- Heparin versus DNA: Chiral preferences in polyanion binding to self-assembled multivalent (SAMul) nanostructures
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This communication presents simple cationic self-assembling multivalent (SAMul) first generation dendrons based on l or d lysine, which form identical nanoscale assemblies in terms of dimensions and charge densities but toward which DNA and heparin exhibit different chiral binding preferences. However, higher generation dendrons with larger hydrophilic head groups are bound identically by these polyanions, irrespective of chirality. We propose that well-organized chiral ligands on the surface of self-assembled nanostructures can exhibit enantioselective polyanion binding. This demonstrates that small structural changes can be amplified by self-assembly and impact on nanoscale binding.
- Bromfield, Stephen M.,Smith, David K.
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- PH-sensitive cationic lipopeptides for the design of drug-delivery systems
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Lipopeptides on the basis of L-glutamic acid and glutamine di-and monoesters with aliphatic alcohols of various lengths that contain L-arginine, L-ornithine, and L-lysine were synthesized. The behavior of these amphiphiles in aqueous medium was shown to depend on their structure. Pleiades Publishing, Inc., 2006.
- Sebyakin,Budanova
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- A Collaborative Assembly Strategy for Tumor-Targeted siRNA Delivery
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A novel "collaborative assembly" approach was reported for the synthesis of an siRNA delivery system via a combination of an electrostatically driven physical assembly and a facile click reaction-mediated chemical assembly, which showed various advantages
- Sun, Qiong,Kang, Zisheng,Xue, Lingjing,Shang, Yunkai,Su, Zhigui,Sun, Hongbin,Ping, Qineng,Mo, Ran,Zhang, Can
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- Ynamide-Mediated Thiopeptide Synthesis
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Exploration of the full potential of thioamide substitution as a tool in the chemical biology of peptides and proteins has been hampered by insufficient synthetic strategies for the site-specific introduction of a thioamide bond into a peptide backbone. A novel ynamide-mediated two-step strategy for thiopeptide bond formation with readily available monothiocarboxylic acids as thioacyl donors is described. The α-thioacyloxyenamide intermediates formed from the ynamides and monothiocarboxylic acids can be purified, characterized, and stored. The balance between their activity and stability enables them to act as effective thioacylating reagents to afford thiopeptide bonds under mild reaction conditions. Amino acid functional groups such as OH, CONH2, and indole NH groups need not be protected during thiopeptide synthesis. The modular nature of this strategy enables the site-specific incorporation of a thioamide bond into peptide backbones in both solution and the solid phase.
- Yang, Jinhua,Wang, Changliu,Xu, Silin,Zhao, Junfeng
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supporting information
p. 1382 - 1386
(2019/01/08)
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- Self-assembling tryptophan-based designer peptides as intracellular delivery vehicles
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A series of tryptophan-based peptides W1a, b-W4a, b, with diverse architectures were designed and synthesized. These tryptophan containing peptides can self-assemble to spherical particle. This self-assembled system was demonstrated to encapsulate rhodamine B and penetrate the cell membrane.
- Bhardwaj, Ishanki,Jha, Divya,Admane, Prasad,Panda, Amulya K.,Haridas
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supporting information
p. 672 - 676
(2016/01/09)
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- One-pot orthogonal copper-catalyzed synthesis and self-assembly of l-lysine-decorated polymeric dendrimers
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Synthetic peptides, including cyclic peptides and peptidomimetics, provide stability, protection, and long circulation times compared to free-circulating peptides. Dendritic structures with amino acids or peptides attached to the peripheral layer represent one form of peptidomimetics (i.e., a hybrid peptide/dendrimer construct) that has found use in biological applications. Constructing such dendritic structures from linear polymeric building blocks provides a further advantage of generating a highly ordered and defined structure in the nanoparticle size range. However, the rapid synthesis of such well-defined structures is still a challenge. In this work, we demonstrate that through modulating the copper activity concomitantly of the nitroxide radical coupling (NRC) and the azide-alkyne cycloaddition (CuAAC) reactions, polymeric dendrimers decorated with l-lysine on the periphery could be made rapidly in one pot at 25 °C. Three polymeric dendrimers were constructed with high purity (>94%) and with varying l-lysine density coated on the peripheral generation layer. The self-assembly of these dendrimers in water gave similar sizes to that found in organic solvents, suggesting that the aggregation number of dendritic structures in water was very low and possibly consisting of unimolecular micelles. The findings support the conclusion that the self-assembly of a dendritic architecture in water produces nanoparticles with predictable and well-controlled sizes. This synthetic methodology and the self-assembly properties represent an important step toward synthesizing peptide-decorated dendrimers targeted toward therapeutic applications.
- Lu, Derong,Hossain, Md. D.,Jia, Zhongfan,Monteiro, Michael J.
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p. 1688 - 1702
(2015/03/31)
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- GSH- and pH-responsive drug delivery system constructed by water-soluble pillar[5]arene and lysine derivative for controllable drug release
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Novel GSH- and pH-responsive supramolecular vesicles constructed by an amphiphilic inclusion complex formed from water-soluble pillar[5]arene and lysine derivative have been successfully developed, which can efficiently encapsulate anticancer drug MTZ and show rapid MTZ-release in a simulated acidic tumor environment with high GSH concentration, and exhibit potent antitumor activity.
- Wu, Xuan,Li, Yan,Lin, Chen,Hu, Xiao-Yu,Wang, Leyong
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p. 6832 - 6835
(2015/04/22)
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- Fluorescent dyes
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Chemically reactive carbocyanine dyes that are intramolecularly crosslinked between the 1-position and 3′-position, their bioconjugates and their uses are described. 1,3′-crosslinked carbocyanines are superior to those of conjugates of spectrally similar 1,1′-crosslinked or non-crosslinked dyes. The invention includes derivative compounds having one or more benzo nitrogens.
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Paragraph 0106
(2015/10/05)
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- Facile and universal immobilization of l-lysine inspired by mussels
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A novel functional molecule lysine-dopamine (LDA) was successfully synthesized and explored as a universal modifier for different types of surfaces, inspired by mussel adhesive moiety dopamine and bio-functional moiety l-lysine. The universal, robust, and efficient surface modification based on LDA was achieved through a facile and cost-effective dip-coating process, confirmed by Fourier transform infrared spectroscopy (FTIR), contact angle, X-ray photoelectron spectroscopy (XPS) and scanning electron microscope-energy dispersive spectroscopy (SEM-EDS) measurements. Meanwhile, LDA modification improved cell adhesion, promoted cell growth, and accelerated endothelialization on the substrate surface and provided plasma clot lysis activity. The results indicated that the surface biocompatibility was obviously improved by the one-step modification method for the immobilized l-lysine.
- Sun, Peiyu,Lu, Haoxiang,Yao, Xiong,Tu, Xiaoxiong,Zheng, Zhen,Wang, Xinling
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p. 10035 - 10041
(2012/07/28)
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- Prodrugs comprising an exendin linker conjugate
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The present invention relates to a prodrug or a pharmaceutically acceptable salt thereof comprising an exendin linker conjugate D-L, wherein D represents an exendin moiety; and -L is a non-biologically active linker moiety -L1 represented by formula (I), wherein the dashed line indicates the attachment to one of the amino groups of the exendin moiety by forming an amide bond. The invention further relates to pharmaceutical compositions comprising said prodrugs as well as their use as a medicament for treating or preventing diseases or disorders which can be treated by exendin.
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- Chemical cell-surface receptor engineering using affinity-guided, multivalent organocatalysts
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Catalysts hold promise as tools for chemical protein modification. However, the application of catalysts or catalyst-mediated reactions to proteins has only recently begun to be addressed, mainly in in vitro systems. By radically improving the affinity-guided DMAP (4-dimethylaminopyridine) (AGD) catalysts that we previously reported (Koshi, Y.; Nakata, E.; Miyagawa, M.; Tsukiji, S.; Ogawa, T.; Hamachi, I. J. Am. Chem. Soc.2008, 130, 245.), here we have developed a new organocatalyst-based approach that allows specific chemical acylation of a receptor protein on the surface of live cells. The catalysts consist of a set of 'multivalent DMAP groups (the acyl transfer catalyst) fused to a ligand specific to the target protein. It was clearly demonstrated by in vitro experiments that the catalyst multivalency enables remarkable enhancement of protein acylation efficiency in the labeling of three different proteins: congerin II, a Src homology 2 (SH2) domain, and FKBP12. Using a multivalent AGD catalyst and optimized acyl donors containing a chosen probe, we successfully achieved selective chemical labeling of bradykinin B2 receptor (B2R), a G-protein coupled receptor, on the live cell-surface. Furthermore, the present tool allowed us to construct a membrane protein (B 2R)-based fluorescent biosensor, the fluorescence of which is enhanced (tuned on) in response to the antagonist ligand binding. The biosensor should be applicable to rapid and quantitative screening and assay of potent drug candidates in the cellular context. The design concept of the affinity-guided, multivalent catalysts should facilitate further development of diverse catalyst-based protein modification tools, providing new opportunities for organic chemistry in biological research.
- Wang, Hangxiang,Koshi, Yoichiro,Minato, Daishiro,Nonaka, Hiroshi,Kiyonaka, Shigeki,Mori, Yasuo,Tsukiji, Shinya,Hamachi, Itaru
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supporting information; experimental part
p. 12220 - 12228
(2011/10/04)
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- Oligopeptide delivery carrier for osteoclast precursors
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Dendritic amine and guanidinium group-modified nanoparticles were investigated for the delivery of model peptide drug into primary osteoclast precursor cells (bone marrow macrophages; BMMs). The model peptide drug was encapsulated into the nanoparticle by
- Chi, Bo,Park, So Jeong,Park, Min Hee,Lee, Soo Young,Jeong, Byeongmoon
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experimental part
p. 1473 - 1478
(2011/11/12)
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- ABUSE-RESISTANT AMPHETAMINE PRODRUGS
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The invention describes compounds, compositions, and methods of using the same comprising a chemical moiety covalently attached to amphetamine. These compounds and compositions are useful for reducing or preventing abuse and overdose of amphetamine. These compounds and compositions find particular use in providing an abuse-resistant alternative treatment for certain disorders, such as attention deficit hyperactivity disorder (ADHD), ADD, narcolepsy, and obesity. Oral bioavailability of amphetamine is maintained at therapeutically useful doses. At higher doses bioavailability is substantially reduced, thereby providing a method of reducing oral abuse liability. Further, compounds and compositions of the invention decrease the bioavailability of amphetamine by parenteral routes, such as intravenous or intranasal administration, further limiting their abuse liability.
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Page/Page column 28-29; 2/70
(2008/06/13)
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- STUDIES ON LACTAMS IX. A CONVENIENT SYNTHESIS OF LACTAM RINGS
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The auto-cyclization reaction has been employed for the synthesis of lactam rings by means of reduction from ω-carbobenzoxyamino acid active esters in high dilution method.
- Ogura, Haruo,Takeda, Kazuyoshi
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p. 467 - 468
(2007/10/02)
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