Jan Jezek

Jan Jezek
Institute of Organic Chemistry and Biochemistry of the CAS · Theoretical chemistry

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68
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Introduction
Skills and Expertise

Publications

Publications (68)
Chapter
The Possible biological applications of dendrimers stem from their capacity to influence the cell–cell interactions. These interactions are mediated by branched glycoconjugates forming a structure called glycocalyx present on the cell surface. Glycopeptide dendrimers, which can mimic these structures, thus can be used for detection of important pla...
Chapter
Dendrimers, as hyperbranched synthetic well-defined molecules, have been suggested as potential antivirals from several reasons, such as their small sizes (nanometers) and their ease of preparation and functionalization. Importantly they can be potent inhibitors of virus–cell interactions due to their multivalency and capacity to display multiple c...
Chapter
Basic terms and nomenclature of dendrimers are discussed. Till now, there is not one simple, unambiguous, generally applicable and worldwide acceptable dendrimer nomenclature, like IUPAC-IUB rules, which must be respected in every journal. This chapter explains basic terms of dendrimeric field: dendriplexes, dendrisomes, dendrigraft, glycotope, gly...
Chapter
Carbohydrates are expressed on majority of mammalian cell surfaces. They are bound to glycoproteins, proteins, and glycolipids, or to different cellular constituents, e.g. proteoglycans that are part of the cell membrane in clustered and multiantennary structures. These oligosaccharides represent signal transductors between extra- and intracellular...
Chapter
Various dendrimers can play enormous role in cancer research, diagnosis and treatment. Glycopeptide or peptide dendrimers containing different types of tumor-associated carbohydrate or peptide antigens have been intensively studied for their use as diagnostic or therapeutic tools. Dendrimers possess a great potential that can be utilized in antitum...
Chapter
The terms of toxicity and biocompatibility of dendrimers are closely related. For biomedical applications, dendrimers should be devoid of toxicity and immunogenicity. The first concept—“toxicity”—is mainly applied by pharmacompanies for description of adverse effects to cells, organs, or patients. The second concept—“biocompatibility”—belongs to th...
Chapter
Dendrimers can be prepared by both convergent and divergent approaches. In the convergent approach, first suitable building blocks are prepared and then connected by lego chemistry, ligations or click chemistry. In the divergent approach, the synthesis is done stepwise. The advantage of convergent synthesis is greater difference between product and...
Chapter
Various methods of dendrimers characterization have been elaborated such as NMR, electron paramagnetic resonance, mass spectrometry, UV–VIS spectrometry, time-resolved and nonlinear optical spectroscopy, laser light scattering, optical rotation, circular dichroism, synchrotron radiation-based circular dichroism, IR, Raman, fluorescence, X-ray diffr...
Chapter
Before 1984, three classes of macromolecular architecture (i.e. linear, cross-linked, and branched) were widely accepted for construction of relatively polydisperse products of different molecular weights. Since that year, the “dendritic state” is acknowledged as a new, fourth class of polymer architecture. It can be divided to five subclasses: ran...
Chapter
Peptide, glyco, and glycopeptide dendrimers, capable of binding bacterial polysaccharides, represent attractive tools both for the therapy and for the diagnostics of the diseases of bacterial etiology. Finding new antibacterial drugs, as well as diagnostic tools, is nowadays of particular importance due to enhanced resistance of bacteria toward com...
Chapter
The vast majority of signal transduction processes in most living organisms are caused by four sorts of biomolecules: nucleic acids, proteins, glycoconjugates and lipids. The sequence and structure of nucleic acids, as well as, peptides and proteins have been extensively studied, including different sorts of interactions and functions. Genomics, pr...
Chapter
Solubility is a key property influencing behavior of compounds in nature, science, biomedical applications, etc. Hydrophobicity and poor solubility of drugs and other bioactive compounds limit their possible applications in drug delivery and formulation development. Therefore approximately 40 % of newly developed drugs are rejected by the pharmaceu...
Chapter
Thanks to variable structures and properties, dendrimers are attractive for catalytic applications. They can act as catalytically active species, as well as, soluble supports onto which catalytically active species can be attached. Different sorts of dendrimer-encapsulated nanoparticles are used both in homogeneous and in heterogeneous catalysis. E...
Chapter
It is a difficult task to create a simple, universal, clear, unambiguous, logical, and generally applicable classification or even nomenclature of different sorts of dendrimers. In general, dendrimers contain a core, branches, and surface functional groups. Sometimes the core is missing (e.g., MAPs), or the branches are missing (RAFTs). The classif...
Chapter
Dendrimers can serve also as antiparasitic tools. They can serve for vaccination, as well as, for specific delivery of toxic cargos. As examples, applications of dendrimers for treatment of various diseases caused by Schistosoma mansoni, Fasciola gigantica, Plasmodium falciparum, and Leishmania spp. are briefly mentioned.
Chapter
Due to low affinity of interactions between carbohydrate receptors and modified oligosaccharides, glycopeptides have been explored as alternative mimetics. Glycopeptides are superior ligands with higher affinity for a receptor than the natural carbohydrate ligands.The epoch of peptide libraries started in the late 1980s. The synthesis, functional s...
Chapter
Dendritic macromolecules and dendrimers, pioneered in the 1980s, represent a dynamically expanding area spanning from physics, chemistry, and biology to a broad field of biomedical applications. Dendrimers interpenetrate to till now isolated areas of science and create an interconnected, logical, mutually influencing scientific network, the dendrim...
Article
The size of information that can be stored in nucleic acids, proteins, and carbohydrates was calculated. The number of hexamers for peptides is 64,000,000 (20(6)) and seems to be impressive in comparison with 4,096 (4(6)) hexanucleotides, but the number of isomers of hexasaccharides is 1.44 × 10(15). Carbohydrates are therefore the best high-densit...
Article
Full-text available
The recently described antimicrobial peptide melectin (MEP, GFLSILKKVLPKVMAHMK-NH2) exhibits high antimicrobial activity against Gram-positive and Gram-negative bacteria. Here we describe the synthesis and biological activities of 23 new analogues of MEP. We studied the influence of dimerization and tetramerization (MAP-constructs of MEP) on the an...
Article
Synthetic study on cystinyl peptides using solution and solid phase methodology was carried out with the central hinge region of immunoglobulin IgG1. In the solid phase synthesis of hexadecapeptide 1c, the time necessary for the formation of disulfide bonds between linear precursors was shortened four times by the action of pure oxygen in buffered...
Article
Glycopeptide dendrimers containing different types of tumor associated-carbohydrate antigens (T(N), TF, sialyl-T(N), sialyl-TF, sialyl-Le(x), sialyl-Le(a) etc.) were used in diagnosis and therapy of different sorts of cancer. These dendrimeric structures with incorporated T-cell epitopes and adjuvants can be used as antitumor vaccines. Best results...
Article
Glycopeptide dendrimers are regularly branched structures containing both carbohydrates and peptides. Various types of these compounds differing in composition and structure are mentioned, together with their practical use spanning from catalysis, transport vehicles to synthetic vaccines. This Part II (for Part I see JeZek J, et al., J. Pept. Sci....
Article
Glycopeptide dendrimers are branched structures containing both carbohydrates and peptides. Various classes of these compounds differing in composition and structure are mentioned, together with their practical use spanning from catalysis, transport vehicles to synthetic vaccines. The main stress is given to glycopeptide dendrimers, namely multiple...
Article
Sheep fasciolosis is a devastating burden for the livestock industry. We herein report on immunodiagnosis of fasciolosis, and significant protection of sheep against challenge infection with Fasciola gigantica following immunization with a peptide based on the H-Asp(110)-Lys-Ile-Asp-Trp-Arg-Glu-Ser-Gly-Tyr-Val-Thr-Glu-Val(123)-OH (Fas14p) sequence...
Article
In this paper, we present the detailed synthetic protocol and characterization of Fmoc-Lys(Pac)-OH, its use for the preparation of octapeptides H-Gly-Phe-Tyr-N-MePhe-Thr-Lys(Pac)-Pro-Thr-OH and H-Gly-Phe-Phe-His-Thr-Pro-Lys(Pac)-Thr-OH by solid-phase synthesis, trypsin-catalyzed condensation of these octapeptides with desoctapeptide(B23-B30)-insuli...
Article
Propeptide blocks the active site in the inactive zymogen of cathepsin D and is cleaved off during zymogen activation. We have designed a set of peptidic fragments derived from the propeptide structure and evaluated their inhibitory potency against mature cathepsin D using a kinetic assay. Our mapping of the cathepsin D propeptide indicated two dom...
Article
Dendrimers are branched structures and represent a fast growing field covering many areas of chemistry. Various types of dendrimers differing in composition and structure are mentioned, together with their practical use spanning from catalysis, transport vehicles to synthetic vaccines. The main stress is given to peptide dendrimers, namely, multipl...
Article
Glycopeptide dendrimers containing different types of tumor associated-carbohydrate antigens (T(N), TF, sialyl-T(N), sialyl-TF, sialyl-Le(x), sialyl-Le(a) etc.) were used in diagnosis and therapy of different sorts of cancer. These dendrimeric structures with incorporated T-cell epitopes and adjuvants can be used as antitumor vaccines. Best results...
Article
Glycodendrimers bearing Tn (alpha-D-GalNAc-(1 --> O)-Ser/Thr), an identified tumor-associated carbohydrate antigen, hold promise in the post-surgery treatment of a variety of tumors such as metastatic breast cancer. We used molecular dynamics (MD) techniques to examine structural differences taking place during synthesis of two classes of tetravale...
Article
Four monoepitopic MAPs (MAP A, B, C and E) and one bis-diepitopic MAP B-E derived from the primary sequence of Schistosoma mansoni glyceraldehyde 3-phosphate dehydrogenase, previously tested in BALB/c mice, were examined for their immunogenicity and protective capacity in C57BL/6 mice. Despite multimerization into MAPs, MAP A and MAP C were poorly...
Article
Six peptides, A, B1, B, C, D and E derived from the primary sequence of Schistosoma mansoni glyceraldehyde 3-phosphate dehydrogenase (SG3PDH) were selected based on lowest homology to human G3PDH and used for immunization of BALB/c mice. Peptides B1 and D induced immunoglobulin (Ig) G1, IgG2a and IgG2b antibodies that reacted with native and denatu...
Article
Schistosoma mansoni glyceraldehyde 3-phosphate dehydrogenase (SG3PDH) is a target of cellular and humoral immune responses of Brazilian and Egyptian subjects putatively resistant to reinfection with S. mansoni. In an aim to develop a safe, stable and effective vaccine based on this promising molecule, six peptides derived from its primary sequence...
Article
Glycopeptide dendrimers are branched structures containing both carbohydrates and peptides. Various classes of these compounds differing in composition and structure are mentioned, together with their practical use spanning from catalysis, transport vehicles to synthetic vaccines. The main stress is given to glycopeptide dendrimers, namely multiple...
Article
MN/CA IX is a cell surface protein, strongly associated with several types of human carcinomas. It exerts activity of carbonic anhydrase and capacity of binding to cell surface receptors. In the present work, we used affinity purified MN/CA IX protein to demonstrate that the cells adhere to immobilized MN/CA IX and that the monoclonal antibody M75...
Article
Recent progress in peptide and glycopeptide chemistry make the preparation of peptide and glycopeptide dendrimers of acceptable purity, with designed structural and immunochemical properties reliable. New methodologies using unprotected peptide building blocks have been developed to further increase the possibilities of their design and improve the...
Article
Recent progress in peptide and glycopeptide chemistry make the preparation of peptide and glycopeptide dendrimers of acceptable purity, with designed structural and immunochemical properties reliable. New methodologies using unprotected peptide building blocks have been developed to further increase possibilities of their design and improve their p...
Article
Protection from undesirable effects of radiotherapy or chemotherapy, primarily from myelosuppression, remains still a crucial problem to be studied. Attention has been therefore paid to various immunomodulatory agents that through the monocyte/macrophage system induced production of cytokines, which can induce and operate restoration of haemopoiesi...
Article
Silver triflate-promoted condensation of 3,4,6-tri-O-acetyl-2-deoxy-2- phthalimido-beta-D-glucopyranosyl bromide (1) with benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O- (methoxycarbonyl)methyl-alpha-D-glucopyranoside (4) afforded the key compound, benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O- (methoxy-carbonyl)methyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phth...
Article
With the aim of synthesizing cyclic antagonists of the nonapeptide hormone bradykinin with minimal side chain modification, we performed backbone to backbone and backbone to side chain cyclization. To probe and compare different strategies for this new kind of cyclization, the branched peptide bonds were formed by both reductive alkylation on the s...
Article
Full-text available
Parallel simultaneous synthesis of fifty linear peptides has been carried out in order to compare in detail two promising methodologies of simultaneous multiple peptide synthesis (SMPS): the "T bag" method, utilizing 4-methyl-benzhydrylamine resin (MeBHA), and synthesis on derivatized Fmoc-Gly-O-cotton fabric strips. The basic set of experiments, w...
Article
An alternative synthesis of the known title compound (VIII), an agent exhibiting high immunoadjuvant activity, starts from the benzoylation product (Ib) of the readily available normuramate (Ia).
Article
Full-text available
Rabbits were immunized with a synthetic octadecapeptide corresponding to the sequence ser-91 to leu-108 of the haemagglutinin heavy chain of H3N2 influenza A viruses. They developed antibodies reactive in solid-phase radioimmunoassay (SPRIA) with the peptide and with haemagglutinins of various H3N2 viruses but not of heterotypic H1N1 and H2N2 virus...
Article
A series of 25 synthetic subunits or analogues of streptococcal peptidoglycan was tested for their ability to damage rabbit blood platelets. The morphological changes of the platelets were studied on an ultrastructural level. Minimal subunit structure able to produce a complete lysis of the platelets was found to be muramyldipeptide (MDP). Comparab...
Article
Each of a series of synthetic peptidoglycan subunits and subunit analogues was injected in combination with streptococcus type M24 antigen extract. The substances tested were: (8a) N-acetylmuramyldipeptide (MDP) and the following derivatives thereof: MDP modified in positions C3 and C4, or with L-alanine substituted by L-2-aminobutyric acid or with...
Article
Treatment with synthetic MDP inhibited growth of transplantable, chemically induced tumors in syngeneic mice. The tumor-inhibitory effect was dependent on the schedule of MDP administration. Growth of SC transplants of a nonmetastasizing, MC-induced fibrosarcoma, MC11, was inhibited by local treatment with 200 μg and 1,000 μg MDP given SC 5–7 weeks...
Article
Die Titelverbindung bzw. das Amid (Vb) wird unter Verwendung der Komponenten (I)-(IV) nach der Festphasenmethode [-+ (Va); nachfolgende Deblockierung] synthetisiert.
Article
Die Titelverbindungen (IX), (Xa) bzw. (Xb), über deren biologische Untersuchungsergebnisse noch gesondert berichtet wird, werden synthetisiert: Die Aminozucker (I) bzw. (IV) werden in die Derivate (III) bzw. (VIa), (VIb) übergeführt; Kondensation von (III) mit dem Peptidamin (VII) [(VIII)] und nachfolgende Deblockierung geben (IX).
Article
A series of synthetic subunits and analogues of streptococcal peptidoglycan was prepared and used in fever and tolerance experiments on rabbits. The lengthening of the chain of the peptide moiety of peptidoglycan did not result in pyrogenic activity, except for hexapeptide. Attachment of the muramyl residue rendered the peptides pyrogenic. The acti...
Article
Synthetic MDP administered in an aqueous medium at relatively high doses stimulates non-specific and specific tumour immunity. Non-specific inhibition of tumour growth was observed in B10 mice injected with 1 mg of MDP 14 days before transplantation of 3-Mc-induced sarcoma cells. Muramyl dipeptide in an aqueous medium increases specific tumour immu...
Article
The immunoadjuvant activity of muramyl dipeptide seems to be critically dependent on the type of substitution of the gamma-carboxyl group of the D-isoglutamine residue. Moreover the nonapeptide L-Ala-D-isoGlu-L-lys-D-Ala-(Gly)5-OME also shows a definite effect.

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