112883-29-1Relevant academic research and scientific papers
Cerium oxide nanoparticle-mediated self-assembly of hybrid supramolecular hydrogels
Patil, Avinash J.,Kumar, Ravinash Krishna,Barron, Nicholas J.,Mann, Stephen
, p. 7934 - 7936 (2012)
Hybrid supramolecular hydrogels are prepared by non-enzymatic dephosphorylation of N-fluorenylmethyloxycarbonyl tyrosine-(O)-phosphate (FMOC-Tyr-P) using catalytic cerium oxide nanoparticles. The organic-inorganic hydrogels exhibit enhanced viscoelastic p
Supramolecular Platform Stabilizing Growth Factors
Hendrikse, Simone I. S.,Spaans, Sergio,Meijer,Dankers, Patricia Y. W.
, p. 2610 - 2617 (2018)
High concentrations of supplemented growth factors can cause oversaturation and adverse effects in in vitro and in vivo studies, though these supraphysiological concentrations are often required due to the low stability of growth factors. Here we demonstrate the stabilization of TGF-β1 and BMP4 using supramolecular polymers. Inspired by heparan sulfate, sulfonated peptides were presented on a supramolecular polymer to allow for noncovalent binding to growth factors in solution. After mixing with excipient molecules, both TGF-β1 and BMP4 were shown to have a prolonged half-life compared to the growth factors free in solution. Moreover, high cellular response was measured by a luciferase assay, indicating that TGF-β1 remained highly active upon binding to the supramolecular assembly. The results demonstrate that significant lower concentrations of growth factors can be used when supramolecular polymers bearing growth factor binding moieties are implemented. This approach can also be exploited in hydrogel systems to control growth factor release.
Toward the Rational Design of Galactosylated Glycoclusters That Target Pseudomonas aeruginosa Lectin A (LecA): Influence of Linker Arms That Lead to Low-Nanomolar Multivalent Ligands
Wang, Shuai,Dupin, Lucie,No?l, Mathieu,Carroux, Cindy J.,Renaud, Louis,Géhin, Thomas,Meyer, Albert,Souteyrand, Eliane,Vasseur, Jean-Jacques,Vergoten, Gérard,Chevolot, Yann,Morvan, Fran?ois,Vidal, Sébastien
, p. 11785 - 11794 (2016)
Anti-infectious strategies against pathogen infections can be achieved through antiadhesive strategies by using multivalent ligands of bacterial virulence factors. LecA and LecB are lectins of Pseudomonas aeruginosa implicated in biofilm formation. A series of 27 LecA-targeting glycoclusters have been synthesized. Nine aromatic galactose aglycons were investigated with three different linker arms that connect the central mannopyranoside core. A low-nanomolar (Kd=19 nm, microarray) ligand with a tyrosine-based linker arm could be identified in a structure–activity relationship study. Molecular modeling of the glycoclusters bound to the lectin tetramer was also used to rationalize the binding properties observed.
Mechanistic insights into phosphatase triggered self-assembly including enhancement of biocatalytic conversion rate
Thornton, Kate,Abul-Haija, Yousef M.,Hodson, Nigel,Ulijn, Rein V.
, p. 9430 - 9439 (2013)
We report on the mechanistic investigation of alkaline phosphatase (AP) triggered self-assembly and hydrogelation of Fmoc-tyrosine (Fmoc-Y). We studied separately the biocatalytic conversion using HPLC, changes in supramolecular interactions and chirality
A Neutrophil-Inspired Supramolecular Nanogel for Magnetocaloric–Enzymatic Tandem Therapy
Chen, Mengwei,Cheng, Yu,Lesniak, Maciej S.,Mi, Yongli,Wang, Jingjing,Wang, Qigang,Wang, Xia,Wu, Chu,Wu, Jiaojiao,Wu, Qing,Zhang, Qi
, p. 3732 - 3738 (2020)
Neutrophils can responsively release reactive oxygen species (ROS) to actively combat infections by exogenous stimulus and cascade enzyme catalyzed bio-oxidation. A supramolecular nanogel is now used as an artificial neutrophil by enzymatic interfacial se
Facile solid-phase synthesis of sulfated tyrosine-containing peptides: Total synthesis of human big gastrin-II and cholecystokinin (CCK)-39
Kitagawa,Aida,Fujiwara,Yagami,Futaki,Kogire,Ida,Inoue
, p. 1 - 10 (2001)
Chemical synthesis of tyrosine O-sulfated peptides is still a laborious task for peptide chemists because of the intrinsic acid-lability of the sulfate moiety. An efficient cleavage/deprotection procedure without loss of the sulfate is the critical difficulty remaining to be solved for fluoren-9-ylmethoxycarbonyl (Fmoc)-based solid-phase synthesis of sulfated peptides. To overcome the difficulty, TFA-mediated solvolysis rates of a tyrosine O-sulfate [Tyr(SO3H)] residue and two protecting groups, tBu for the hydroxyl group of Ser and 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl (Pbf) for the guanidino group of Arg, were examined in detail. The desulfation obeyed first-order kinetics with a large entropy (59.6 J·K-1·mol-1) and enthalpy (110.5 kJ·mol-1) of activation. These values substantiated that the desulfation rate of the rigidly solvated Tyr(SO3H) residue was strongly temperature-dependent. By contrast, the SN1-type deprotections were less temperature-dependent and proceeded smoothly in TFA of a high ionizing power. Based on the large rate difference between the desulfation and the SN1-type deprotections in cold TFA, an efficient deprotection protocol for the sulfated peptides was developed. Our synthetic strategy for Tyr(SO3H)containing peptides with this effective deprotection protocol is as follows: (i) a sulfated peptide chain is directly constructed on 2-chlorotrityl resin with Fmoc-based solid-phase chemistry using Fmoc-Tyr(SO3Na)-OH as a building block; (ii) the protected peptide-resin is treated with 90% aqueous TFA at 0 °C for an appropriate period of time for the cleavage and deprotection. Human cholecystokinin (CCK)-12, mini gastrin-II (14 residues), and little gastrin-II (17 residues) were synthesized with this method in 26-38% yields without any difficulties. This method was further applied to the stepwise synthesis of human big gastrin-II (34 residues), CCK-33 and -39. Despite the prolonged acid treatment (15-18 h at 0 °C), the ratios of the desulfated peptides were less than 15%, and the pure sulfated peptides were obtained in around 10% yields.
Synthesis and anticancer activities of proline-containing cyclic peptides and their linear analogs and congeners
Ghosh, Keshab Ch,Duttagupta, Indranil,Bose, Chandra,Banerjee, Priyanjalee,Gayen, Anuran Kumar,Sinha, Surajit
, p. 221 - 236 (2019)
A solution phase method was adopted for the synthesis of proline-containing cyclic pentapeptide 2 and total synthesis of naturally occurring cyclic heptapeptide Reniochalistatin B 3. For the synthesis of 3, both divergent and convergent strategies were used to improve the overall yield from 12 to 25%. Different N and C terminal modified linear analogs and congeners of 2 and 3 were synthesized. Both cyclic peptides 2 and 3 and their linear analogs/congeners were evaluated for anti-cancer activity against HeLa cell line, among which pentapeptide 2 h and hexapeptide 3n with N-terminal protected hexafluoroisopropyl carbamates (HFIPC) interestingly showed higher cytotoxicity with an IC50 of 2.73 and 4.3 μM, respectively compared to their Boc-protected analogs 2a (IC50 20 μM) and 3c (IC50 38.51 μM) and cyclic peptides 2 (>100 μM) and 3 (47 μM). These results were further validated by biological experiments such as colony formation and wound healing assays.
SUPRAMOLECULAR GEL SUPPORTED ON OPEN-CELL POLYMER FOAM
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Page/Page column 16-17; 21, (2021/03/19)
The present invention relates to a polymer foam, said polymer foam comprising pores forming an open-cell polymer foam, said polymer foam comprising a supramolecular gel inside pores, and said polymer foam comprising at least one enzyme. The present invention relates to a supramolecular gel; its preparation and its applications, notably in chemical synthesis and kinetic resolution, in particular of organic compounds. The present invention also relates to flow chemistry.
Enzyme Instructed Self-assembly of Naphthalimide-dipeptide: Spontaneous Transformation from Nanosphere to Nanotubular Structures that Induces Hydrogelation
Chakravarthy, Rajan Deepan,Lin, Hsin-Chieh,Mohammed, Mohiuddin
, (2020/08/03)
Understanding the structure-morphology relationships of self-assembled nanostructures is crucial for developing materials with the desired chemical and biological functions. Here, phosphate-based naphthalimide (NI) derivatives have been developed for the
Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety
Zhu, Lunan,Zhu, Junchen,Sun, Xiaotong,Wu, Yaling,Wang, Huiying,Cheng, Lingping,Shen, Jiawei,Ke, Yanxiong
, p. 1080 - 1090 (2020/05/25)
Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples.
