105589-77-3Relevant articles and documents
Synthesis of gemini surfactants with twelve symmetric fluorine atoms and one singlet 19F MR signal as novel 19F MRI agents
Li, Yu,Thapa, Bijaya,Zhang, Hua,Li, Xuefei,Yu, Fanghua,Jeong, Eun-Kee,Yang, Zhigang,Jiang, Zhong-Xing
, p. 9586 - 9590 (2013)
A family of fluorinated gemini surfactants derived from perfluoropinacol has been synthesized as novel 19F magnetic resonance imaging ( 19F MRI) agents. These fluorinated surfactants with 12 symmetric fluorine atoms and one singlet
Synthesis of New Glycerolipids Linked to Hydroxamate Derivatives Designed for Two-Dimensional Crystallization of Aminopeptidase M
Altenburger, Jean-Michel,Lebeau, Luc,Mioskowski, Charles,Schirlin, Daniel
, p. 2538 - 2544 (1992)
The synthesis of glycerolipids linked to hydroxamate derivatives designed for two-dimensional crystallization of aminopeptidase M is reported.The lipid moieties are readily obtained using a convergent pathway.Their structure allows the introduction of a w
An ion conductor that recognizes osmotically-stressed phospholipid bilayers
Bandyopadhyay, Prasun,Bandyopadhyay, Punam,Regen, Steven L.
, p. 11254 - 11255 (2002)
A synthetic ion conductor (1), derived from cholic acid and spermine, has been found capable of recognizing osmotic stress in liposomes made from 1,2-dipalmitoleoyl-sn-glycero-3-phosphocholine [(C16:1)PC]. Thus, when large unilamellar vesicles of (C16:1)PC are placed under hypotonic conditions, the Na+/Li+ transport activity of 1 increases by as much as 1 order of magnitude, relative to isotonic conditions Copyright
Synthesis of a library of propargylated and PEGylated α-hydroxy acids toward "clickable" polylactides via hydrolysis of cyanohydrin derivatives
Zhang, Quanxuan,Ren, Hong,Baker, Gregory L.
, p. 9546 - 9555 (2014)
A new simple and practical protocol for scalable synthesis of a novel library of propargylated and PEGylated α-hydroxy acids toward the preparation of "clickable" polylactides was described. The overall synthesis starting from readily available propargyl alcohol, bromoacetaldehyde diethyl acetal, and OEGs or PEGs was developed as a convenient procedure with low cost and no need of column chromatographic purification. The terminal alkyne functionality survives from hydrolysis of the corresponding easily accessible cyanohydrin derivatives in methanolic sulfuric acid. Facile desymmetrization, monofunctionalization, and efficient chain-elongation coupling of OEGs further enable the incorporation of OEGs to α-hydroxy acids in a simple and efficient manner. At the end, synthesis of allyloxy lactic acid indicates that an alkene group is also compatible with the developed method. (Chemical Equation Presented).
Hydrophilic and Cell-Penetrable Pyrrolidinyl Peptide Nucleic Acid via Post-synthetic Modification with Hydrophilic Side Chains
Pansuwan, Haruthai,Ditmangklo, Boonsong,Vilaivan, Chotima,Jiangchareon, Banphot,Pan-In, Porntip,Wanichwecharungruang, Supason,Palaga, Tanapat,Nuanyai, Thanesuan,Suparpprom, Chaturong,Vilaivan, Tirayut
, p. 2284 - 2292 (2017)
Peptide nucleic acid (PNA) is a nucleic acid mimic in which the deoxyribose-phosphate was replaced by a peptide-like backbone. The absence of negative charge in the PNA backbone leads to several unique behaviors including a stronger binding and salt independency of the PNA-DNA duplex stability. However, PNA possesses poor aqueous solubility and cannot directly penetrate cell membranes. These are major obstacles that limit in vivo applications of PNA. In previous strategies, the PNA can be conjugated to macromolecular carriers or modified with positively charged side chains such as guanidinium groups to improve the aqueous solubility and cell permeability. In general, a preformed modified PNA monomer was required. In this study, a new approach for post-synthetic modification of PNA backbone with one or more hydrophilic groups was proposed. The PNA used in this study was the conformationally constrained pyrrolidinyl PNA with prolyl-2-aminocyclopentanecarboxylic acid dipeptide backbone (acpcPNA) that shows several advantages over the conventional PNA. The aldehyde modifiers carrying different linkers (alkylene and oligo(ethylene glycol)) and end groups (-OH, -NH2, and guanidinium) were synthesized and attached to the backbone of modified acpcPNA by reductive alkylation. The hybrids between the modified acpcPNAs and DNA exhibited comparable or superior thermal stability with base-pairing specificity similar to those of unmodified acpcPNA. Moreover, the modified apcPNAs also showed the improvement of aqueous solubility (10-20 folds compared to unmodified PNA) and readily penetrate cell membranes without requiring any special delivery agents. This study not only demonstrates the practicality of the proposed post-synthetic modification approach for PNA modification, which could be readily applied to other systems, but also opens up opportunities for using pyrrolidinyl PNA in various applications such as intracellular RNA sensing, specific gene detection, and antisense and antigene therapy.
Preparation of monotritylated symmetric 1,n-diols
Komiotis,Currie,LeBreton,Venton
, p. 531 - 534 (1993)
A convenient method has been developed to selectively form the monotriphenylmethyl derivatives of symmetric 1,n-diols, both straight chain and cyclic, in moderate to high yields.
Ligand-Phospholipid Conjugation: A Versatile Strategy for Developing Long-Acting Ligands That Bind to Membrane Proteins by Restricting the Subcellular Localization of the Ligand
Kawamura, Shuhei,Ito, Yoshihiko,Hirokawa, Takatsugu,Hikiyama, Eriko,Yamada, Shizuo,Shuto, Satoshi
supporting information, p. 4020 - 4029 (2018/05/07)
We hypothesized that if drug localization can be restricted to a particular subcellular domain where their target proteins reside, the drugs could bind to their target proteins without being metabolized and/or excreted, which would significantly extend the half-life of the corresponding drug-target complex. Thus, we designed ligand-phospholipid conjugates in which the ligand is conjugated with a phospholipid through a polyethylene glycol linker to restrict the subcellular localization of the ligand in the vicinity of the lipid bilayer. Here, we present the design, synthesis, pharmacological activity, and binding mode analysis of ligand-phospholipid conjugates with muscarinic acetylcholine receptors as the target proteins. These results demonstrate that ligand-phospholipid conjugation can be a versatile strategy for developing long-acting ligands that bind to membrane proteins in drug discovery.
A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: Hydrophobic interactions alone can mediate gelation
Singh, Wangkhem P.,Singh, Rajkumar S.
supporting information, p. 138 - 149 (2017/02/15)
In the present work, we have explored the use of the triphenylmethyl group, a commonly used protecting group for primary alcohols as a gelling structural component in the design of molecular gelators. We synthesized a small library of triphenylmethyl deri
Highly efficient synthesis of monodisperse poly(ethylene glycols) and derivatives through macrocyclization of oligo(ethylene glycols)
Zhang, Hua,Li, Xuefei,Shi, Qiuyan,Li, Yu,Xia, Guiquan,Chen, Long,Yang, Zhigang,Jiang, Zhong-Xing
supporting information, p. 3763 - 3767 (2015/03/18)
A macrocyclic sulfate (MCS)-based approach to monodisperse poly(ethylene glycols) (M-PEGs) and their monofunctionalized derivatives has been developed. Macrocyclization of oligo(ethylene glycols) (OEGs) provides MCS (up to a 62-membered macrocycle) as versatile precursors for a range of monofunctionalized M-PEGs. Through iterative nucleophilic ring-opening reactions of MCS without performing group protection and activation, a series of M-PEGs, including the unprecedented 64-mer (2850Da), can be readily prepared. Synthetic simplicity coupled with versatility of this new strategy may pave the way for broader applications of M-PEGs. Macrocycles make synthesis easier: Convenient macrocyclization of the OEGs provides versatile macrocyclic sulfates. These compounds are cornerstones for both monofunctionalization of OEGs and highly efficient synthesis of monodisperse PEGs and derivatives, including an unprecedented 64-mer.
Synthesis and the structure to property relationship of monoperfluoroalkyl polyethylene glycol
Jaoued-Grayaa, Najeh,Boughariou-Charrada, Boutheina,Hedhli, Ahmed
, p. 767 - 772 (2014/07/08)
Monoprotected polyethylene glycols (PEG) react with epichlorohydrin to furnish PEGylated epoxides. The latter were converted into the corresponding α-(2-F-alkylethyl)thiomethyl polyethylene glycols by treatment with 2-F-alkylethanethiol. Surface activity
