Phosmidosine and a variety of its analogs were synthesized by reaction of N-diisopropyl-N'-(N tritylaminoacyl)phosphorodiamidite derivatives with appropriately protected 8-oxoadenosine derivatives. It was found that replacement of the methyl group of the N-acylphosphoramidate linkage with longer alkyl groups resulted in significant stabilization of the ester linkage. Among the phosmidosine analogs synthesized, the O-ethyl derivative was easily synthesized and was found to be sufficiently stable under acidic and neutral conditions. These stable phosmidosine analogs exhibited similar antitumor activities against several cancer cell lines. The structure-activity relationship is also discussed.
{"title":"Synthesis and biological properties of stable phosmidosine analogs.","authors":"Kazuhisa Okada, Haruhiko Taguchi, Kohji Seio, Hideaki Kakeya, Hiroyuki Osada, Takuma Sasaki, Mitsuo Sekine","doi":"10.1093/nass/3.1.105","DOIUrl":"https://doi.org/10.1093/nass/3.1.105","url":null,"abstract":"<p><p>Phosmidosine and a variety of its analogs were synthesized by reaction of N-diisopropyl-N'-(N tritylaminoacyl)phosphorodiamidite derivatives with appropriately protected 8-oxoadenosine derivatives. It was found that replacement of the methyl group of the N-acylphosphoramidate linkage with longer alkyl groups resulted in significant stabilization of the ester linkage. Among the phosmidosine analogs synthesized, the O-ethyl derivative was easily synthesized and was found to be sufficiently stable under acidic and neutral conditions. These stable phosmidosine analogs exhibited similar antitumor activities against several cancer cell lines. The structure-activity relationship is also discussed.</p>","PeriodicalId":86149,"journal":{"name":"Nucleic acids research. Supplement (2001)","volume":" 3","pages":"105-6"},"PeriodicalIF":0.0,"publicationDate":"2003-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1093/nass/3.1.105","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"40825074","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}
Stretched single DNA molecules were prepared on substrates by Langmuir-Blodgett (LB) method for the restriction site mapping. Stretched single Lambda DNA and EcoRI bound to the DNA were observed by scanning near-field optical microscope (SNOM). As a result, the specific binding sites of EcoRI on the Lambda DNA molecules were determined.
{"title":"Stretching of single DNA molecules by LB technique for restriction site mapping.","authors":"Kuniharu Ijiro, Yasutaka Matsuo, Masatsugu Shimomura","doi":"10.1093/nass/3.1.47","DOIUrl":"https://doi.org/10.1093/nass/3.1.47","url":null,"abstract":"<p><p>Stretched single DNA molecules were prepared on substrates by Langmuir-Blodgett (LB) method for the restriction site mapping. Stretched single Lambda DNA and EcoRI bound to the DNA were observed by scanning near-field optical microscope (SNOM). As a result, the specific binding sites of EcoRI on the Lambda DNA molecules were determined.</p>","PeriodicalId":86149,"journal":{"name":"Nucleic acids research. Supplement (2001)","volume":" 3","pages":"47-8"},"PeriodicalIF":0.0,"publicationDate":"2003-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1093/nass/3.1.47","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"40825180","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}
N-terminal specific radioisotope (RI) labelling of a protein posessing lysine as the N-terminal residue (Lys-XBD) was achieved under mild enzymatic reaction condition using L/F-tRNA-protein transferase. To expose a single lysine moiety only at the N-teminal site, we overexpressed pelB signal peptide-Lys-XBD fusion protein using the bacterial expression host BL21(DE3). The pelB signal peptide was sponteneously cleaved in E. coli to obtain the desired Lys-XBD.
利用L/ f - trna -蛋白转移酶在温和的酶促反应条件下,实现了以赖氨酸为n端残基的蛋白质(Lys-XBD)的n端特异性放射性同位素(RI)标记。为了仅在n端暴露单个赖氨酸片段,我们使用细菌表达宿主BL21(DE3)过表达pelB信号肽-赖氨酸- xbd融合蛋白。pelB信号肽在大肠杆菌中自发裂解得到所需的Lys-XBD。
{"title":"Leucyl/phenylalanyl (L/F)-tRNA-protein transferase-mediated N-terminal specific labelling of a protein in vitro.","authors":"Atsushi Kuno, Masumi Taki, Satoshi Kaneko, Kazunari Taira, Tsunemi Hasegawa","doi":"10.1093/nass/3.1.259","DOIUrl":"https://doi.org/10.1093/nass/3.1.259","url":null,"abstract":"<p><p>N-terminal specific radioisotope (RI) labelling of a protein posessing lysine as the N-terminal residue (Lys-XBD) was achieved under mild enzymatic reaction condition using L/F-tRNA-protein transferase. To expose a single lysine moiety only at the N-teminal site, we overexpressed pelB signal peptide-Lys-XBD fusion protein using the bacterial expression host BL21(DE3). The pelB signal peptide was sponteneously cleaved in E. coli to obtain the desired Lys-XBD.</p>","PeriodicalId":86149,"journal":{"name":"Nucleic acids research. Supplement (2001)","volume":" 3","pages":"259-60"},"PeriodicalIF":0.0,"publicationDate":"2003-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1093/nass/3.1.259","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"40903184","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}
The ODNs containing (MD)A, which effectively mediate hole transport, were enzymatically ligated, and photo-induced hole transport reaction proceeded efficiently through a ligated long duplex. The ligated duplex showed high hole transport efficiency.
{"title":"Enzymatic ligation and extension of DNA wire.","authors":"Kazuo Tanaka, Ken-ichiro Nishiza, Akimitsu Okamoto, Isao Saito","doi":"10.1093/nass/3.1.39","DOIUrl":"https://doi.org/10.1093/nass/3.1.39","url":null,"abstract":"The ODNs containing (MD)A, which effectively mediate hole transport, were enzymatically ligated, and photo-induced hole transport reaction proceeded efficiently through a ligated long duplex. The ligated duplex showed high hole transport efficiency.","PeriodicalId":86149,"journal":{"name":"Nucleic acids research. Supplement (2001)","volume":" 3","pages":"39-40"},"PeriodicalIF":0.0,"publicationDate":"2003-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1093/nass/3.1.39","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"40903180","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}
Gerd K Wagner, Andrew M Riley, Heidi J Rosenberg, Colin W Taylor, Andreas H Guse, Barry V L Potter
Nicotinamide 8-Br-hypoxanthine dinucleotide (8-Br-NHD+) was cyclised at the N-1 position by ADP-ribosyl cyclase from Aplysia californica to give cyclic 8-Br-inosine diphosphoribose, a novel membrane-permeant analogue of cyclic-ADP ribose and agonist in human T cells. Adenine-substituted analogues of adenophostin A with potent Ca2+ releasing activity were synthesized; docking studies using the binding core of the Ins(1,4,5)P3 receptor identified specific residues that could be of importance in determining the hyperagonist nature of adenophostin activity.
{"title":"Analogues of cyclic adenosine 5'-diphosphate ribose and adenophostin A, nucleotides in cellular signal transduction.","authors":"Gerd K Wagner, Andrew M Riley, Heidi J Rosenberg, Colin W Taylor, Andreas H Guse, Barry V L Potter","doi":"10.1093/nass/3.1.1","DOIUrl":"https://doi.org/10.1093/nass/3.1.1","url":null,"abstract":"<p><p>Nicotinamide 8-Br-hypoxanthine dinucleotide (8-Br-NHD+) was cyclised at the N-1 position by ADP-ribosyl cyclase from Aplysia californica to give cyclic 8-Br-inosine diphosphoribose, a novel membrane-permeant analogue of cyclic-ADP ribose and agonist in human T cells. Adenine-substituted analogues of adenophostin A with potent Ca2+ releasing activity were synthesized; docking studies using the binding core of the Ins(1,4,5)P3 receptor identified specific residues that could be of importance in determining the hyperagonist nature of adenophostin activity.</p>","PeriodicalId":86149,"journal":{"name":"Nucleic acids research. Supplement (2001)","volume":" 3","pages":"1-2"},"PeriodicalIF":0.0,"publicationDate":"2003-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1093/nass/3.1.1","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"40824167","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}
We could obtain the DNA aptamers that can bind strongly and selectively to ATP (Ka = 6.7 x 10(7) M(-1)) from four way junction random DNAs by using in vitro selection on a quartz-crystal microbalance.
在石英晶体微天平上进行体外筛选,从四向结随机DNA中获得了能与ATP (Ka = 6.7 x 10(7) M(-1))强选择性结合的核酸适体。
{"title":"In vitro selection of four way junction DNA.","authors":"Tomomitsu Ozeki, Hiroyuki Furusawa, Yoshio Okahata","doi":"10.1093/nass/3.1.257","DOIUrl":"https://doi.org/10.1093/nass/3.1.257","url":null,"abstract":"<p><p>We could obtain the DNA aptamers that can bind strongly and selectively to ATP (Ka = 6.7 x 10(7) M(-1)) from four way junction random DNAs by using in vitro selection on a quartz-crystal microbalance.</p>","PeriodicalId":86149,"journal":{"name":"Nucleic acids research. Supplement (2001)","volume":" 3","pages":"257-8"},"PeriodicalIF":0.0,"publicationDate":"2003-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1093/nass/3.1.257","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"40824187","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}
To array Cu2+ ions within a double-stranded DNA along the helix axis in a controllable manner, a series of artificial oligonucleotides, d(5'-GHnC-3') (n = 1-5), were synthesized, where H is a hydroxypyridone nucleobase. Right-handed double helices of the oligonucleotides, nCu2+ x d(5'-GHnC-3')2 (n = 1-5), were quantitatively formed through Cu2+-mediated metallo-base pairing (H-Cu2+-H). The Cu2+ ions incorporated into each duplex were aligned along the helix axes with the Cu2+-Cu2+ distance of 3.7 +/- 0.1 A. The unpaired d electrons of the Cu2+ ions were coupled ferromagnetically with one another to form magnetic chains.
{"title":"Artificial metallo-DNA: structural control and discrete metal assembly.","authors":"Kentaro Tanaka, Yasuyuki Yamada, Atsushi Tengeiji, Tatsuhisa Kato, Namiki Toyama, Yusuke Takezawa, Maiko Yori, Motoo Shiro, Mitsuhiko Shionoya","doi":"10.1093/nass/3.1.121","DOIUrl":"https://doi.org/10.1093/nass/3.1.121","url":null,"abstract":"<p><p>To array Cu2+ ions within a double-stranded DNA along the helix axis in a controllable manner, a series of artificial oligonucleotides, d(5'-GHnC-3') (n = 1-5), were synthesized, where H is a hydroxypyridone nucleobase. Right-handed double helices of the oligonucleotides, nCu2+ x d(5'-GHnC-3')2 (n = 1-5), were quantitatively formed through Cu2+-mediated metallo-base pairing (H-Cu2+-H). The Cu2+ ions incorporated into each duplex were aligned along the helix axes with the Cu2+-Cu2+ distance of 3.7 +/- 0.1 A. The unpaired d electrons of the Cu2+ ions were coupled ferromagnetically with one another to form magnetic chains.</p>","PeriodicalId":86149,"journal":{"name":"Nucleic acids research. Supplement (2001)","volume":" 3","pages":"121-2"},"PeriodicalIF":0.0,"publicationDate":"2003-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1093/nass/3.1.121","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"40824472","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}
Naoto Kishi, Masayuki Ogino, Isao Saito, Yoshinaga Yoshimura, Kenzo Fujimoto
The photochemical DNA computing of 5-vinyluracil ((V)U) containing oligodeoxynucleotides (ODNs) tethered multiple "DNA words" is demonstrated. A new MARK and UNMARK operation based on the (V)U mediated reversible DNA photoligation has been developed for multiple-word DNA computing. The utility of this operation for DNA computing is demonstrated by solving a small Satisfiability problem (SAT problem) in which information was encoded in three tandem words.
{"title":"Photochemical ligation of DNA \"words\" for DNA computing.","authors":"Naoto Kishi, Masayuki Ogino, Isao Saito, Yoshinaga Yoshimura, Kenzo Fujimoto","doi":"10.1093/nass/3.1.183","DOIUrl":"https://doi.org/10.1093/nass/3.1.183","url":null,"abstract":"<p><p>The photochemical DNA computing of 5-vinyluracil ((V)U) containing oligodeoxynucleotides (ODNs) tethered multiple \"DNA words\" is demonstrated. A new MARK and UNMARK operation based on the (V)U mediated reversible DNA photoligation has been developed for multiple-word DNA computing. The utility of this operation for DNA computing is demonstrated by solving a small Satisfiability problem (SAT problem) in which information was encoded in three tandem words.</p>","PeriodicalId":86149,"journal":{"name":"Nucleic acids research. Supplement (2001)","volume":" 3","pages":"183-4"},"PeriodicalIF":0.0,"publicationDate":"2003-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1093/nass/3.1.183","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"40824483","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}
RNA molecules express the specific structure containing A-form helices and non-helical regions, such as loops and bulges. The adenosine moiety plays a key role in helical packing and/or loop and/or bulge interactions. It is well known as A-platform, tetraloop, and A-minor motif. For the formation of these motifs, there are specific interactions to the adjacent RNA segments and/or protein and/or metal ions beside the specific base sequences. The database focusing on adenine's structural roles, structural information about the assemblage and the space distribution of base moieties can be a useful tool. The user can obtain the selected list with the several descriptors including kink parameters for the structure definition and sequence properties. In addition to this nucleic acid system, RNA-drug related compound system would be included.
{"title":"Structural characterization of adenine moiety in functional RNA molecules.","authors":"Satoshi Fujii","doi":"10.1093/nass/3.1.195","DOIUrl":"https://doi.org/10.1093/nass/3.1.195","url":null,"abstract":"<p><p>RNA molecules express the specific structure containing A-form helices and non-helical regions, such as loops and bulges. The adenosine moiety plays a key role in helical packing and/or loop and/or bulge interactions. It is well known as A-platform, tetraloop, and A-minor motif. For the formation of these motifs, there are specific interactions to the adjacent RNA segments and/or protein and/or metal ions beside the specific base sequences. The database focusing on adenine's structural roles, structural information about the assemblage and the space distribution of base moieties can be a useful tool. The user can obtain the selected list with the several descriptors including kink parameters for the structure definition and sequence properties. In addition to this nucleic acid system, RNA-drug related compound system would be included.</p>","PeriodicalId":86149,"journal":{"name":"Nucleic acids research. Supplement (2001)","volume":" 3","pages":"195-6"},"PeriodicalIF":0.0,"publicationDate":"2003-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1093/nass/3.1.195","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"40824489","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}
To select antisense oligonucleotides (AONs) that specifically target the genes of rat organic anion transporting polypeptide (oatp) subtypes, in vitro selection and an alignment program were used. When we incorporated a couple of our original 2'-O,4'-C-ethylene nucleoside (ENA) residues into the AONs at both the 3' and 5' ends, the inhibitory activity of these oatp subtype-specific AONs was enhanced. This strategy of combining in vitro selection with the use of an alignment program as well as incorporating ENA residues, was effective in synthesizing oatp subtype-specific AONs.
采用体外筛选和比对程序筛选大鼠有机阴离子转运多肽(oatp)亚型基因的反义寡核苷酸(AONs)。当我们在AONs的3'和5'端同时加入两个原始的2'-O,4'- c -乙烯核苷(ENA)残基时,这些oatp亚型特异性AONs的抑制活性得到增强。这种结合体外选择与使用比对程序以及纳入ENA残基的策略,在合成oatp亚型特异性aon方面是有效的。
{"title":"Design and synthesis of oatp subtype-specific antisense oligonucleotides having 2'-O,4'-C-ethylene-bridged nucleic acids (ENA).","authors":"Miho Takagi, Koji Morita, Daisuke Nakai, Rie Nakagomi, Taro Tokui, Makoto Koizumi","doi":"10.1093/nass/3.1.83","DOIUrl":"https://doi.org/10.1093/nass/3.1.83","url":null,"abstract":"<p><p>To select antisense oligonucleotides (AONs) that specifically target the genes of rat organic anion transporting polypeptide (oatp) subtypes, in vitro selection and an alignment program were used. When we incorporated a couple of our original 2'-O,4'-C-ethylene nucleoside (ENA) residues into the AONs at both the 3' and 5' ends, the inhibitory activity of these oatp subtype-specific AONs was enhanced. This strategy of combining in vitro selection with the use of an alignment program as well as incorporating ENA residues, was effective in synthesizing oatp subtype-specific AONs.</p>","PeriodicalId":86149,"journal":{"name":"Nucleic acids research. Supplement (2001)","volume":" 3","pages":"83-4"},"PeriodicalIF":0.0,"publicationDate":"2003-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1093/nass/3.1.83","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"40824647","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}