13122-90-2Relevant articles and documents
Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them
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.
supporting information, p. 4532 - 4552 (2021/05/06)
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.
A Comprehensive Landscape for Fibril Association Behaviors Encoded Synergistically by Saccharides and Peptides
Liu, Rongying,Zhang, Ran,Li, Long,Kochovski, Zdravko,Yao, Lintong,Nieh, Mu-Ping,Lu, Yan,Shi, Tongfei,Chen, Guosong
supporting information, p. 6622 - 6633 (2021/05/29)
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-
A catalytic one-step synthesis of peptide thioacids: the synthesis of leuprorelin via iterative peptide-fragment coupling reactions
Matsumoto, Takuya,Sasamoto, Koki,Hirano, Ryo,Oisaki, Kounosuke,Kanai, Motomu
supporting information, p. 12222 - 12225 (2018/12/01)
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.
On the Role of Chirality in Guiding the Self-Assembly of Peptides
Basak, Shibaji,Singh, Ishwar,Ferranco, Annaleizle,Syed, Jebreil,Kraatz, Heinz-Bernhard
supporting information, p. 13288 - 13292 (2017/10/07)
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
Synthesis and photochemical reactivity of phthalimidoadamantane–tyrosine conjugates
Sohora, Margareta,Vidovi?, Nikolina,Mlinari?-Majerski, Kata,Basari?, Nikola
, p. 5305 - 5320 (2017/09/23)
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.
NOVEL SHORT-CHAIN PEPTIDES AS KAPPA (κ) OPIOID RECEPTORS (KOR) AGONIST
-
Page/Page column 32, (2016/12/01)
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
Peptide based hydrogels for cancer drug release: Modulation of stiffness, drug release and proteolytic stability of hydrogels by incorporating d-amino acid residue(s)
Basu, Kingshuk,Baral, Abhishek,Basak, Shibaji,Dehsorkhi, Ashkan,Nanda, Jayanta,Bhunia, Debmalya,Ghosh, Surajit,Castelletto, Valeria,Hamley, Ian W.,Banerjee, Arindam
supporting information, p. 5045 - 5048 (2016/04/19)
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
Building Nanowires from Micelles: Hierarchical Self-Assembly of Alternating Amphiphilic Glycopolypeptide Brushes with Pendants of High-Mannose Glycodendron and Oligophenylalanine
Liu, Yijiang,Zhang, Yufei,Wang, Zheyu,Wang, Jue,Wei, Kongchang,Chen, Guosong,Jiang, Ming
supporting information, p. 12387 - 12394 (2016/10/09)
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
Redox-triggered changes in the self-assembly of a ferrocene-peptide conjugate
Adhikari, Bimalendu,Kraatz, Heinz-Bernhard
supporting information, p. 5551 - 5553 (2014/05/20)
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.
A synthetic amino acid residue containing a new oligopeptide-based photosensitive fluorescent organogel
Maiti, Dibakar Kumar,Banerjee, Arindam
supporting information, p. 113 - 120 (2013/02/26)
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