5454-83-1Relevant academic research and scientific papers
The Cyclopentyl Group, As a Small but Bulky Terminal Group, Allows Rapid and Efficient Active Transport
Nishiyama, Junya,Makita, Yoshimasa,Kihara, Nobuhiro
, p. 138 - 141 (2015)
Secondary ammonium salts bearing a cyclopentyl terminal group rapidly formed pseudorotaxane with 1.5 equiv of DB24C8. Acylation of the pseudorotaxane with 50 equiv of benzoyl chloride in the presence of 50 equiv of triethylamine in toluene afforded rotaxane, the product of active transport, in 95% yield. The cyclopentyl group is small enough to allow rapid formation of pseudorotaxane, and bulky enough to facilitate the quantitative active transport by steric repulsion. (Chemical Equation Presented).
A convenient asymmetric synthesis of a β-amino ester with additional functionalization as a precursor for peptide nucleic acid (PNA) monomers
Garrido, Narciso M.,Diez, David,Dominguez, Sara H.,Rosa Sanchez,Garcia, Mercedes,Urones, Julio G.
, p. 435 - 443 (2006)
We report the asymmetric synthesis of di-3-pentyl (3S,αS,7E)-3-N- benzyl-N-α-methylbenzylamino-dec-7-enedioate (9), which contains the correct functionalization to produce δ-amino acid derivatives to be used as monomers for Peptide Nucleic Acid (PNA) formation With this aim, thymine-pentanoic acid 15 and some of its ester derivatives were obtained, their reactivity was studied and the noteworthy ethyl ester 12 was quantitatively produced by transesterification of methyl ester 11, thus paving the way for the synthesis of the thymine-containing amino ester IV, which has been designed as a building block for a Nucleic-Acid analog with a chiral, flexible peptide backbone
Synthesis and spectral properties of 6′-triazolyl-dihydroxanthene-hemicyanine fused near-infrared dyes
Gu, Lingyue,Renault, Kévin,Romieu, Anthony,Richard, Jean-Alexandre,Srinivasan, Rajavel
supporting information, p. 12208 - 12215 (2020/07/30)
We describe the synthesis of a range of 6′-triazolyl-dihydroxanthene-hemicyanine (DHX-hemicyanine) fused dyes through an effective copper-catalyzed azide-alkyne cycloaddition (CuAAC) "click"reaction, with the aim of providing molecular diversity and evaluating the spectral properties of these near-infrared (NIR)-active materials. This was implemented by reacting 15 different aliphatic and aromatic azides with a terminal alkynyl-based DHX-hemicyanine hybrid scaffold prepared in four steps and 35% overall yield from 4-bromosalicylaldehyde. The resulting triazole derivatives have been fully characterized and their optical properties determined both in organic solvents and under simulated physiological conditions (phosphate buffered saline containing 5% of bovine serum albumin protein). This systematic study is a first important step towards the development of NIR-I fluorogenic "click-on"dyes or related photoactive agents for light-based diagnostic and/or therapeutic applications.
Design, synthesis, and biological evaluation of dual targeting inhibitors of histone deacetylase 6/8 and bromodomain BRPF1
Erdmann, Frank,Günther, Stefan,Ghazy, Ehab,Hügle, Martin,Herp, Daniel,Jung, Manfred,Morales, Elizabeth R.,Robaa, Dina,Romier, Christophe,Schmidt, Matthias,Schmidtkunz, Karin,Sippl, Wolfgang,Zeyen, Patrik
supporting information, (2020/06/03)
Histone modifying proteins, specifically histone deacetylases (HDACs) and bromodomains, have emerged as novel promising targets for anticancer therapy. In the current work, based on available crystal structures and docking studies, we designed dual inhibitors of both HDAC6/8 and the bromodomain and PHD finger containing protein 1 (BRPF1). Biochemical and biophysical tests showed that compounds 23a,b and 37 are nanomolar inhibitors of both target proteins. Detailed structure-activity relationships were deduced for the synthesized inhibitors which were supported by extensive docking and molecular dynamics studies. Cellular testing in acute myeloid leukemia (AML) cells showed only a weak effect, most probably because of the poor permeability of the inhibitors. We also aimed to analyse the target engagement and the cellular activity of the novel inhibitors by determining the protein acetylation levels in cells by western blotting (tubulin vs histone acetylation), and by assessing their effects on various cancer cell lines.
Nanostructured Micelle Nanotubes Self-Assembled from Dinucleobase Monomers in Water
Aparicio, Fátima,Casado, Santiago,Chamorro, Paula B.,Chamorro, Raquel,González-Rodríguez, David
supporting information, p. 17091 - 17096 (2020/07/30)
Despite the central importance of aqueous amphiphile assemblies in science and industry, the size and shape of these nano-objects is often difficult to control with accuracy owing to the non-directional nature of the hydrophobic interactions that sustain them. Here, using a bioinspired strategy that consists of programming an amphiphile with shielded directional Watson–Crick hydrogen-bonding functions, its self-assembly in water was guided toward a novel family of chiral micelle nanotubes with partially filled lipophilic pores of about 2 nm in diameter. Moreover, these tailored nanotubes are successfully demonstrated to extract and host molecules that are complementary in size and chemical affinity.
Efficient flow fischer esterification of carboxylic acids with alcohols using sulfonic acid-functionalized silica as supported catalyst
Furuta, Akihiro,Fukuyama, Takahide,Ryu, Ilhyong
, p. 607 - 612 (2017/06/19)
Flow Fischer esterification of carboxylic acids using hydroxy-substituted sulfonic acid-functionalized silica (HOSAS) packed into a stainless steel column reactor was investigated. HO-SAS well catalyzed flow esterification of long chain carboxylic acids with methanol within 3min of residence time at 110°C, and the methyl esters were quantitatively obtained. The flow esterification protocol was applied to the synthesis of a variety of esters (19 examples) and scalable synthesis was also successful.
Synthesis of long-wavelength absorbing porphyrin m-benzoic acids as molecular tectons for surface studies
Meindl, Alina,Ryan, Aoife A.,Flanagan, Keith J.,Senge, Mathias O.
, p. 1518 - 1541 (2017/08/02)
Porphyrins are becoming increasingly important building blocks in material science. This is due in part to several favorable characteristics; such as strong absorption into the infrared region, tunable electronic properties and the possibility to modify and define the porphyrin core in multiple ways. Herein we report synthetic methodologies for porphyrin-based molecular tectons for surface studies. The study aims to generate porphyrins with directional anchoring groups of different length and we report a library of long-wavelength absorbing porphyrins with a special focus on organometallic coupling reactions for the introduction of benzoic acid moieties as anchor groups.
Dual stimuli-responsive self-assembled supramolecular nanoparticles
Stoffelen, Carmen,Voskuhl, Jens,Jonkheijm, Pascal,Huskens, Jurriaan
supporting information, p. 3400 - 3404 (2014/04/03)
Supramolecular nanoparticles (SNPs) encompass multiple copies of different building blocks brought together by specific noncovalent interactions. The inherently multivalent nature of these systems allows control of their size as well as their assembly and disassembly, thus promising potential as biomedical delivery vehicles. Here, dual responsive SNPs have been based on the ternary host-guest complexation between cucurbit[8]uril (CB[8]), a methyl viologen (MV) polymer, and mono- and multivalent azobenzene (Azo) functionalized molecules. UV switching of the Azo groups led to fast disruption of the ternary complexes, but to a relatively slow disintegration of the SNPs. Alternating UV and Vis photoisomerization of the Azo groups led to fully reversible SNP disassembly and reassembly. SNPs were only formed with the Azo moieties in the trans and the MV units in the oxidized states, respectively, thus constituting a supramolecular AND logic gate. A guiding light: UV/Vis irradiation and chemical reduction have been used for the reversible disassembly/reassembly and irreversible disintegration, respectively, of responsive supramolecular nanoparticles stabilized by ternary host-guest complexes (see picture). The disassembly proceeds through an initial aggregation phase that is attributed to different response times of the multivalent core and the monovalent shell upon photoswitching.
Synthesis of new calix[4]arene amide derivatives and investigation of their DNA cleavage activity
Oezkan, Seyda Cigdem,Yilmaz, Aydan,Oezmen, Ismail
, p. 25 - 31 (2014/01/17)
This study comprises the synthesis of new p-tert-butylcalix[4]arene with different amide functional groups and summarises an investigation of their DNA cleavage activities. The structural investigations of the synthesised compounds were examined by FTIR, 1H NMR, 13C NMR, elemental analysis and FAB-MS techniques. The interaction between these compounds and pBR322 plasmid DNA has been investigated via agarose gel electrophoresis and, according to the results, compounds 5, 7, 8 and 13 exhibit efficient DNA cleavage activity. In the electrophoresis images of 5, 7 and 8, Form IV which is small DNA fragment was observed in addition to supercoiled Form I, open circular Form II and linear Form III. 2013
Cancer phototherapy in living cells by multiphoton release of doxorubicin from gold nanospheres
Voliani, Valerio,Signore, Giovanni,Vittorio, Orazio,Faraci, Paolo,Luin, Stefano,Perez-Prieto, Julia,Beltram, Fabio
, p. 4225 - 4230 (2013/09/02)
Doxorubicin is a widely used but toxic cancer chemotherapeutic agent. In order to localize its therapeutic action and minimize side effects, it was covalently conjugated to peptide-encapsulated gold nanospheres by click-chemistry and then photo-released in a controlled fashion by a multiphoton process. Selective treatment of a chosen region in a 2D layer of U2Os cancer cells is shown by driving photorelease with 561 nm irradiation at μW power. These results show promising directions for the development of practical applications based on nanocarriers that can ensure drug delivery with high spatial and temporal control. The Royal Society of Chemistry 2013.
