370564-68-4Relevant academic research and scientific papers
A convenient protocol for the synthesis of ligands from a 4-methyl-3,5-diacylaminophenyl platform
Pickaert, Guillaume,Cesario, Michele,Ziessel, Raymond
, p. 5335 - 5341 (2004)
The synthesis of stable and highly organized phenanthroline, terpyridine, and pyridino-oxazoline ligands bearing one or two 4-methyl-3,5-diacylaminophenyl modules equipped with two lateral dialkoxyphenyl groups has been performed using EDC·HCl and DMAP reagents in the final coupling reaction. Evidently, in the final ligands and in the solid state intermolecular hydrogen bonding maintains the coherence of the tridimensional structure as clearly evidenced by FT-IR and X-ray diffraction spectroscopy in the cases of the methoxy ligands. The supramolecular packing is also maintained by additional π-π stacking interactions.
Targeted Delivery of mRNA with One-Component Ionizable Amphiphilic Janus Dendrimers
Zhang, Dapeng,Atochina-Vasserman, Elena N.,Maurya, Devendra S.,Liu, Matthew,Xiao, Qi,Lu, Juncheng,Lauri, George,Ona, Nathan,Reagan, Erin K.,Ni, Houping,Weissman, Drew,Percec, Virgil
supporting information, p. 17975 - 17982 (2021/11/10)
Targeted and efficient delivery of nucleic acids with viral and synthetic vectors is the key step of genetic nanomedicine. The four-component lipid nanoparticle synthetic delivery systems consisting of ionizable lipids, phospholipids, cholesterol, and a PEG-conjugated lipid, assembled by microfluidic or T-tube technology, have been extraordinarily successful for delivery of mRNA to provide Covid-19 vaccines. Recently, we reported a one-component multifunctional sequence-defined ionizable amphiphilic Janus dendrimer (IAJD) synthetic delivery system for mRNA relying on amphiphilic Janus dendrimers and glycodendrimers developed in our laboratory. Amphiphilic Janus dendrimers consist of functional hydrophilic dendrons conjugated to hydrophobic dendrons. Co-assembly of IAJDs with mRNA into dendrimersome nanoparticles (DNPs) occurs by simple injection in acetate buffer, rather than by microfluidic devices, and provides a very efficient system for delivery of mRNA to lung. Here we report the replacement of most of the hydrophilic fragment of the dendron from IAJDs, maintaining only its ionizable amine, while changing its interconnecting group to the hydrophobic dendron from amide to ester. The resulting IAJDs demonstrated that protonated ionizable amines play dual roles of hydrophilic fragment and binding ligand for mRNA, changing delivery from lung to spleen and/or liver. Replacing the interconnecting ester with the amide switched the delivery back to lung. Delivery predominantly to liver is favored by pairs of odd and even alkyl groups in the hydrophobic dendron. This simple structural change transformed the targeted delivery of mRNA mediated with IAJDs, from lung to liver and spleen, and expands the utility of DNPs from therapeutics to vaccines.
Impact of substitution pattern and chain length on the thermotropic properties of alkoxy-substituted triphenyl-tristriazolotriazines
Detert, Heiner,Glang, Stefan,Haspel, Tobias,Lehmann, Matthias,Limbach, Daniel,Rieth, Thorsten,Schupp, Niklas,Sperner, Marcel,Tober, Natalie,Wicker, Philipp
supporting information, (2021/06/14)
Tristriazolotriazines (TTTs) with a threefold alkoxyphenyl substitution were prepared and studied by DSC, polarized optical microscopy (POM) and X-ray scattering. Six pentyloxy chains are sufficient to induce liquid-crystalline behavior in these star-shap
Functionalization of pristine graphene with conjugated polymers through diradical addition and propagation
Ma, Xiaowei,Li, Fei,Wang, Youfu,Hu, Aiguo
, p. 2547 - 2550,4 (2020/09/02)
Hanging on: Pristine graphene was grafted with conjugated polymers through addition and propagation of diradicals generated from Bergman cyclization of enediyne-containing dendrimers. The surface functionalization was confirmed with TGA, FTIR and Raman spectroscopy, and AFM analysis. The sp2 network of graphene is only slightly destroyed, as revealed by conductivity measurements. Copyright
Covalent surface functionalization of multiwalled carbon nanotubes through bergman cyclization of enediyne-containing dendrimers
Ma, Jianguo,Deng, Sheng,Cheng, Xin,Wei, Wei,Hu, Aiguo
experimental part, p. 3951 - 3959 (2012/07/14)
A method for covalent functionalization of multiwalled carbon nanotubes (MWCNTs) was developed using the free radicals generated through Bergman cyclization of enediyne-containing compounds. Four enediyne-bearing Frechet type dendrimers were synthesized in good quantities and characterized. Then, the enediyne-containing molecules were reacted with MWCNTs in N-methyl-2- pyrrolidinone at 206 °C under nitrogen. The structure and morphology of the resulting products were characterized by thermogravimetric analysis, ultraviolet-visible spectroscopy, Fourier transform infrared spectroscopy, Raman spectroscopy, and transmission electron microscopy. The dendrimer- functionalized MWCNTs showed good solubility/dispersibility in common organic solvents and polymer solutions. They were used in the formation of polymer composites through electrospinning with polycaprolactone. The results confirmed the surface functionalization of MWCNTs.
Synthesis of oligopyridinic scaffolds from amido substituted phenyl rings for extended hydrogen bonding
Pickaert, Guillaume,Ziessel, Raymond
, p. 2716 - 2726 (2007/10/03)
A series of phenanthroline, terpyridine and pyridino-oxazoline ligands combining a 4-methyl-3,5-diacylaminophenyl platform and two dialkoxyphenyl groups has been prepared by a linear multistep protocol. The synthetic potential of 4-methyl-3,5-(diacyl-amin
Tuning organogels and mesophases will phenanthroline ligands and their copper complexes by inter- to intramolecular hydrogen bonds
Ziessel, Raymond,Pickaert, Guillaume,Camerel, Franck,Donnio, Bertrand,Guillon, Daniel,Cesario, Michele,Prange, Thierry
, p. 12403 - 12413 (2007/10/03)
A novel family of highly functionalized molecules consisting of a central 4-methyl-3,5-diacylaminobenzene platform linked in close proximity to the methyl group by two lateral aromatic rings each equipped with two long alkoxy chains has been rationally de
Facile synthesis of stable lipid analogues possessing a range of alkyl groups: Application to artificial glycolipids
Azefu, Yasuo,Tamiaki, Hitoshi,Sato, Reiko,Toma, Kazunori
, p. 4013 - 4022 (2007/10/03)
Efficient preparation of lipid analogues is described in which various long alkoxy chains and 2-hydroxyethyl group were covalently linked with benzoic acid derivatives. An α-mannopyranosyl group was stereoselectively introduced by the conventional imidate
