{"title":"[A convenient approach to the synthesis of the phosphoramidite non-nucleotide monomers for the preparation of functionalized oligonucleotide derivatives].","authors":"M S Kopriushkin, D V Pyshnyĭ","doi":"","DOIUrl":"","url":null,"abstract":"<p><p>A simple approach to the synthesis of phosphoramidite synthons for non-nucleotide inserts using 4-(2-(4,4'-dimethoxytrityloxy)ethyl)morpholine-2,3-dione as a key precursor is suggested. Using the method developed various inserts have been introduced into oligonucleotides to obtain intercalator-containing (acridine) as well as branched oligonucleotides.</p>","PeriodicalId":9325,"journal":{"name":"Bioorganicheskaia khimiia","volume":"38 6","pages":"745-9"},"PeriodicalIF":0.0,"publicationDate":"2012-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"40242828","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"[Oligonucleotide derivatives in the nucleic acid hybridization analysis. III. Synthesis and investigation of properties of oligonucleotides, bearing bifunctional non-nucleotide insert].","authors":"M S Kupriushkin, D V Pyshnyĭ","doi":"","DOIUrl":"","url":null,"abstract":"<p><p>Non-nucleotide phosporamidites were synthetized, having branched backbone with different position of functional groups. Obtained phosphoramidite monomers contain intercalator moiety--6-chloro-2-methoxyacridine, and additional hydroxyl residue protected with dimethoxytrityl group or with tert-butyldimethylsilyl group for post-synthetic modification. Synthesized oligothymidilates contain one or more modified units in different positions of sequence. Melting temperature and thermodynamic parameters of formation of complementary duplexes formed by modified oligonucleotides was defined (change in enthalpy and entropy). The introduction of intercalating residue causes a significant stabilization of DNA duplexes. It is shown that the efficiency of the fluorescence of acridine residue in the oligonucleotide conjugate significantly changes upon hybridization with DNA.</p>","PeriodicalId":9325,"journal":{"name":"Bioorganicheskaia khimiia","volume":"38 6","pages":"706-20"},"PeriodicalIF":0.0,"publicationDate":"2012-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"40242822","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"[Binding of human serum low-density lipoprotein cholesterol in vitro by sulfated pectin derivatives].","authors":"F V Vitiazev, N M Paderin, V V Golovchenko","doi":"","DOIUrl":"","url":null,"abstract":"<p><p>The ability to bind human serum LDL-C in vitro by the native pectins is lower than that of their sulfation derivatives. The number of sulfate groups and molecular weight of the sulfated derivatives are assumed to be crucial factors. The sulfated derivatives of pectin with molecular weight above 200 kDa containing 45 wt % sulfate groups possess the highest ability to bind atherogenic lipids, the lowest activity was estimated for the derivatives with molecular weight below 50 kDa containing 5 wt % of sulfate groups.</p>","PeriodicalId":9325,"journal":{"name":"Bioorganicheskaia khimiia","volume":"38 3","pages":"365-9"},"PeriodicalIF":0.0,"publicationDate":"2012-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"30922912","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
D A Andriianova, G P Smirnova, L A Galanina, E P Feofilova, A I Usov
{"title":"[Polysaccharides of the fungus Cunninghamella japonica mycelium].","authors":"D A Andriianova, G P Smirnova, L A Galanina, E P Feofilova, A I Usov","doi":"","DOIUrl":"","url":null,"abstract":"<p><p>Preliminary data on the polysaccharide composition of mycelium of the submerged grown fungus Cunninghamella japonica (synonymous with C. echinulata) were obtained. Mild acid hydrolysis of the mycelium led to formation of glucose, mannose and galactose, whereas acid treatment under drastic conditions afforded glucosamine as the hydrolysis product of chitin and chitosan, the summary content of both glucosaminoglycans being estimated as about 35%. Sequential treatment of the mycelium with hot water, 2% aqueous NaOH and 10% AcOH gave rise to several polysaccharide fractions, which were characterized by their monosaccharide composition. The yield ofchitosan extracted by AcOH was negligible. Additional purification of the fraction obtained by the action of alkali afforded a polysaccharide preparation, which was shown to be a linear (1-->3)-alpha-D-glucopyranan according to the data of chemical methods of structural analysis and NMR spectroscopy. It was concluded that Cunninghamella japonica differs from several other known representatives of Mucorales by the presence of this alpha-D-glucan, as well as by low content of chitosan and polyuronides.</p>","PeriodicalId":9325,"journal":{"name":"Bioorganicheskaia khimiia","volume":"38 2","pages":"251-6"},"PeriodicalIF":0.0,"publicationDate":"2012-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"30759940","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
D V Ianvarev, A N Korovina, N N Usanov, S N Kochetkov
{"title":"[Non-hydrolysable analogs of inorganic pyrophosphate as inhibitors of hepatitis C virus RNA-dependent RNA-polymerase].","authors":"D V Ianvarev, A N Korovina, N N Usanov, S N Kochetkov","doi":"","DOIUrl":"","url":null,"abstract":"<p><p>Inorganic pyrophosphate (PPi) is a product of the polymerization reaction catalyzed by DNA- and RNA-polymerases. We have synthesized a number of novel non-hydrolysable PPi analogues, some of them have demonstrated inhibition of polymerization reaction catalyzed by hepatitis C virus RNA-dependent RNA-polymerase (NS5B). A new pharmacophore has been developed based on non-hydrolysable methylene-diphosphonate backbone. Structure-activity relationship analysis of 12 bisphosphonates is presented and structural features crucial for the ability of molecule to inhibit NS5B polymerase activity are ascertained.</p>","PeriodicalId":9325,"journal":{"name":"Bioorganicheskaia khimiia","volume":"38 2","pages":"257-62"},"PeriodicalIF":0.0,"publicationDate":"2012-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"30760935","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"[Theoretical possibilities and limitations of protease primary specificity determination by statistical analysis of MALDI mass-spectra of proteolysis products].","authors":"M I Drachevskaia, A V Borzenkova, N L Eremeev","doi":"","DOIUrl":"","url":null,"abstract":"<p><p>Possibilities and limitations of method examination of proteolytic enzymes' primary specificity by statistical analysis of MALDI (matrix-assisted laser desorption/ionization) mass spectra of products obtained by protein substrates proteolysis without direct determination of their amino acid sequences were investigated theoretically. The optimum ranges given by the errors of the peptides masses measuring for the fabrication of statistical set of the events and the form of statistical data presentation were chosen. It was shown that the proposed method can be applied only for proteases with a relatively narrow primary specificity (two or three amino acids). The influence of protein substrate molecular weight and amino acid composition on the efficiency of specific to a particular protease amino acids display under statistical treatment of the set of proteolysis products masses was studied on the model of trypsin, chymotrypsin, glutamylendopeptidase, pepsin (pH 1.3).</p>","PeriodicalId":9325,"journal":{"name":"Bioorganicheskaia khimiia","volume":"38 1","pages":"111-8"},"PeriodicalIF":0.0,"publicationDate":"2012-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"30760072","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
T V Iablokova, P S Chelushkin, M Iu Dorosh, A M Efremov, S V Orlov, S V Burov
{"title":"[Synthesis of GnRH analogs and their application in targeted gene delivery systems].","authors":"T V Iablokova, P S Chelushkin, M Iu Dorosh, A M Efremov, S V Orlov, S V Burov","doi":"","DOIUrl":"","url":null,"abstract":"<p><p>A set of GnRH analogues containing nuclear localization signal (NLS) of SV-40 virus large T-antigen have been synthesized using solid phase peptide synthesis and chemical ligation technique. Selective chemical ligation was achieved as a result of hydrazone formation in the course of interaction between NLS hydrazide and GnRH analog modified by pyruvic acid. The efficiency of synthesized peptide carriers was demonstrated in experiments with human cancer cells transfected by reporter luciferase and beta-galactosidase genes or suicide HSV-1 thymidine kinase gene. It was shown that selectivity of action on cancer cells can be achieved as a result of peptide/DNA complex penetration through the cell membrane by GnRH receptor-mediated endocytosis pathway.</p>","PeriodicalId":9325,"journal":{"name":"Bioorganicheskaia khimiia","volume":"38 1","pages":"31-9"},"PeriodicalIF":0.0,"publicationDate":"2012-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"30760631","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
R U Ostrovskaia, T A Gudasheva, N A Krupina, S B Seredin
{"title":"[The search of small molecules with antipsychotic activity on the background of neurotensin].","authors":"R U Ostrovskaia, T A Gudasheva, N A Krupina, S B Seredin","doi":"","DOIUrl":"","url":null,"abstract":"<p><p>Tridecapeptide neurotensin (NT) is known to exert the neuroleptic-like effects in case of its intracerebral administration. The group of systemically active dipeptides , acylprolyltyrosines, was constructed on the background of NT. Methyl ester of N-caproyl-L-prolyl-L-tyrosine (Dilept) was chosen for further development. The paper is dealing with main principles of Dilept'design and with analysis of the experimental data concerning its effect on the \"translational\" model of schizophrenia--the deficit of prepulse inhibition of the acoustic startle-reaction caused by either dopamine-mimetic, apomorphine, or by the uncompetitive NMDA-blocker, ketamine. Dilept was shown to attenuate these deficits both in case ofintraperitoneal and peroral administration. Dilept is considered as a potential antipsychotic.</p>","PeriodicalId":9325,"journal":{"name":"Bioorganicheskaia khimiia","volume":"38 1","pages":"119-26"},"PeriodicalIF":0.0,"publicationDate":"2012-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"30760073","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"[Methoxymethyl and (p-nitrobenzyloxy)methyl groups in the synthesis of oligoribonucleotides by the phosphotriester method].","authors":"V A Efimov, A V Aralov, O G Chakhmakhcheva","doi":"","DOIUrl":"","url":null,"abstract":"<p><p>An efficient synthetic method for monomer ribonucleotide synthons containing 2'-O-methoxymethyl and 2'O-(p-nitrobenzyloxy)methyl groups used for oligonucleotide phosphotriester method with O-nucleophilic intramolecular catalysis at the stage of formation of internucleotide bond is developed. It is shown that synthons containing protecting 2'-O-(p-nitrobenzyloxy)methyl group may be used for automatic synthesis of phosphotriester oligoribonucleotides with high yields and synthons containing methoxymethyl group--to get 2'-O-modified oligonucleotides.</p>","PeriodicalId":9325,"journal":{"name":"Bioorganicheskaia khimiia","volume":"37 2","pages":"284-8"},"PeriodicalIF":0.0,"publicationDate":"2011-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"29977446","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"[Application of BODIPY-trimethylmelamine conjugate for DNA cross-linking in vitro].","authors":"V A Efimov, S V Fediunin, O G Chakhmakhcheva","doi":"","DOIUrl":"","url":null,"abstract":"<p><p>Conjugate the fluorescent dye 4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indatsen-8-propionic acid (BODIPY) and N2,N4,N6-trimethylmelamine was obtained. It was shown that this compound in the presence of formaldehyde generates covalent cross-links of DNA strands in vitro.</p>","PeriodicalId":9325,"journal":{"name":"Bioorganicheskaia khimiia","volume":"37 2","pages":"278-83"},"PeriodicalIF":0.0,"publicationDate":"2011-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"29977445","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}