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2 S DDS sira DDS RA 2012 sira mipomersenapo ISIS 2 S DDS 200 mg/ EMA S 2 --methyl-4 -thioribonucleosidesms MS 5 -GCattggtatTCA-3, Apo100 LA, DA, RA sira S Table 1, 2014 MS mra S-AS 5%3 choleve (2) ch;msa LG; -acetylgalactosamine 3 3GalAc18, 21, 33% 3GalAc MS 1) 80% STAT3 Table 1. S mra (Stat3)siRA microramira GCattggtatTCA-3 S mir-122 LA DA LA AS chol V E RAAM 3GalAc (%) ) 90% 41 (%) CpG DMT1 de novo DMT3 dumbbel DA dmda (1)
3 (1) MSJ. Am. Chem. Soc. 2000, 122, thioribonucleosides2 - ucleic Acids Res. 2013, 41, DA/RA RA(2) SMA MSAGL J. Am. Chem. Soc. 2009, 131, (3) CpG DMT1DMT3 5-formylCpG (fcpg)dumbbel dmdafig. 13, Fig. 1. SMADA 5 C C T T T T CCTCCCGGAAGT T T T T CuAAC C C T T T GGAGGGCCTTCA T T T T 3 C 3 ai 4 5-(1,2-dihydroxyethyl)CpG-hpDA 5 T T T T CCTCCCGGAAGT T T T T T GGAGGGCCTTCA T T T T T T 3 C 3 SMA fcpg-dmda (DMT1) C C 5 T T CCTCCCGGAAGT T T T T T T T T T GGAGGGCCTTCA T T T T 3 C 3 C 5 T T T T CCTTGCGCAAGT T T T T T GGAACGCGTTCA T T T T T T 3 C 3 fcpg-dmda (DMT3) GL-fCpG-dmDA (DMT1) 5 T T T T CCTCCCGGAAGT T T T T T T T GGAGGGCCTTCA T T T T 3 C 3 5-(1,2-dihydroxyethyl)CpG-dmDA SAAC 0.05% DMS r.t h fcpg 5-(1,2-dihydroxyethyl)CpG-hpDA tris(azidoethyl)aminecuaac Cu(I) catalyzed alkyne-azide cycloaddition 5-(1,2-dihydroxyethyl)CpG-dmDA rg. Lett. 2013, 15, aI4 fcpg-dmda 3 C C ai 4 5 T T T T CCTCCCGGAAGT T T T T T T T GGAGGGCCTTCA T T T T 3 C 3 C GL-5-(1,2-dihydroxyethyl)- CpG-dmDA J. Control. Release. 2012, 163, ucleic Acids Res. 2001, 29, Fig. (4) 5-(1,2-dihydroxy- ethyl)cpg-dmda 2AM-122 SMASAACstrain- promoted azide alkyne cycloadditions ai4gl-fcpg-dmda 2 --Me-ribonucleosidesFig. 3 STAT3 mra (Stat3)siRA -mm6m- 3 GL 2466% (5) MS-60% pysk05 72 (1) microra- 122 (mir-122)mir-122 mir-122 AM AM mira mirisc miramirisc mramira miramraam mra AM AMmiRA AM mira mirain vivo Fig. 2. mir-122 sense Evaluation of AM-122 activity 3 -GUUUGUGGUAACAGUGUGAGG-5 Antisense (23mer) sequences Tm ( C) MS- 5 -A o C o A o A o A o C o A o C o C o A o U o U o G o U o C o A o C o A o C o U o C o C o A A s C s A s A s A s C s A s C s C s A s U s U s G s U s C s A s C s A s C s U s C s C s A mm6 5 -A s C s A s U s A s C s U s C s C s U s U s U s C s U s C s A s G s A s G s U s C s C s A-3 n. d. M- 5 -A o C o A o A o A o C o A o C o C o A o U o U o G o U o C o A o C o A o C o U o C o C o A A s C s A s A s A s C s A s C s C s A s U s U s G s U s C s A s C s A s C s U s C s C s A mm6 5 -A s C s A s U s A s C s U s C s C s U s U s U s C s U s C s A s G s A s G s U s C s C s A-3 n. d. T m ; 10 mm phosphate buffer (p 7.0), 0.1 mm EDTA, 1 mm acl, 3 µm strand concentration mm; mismatch S MS- C 3 S S S C 3 86% M- C 3 S S C 3
4 MS-50% S Relative Fluc/Rluc ratios (%) Fig pmirgl 24h pmirgl mir122 Scr Evaluation of AM-122 activity 24 h after transfection to uh-7 cells 5 -ACAAACACCAUUGUCACACUCCA-3 (23mer) pmirgl mir122 Me- M- -AM-122 -AM-1225 chol Toc3 chol in vitro (2)CpGC5 -AM-122 SM122-S -AM-122p YSK05 (Fig. 4) E:chol:EG-DMG (50:25:25:3) in vivo ppka6.5 p 7.4 p 6.5~6.8 1 mg/kg-am mir-122 mras AldoA, Me-S 0.5 nm 1 nm 5 nm Me-S-mm6 -mm6 SMe- MS- SMe-S SMe-S-mm6 -mm6 Fig. 5. Gene expression of AldoA, cldk, & drg3 in vivo Relative AldoA expression Cholesterol concentration (mg/dl) 3.0" 2.5" 2.0" 1.5" 1.0" 0.5" 0.0" T Fig. 6. ##" *" AldoA MED Relative ckdk expression 4.5" 4.0" 3.5" 3.0" 2.5" 2.0" 1.5" 1.0" 0.5" 0.0" T ##" MED lood cholesterol level Day 1 not.significant. Day 6 **< " 80" 80" 70" 60" 60" *" 50" 40" 40" 30" 20" 20" 10" 0" 0" T MED T MED cldk Fig. 4. YSK05 Relative drg3 expression 2.5( 2.0( 1.5( 1.0( 0.5( 0.0( T drg3 MED ckdk, drg3mir-122 mras AM-122 -AM-122 -AM-122Fig. 5 chol653%fig %-AM-122 1:1Table 1 CpG T CpGDMT SMA 5Me CpG5 TET 5-C25-C=5-C2 DA ER DMT S 5-C= (f) 6DMT fcpg DAfCpG-dsDA DMTM. paii S-adenosylmethionine (SAM) M. paii-fcpg-dsdacpg DMT1 (MW; 183kDa) Fig.
5 1fCpG-dmDASMA GL-fCpG-dmDASMA LCa C-3eLa ela fcpg DA fcpg-dmda (DMT1)fCpG-dmDA (DMT3 )lipofectamin IC50 66, 41, 18 nmfig. 7DMT1 DMT3Fig. 1 dmdaela cell proliferation (% of control) Fig LF (nm) (cont.) fo C DMT1 DMT3 duplex fcpg-dmda fcpg-dmda DMT1 183kDaDMT3 100kDa DMT1 SMA Fig. 8DL-fCpG-dmDA LCap100 nm90% C-3 30% GL SMA in vivo STAT3DL sira Cell growth inhibitory activity 34 1) atakeyama,.; Murata, M.; Sato, Y.; Takahashi, M.; Minakawa,.; Matsuda, A.; arashima,. The systemic administration of an anti-mira oligonucleotide encapsulated p-sensitive liposome results in reduced level of hepatic microra-122 in mice. J. Control. Release 2014, 173, (DI, /j.jconrel ) omura, Y.; Kashiwagi, S.; Sato, K.; Matsuda, A. Selective transcription of an unnatural cell proliferation (% of control) Fig Cell growth inhibitory activity LCa cells (SMA+) C-3 cells (SMA ) (nm) DMT1 fcpg-dmda naphthyridine:imidazopyrimidine base pair containing four hydrogen bonds by using T7 RA polymerase. Angew. Chem. Int. Ed. Engl. 2014, 53, (DI, /anie ) Saito, Y.; ashimoto, Y.; Arai, M.; Tarashima,.; Miyazawa, T.; Miki, K.; Takahashi, M.; Furukawa, K. Yamazaki,.; Matsuda, A. Ishida, T.; Minakawa,. Chemistry, properties, and in vitro and in vivo applications of 2 --methoxyethyl-4 - thiora, a novel hybrid type of chemically-modified RA. ChemioChem. 2014, 15, (DI, /cbic ) Tarashima,.; ayashi, K.; Terasaki, M.; Taniike,.; Inagaki, Y.; irose, K.; Furukawa, K.; Matsuda, A.; Minakawa,. First synthesis of fully-modified 4 -selenora and 2 -Me-4 -selenora based on the mechanistic considerations of an unexpected strand-break. rg. Lett. 2014, 16, (DI, /ol502077h) Maruyama,.; akashima, Y.; Shuto, S.; Matsuda, A.; Itoh, Y.; Abe,. An intracellular buildup reaction of active sira species from short RA fragments. Chem. Commun. 2014, 50, (DI, /c3cc47529h) Takahashi, M.; Yamada,.; atakeyama,.; Murata, M.; Sato, Y.; Minakawa,.; arashima,.; Matsuda, A. In vitro optimization of 2 -Me-4 -thioribonucleoside modified anti-micro- RA oligonucleotides (AMs) and its targeting delivery to mouse liver using a liposomal nanoparticle. ucleic Acids Res. 2013, 41, (DI, /nar/gkt823) Abe,.; iroshima, M.; Maruyama,.; akashima, Y.; akano, Y.; Matsuda, A.; Sako, Y.; Ito, Y.; Abe,. Rolling circle amplification in a prokaryotic translation system using small circular RA. Angew. Chem. Int. Ed. Engl. 2013, 52, (DI, /anie ) Kojima, T.; Furukawa, K.; Maruyama,.; Inoue,.; Tarashima,.; Matsuda, A.; Minakawa,. CR amplification of 4 -thioda using 2 -deoxy-4 -thionucleoside 5 -triphosphates. ACS Synthetic iol. 2013, 2, (DI, /sb400074w) Ichikawa, S.; Ueno,.; Sunadome, T.; Sato, K.; Matsuda, A. Tris(azidoethyl)amine hydrochloride; a versatile reagent for synthesis of functionalized dumbbell oligonucleotides. rg. Lett. 2013, 15, (DI, /ol400001w) Takahashi, M.; agai, C.; atakeyama,.; Minakawa,.; arashima,.; Matsuda, A. Intracellular stability of 2 -Me-4 -thioribonucleoside modified sira leads to long-term RAi effect. ucleic Acids Res. 2012, 40, (DI, /nar/gks204) Shibata, A.; Ueno, Y.; Iwata, M.; Wakita,.; Matsuda, A.; Kitade, Y. Double-stranded oligonucleotides containing 5-aminomethyl-2 - deoxyuridine form thermostable anti-parallel
6 triplexes with single-stranded DA or RA. ioorg. Med. Chem. Lett. 2012, 22, (DI, /j.bmcl ) Sato, K.; Sasaki, A.; Matsuda, A. ighly fluorescent 5-(5,6-dimethoxybenzothiazol-2-yl)-2'- deoxyuridine 5'-triphosphate as an efficient substrate for DA polymerases. ChemioChem 2011, 12, (DI, /cbic ) irose, W.; Sato, K.; Matsuda, A. Fluorescence properties of 5-(5,6-dimethoxybenzothiazol-2-yl)- 2'-deoxyuridine ( bt du) and oligodeoxyribonucleotides containing bt du. Eur. J. rg. Chem. 2011, (DI, /ejoc ) Kuramoto, K.; Tarashima,.; irama, Y.; Kikuchi, Y.; Minakawa,.; Matsuda, A. ew imidazopyridopyrimidine:naphthyridine basepairing motif, Im :a, consisting of a DAAD:ADDA hydrogen bonding pattern, markedly stabilize DA duplexes. Chem. Commun. 2011, 47, (DI, /c1cc13805g) Kataoka, M.; Kouda, Y.; Sato, K.; Minakawa,.; Matsuda, A. ighly efficient enzymatic synthesis of 3 -deoxyapionucleic acid (apioa) having the four natural nucleobases. Chem. Commun. 2011, 47, (DI, /c1cc12980e) Furuita, K.; Murata, S.; Jee, G-J.; Ichikawa, S.; Matsuda, A.; Kojima, C. Structural feature of bent DA recongnized by MG1. J. Am. Chem. Soc. 2011, 133, (DI, /ja ) 31 白金シンポジウム 創薬研究の最前線 Akira Matsuda, Development of sugar-modified cytosine nucleosides as antitumor agents-old stories for future success-, The 20 th International Round Table for ucleosides, ucleotides, & ucleic Acids, August 8, 2012, Montreal, Canada 4 Minakawa,.; Matsuda, A. Design, characterization, and application of imidazopyridopyrimidine: naphthyridine basepairing motifs consisting of four hydrogen bonds. In Chemical iology of ucleic Acids, RA Technologies, Eds. by V. A. Erdman, W. T. Markiewicz & J. arciszewski, Springer eidelberg ew York Dordrecht London, pp , (total 599 pages), ) update 革新的シーズ育成に向けて IV... pp , 375(2013) CSJ 06 pp CT/J2012/ MATSUDA Akira SAT Kosuke SAT Yusuke
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