862121-45-7Relevant academic research and scientific papers
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.
Screening Libraries of Amphiphilic Janus Dendrimers Based on Natural Phenolic Acids to Discover Monodisperse Unilamellar Dendrimersomes
Buzzacchera, Irene,Xiao, Qi,Han, Hong,Rahimi, Khosrow,Li, Shangda,Kostina, Nina Yu.,Toebes, B. Jelle,Wilner, Samantha E.,M?ller, Martin,Rodriguez-Emmenegger, Cesar,Baumgart, Tobias,Wilson, Daniela A.,Wilson, Christopher J.,Klein, Michael L.,Percec, Virgil
, p. 712 - 727 (2018/11/23)
Natural, including plant, and synthetic phenolic acids are employed as building blocks for the synthesis of constitutional isomeric libraries of self-assembling dendrons and dendrimers that are the simplest examples of programmed synthetic macromolecules.
Compound containing diphenylmethane structure
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Paragraph 0114; 0115; 0116; 0117, (2019/05/08)
The invention relates to a compound containing a diphenylmethane structure, and belongs to the technical field of compounds and polypeptide synthesis. The structure of the compound containing the diphenylmethane structure is shown in general formula (1).
Anhydrous proton conduction in self-assembled and disassembled ionic molecules
Kumar, Avneesh,Pisula, Wojciech,Sieber, Christoph,Klapper, Markus,Müllen, Klaus
, p. 6074 - 6084 (2018/04/12)
In polymer based ionic conductors, the conductivity is suppressed by a low degree of chain mobility, therefore it is imperative to design a molecular system in which ionic groups can be mobilized and immobilized as a function of temperature to allow ions
MODULAR SYNTHESIS OF AMPHIPHILIC JANUS GLYCODENDRIMERS AND THEIR SELF-ASSEMBLY INTO GLYCODENDRIMERSOMES
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Paragraph 0088, (2014/12/12)
The invention concerns compounds of the formula (I) wherein: Y1 and Y2 are independently a monosaccharide or disaccharide; X1 and X2 are independently -(R9-O)m-, -(R10)P-, -O-(R11-O)q-, -R16-O-R17-O- or a covalent bond; Q1 and Q2 are independently a nitrogen-containing heterocycle moiety; Z1 and Z2 are independently -(O-R7)-, -(O-C(=O)-R8)a-, -O-C(=O)-R12-C(=0)-R13-, -O- C(=O)-R14-C(=O)-R15 or a covalent bond; R7-R17 are each independently C1-C6 alkyl; R1-R6 are each independently a linear or branched alkly group; b, c, d, e, f, and g are 0 or 1, provided b + c + d equals at least 2 and e + f + g equals at least 2; and a, m, p, and q are each an integer from 1-6.
Modular synthesis of amphiphilic Janus glycodendrimers and their self-assembly into glycodendrimersomes and other complex architectures with bioactivity to biomedically relevant lectins
Percec, Virgil,Leowanawat, Pawaret,Sun, Hao-Jan,Kulikov, Oleg,Nusbaum, Christopher D.,Tran, Tam M.,Bertin, Annabelle,Wilson, Daniela A.,Peterca, Mihai,Zhang, Shaodong,Kamat, Neha P.,Vargo, Kevin,Moock, Diana,Johnston, Eric D.,Hammer, Daniel A.,Pochan, Darrin J.,Chen, Yingchao,Chabre, Yoann M.,Shiao, Tze C.,Bergeron-Brlek, Milan,Andre, Sabine,Roy, Rene,Gabius, Hans-J.,Heiney, Paul A.
, p. 9055 - 9077 (2013/07/26)
The modular synthesis of 7 libraries containing 51 self-assembling amphiphilic Janus dendrimers with the monosaccharides d-mannose and d-galactose and the disaccharide d-lactose in their hydrophilic part is reported. These unprecedented sugar-containing dendrimers are named amphiphilic Janus glycodendrimers. Their self-assembly by simple injection of THF or ethanol solution into water or buffer and by hydration was analyzed by a combination of methods including dynamic light scattering, confocal microscopy, cryogenic transmission electron microscopy, Fourier transform analysis, and micropipet-aspiration experiments to assess mechanical properties. These libraries revealed a diversity of hard and soft assemblies, including unilamellar spherical, polygonal, and tubular vesicles denoted glycodendrimersomes, aggregates of Janus glycodendrimers and rodlike micelles named glycodendrimer aggregates and glycodendrimermicelles, cubosomes denoted glycodendrimercubosomes, and solid lamellae. These assemblies are stable over time in water and in buffer, exhibit narrow molecular-weight distribution, and display dimensions that are programmable by the concentration of the solution from which they are injected. This study elaborated the molecular principles leading to single-type soft glycodendrimersomes assembled from amphiphilic Janus glycodendrimers. The multivalency of glycodendrimersomes with different sizes and their ligand bioactivity were demonstrated by selective agglutination with a diversity of sugar-binding protein receptors such as the plant lectins concanavalin A and the highly toxic mistletoe Viscum album L. agglutinin, the bacterial lectin PA-IL from Pseudomonas aeruginosa, and, of special biomedical relevance, human adhesion/growth-regulatory galectin-3 and galectin-4. These results demonstrated the candidacy of glycodendrimersomes as new mimics of biological membranes with programmable glycan ligand presentations, as supramolecular lectin blockers, vaccines, and targeted delivery devices.
Benzothiadiazole-based dyes that emit red light in solution, solid, and liquid state
Ishi-I, Tsutomu,Sakai, Miki,Shinoda, Chihiro
, p. 9475 - 9480 (2013/10/08)
In this paper, we report the preparation and red-light-emitting behavior of benzothiadiazole-tris(alkyloxy)phenylethene dyes. In solution, we observed an efficient red light emission with high fluorescence quantum yields (up to 0.78). With increase in solvent polarity, the emission bands shifted to longer wavelengths accompanied by a large Stokes shift of up to 152 nm. A moderate fluorescence quantum yield of 0.52 could be achieved even in the polar solvent dimethylformamide. Red light emission with good fluorescence quantum yields (up to 0.50) was also observed in the bulk solid, liquid, and film state.
Self-assembly and orientation of hydrogen-bonded oligothiophene polymorphs at liquid-membrane-liquid interfaces
Tevis, Ian D.,Palmer, Liam C.,Herman, David J.,Murray, Ian P.,Stone, David A.,Stupp, Samuel I.
supporting information; experimental part, p. 16486 - 16494 (2011/12/14)
One of the challenges in organic systems with semiconducting function is the achievement of molecular orientation over large scales. We report here on the use of self-assembly kinetics to control long-range orientation of a quarterthiophene derivative des
Control of H- and J-type π stacking by peripheral alkyl chains and self-sorting phenomena in perylene bisimide homo- and heteroaggregates
Ghosh, Suhrit,Li, Xue-Qing,Stepanenko, Vladimir,Wuerthner, Frank
experimental part, p. 11343 - 11357 (2009/10/25)
The synthesis, self-assembly, and gelation ability of a series of organogelators based on perylene bisimide (PBI) dyes containing amide groups at imide positions are reported. The synergetic effect of intermolecular hydrogen bonding among the amide functi
Spontaneous colorimetric sensing of the positional isomers of dihydroxynaphthalene in a 1D organogel matrix
Mukhopadhyay, Pritam,Iwashita, Yuya,Shirakawa, Michihiro,Kawano, Shin-Ichiro,Fujita, Norifumi,Shinkai, Seiji
, p. 1592 - 1595 (2007/10/03)
(Figure Presented) Like a color palette: A naphthalenediimide-based organogel colorimetric sensor allows recognition of the positional isomers of dihydroxynaphthalene in the gel phase with the naked eye. Intercalation of the dihydroxynaphthalene into the gel matrix produces a donor-acceptor interaction, which gives the gel a distinct color that depends on the strength of noncovalent (H-bonding, π-stacking, van der Waals) interactions.
