146292-90-2Relevant articles and documents
Cationic poly(ester amide) dendrimers: Alluring materials for biomedical applications
Lancelot, Alexandre,González-Pastor, Rebeca,Clavería-Gimeno, Rafael,Romero, Pilar,Abian, Olga,Martín-Duque, Pilar,Serrano, José L.,Sierra, Teresa
, p. 3956 - 3968 (2018)
Novel cationic poly(ester amide) dendrimers have been synthesized by copper(i) azide-alkyne cycloaddition (CuAAC) of a tripropargylamine core and azide-terminated dendrons, in turn prepared by iterative amide coupling of the new monomer 2,2′-bis(glycyloxymethyl)propionic acid (bis-GMPA). The alternation of ester and amide groups provided a dendritic scaffold that was totally biocompatible and degradable in aqueous media at physiological and acidic pH. The tripodal dendrimers naturally formed rounded aggregates with a drug that exhibited low water solubility, camptothecin, thus improving its cell viability and anti-Hepatitis C virus (anti-HCV) activity. The presence of numerous peripheral cationic groups enabled these dendrimers to form dendriplexes with both pDNA and siRNA and they showed effective in vitro siRNA transfection in tumoral and non-tumoral cell lines.
Semisynthesis of Chondroitin Sulfate e Tetrasaccharide from Hyaluronic Acid
Yao, Wang,Zhu, Yong,Zhang, Xiao,Sha, Meng,Meng, Xiangbao,Li, Zhongjun
, p. 14069 - 14077 (2018)
Chondroitin sulfate (CS) is crucial glycosaminoglycan that regulates key functions of the nervous system. CS-E is one of the key CS subtypes that modulates the biological function of CS. Herein, N-protecting-group-free semisynthesis of CS-E tetrasaccharid
Synthesis of a novel polymeric material folate-poly(2-ethyl-2-oxazoline)- distearoyl phosphatidyl ethanolamine tri-block polymer for dual receptor and pH-sensitive targeting liposome
Xia, Gui Min,An, Zhi Jiao,Wang, Yang,Zhao, Chen,Li, Mei,Li, Zi Chen,Ma, Jie
, p. 390 - 398 (2013)
The in vivo distribution of antitumor drugs is usually lack of selectivity, and thus, leading to a low efficacy of chemotherapy on cancers and high toxicity to normal cells. Receptor-mediated targeting liposome with pH-sensitivity as a dual drug delivery
Efficient click chemistry towards fatty acids containing 1,2,3-triazole: Design and synthesis as potential antifungal drugs for Candida albicans
Fu, Nina,Wang, Suiliang,Zhang, Yuqian,Zhang, Caixia,Yang, Dongliang,Weng, Lixing,Zhao, Baomin,Wang, Lianhui
, p. 596 - 602 (2017)
Candida is an important opportunistic human fungal pathogen. The cis-2-dodecenoic acid (BDSF) showing in vitro activity of against C. albicans growth, germ-tube germination and biofilm formation has been a potential inhibitor for Candida and other fungi.
Macrocyclic polyamine [12]aneN3modified triphenylamine-pyrazine derivatives as efficient non-viral gene vectors with AIE and two-photon imaging properties
Gao, Yong-Guang,He, Lan,Liu, Ming-Xuan,Liu, Xu-Ying,Lu, Zhong-Lin,Ma, Le-Le,Sun, Wan
, p. 3869 - 3879 (2020)
With the aim to develop a novel multifunctional gene delivery system that may overcome the common barriers of gene transfection, near-infrared fluorescent triphenylamine-pyrazine was modified with a DNA condensing triazole-[12]aneN3moiety through different length alkyl ester linkages to afford three new non-viral gene vectors,TDM-A/B/C. All compounds showed prominent solvatochromic fluorescence (Stokes shift of up to 383 nm) and two-photon absorption properties (σ2P to 101 GM), and exhibited strong aggregation-induced emission (AIE). Gel electrophoresis demonstrated that plasmid DNA was completely condensed at a concentration of 10 μM (TDM-A), 14 μM (TDM-B) and 16 μM (TDM-C), and released in esterase and acidic environment. SEM demonstrated that the three compounds were able to self-assemble and co-aggregate with DNA to form regular nanoparticles. Experiments demonstrated thatTDM-A/B/Cwas able to integrate with DNA through electrostatic interactions and supramolecular stacking, and the short alkyl linkage favored the strong interaction with DNA. Among the three compounds,TDM-Bshowed the best luciferase and GFP transfection activities in the presence of DOPE, which were 156% and 310% higher than those of Lipo2000, respectively. The transfection process of DNA was clearly traced through one- and two-photon fluorescence microscopy imaging. Cellular uptake inhibition assay indicated that the DNA complex entered the cell mainlyviaclathrin-independent endocytosis. Furthermore, thein vivotransfection experiments ofTDM-B/DOPE were successfully implemented in zebra fish embryos, and the GFP gene expression level was superior to that of Lipo2000 (200%). Finally, this study clearly unraveled that the length of the alkyl linkage affected the DNA condensation and transfection activity, which can serve as a base for the future rational design of non-viral gene vectors.
Intracellular location matters: Rationalization of the anti-inflammatory activity of a manganese(ii) superoxide dismutase mimic complex
Bernard, Anne-Sophie,Delsuc, Nicolas,Henry, Lucas,Iriart, Sébastien,Ivanovi?-Burmazovi?, Ivana,Lai, Barry,Lung-Soong, Caroline,Marco, Sergio,Mathieu, Emilie,Medjoubi, Kadda,Nagarajan, Sounderya,Policar, Clotilde,Poyer, Florent,Quévrain, Elodie,Scheitler, Andreas,Seksik, Philippe,Somogyi, Andrea,Zoumpoulaki, Martha
, p. 7885 - 7888 (2020)
A conjugate of a Mn-based superoxide dismutase mimic with a Re-based multimodal probe 1 was studied in a cellular model of oxidative stress. Its speciation was investigated using Re and Mn X-fluorescence. Interestingly, 1 shows a distribution different fr
Modular Toolkit of Multifunctional Block Copoly(2-oxazoline)s for the Synthesis of Nanoparticles
Keckeis, Philipp,Zeller, Enriko,Jung, Carina,Besirske, Patricia,Kirner, Felizitas,Ruiz-Agudo, Cristina,Schlaad, Helmut,C?lfen, Helmut
, p. 8283 - 8287 (2021)
Post-polymerization modification provides an elegant way to introduce chemical functionalities onto macromolecules to produce tailor-made materials with superior properties. This concept was adapted to well-defined block copolymers of the poly(2-oxazoline) family and demonstrated the large potential of these macromolecules as universal toolkit for numerous applications. Triblock copolymers with separated water-soluble, alkyne- and alkene-containing segments were synthesized and orthogonally modified with various low-molecular weight functional molecules by copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) and thiol-ene (TE) click reactions, respectively. Representative toolkit polymers were used for the synthesis of gold, iron oxide and silica nanoparticles.
Activity-based protein profiling in vivo using a copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition
Speers, Anna E.,Adam, Gregory C.,Cravatt, Benjamin F.
, p. 4686 - 4687 (2003)
Toward the goal of assigning function to the tens of thousands of protein products encoded by eukaryotic and prokaryotic genomes, the field of proteomics requires new technologies that can functionally characterize proteins within the dynamic environment
Structurally diverse dendritic libraries: A highly efficient functionalization approach using click chemistry
Malkoch, Michael,Schleicher, Kristin,Drockenmuller, Eric,Hawker, Craig J.,Russell, Thomas P.,Wu, Peng,Fokin, Valery V.
, p. 3663 - 3678 (2005)
The high fidelity and efficiency of Click chemistry are exploited in the synthesis of a library of chain end functionalized dendritic macromolecules. In this example, the selectivity of the Cu-catalyzed [3 + 2π] cycloaddition reaction of azides with termi
A new homobifunctional p-nitro phenyl ester coupling reagent for the preparation of neoglycoproteins
Wu, Xiangyang,Ling, Chang-Chun,Bundle, David R.
, p. 4407 - 4410 (2004)
(Chemical equation presented) A new linker system has been designed and applied to neoglycoprotein synthesis. Reaction of oligosaccharide ω-aminoalkyl glycosides with homobifunctional adipic acid p-nitrophenyl diesters in dry DMF gave the corresponding am
Design, synthesis and antiparasitic evaluation of click phospholipids
Afroudakis, Pantelis,Barrias, Emile,Bifeld, Eugenia,Borsari, Chiara,Calogeropoulou, Theodora,Clos, Joachim,Costi, Maria Paola,Ellinger, Bernhard,Fotopoulou, Theano,Fragiadaki, Irini,Georgikopoulou, Kalliopi,Gul, Sheraz,Hachenberg, Julia,Kuzikov, Maria,Magoulas, George E.,Prousis, Kyriakos C.,Roussaki, Marina,Santarem, Nuno,Scoulica, Effie,Tejera Nevado, Paloma,da Silva, Anabela Cordeiro,de Souza, Wanderley
, (2021/07/26)
A library of seventeen novel ether phospholipid analogues, containing 5-membered heterocyclic rings (1,2,3-triazolyl, isoxazolyl, 1,3,4-oxadiazolyl and 1,2,4-oxadiazolyl) in the lipid portion were designed and synthesized aiming to identify optimised miltefosine analogues. The compounds were evaluated for their in vitro antiparasitic activity against Leishmania infantum and Leishmania donovani intracellular amastigotes, against Trypanosoma brucei brucei and against different developmental stages of Trypanosoma cruzi. The nature of the substituents of the heterocyclic ring (tail) and the oligomethylene spacer between the head group and the heterocyclic ring was found to affect the activity and toxicity of these compounds leading to a significantly improved understanding of their structure–activity relationships. The early ADMET profile of the new derivatives did not reveal major liabilities for the potent compounds. The 1,2,3-triazole derivative 27 substituted by a decyl tail, an undecyl spacer and a choline head group exhibited broad spectrum antiparasitic activity. It possessed low micromolar activity against the intracellular amastigotes of two L. infantum strains and T. cruzi Y strain epimastigotes, intracellular amastigotes and trypomastigotes, while its cytotoxicity concentration (CC50) against THP-1 macrophages ranged between 50 and 100 μM. Altogether, our work paves the way for the development of improved ether phospholipid derivatives to control neglected tropical diseases.
Synthesis of the Fungal Metabolite YWA1 and Related Constructs as Tools to Study MelLec-Mediated Immune Response to Aspergillus Infections ?
Piras, Monica,Patruno, Ilaria,Nikolakopoulou, Christina,Willment, Janet A.,Sloan, Nikki L.,Zanato, Chiara,Brown, Gordon D.,Zanda, Matteo
, p. 6044 - 6055 (2021/05/29)
We describe the chemical synthesis of the fungal naphthopyrones YWA1 and fonsecin B, as well as their functionalization with an amine-spacer arm and the conjugation of the resulting molecules to three different functional tags (i.e., biotin, Oregon green, 1-[3-(succinimidyloxycarbonyl)benzyl]-4-[5-(4-methoxyphenyl)-2-oxazolyl]pyridinium bromide (PyMPO)). The naphthopyrone-biotin and -PyMPO constructs maintained the ability to bind the C-type lectin receptor MelLec, whose interaction with immunologically active fungal metabolites (i.e., 1,8-dihydroxynaphthalene-(DHN)-melanin and YWA1) is a key step in host recognition and induction of protective immune responses against Aspergillus fumigatus. The fluorescent Fonsecin B-PyMPO construct 21 was used to selectively visualize MelLec-expressing cells, thus validating the potential of this strategy for studying the role and functions of MelLec in immunity.
