Enzyme-instructed morphological transition of the supramolecular assemblies of branched peptides

• Dongsik Yang,
• Hongjian He and
• Bing Xu

Beilstein J. Org. Chem. 2020, 16, 2709–2718, doi:10.3762/bjoc.16.221

• role in endocytic pathways. Figure 1A shows the molecular design of the branched peptides, which also act as hydrogelator precursors [44][45]. The branch consists of (i) a hydrophilic ʟ-peptide segment for enzymatic recognition and cleavage, (ii) a self-assembling ᴅ-peptide sequence composed of a 2

The conjugation of nonsteroidal anti-inflammatory drugs (NSAID) to small peptides for generating multifunctional supramolecular nanofibers/hydrogels

• Jiayang Li,
• Yi Kuang,
• Junfeng Shi,
• Yuan Gao,
• Jie Zhou and
• Bing Xu

Beilstein J. Org. Chem. 2013, 9, 908–917, doi:10.3762/bjoc.9.104

• covalent linkage of Phe–Phe and NSAIDs results in conjugates that self-assemble in water to form molecular nanofibers as the matrices of hydrogels. When the NSAID is naproxen (1), the resultant hydrogelator 1a forms a hydrogel at a critical concentration (cgc) of 0.2 wt % at pH 7.0. Hydrogelator 1a, also

• acting as a general motif, enables enzymatic hydrogelation in which the precursor turns into a hydrogelator upon hydrolysis catalyzed by a phosphatase at physiological conditions. The conjugates of Phe–Phe with other NSAIDs, such as (R)-flurbiprofen (2), racemic flurbiprofen (3), and racemic ibuprofen (4

• of small molecule hydrogels formed by NSAID derivatives [48][54][55][56] we intend to explore supramolecular hydrogels of other NSAIDs. Specifically, we use naproxen (denoted as Npx in this report), an over-the-counter NSAID, to generate a new hydrogelator 1a that only consists of naproxen and

A peptidic hydrogel that may behave as a “Trojan Horse”

• Nicola Castellucci,
• Giorgio Sartor,
• Natalia Calonghi,
• Carola Parolin,
• Giuseppe Falini and
• Claudia Tomasini

Beilstein J. Org. Chem. 2013, 9, 417–424, doi:10.3762/bjoc.9.44

• 10.3762/bjoc.9.44 Abstract A physical hydrogel prepared with the low-molecular-weight hydrogelator (LMWHG) CH2(C3H6CO-L-Phe-D-Oxd-OH)2 and water/ethanol mixture was applied as a potential “Trojan Horse” carrier into cells. By SEM and XRD analysis we could demonstrate that a fibrous structure is present in

• confocal microscopy, fluorescent hydrogels were prepared, introducing the fluorescent dansyl moiety into the mixture. Keywords: amino acids; confocal microscopy; controlled release; hydrogel; low molecular weight hydrogelator; Introduction Drug delivery is an important topic in the finding of successful

Protonation and deprotonation induced organo/hydrogelation: Bile acid derived gelators containing a basic side chain

• Uday Maitra and
• Arkajyoti Chakrabarty

Beilstein J. Org. Chem. 2011, 7, 304–309, doi:10.3762/bjoc.7.40

• . Keywords: bile acid derived amines; organogelator and hydrogelator; protonation and deprotonation induced gelation; SEM and POM; thermal stability; Introduction Low molecular mass organo- and hydrogelators (LMOG) have attracted considerable attention in recent years due to their tunable physical

• conclusion, we have demonstrated an interesting protonation and deprotonation induced gelation of an organogelator and a hydrogelator, respectively. Using cresol red as an indicator, it was possible to illustrate the acid-stability and base-instability of the organogel and the acid-instability and base

• tapes pasted on aluminium stubs and allowed to dry at room temperature in a desiccator connected to vacuum pump. Brief synthetic procedure Organogelator 1 and hydrogelator 2 were synthesized starting from lithocholic acid and deoxycholic acid, respectively, as shown in Scheme 2. Formylated lithocholic

Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators

• Guijun Wang,
• Hao Yang,
• Sherwin Cheuk and
• Sherman Coleman

Beilstein J. Org. Chem. 2011, 7, 234–242, doi:10.3762/bjoc.7.31

• synthesis and characterization of these novel analogs are reported. Keywords: 1,5-anhydroglucitol; carbohydrate; hydrogelator; organogelator; self-assembly; Introduction In recent years, the field of low molecular weight gelators (LMWGs) has received a great deal of attention. LMWGs are an interesting

Exceptionally small supramolecular hydrogelators based on aromatic–aromatic interactions

• Junfeng Shi,
• Yuan Gao,
• Zhimou Yang and
• Bing Xu

Beilstein J. Org. Chem. 2011, 7, 167–172, doi:10.3762/bjoc.7.23

• /bjoc.7.23 Abstract We report herein the use of an aromatic–aromatic interaction to produce small molecule hydrogelators that self-assemble in water and form molecular nanofibers in the resulting hydrogels. Among these hydrogelators, a hydrogelator (6) made from a phenylalanine and a cinnamoyl group

• represents the lowest molecular weight (MW = 295.33 g/mol) peptide-based hydrogelator prepared to date. The supramolecular hydrogels were characterized by transmission electron micrograph (TEM) and fluorescence spectroscopy, and the results obtained by both techniques correlate well with their rheological

• properties. Notably, compound 6 can undergo cis/trans-isomerization upon UV irradiation. Keywords: aromatic–aromatic interaction; cinnamoyl; hydrogel; hydrogelator; supramolecular; Introduction Gels formed by three-dimensional, elastic networks to encapsulate a liquid [1], have many useful properties (e.g

Differences between β-Ala and Gly-Gly in the design of amino acids-based hydrogels

• Andreea Pasc,
• Firmin Obounou Akong,
• Sedat Cosgun and
• Christine Gérardin

Beilstein J. Org. Chem. 2010, 6, 973–977, doi:10.3762/bjoc.6.109

• including, NMR, FT-IR, scanning electron microscopy, SAXS/WAXS. Results and Discussion Molecular design A hydrogelator generally contains three functional domains: a hydrogen or electron donor and acceptor domain as the main organiser, a hydrophilic domain to adjust the solubility in water or in organic