- A Comprehensive Landscape for Fibril Association Behaviors Encoded Synergistically by Saccharides and Peptides
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Nature provides us a panorama of fibrils with tremendous structural polymorphism from molecular building blocks to hierarchical association behaviors. Despite recent achievements in creating artificial systems with individual building blocks through self-
- Liu, Rongying,Zhang, Ran,Li, Long,Kochovski, Zdravko,Yao, Lintong,Nieh, Mu-Ping,Lu, Yan,Shi, Tongfei,Chen, Guosong
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p. 6622 - 6633
(2021/05/29)
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- Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them
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Prostate-specific membrane antigen (PSMA), also known as glutamate carboxypeptidase II (GCPII), is a suitable target for specific delivery of antitumor drugs and diagnostic agents due to its overexpression in prostate cancer cells. In the current work, we describe the design, synthesis, and biological evaluation of novel low-molecular PSMA ligands and conjugates with fluorescent dyes FAM-5, SulfoCy5, and SulfoCy7. In vitro evaluation of synthesized PSMA ligands on the activity of PSMA shows that the addition of aromatic amino acids into a linker structure leads to a significant increase in inhibition. The conjugates of the most potent ligand with FAM-5 as well as SulfoCy5 demonstrated high affinities to PSMA-expressing tumor cells in vitro. In vivo biodistribution in 22Rv1 xenografts in Balb/c nude mice of PSMA-SulfoCy5 and PSMA-SulfoCy7 conjugates with a novel PSMA ligand demonstrated good visualization of PSMA-expressing tumors. Also, the conjugate PSMA-SulfoCy7 demonstrated the absence of any explicit toxicity up to 87.9 mg/kg.
- Machulkin, Aleksei E.,Shafikov, Radik R.,Uspenskaya, Anastasia A.,Petrov, Stanislav A.,Ber, Anton P.,Skvortsov, Dmitry A.,Nimenko, Ekaterina A.,Zyk, Nikolay U.,Smirnova, Galina B.,Pokrovsky, Vadim S.,Abakumov, Maxim A.,Saltykova, Irina V.,Akhmirov, Rauf T.,Garanina, Anastasiia S.,Polshakov, Vladimir I.,Saveliev, Oleg Y.,Ivanenkov, Yan A.,Aladinskaya, Anastasiya V.,Finko, Alexander V.,Yamansarov, Emil U.,Krasnovskaya, Olga O.,Erofeev, Alexander S.,Gorelkin, Petr V.,Dontsova, Olga A.,Beloglazkina, Elena K.,Zyk, Nikolay V.,Khazanova, Elena S.,Majouga, Alexander G.
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supporting information
p. 4532 - 4552
(2021/05/06)
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- A catalytic one-step synthesis of peptide thioacids: the synthesis of leuprorelin via iterative peptide-fragment coupling reactions
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A catalytic one-step synthesis of peptide thioacids was developed. The oxygen-sulfur atom exchange reaction converted the carboxy group at the C-terminus of the peptides into a thiocarboxy group with suppressed epimerization. This method was successfully applied to the synthesis of the peptide drug leuprorelin via an iterative fragment-coupling protocol.
- Matsumoto, Takuya,Sasamoto, Koki,Hirano, Ryo,Oisaki, Kounosuke,Kanai, Motomu
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supporting information
p. 12222 - 12225
(2018/12/01)
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- Synthesis and photochemical reactivity of phthalimidoadamantane–tyrosine conjugates
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Abstract: Dipeptide 3, tetrapeptide 4 and pentapeptide 5, containing adamantylphthalimide and tyrosine, were synthesized and their photochemical reactivity investigated. Upon excitation to the triplet excited state, 3 does not give any photoproduct, although the photoinduced electron transfer (PET) should take place based on the thermodynamic properties. Tetrapeptide 4 and pentapeptide 5 are photochemically reactive, undergoing decomposition upon excitation. The lack of anticipated photodecarboxylation reactivity is explained by PET between the tyrosine and the phthalimide. However, deprotonation of the phenoxyl radical-cation giving phenoxyl radicals or back electron transfer giving starting material are probably faster than intrastrand single electron transfer which would lead to carboxyl radical and decarboxylation. The results indicate the importance of fine-tuning the molecular structure to attain the desired photoreactivity by the right choice of the reactants redox potential, as well as their acid/base properties.
- Sohora, Margareta,Vidovi?, Nikolina,Mlinari?-Majerski, Kata,Basari?, Nikola
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p. 5305 - 5320
(2017/09/23)
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- On the Role of Chirality in Guiding the Self-Assembly of Peptides
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Homochirality in peptides is crucial in sustaining “like–like” intermolecular interactions that allow the formation of assemblies and aggregates and is ultimately responsible for the resulting material properties. With the help of a series of stereoisomer
- Basak, Shibaji,Singh, Ishwar,Ferranco, Annaleizle,Syed, Jebreil,Kraatz, Heinz-Bernhard
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p. 13288 - 13292
(2017/10/07)
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- Peptide based hydrogels for cancer drug release: Modulation of stiffness, drug release and proteolytic stability of hydrogels by incorporating d-amino acid residue(s)
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Synthetic tripeptide based noncytotoxic hydrogelators have been discovered for releasing an anticancer drug at physiological pH and temparature. Interestingly, gel stiffness, drug release capacity and proteolytic stability of these hydrogels have been suc
- Basu, Kingshuk,Baral, Abhishek,Basak, Shibaji,Dehsorkhi, Ashkan,Nanda, Jayanta,Bhunia, Debmalya,Ghosh, Surajit,Castelletto, Valeria,Hamley, Ian W.,Banerjee, Arindam
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p. 5045 - 5048
(2016/04/19)
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- Building Nanowires from Micelles: Hierarchical Self-Assembly of Alternating Amphiphilic Glycopolypeptide Brushes with Pendants of High-Mannose Glycodendron and Oligophenylalanine
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Mimicking the diverse glyco-conjugate structures in nature is always the dream of scientists. Right now, hierarchical self-assembled structures of natural conjugates of peptides and sugars could not easily be achieved via linear glycopolypeptide with mono
- Liu, Yijiang,Zhang, Yufei,Wang, Zheyu,Wang, Jue,Wei, Kongchang,Chen, Guosong,Jiang, Ming
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p. 12387 - 12394
(2016/10/09)
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- NOVEL SHORT-CHAIN PEPTIDES AS KAPPA (κ) OPIOID RECEPTORS (KOR) AGONIST
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The present invention relates to novel short-chain peptides of the general formula (I), which are selective and peripherally acting KOR agonist, their tautomeric forms, their enantiomers, their diastereoisomers, their stereoisomers, their pharmaceutically
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- Redox-triggered changes in the self-assembly of a ferrocene-peptide conjugate
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Ultrasonication of a ferrocene conjugate of a short amyloid peptide (Aβ18-20) in toluene causes formation of an organogel, which undergoes dramatic structural changes upon oxidation from a nanofibrillar network to spherical micelles. This morphological change is redox-controlled and reversible. the Partner Organisations 2014.
- Adhikari, Bimalendu,Kraatz, Heinz-Bernhard
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p. 5551 - 5553
(2014/05/20)
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- A synthetic amino acid residue containing a new oligopeptide-based photosensitive fluorescent organogel
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A synthetic amino acid (with a stilbene residue in the main chain) containing a tripeptide-based organogelator has been discovered. This peptide-based synthetic molecule 1 self-assembles in various organic solvents to form an organogel. The gel has been thoroughly characterized by using various microscopic techniques including field-emission scanning electron microscopy (FESEM), atomic force microscopy (AFM), X-ray diffraction (XRD), UV-visible and fluorescence spectroscopy, and rheology. Morphological investigations using FESEM and AFM show a nanofibrillar network structure. Interestingly, the organogel is photoresponsive and a gel-sol transition occurred by irradiating the gel with UV light of 365 nm for 2 h as shown by the UV and fluorescence study. This photoresponsive fluorescent gel holds promise for new peptide-based soft materials with interesting applications. Copyright
- Maiti, Dibakar Kumar,Banerjee, Arindam
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p. 113 - 120
(2013/02/26)
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- Epimerization-free C-terminal peptide activation
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Smooth operation: C-terminal peptide activation with full stereointegrity was accomplished using a copper(II)-mediated coupling reaction of carboxylic acids with arylboroxines (see scheme, NCL = native chemical ligation, Boc = tert-butoxycarbonyl). This method allows epimerization-free activation and ligation of peptides with racemization-prone phenylglycine at the C terminus.
- Popovic, Stanimir,Bieraeugel, Hans,Detz, Remko J.,Kluwer, Alexander M.,Koole, Jelmer A. A.,Streefkerk, Dieuwertje E.,Hiemstra, Henk,Van Maarseveen, Jan H.
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supporting information
p. 16934 - 16937
(2014/01/06)
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- Spacer driven morphological twist in Phe-Phe dipeptide conjugates
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Chemists and material scientists are interested in complex biological systems and morphologies for fabrication of new materials. Bioinspired design of short peptide conjugates produces various self-assembled structures, depending on their structural diver
- Ghosh, Surajit,Adler-Abramovich, Lihi,Gazit, Ehud,Verma, Sandeep
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p. 2004 - 2009
(2013/03/13)
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- Photo-induced charge-transfer complex formation and organogelation by a tripeptide
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A terminally protected tripeptide Boc-Phe-Phe-Tyr-OMe 1 and picric acid form a photo induced charge-transfer complex and organogels. The interactions between stacked aromatic units play a key role in the assembly process. UV light (366 nm) has been used a
- Jana, Poulami,Maity, Sibaprasad,Maity, Suman Kumar,Ghorai, Pradip Kumar,Haldar, Debasish
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p. 5621 - 5628
(2012/08/14)
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- PEG prodrug of gambogic acid: Amino acid and dipeptide spacer effects
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The clinical application of gambogic acid (GA), a natural component with promising antitumor activity, was limited due to its extremely poor aqueous solubility, rapid elimination in vivo, and wide biodistribution. To solve these problems, 30 poly(ethylene
- Ding, Ya,Zhang, Peng,Tang, Xiao-Yan,Zhang, Can,Ding, Song,Ye, Hai,Ding, Qi-Long,Shen, Wen-Bin,Ping, Qi-Neng
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p. 1694 - 1702
(2012/08/08)
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- Supramolecular hydrogelators of N-terminated dipeptides selectively inhibit cancer cells
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Consisting of N-terminated diphenylalanine, a new type of supramolecular hydrogelators forms hydrogels within a narrow pH window (pH 5.0 to 6.0) and selectively inhibits growth of HeLa cells, which provides important and useful insights for designing molecular nanofibers as potential nanomedicines. The Royal Society of Chemistry 2011.
- Kuang, Yi,Gao, Yuan,Xu, Bing
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supporting information; experimental part
p. 12625 - 12627
(2012/01/12)
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- Multigram-scale synthesis of short peptides via a simplified repetitive solution-phase procedure
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(Chemical Equation Presented) A rapid repetitive solution-phase synthesis of peptides is described. The procedure involves coupling of amino acids and peptide acids, instead of the usual amino esters and peptide esters, to slight excesses of pentafluoroph
- Meneses, Celia,Nicoll, Sarah L.,Trembleau, Laurent
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supporting information; experimental part
p. 564 - 569
(2010/04/29)
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- Design, synthesis and inhibition activity of novel cyclic peptides against protein tyrosine phosphatase A from Mycobacterium tuberculosis
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Mycobacterium tuberculosis, the causative agent for tuberculosis has employed several signalling molecules to sense the host cellular environment and act accordingly. For example, protein tyrosine phosphatase A (MPtpA) of M. tuberculosis, a signalling pro
- Chandra, Koushik,Dutta, Debajyoti,Das, Amit K.,Basak, Amit
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supporting information; scheme or table
p. 8365 - 8373
(2011/02/25)
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- Fabrication of luminescent cds nanoparticles on short-peptide-based hydrogel nanofibers: Tuning of Optoelectronic Properties
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The pH-induced self-assembly of three synthetic tripeptides in water medium is used to immobilize luminescent CdS nanoparticles. These peptides form a nanofibrillar network structure upon gelation in aqueous medium at basic pH values (pH 11.013.0), and th
- Palui, Goutam,Nanda, Jayanta,Ray, Sudipta,Banerjee, Arindam
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supporting information; experimental part
p. 6902 - 6909
(2010/03/02)
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- Biomimetic catalysis of diketopiperazine and dipeptide syntheses
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Modular supramolecular catalysts with a coiled-coil peptide scaffold, designed to mimic nonribosomal peptide synthetases, catalyze the formation of diketopiperazines and linear dipeptides for several aminoacyl substrates (see scheme). The nature of the ac
- Huang, Zheng-Zheng,Leman, Luke J.,Ghadiri, M. Reza
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supporting information; experimental part
p. 1758 - 1761
(2009/02/06)
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- Design and synthesis of a novel class of furan-based molecules as potential 20S proteasome inhibitors
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A novel class of furan-based compounds as potential 20S proteasome inhibitors have been designed and synthesized, among which nine compounds are peptide derivatives and six molecules are statine peptidomimetics. The C-terminal furanyl moiety was introduced to target molecules as furan-based amino acids. All the compounds were obtained steadily with moderate to high yield. Compound 12 was a selective moderate potent proteasome peptidomimetic inhibitor. It inhibited HepG2 and HL-60 proliferation effectively.
- Fu, Yiqiu,Xu, Bo,Zou, Xiaomin,Ma, Chao,Yang, Xiaoming,Mou, Ke,Fu, Gang,Lue, Yang,Xu, Ping
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p. 1102 - 1106
(2007/10/03)
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- Functional and mechanistic analyses of biomimetic aminoacyl transfer reactions in de novo designed coiled coil peptides via rational active site engineering
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Ribosomes and nonribosomal peptide synthetases (NRPSs) carry out instructed peptide synthesis through a series of directed intermodular aminoacyl transfer reactions. We recently reported the design of coiled-coil assemblies that could functionally mimic t
- Leman, Luke J.,Weinberger, Dana A.,Huang, Zheng-Zheng,Wilcoxen, Keith M.,Ghadiri, M. Reza
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p. 2959 - 2966
(2007/10/03)
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- Synthesis and characterization of peptide-cationic steroid antibiotic conjugates
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(Chemical Equation Presented) New cationic steroid antibiotics have been prepared by conjugating tripeptides to a triamino analogue of cholic acid. These compounds were synthesized on a solid phase in an indexed library that was screened for antibacterial
- Ding, Bangwei,Taotofa, Uale,Orsak, Thomas,Chadwell, Matthew,Savage, Paul B.
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p. 3433 - 3436
(2007/10/03)
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- METHODS AND COMPOSITIONS FOR TREATING AMYLOID-RELATED DISEASES
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Methods, compounds, pharmaceutical compositions and kits are described for treating or preventing amyloid-related disease.
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Page 158; 159
(2008/06/13)
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- Phenylhydrazide as an enzyme-labile protecting group in peptide synthesis
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The enzymatic cleavage of amino acid phenylhydrazides with the enzyme tyrosinase (EC 1.14.18.1) offers a new, mild, and selective method for C-terminal deprotection of peptides. The advantages of the described methodology are the very mild oxidative removal of the protecting group at room temperature and pH 7, a high chemo- and regioselectivity, and the availability of the biocatalyst. Even in oxygen-saturated solution, the oxidation of sensitive methionine residues was not observed. These features make the methodology suitable for the synthesis of sensitive peptide conjugates. Mechanistic data suggest that the hydrolysis of the oxidized adducts proceeds by a free-radical mechanism.
- Voelkert, Martin,Koul, Surrinder,Mueller, Gernot H.,Lehnig, Manfred,Waldmann, Herbert
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p. 6902 - 6910
(2007/10/03)
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- Application of AlMe3-mediated amidation reactions to solution phase peptide synthesis
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A practical modification of the Weinreb amidation protocol employing amino acids as the amine reaction partner has been developed that allows for the facile synthesis of oligopeptides in solution.
- Martin, Stephen F.,Dwyer, Michael P.,Lynch, Christopher L.
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p. 1517 - 1520
(2007/10/03)
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- Enzymatische Synthese von Peptiden und Ras-Lipopeptiden unter Verwendung des Cholinesters als loeslichkeitsvermittelnder Schutz- und Aktivierungsgruppe
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Keywords: Cholinesterase; Enzymkatalyse; Peptidsynthesen; Ras-Proteine
- Schelhaas, Michael,Glomsda, Simone,Haensler, Marion,Jakubke, Hans-Dieter,Waldmann, Herbert
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- Synthesis and biological activity of peptide hydroxamate inhibitors of degradation of substance P analogues
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A series of hydroxamic acid derivatives of peptides related to fragments of substance P (SP) were synthesized.Methyl, ethyl or N-hydroxy-succinimide ester precursors of the desired peptides were prepared by using classical peptide synthesis methodology an
- Ewenson, A,Laufer, R,Frey, J,Chorev, M,Selinger, Z,Gilon, C
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p. 179 - 186
(2007/10/02)
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- Diacylamines - Perfect Acylating Agents for Peptide Synthesis
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A new series of diacylamines containing N-protected amino acids have been synthesized.These diacylamines, possessing ortho-substituted benzoyl groups were found to be excellent acylating agents for peptide synthesis.In this reaction the 2,6-dichlorobenzoy
- Gruszecki, Wojciech,Gruszecka, Maria,Bradaczek, Hans
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p. 331 - 336
(2007/10/02)
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