58320-73-3Relevant academic research and scientific papers
Post-modification of helical dipeptido polyisocyanides using the 'click' reaction
Kitto, Heather J.,Schwartz, Erik,Nijemeisland, Marlies,Koepf, Matthieu,Cornelissen, Jeroen J. L. M.,Rowan, Alan E.,Nolte, Roeland J. M.
, p. 5615 - 5624 (2008)
Polyisocyanopeptides have been synthesised containing acetylene groups on the side arms as scaffolds for multifunctional derivatisation by the copper-catalysed click reaction with a variety of azides. By using ethylene glycol azide and perylene azide chro
Fragment-based solid-phase assembly of oligonucleotide conjugates with peptide and polyethylene glycol ligands
Dirin, Mehrdad,Urban, Ernst,Noe, Christian R.,Winkler, Johannes
, p. 132 - 142 (2016)
Ligand conjugation to oligonucleotides is an attractive strategy for enhancing the therapeutic potential of antisense and siRNA agents by inferring properties such as improved cellular uptake or better pharmacokinetic properties. Disulfide linkages enable dissociation of ligands and oligonucleotides in reducing environments found in endosomal compartments after cellular uptake. Solution-phase fragment coupling procedures for producing oligonucleotide conjugates are often tedious, produce moderate yields and reaction byproducts are frequently difficult to remove. We have developed an improved method for solid-phase coupling of ligands to oligonucleotides via disulfides directly after solid-phase synthesis. A 2′-thiol introduced using a modified nucleotide building block was orthogonally deprotected on the controlled pore glass solid support with N-butylphosphine. Oligolysine peptides and a short monodisperse ethylene glycol chain were successfully coupled to the deprotected thiol. Cleavage from the resin and full removal of oligonucleotide protection groups were achieved using methanolic ammonia. After standard desalting, and without further purification, homogenous conjugates were obtained as demonstrated by HPLC, gel electrophoresis, and mass spectrometry. The attachment of both amphiphilic and cationic ligands proves the versatility of the conjugation procedure. An antisense oligonucleotide conjugate with hexalysine showed pronounced gene silencing in a cell culture tumor model in the absence of a transfection reagent and the corresponding ethylene glycol conjugate resulted in down regulation of the target gene to nearly 50% after naked application.
Luminescent gels by self-assembling platinum complexes
Allampally, Naveen Kumar,Strassert, Cristian A.,De Cola, Luisa
, p. 13132 - 13137 (2012)
A platinum complex bearing a tetraethylene glycol chain has been designed and its self-assembly properties investigated. In solution, only a yellow phosphorescence of the aggregated species is observed. The complex gives luminescent gels of different colo
Spectroscopy, binding to liposomes and production of singlet oxygen by porphyrazines with modularly variable water solubility
Sholto, Alan,Lee, Sangwan,Hoffman, Brian M.,Barrett, Anthony G. M.,Ehrenberg, Benjamin
, p. 764 - 773 (2008)
Three novel classes of porphyrazine-like structures were synthesized to form modular structures in which lipophilicity and water solubility can be tuned. Subtle modification of solubility is an important criterion in selecting a compound for biological ph
Chirality Synchronization of Hydrogen-Bonded Complexes of Achiral N-Heterocycles
Buchs, Jens,Vogel, Laura,Janietz, Dietmar,Prehm, Marko,Tschierske, Carsten
, p. 280 - 284 (2017)
2,4-Diamino-6-phenyl-1,3,5-triazines carrying a single oligo(ethylene oxide) (EO) chain form an optically isotropic mesophase composed of a conglomerate of macroscopic chiral domains with opposite sense of chirality even though the constituent molecules are achiral. This mesophase was proposed to result from the helical packing of hydrogen-bonded triazine aggregates, providing long-range chirality synchronization. The results provide first evidence for macroscopic achiral symmetry breaking upon conglomerate formation in an amorphous isotropic phase formed by hydrogen-bonded associates of simple N-heterocycles that are related to prebiotic molecules.
Hydrophilic and lipophilic iron chelators with the same complexing abilities
Imbert, Daniel,Baret, Paul,Gaude, Didier,Gautier-Luneau, Isabelle,Gellon, Gisele,Thomas, Fabrice,Serratrice, Guy,Pierre, Jean-Louis
, p. 1091 - 1100 (2002)
A new series of iron chelators with the same coordination sphere as the water-soluble ligand O-trensox, but featuring a variable hydrophilic-lipophilic balance, have been obtained by grafting oxyethylene chains of variable length on a C-pivot tripodal sca
TPE based aggregation induced emission fluorescent sensors for viscosity of liquid and mechanical properties of hydrogel
Wang, Na,Yao, Hang,Tao, Qi,Sun, Jing,Ma, Hao,Wang, Yang,Zhou, ChengCheng,Fan, Hongying,Shao, Hongxia,Qin, Aijian,Su, Dawei,Wang, Chenyin,Chong, Hui
supporting information, p. 252 - 256 (2021/08/13)
Two amphiphilic TPE E/Z isomers with aggregation induced emission (AIE) property have been synthesized and characterized. The logarithmic fluorescent intensity of the two molecules was in positive relationship with logarithmic viscosity of liquid. To note
FLUORINATED AMINE OXIDE SURFACTANTS
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, (2022/02/27)
Compositions including one or more fluorochemical surfactants of the formula: (I) where Rf is a perfluoroalkyl group, each of R1, R2 and R3 are C1-C20 alkyl, alkoxy, or aryl; and R4 is alkylene, arylene of a combination thereof. R4 is preferably an alkylene of 1-20 carbons that may be cyclic or acyclic, may optionally contain catenated or terminal heteroatoms selected from the group consisting of N, O, and S. Most preferably R4 is an alkylene of 2-10 carbon atoms. Described are anionic N-substituted fluorinated amine oxide surfactants, and use thereof in cleaning and in acid etch solutions. The cleaning and etch solutions are used with a wide variety of substrates, for example, in the cleaning and etching of silicon oxide-containing substrates.
A Modular Synthetic Route Involving N-Aryl-2-nitrosoaniline Intermediates Leads to a New Series of 3-Substituted Halogenated Phenazine Antibacterial Agents
Yang, Hongfen,Kundra, Shivani,Chojnacki, Michaelle,Liu, Ke,Fuse, Marisa A.,Abouelhassan, Yasmeen,Kallifidas, Dimitris,Zhang, Peilan,Huang, Guangtao,Jin, Shouguang,Ding, Yousong,Luesch, Hendrik,Rohde, Kyle H.,Dunman, Paul M.,Lemos, José A.,Huigens, Robert W.
supporting information, p. 7275 - 7295 (2021/05/29)
Pathogenic bacteria demonstrate incredible abilities to evade conventional antibiotics through the development of resistance and formation of dormant, surface-attached biofilms. Therefore, agents that target and eradicate planktonic and biofilm bacteria are of significant interest. We explored a new series of halogenated phenazines (HP) through the use of N-aryl-2-nitrosoaniline synthetic intermediates that enabled functionalization of the 3-position of this scaffold. Several HPs demonstrated potent antibacterial and biofilm-killing activities (e.g., HP 29, against methicillin-resistant Staphylococcus aureus: MIC = 0.075 μM; MBEC = 2.35 μM), and transcriptional analysis revealed that HPs 3, 28, and 29 induce rapid iron starvation in MRSA biofilms. Several HPs demonstrated excellent activities against Mycobacterium tuberculosis (HP 34, MIC = 0.80 μM against CDC1551). This work established new SAR insights, and HP 29 demonstrated efficacy in dorsal wound infection models in mice. Encouraged by these findings, we believe that HPs could lead to significant advances in the treatment of challenging infections.
Photo-responsive host-guest complexation directs dynamic covalent condensation of phenyl boronic acid andd-fructose
Klepel, Florian,Ravoo, Bart Jan
supporting information, p. 3207 - 3210 (2021/04/07)
Inspired by the way templates have been used to drive dynamic combinatorial libraries by molecular recognition, we exploited the photo-responsive host-guest interaction of an azo-based photoswitch with permethylated cyclodextrin to reversibly manipulate t
