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.
Luminescence modulations of rhenium tricarbonyl complexes induced by structural variations
Bertrand, Helene C.,Clede, Sylvain,Guillot, Regis,Lambert, Francois,Policar, Clotilde
, p. 6204 - 6223 (2014)
Octahedral d6 low-spin Re(I) tricarbonyl complexes are of considerable interest as noninvasive imaging probes and have been deeply studied owing to their biological stability, low toxicity, large Stokes shifts, and long luminescence lifetimes. We reported recently the bimodal IR and luminescence imaging of a Re(I) tricarbonyl complex with a Pyta ligand (4-(2-pyridyl)-1,2,3-triazole) in cells and labeled such metal-carbonyl complexes SCoMPIs for single-core multimodal probes for imaging. Re(I) tricarbonyl complexes have unique photophysical properties allowing for their unequivocal detection in cells but also present some weaknesses such as a very low luminescence quantum yield in aqueous medium. Further optimizations would thus be desirable. We therefore developed new Re(I) tricarbonyl complexes prepared from different ancillary ligands. Complexes with benzothiadiazole- triazole ligands show interesting luminescent quantum yields in acetonitrile and may constitute valuable luminescent metal complexes in organic media. A series of complexes with bidentate 1-(2-quinolinyl)-1,2,3-triazole (Taquin) and 1-(2-pyridyl)-1,2,3-triazole (Tapy) ligands bearing various 4-substituted alkyl side chains has been designed and synthesized with efficient procedures. Their photophysical properties have been characterized in acetonitrile and in a H 2O/DMSO (98/2) mixture and compared with those of the parent Quinta- and Pyta-based complexes. Tapy complexes bearing long alkyl chains show impressive enhancement of their luminescent properties relative to the parent Pyta complex. Theoretical calculations have been performed to further characterize this new class of rhenium tricarbonyl complexes. Preliminary cellular imaging studies in MDA-MB231 breast cancer cells reveal a strong increase in the luminescence signal in cells incubated with the Tapy complex substituted with a C12 alkyl chain. This study points out the interesting potential of the Tapy ligand in coordination chemistry, which has been so far underexploited.
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
One-pot tandem living radical polymerisation-Huisgens cycloaddition process ("click") catalysed by N-alkyl-2-pyridylmethanimine/Cu(I)Br complexes
Mantovani, Giuseppe,Ladmiral, Vincent,Tao, Lei,Haddleton, David M.
, p. 2089 - 2091 (2005)
Azide terminally functional poly(methyl methacrylate)s (Mn = 4000-6000, PDI = 1.21-1.28) have been prepared by living radical polymerization and successfully reacted with alkynes in a Huisgen cycloaddition (click) reaction in one pot using the same catalyst for both processes. The Royal Society of Chemistry 2005.
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
Competitive Affinity Release for Long-Term Delivery of Antibodies from Hydrogels
Huynh, Vincent,Wylie, Ryan G.
, p. 3406 - 3410 (2018)
With increased clinical use of antibodies, long-term delivery strategies are needed to decrease injection frequency and improve health outcomes. A three-component drug-delivery system was developed for competitive affinity release of a streptavidin–antibody conjugate from agarose–desthiobiotin hydrogels via controlled dissolution of sparingly soluble biotin derivatives. The antibody conjugate was localized in the hydrogel through streptavidin–desthiobiotin complexation. Dissolution of sparingly soluble biotin derivatives disrupts streptavidin–desthiobiotin complexation for controlled release of the antibody conjugate. Release was tuned by altering the total biotin derivative concentration without further hydrogel or antibody modification. First-order tunable release of bioactive Avastin, a therapeutic anti-VEGF antibody, was demonstrated from a non-cytotoxic system for over 100 days.
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.
Facile Synthesis of Sequence-Regulated Synthetic Polymers Using Orthogonal SuFEx and CuAAC Click Reactions
Yang, Cangjie,Flynn, James P.,Niu, Jia
, p. 16194 - 16199 (2018)
The orthogonal sulfur–fluoride exchange reaction (SuFEx) and copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) are employed to synthesize sequence-regulated synthetic polymers. The high efficiency and broad tolerance of SuFEx and CuAAC to diverse chemical functionalities enable the one-pot synthesis of polydispersed sequence-controlled polymers by step-growth copolymerization in high yield and sequence complexity. Furthermore, iterative SuFEx and CuAAC coupling reactions on a solid support, without the need of protecting groups, afford monodispersed sequence-defined oligomers. The use of this orthogonal pair of click reactions provides new opportunities to facilely access sequence-regulated synthetic polymers with a high degree of structural diversity.
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.
Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners
El Sayed Aly, Mohamed Ramadan,Saad, Hosam Ali,Abdel-Hafez, Shams Hashim
, p. 1922 - 1932 (2015)
3β-Azidocholest-5-ene (3) and (3β)-3-(prop-2-yn-1-yloxy)cholest-5-ene (10) were prepared as substrates to synthesize a variety of three-motif pharmacophoric conjugates through CuAAC. Basically, these conjugates included cholesterol and 1,2,3-triazole moie
