199192-20-6Relevant academic research and scientific papers
Cyclopropanation of C60 with malonic acid mono-esters
Nierengarten, Jean-Francois,Nicoud, Jean-Francois
, p. 7737 - 7740 (1997)
Reaction of C69 with malonic acid mono-esters in the presence of iodine and diazabicyclo[5.4.0]undec-7-ene (DBU) provides the corresponding 61-iodo- 1,2-methano[60]fullerene-61-carboxylates. This cyclopropanation of C60 seems to occur via a carbenoid intermediate.
Metal-free C-H functionalization of pyrrolidine to pyrrolinium-based room temperature ionic liquid crystals
Mandal, Sumana,Gupta, Ravindra Kumar,Pathak, Suraj Kumar,Rao, D. S. Shankar,Prasad, S. Krishna,Ammathnadu Sudhakar, Achalkumar,Jana, Chandan K.
supporting information, p. 8064 - 8071 (2021/05/21)
The development of ionic liquid crystals (ILCs) using pyrrolidinium cation has received considerable interest due to their higher electrochemical stability. However, high charge density associated with low charge distribution in the fully saturated pyrrol
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
, 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.
One-Component Multifunctional Sequence-Defined Ionizable Amphiphilic Janus Dendrimer Delivery Systems for mRNA
Atochina-Vasserman, Elena N.,Billingsley, Margaret M.,Huang, Ning,Kim, Kyunghee,Liu, Matthew,Maurya, Devendra S.,Mitchell, Michael J.,Ni, Houping,Ona, Nathan,Percec, Virgil,Pochan, Darrin J.,Shahnawaz, Hamna,Weissman, Drew,Xiao, Qi,Zhang, Dapeng
supporting information, p. 12315 - 12327 (2021/08/20)
Efficient viral or nonviral delivery of nucleic acids is the key step of genetic nanomedicine. Both viral and synthetic vectors have been successfully employed for genetic delivery with recent examples being DNA, adenoviral, and mRNA-based Covid-19 vaccines. Viral vectors can be target specific and very efficient but can also mediate severe immune response, cell toxicity, and mutations. Four-component lipid nanoparticles (LNPs) containing ionizable lipids, phospholipids, cholesterol for mechanical properties, and PEG-conjugated lipid for stability represent the current leading nonviral vectors for mRNA. However, the segregation of the neutral ionizable lipid as droplets in the core of the LNP, the "PEG dilemma", and the stability at only very low temperatures limit their efficiency. Here, we report the development of a one-component multifunctional ionizable amphiphilic Janus dendrimer (IAJD) delivery system for mRNA that exhibits high activity at a low concentration of ionizable amines organized in a sequence-defined arrangement. Six libraries containing 54 sequence-defined IAJDs were synthesized by an accelerated modular-orthogonal methodology and coassembled with mRNA into dendrimersome nanoparticles (DNPs) by a simple injection method rather than by the complex microfluidic technology often used for LNPs. Forty four (81%) showed activity in vitro and 31 (57%) in vivo. Some, exhibiting organ specificity, are stable at 5 °C and demonstrated higher transfection efficiency than positive control experiments in vitro and in vivo. Aside from practical applications, this proof of concept will help elucidate the mechanisms of packaging and release of mRNA from DNPs as a function of ionizable amine concentration, their sequence, and constitutional isomerism of IAJDs.
Rational Design of Supramolecular Dynamic Protein Assemblies by Using a Micelle-Assisted Activity-Based Protein-Labeling Technology
Sandanaraj, Britto S.,Reddy, Mullapudi Mohan,Bhandari, Pavankumar Janardhan,Kumar, Sugam,Aswal, Vinod K.
supporting information, p. 16085 - 16096 (2018/10/15)
The self-assembly of proteins into higher-order superstructures is ubiquitous in biological systems. Genetic methods comprising both computational and rational design strategies are emerging as powerful methods for the design of synthetic protein complexes with high accuracy and fidelity. Although useful, most of the reported protein complexes lack a dynamic behavior, which may limit their potential applications. On the contrary, protein engineering by using chemical strategies offers excellent possibilities for the design of protein complexes with stimuli-responsive functions and adaptive behavior. However, designs based on chemical strategies are not accurate and therefore, yield polydisperse samples that are difficult to characterize. Here, we describe simple design principles for the construction of protein complexes through a supramolecular chemical strategy. A micelle-assisted activity-based protein-labeling technology has been developed to synthesize libraries of facially amphiphilic synthetic proteins, which self-assemble to form protein complexes through hydrophobic interaction. The proposed methodology is amenable for the synthesis of protein complex libraries with molecular weights and dimensions comparable to naturally occurring protein cages. The designed protein complexes display a rich structural diversity, oligomeric states, sizes, and surface charges that can be engineered through the macromolecular design. The broad utility of this method is demonstrated by the design of most sophisticated stimuli-responsive systems that can be programmed to assemble/disassemble in a reversible/irreversible fashion by using the pH or light as trigger.
Self-assembled and Alkyl-substituted Porphyrin derivatives and Preparing Method Thereof
-
, (2017/08/03)
The present invention relates to a self-assembled alkyl-substituted porphyrin derivative and a production method thereof. More specifically, the present invention relates to a self-assembled alkyl-substitued porphyrin derivative which is applicable as a c
Mesoscopic helical architectures: Via self-assembly of porphyrin-based discotic systems
Vela, Sonia,Berrocal, José Augusto,Atienza, Carmen,Meijer,Martín, Nazario
supporting information, p. 4084 - 4087 (2017/04/13)
Mesoscopic super-helices with preferred helicity have been serendipitously formed from the self-assembly of electroactive extended core discotic molecules. The investigation at dilute concentrations reveals intramolecular hydrogen-bonding and π-π stacking
Polycatenar Ligand Control of the Synthesis and Self-Assembly of Colloidal Nanocrystals
Diroll, Benjamin T.,Jishkariani, Davit,Cargnello, Matteo,Murray, Christopher B.,Donnio, Bertrand
, p. 10508 - 10515 (2016/09/04)
Hydrophobic colloidal nanocrystals are typically synthesized and manipulated with commercially available ligands, and surface functionalization is therefore typically limited to a small number of molecules. Here, we report the use of polycatenar ligands d
Synthesis, characterization and aggregation induced emission properties of anthracene based conjugated molecules
Balasaravanan, Rajendiran,Siva, Ayyanar
, p. 5099 - 5106 (2016/07/06)
Aggregation induced emission-active branched and linear 9,10-distyrylanthracene derivatives with different length alkoxy chains have been designed, synthesized and the effect of chain length on the solid-state fluorescence properties systematically investigated. All the three anthracene derivatives possess typical aggregation induced emission (AIE) properties, i.e., they exhibit faint emission in their solutions, but intense emission in their aggregate states, as a result of the dominant nonradiative decay of free intramolecular torsion in the solution and also the restricted torsional motion from supramolecular interaction in the solid states. The results show that these materials exhibit not only AIE properties, but also observed were position and chain length dependent fluorescence properties. The shorter alkoxy chains were more red shifted than the longer ones and also different aggregation behaviours for branched and linear molecules were observed. This work demonstrates once again the accessibility of tuning the solid-state optical properties of organic fluorophores by combining the simple alternation of molecular chemical structures and the physical change of aggregate morphology under external stimuli.
Synthesis and photophysical properties of triphenylamine-based multiply conjugated star-like molecules
Balasaravanan, Rajendiran,Duraimurugan, Kumaraguru,Sivamani, Jayaraman,Thiagarajan, Viruthachalam,Siva, Ayyanar
, p. 7472 - 7480 (2015/09/02)
Novel triphenylamine-based star-like molecules 11 were synthesized and characterized using FT-IR, 1H, 13C, and DEPT-135 NMR spectroscopy, and MALDI-TOF mass spectrometry. The absorption and emission spectra of star-like molecules were studied in different solvents. The effect of solvent polarity and aggregation studies on the absorption and emission spectra has also been studied. The new star-like molecules are found to exhibit broad absorption and emission band along with intramolecular charge transfer character. The fluorescence spectra of triphenylamine derivatives shift from blue to green wavelength on increasing the extended conjugation of the molecule. The experimental results indicate that there is cooperative enhancement originating from the inter-branch coupling and an increase in the light-harvesting ability upon increasing the conjugated molecule size.
