 as an immobilized photocatalyst in a continuous-flow microreactor
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Titanium dioxide was applied as an immobilized photocatalyst in a microstructured falling film reactor for the continuous-flow C-H arylation of heteroarenes with aryldiazonium salts as the starting material. Detailed investigations of the catalyst and a successful long-term run proved its excellent usability for this process. Very good yields up to 99% were achieved with broad substrate scope and were compared with batch synthesis. The transfer to the continuous-flow mode revealed an impressive boost in reactor performance solely resulting from the improved irradiation and contact of the catalyst, substrate and light.
- Fabry, David C.,Ho, Yee Ann,Zapf, Ralf,Tremel, Wolfgang,Panth?fer, Martin,Rueping, Magnus,Rehm, Thomas H.
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supporting information
p. 1911 - 1918
(2017/06/09)
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- Direct C–H Arylation of Heteroarenes with Aryl Chlorides by Using an Abnormal N-Heterocyclic-Carbene–Palladium Catalyst
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Herein, we report a versatile catalytic system for the direct C–H arylation of heteroarenes with activated aryl chloride substrates. The catalyst works successfully for a variety of heteroarenes and aryl chloride coupling partners under very low catalyst-loading conditions. We have successfully performed the direct C–H arylations of 1-methylpyrrole, 1-methylindole, furan, thiophene, furfural, and N-benzyl-1,2,3-triazole with aryl chloride partners in good yields without the use of any additives. Furthermore, we used this catalytic process to develop a one-pot synthetic protocol for the muscle relaxant dantrolene on a gram scale. Additionally, the present catalytic system can be used to perform consecutive arylations in one pot.
- Ahmed, Jasimuddin,Sau, Samaresh Chandra,Sreejyothi,Hota, Pradip Kumar,Vardhanapu, Pavan K.,Vijaykumar, Gonela,Mandal, Swadhin K.
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p. 1004 - 1011
(2017/02/15)
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- Ascorbic acid as an initiator for the direct C-H arylation of (hetero)arenes with anilines nitrosated in situ
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Ascorbic acid (vitaminC) has been used as a radical initiator in a metal-free direct C-H arylation of (hetero)arenes. Starting from an aniline, the corresponding arenediazonium ion is generated in situ and immediately reduced by vitaminC to an aryl radical that undergoes a homolytic aromatic substitution with a (hetero)arene. Notably, neither heating nor irradiation is required. This procedure is mild, operationally simple, and constitutes a greener approach to arylation. Copyright
- Crisostomo, Fernando Pinacho,Martin, Tomas,Carrillo, Romen
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supporting information
p. 2181 - 2185
(2014/03/21)
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