論文・総説・著書

 2017年

原著論文

 

Synthesis and evaluation of c-di-4’-thioAMP as an artificial ligand for c-di-AMP riboswitch

  • Kazuto Shiraishi,Noriko Saito-Tarashima, 
  • Yosuke Igata, 
  • Keiji Murakami, 
  • Yasuko Okamoto, 
  • Yoichiro Miyake, 
  • Kazuhiro Furukawa, 
  • Noriaki Minakawa

Bioorg. Med. Chem., in press [DOI: 10.1016/j.bmc.2017.05.042]

2017_Bioorg_Med_Chem_1.jpg

 

The AMPK/mTOR pathway is involved in D-dopachrome tautomerase gene transcription in adipocytes differentiated from SGBS cells, a human preadipocyte cell line

Takeo Iwata, Kyoko Kuribayashi, Masahiko Nakasono, Noriko Saito-Tarashima, Noriaki Minakawa, Noriko Mizusawa, Rie Kido, Katsuhiko Yoshimoto

Cytokine, 2017, 96, 195–202 [DOI: 10.1016/j.cyto.2017.04.017]

 

2016年

原著論文

Groove modification of siRNA duplexes to elucidate siRNA–protein interactions using 7-bromo-7-deazaadenosine and 3-bromo-3-deazaadenosine as chemical probes
Noriko Saito-Tarashima, Hirotaka Kira, Tomoya Wada, Kazuya Miki, Shiho Ide, Naoshi Yamazaki, Akira Matsuda and Noriaki
Minakawa
Org. Biomol. Chem., 2016,14, 11096-11105 [DOI:10.1039/C6OB01866A]

2016_Org. Biomol. Chem._1.jpg

 

Practical synthesis of 4′-selenopurine nucleosides by combining chlorinated purines and ‘armed’ 4-selenosugar
Kazuki Ishii, Noriko Saito-Tarashima, Masashi Ota, Seigi Yamamoto, Yasuko Okamoto, Yoshiyuki Tanaka and Noriaki Minakawa
Tetrahedron, 2016, 72, 6589-6594 [DOI:10.1016/j.tet.2016.08.071]

2016_tetrahedron_1.jpg

 

The novel functional nucleic acid iRed effectively regulates target genes following cytoplasmic delivery by faint electric treatment

Mahadi Hasan, Noriko Tarashima, Koki Fujikawa, Takashi Ohgita, Susumu Hama, Tamotsu Tanaka, Hiroyuki Saito, Noriaki Minakawa and Kentaro Kogure

Sci. Tech. Adv. Mater., 2016, 17, 554-562 [DOI:10.1080/14686996.2016.1221726]

2016_Sci. Technol. Adv. Mater._1_result.jpg

 

Gene Silencing Using 4′-thioDNA as an Artificial Template to Synthesize Short Hairpin RNA Without Inducing a Detectable Innate Immune Response

Noriko Tarashima, Hidenori Ando, Takamitsu Kojima, Nozomi Kinjo, Yosuke Hashimoto, Kazuhiro Furukawa, Tatsuhiro Ishida and Noriaki Minakawa

Mol. Ther. Nucleic Acids, 2016, 5, e274 [DOI:10.1038/mtna.2015.48]

2016_Mol. Ther. Nucleic Acids_1_result.jpg

 

総説・著書

1. 田良島典子、南川典昭

生物学的等価性を指向した化学修飾DNAによる核酸創薬研究

核酸医薬の創製と応用展開』(シーエムシー出版) 2016年, pp70-78.

 

2015年

原著論文

Faithful PCR Amplification of an Unnatural Base-Pair Analogue with Four Hydrogen Bond

Noriko Tarashima,Yasuo Komatsu,Kazuhiro Furukawa,and Noriaki Minakawa

Chem. Eur.J.,2015,21,10688-10695 [DOI: 10.1002/chem.201583062]

 

図2.gif                    

 

                                

 

Synthesis of DNA fragments containing 2’-deoxy-4’-selenonucleoside units using DNA polymerases:

comparison of dNTPs with O, S and Se at the 4’-position in replication

Noriko Tarashima, Tatsuya  Sumitomo, Hidenori Ando, Kazuhiro Furukawa, Tatsuhiro Ishida and Noriaki Minakawa*

Organic & Biomolecular Chemistry.,2015,13,6949-6952  [DOI: 10.1039/c5ob00941c ]

 図.gif

 
 

 

Transcription of 4′-thioDNA templates to natural RNA in vitro and in mammalian cells

Hideto Maruyama, Kazuhiro Furukawa, Hiroyuki Kamiya, Noriaki Minakawa and  Akira Matsuda  

Chem. Commun. 2015,51, 7887-7890 [DOI: 10.1039/C4CC08862J]

 

 Graphical abstract: Transcription of 4′-thioDNA templates to natural RNA in vitro and in mammalian cells

Bacterial riboswitches cooperatively bind Ni2+ or Co2+ ions and control expression of heavy metal transporters

Kazuhiro Furukawa, Arati Ramesh, Zhiyuan Zhou, Zasha Weinberg,Tenaya Vallery, Wade C. Winkler, Ronald R. Breaker

Mol. Cell.19, 2015, 57, 1088–1098 [DOI10.1016/j.molcel.2015.02.009]

 
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2014年

原著論文

Chemistry, properties, and in vitro and in vivo applications of 2-O-methoxyethyl-4-thioRNA, a novel hybrid type of chemically modified RNA

Yota Saito,Yosuke Hashimoto, Mai Arai, Noriko Tarashima, Tadashi Miyazawa, Kazuya Miki, Mayumi Takahashi, Kazuhiro Furukawa, Naoshi Yamazaki, Akira Matsuda,Tatsuhiro Ishida, Noriaki Minakawa

ChemBioChem, 2014,152535–2540 [DOI: 10.1002/cbic.201402398] 

 


Link to full-size graphical abstract

 

 

First synthesis of fully modified 4'-selenoRNA and 2'-OMe-4'-selenoRNA based on the mechanistic considerations of an unexpected strand break

Noriko Tarashima, Koya Hayashi, Maki Terasaki, Hirotsugu Taniike, Yusuke Inagaki, Kenji Hirose, Kazuhiro Furukawa, Akira Matsuda, Noriaki Minakawa

Org. Lett. 2014,16, 4710–4713 [DOI: 10.1021/ol502077h]

 

Abstract Image

 

 

Development of a new dumbbell-shaped decoy DNA using a combination of the unnatural base pair ImON:NaNO and a CuAAC reaction

Yosuke Higuchi, Kazuhiro Furukawa, Tadashi Miyazawa, Noriaki Minakawa

Bioconjugate Chem. 2014, 25, 1360–1369 [DOI: 10.1021/bc500225r]

 

 Abstract Image

 

 

Allosteric control of a DNA-hydrolyzing deozyribozyme with short oligonucleotides and its application in DNA logic gates

Kazuhiro Furukawa, Noriaki Minakawa

Org. Biomol. Chem. 2014, 12, 3344–3348 [DOI: 10.1039/C4OB00451E]

 

Graphical abstract: Allosteric control of a DNA-hydrolyzing deoxyribozyme with short oligonucleotides and its application in DNA logic gates

 

 

 5.  The systemic administration of an anti-miRNA oligonucleotide encapsulated pH-sensitive liposome results in reduced level of hepatic microRNA-122 in mice

   Hiroto Hatakeyama, Manami Murata, Yusuke Sato, Mayumi Takahashi, Noriaki Minakawa, Akira Matsuda, Hideyoshi Harashima

   Jounal of Controlled Release, 2014, 173, 43-50

 

Full-size image (38 K)

 

 

総説・著書

1. Minakawa N, Matsuda A

   Design,Characterization,and Application of Imidazopyridopyrimidine:Naphthyridine Base-Pairing Motifs Consisting of Four Hydroren Bonds

   Chemical Biology of Nucleic Acids:Volker.A Erdmann,Wojciech T.Markiewicz,Jan Barciszewski,Eds:Springer 2014 p113-129

 

2  Kazuhiro Furukawa, Hongzhou Gu, Ronald Breaker
   In Vitro Selection of allosteric ribozymes that sense the bacterial second messenger c-di-GMP
   Methods in Molecular Biology, 2014, 1111, 209-220

 

 

2013年

原著論文

 1. James W Nelson, Narasimhan Sudarsan, Kazuhiro Furukawa, Zasha Weinberg, Joy X Wang, Ronald R Breaker

  Riboswitches in eubacteria sence the second messenger c-di AMP

  Nat. Chem. Biol., 2013, 9, 834-839

 

 2.  Mayumi Takahashi, Naoki Yamada, Hiroto Hatakeyama, Manami Murata, Yusuke Sato, Noriaki Minakawa, Hideyoshi Harashima, and Akira Matsuda

  In vitoro optimization of 2'-OMe-4'-thioribonucleoside-modified anti-microRNA oligonucleotides and its targeting delivery to mouse liver using a liposomal nanoparticle

  Nucleic Acids Res. 2013, 1-9

 

 3.  Takamitsu Kojima, Kazuhiro Furukawa, Hideto Maruyama, Naonori Inoue, Noriko Tarashima, Akira Matsuda, Noriaki Minakawa

     PCR Amplification of 4'-ThioDNA Using 2'-Deoxy-4'-thionucleoside 5'-triphosphates

    ACS Synth. Biol. 2013, 2 (9), 529–536

 

 

  4. Tadashi Miyazawa, Kouhei Umezaki, Noriko Tarashima, Kazuhiro Furukawa, Takashi Ooi and Noriaki Minakawa

Synthesis of a novel 1,2-dithianenucleoside via Pummerer-like reaction, followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracil

Chem. Commun. 2013, 49, 7851-7853

 

Graphical abstract: Synthesis of a novel 1,2-dithianenucleoside via Pummerer-like reaction, followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracil

 

 5. Yusaku Kikuchi, Naoshi Yamazaki, Noriko Tarashima, Kazuhiro Furukawa, Yoshiharu Takiguchi, Kohji Itoh, and Noriaki Minakawa
Gene suppression via U1 small nuclear RNA interference (U1i) machinery using oligonucleotides containing 2'-modified-4'-thionucleosides
Bioorg. Med. Chem. 2013, 21, 5292-5296

Full-size image (16 K)

 6. Hongzhou Gu, Kazuhiro Furukawa, Zasha Weinberg, Daniel Berenson, Ronald Breaker

Small, Highly Active DNAs That Hydrolyze DNA
J. Am. Chem. Soc., 2013, 135 (24) 9121-9129

            Abstract Image

 

 

総説・著書

1. 古川和寛

病原性細菌の抗生物質耐性を司るRNAスイッチ
ファルマシア, 2013, 49, 905

 

2. Minakawa N

Development of RNA Medicine Using 4'-thioDNA.

Yakugaku Zasshi. 2013, 133, 53-60. (in Japanese)


3. 野村勇作、柏木怜、佐藤浩輔、南川典昭、松田彰

4本の水素結合対を持つ核酸塩基の設計(2)-DNA,RNAポリメラーゼによる認識-

Antisense  2013, 17 , 2,  3-13

 

2012年

原著論文

 1. Tarashima N, Higuchi Y, Komatsu Y, Minakawa N.

A practical post-modification synthesis of oligodeoxynucleotides containing 4,7-diaminoimidazo[5',4':4,5]pyrido[2,3-d]pyrimidine nucleoside.

Bioorg Med Chem. 2012, 20, 7095-7100

 

Full-size image (21 K)

 

 2. Takahashi M, Nagai C, Hatakeyama H, Minakawa N, Harashima H, Matsuda A.

Intracellular stability of 2'-OMe-4'-thioribonucleoside modified siRNA leads to long-term RNAi effect.

Nucleic Acids Res. 2012, 40, 5787-5793

 

 3. Tamura Y, Furukawa K, Yoshimoto R, Kawai Y, Yoshida M, Tsuneda S, Ito Y, Abe H.

Detection of pre-mRNA splicing in vitro by an RNA-templated fluorogenic reaction.

Bioorg Med Chem Lett. 2012, 22,7248-7251

 

 Full-size image (26 K)

 

4. Furukawa K, Gu H, Sudarsan N, Hayakawa Y, Hyodo M, Breaker RR.

Identification of ligand analogues that control c-di-GMP riboswitches.

ACS Chem. Biol. 2012, 7, 1436-1443

 

Abstract Image

 

 

5. Gu H, Furukawa K, Breaker RR.

Engineered allosteric ribozymes that sense the bacterial second messenger cyclic diguanosyl 5'-monophosphate.

Anal. Chem. 2012, 84, 4935-4941

 

Abstract Image

 

 

2011年

原著論文

 1. K. Kuramoto, N. Tarashima, Y. Hirama, Y. Kikuchi, N. Minakawa, and A. Matsuda

New imidazopyridopyrimidine:naphthyridine base-pairing motif, ImNN:NaOO, consisting of a DAAD:ADDA hydrogen bonding pattern, markedly stabilize DNA duplexes

Chem. Commun. 2011,47,10818-10820

 

 Graphical abstract: New imidazopyridopyrimidine:naphthyridine base-pairing motif, ImNN:NaOO, consisting of a DAAD:ADDA hydrogen bonding pattern, markedly stabilize DNA duplexes

 

 

2. H. Taniike, Y. Inagaki, A. Matsuda, and N. Minakawa

Practical synthesis of 4′-selenopyrimidine nucleosides using hypervalent iodine

Tetrahedron. 2011,67,7977-7982.

 

Full-size image (16 K)

 

 

3. M. Hori, T. Suzuki, N. Minakawa, A. Matsuda, H. Harashima, H. Kamiya

Mutagenecity of secondary oxidation products of 8-oxo-7,8-dihydro-2’-deoxyguanosine 5’-triphosphate (8-hydroxy-2’-deoxyguanosine 5’-triphosphate)

Mut. Res. 2011, 714, 11-16.

 

Full-size image (7 K)

 

 

4. Y. Hirama, N. Minakawa, and A. Matsuda

Synthesis and characterization of oligodeoxynucleotides containing a novel tetraazabenzo[cd]azulene:naphthyridine base pair

Bioorg. Med. Chem. 2011, 19, 352-358.

2011 hirama bmc.jpg

 

5. M. Kataoka, Y. Kouda, K. Sato,N. Minakawa, and A. Matsuda

Highlhy efficient enzymatic synthesis of 3'-deoxyapionucleic acid (apioNA) having the four natural nucleobases

Chem. Commun. 2011, 47, 8700-8702.

 

Graphical abstract: Highly efficient enzymatic synthesis of 3′-deoxyapionucleic acid (apioNA) having the four natural nucleobases

 

 

2010年

原著論文

1. K. Tomaya, M. Takahashi, N. Minakawa, and A. Matsuda

A convenient RNA synthesis using a phosphoramidite possessing a biotinylated photocleavable group

Org. Lett. 2010, 12, 3836-3839

Abstract Image

2. Y. Hirama, H. Abe, N. Minakawa, and A. Matsuda

Synthesis and properties of a novel nucleoside derivative possessing a 2,3,5,6-tetraazabenzo[cd]azulene skeleton

Tetrahedron 2010, 66, 8402-8406.

 Full-size image (20 K)

2009年

原著論文

 1. N. Minakawa, S. Ogata, M. Takahashi, A. Matsuda

Selective recognition of unnatural imidazopyridopyrimidine:naphthyridine base pairs consisting of four hydrogen bonds by the Klenow fragment

J. Am. Chem. Soc., 2009, 131, 1644-1645.

 Abstract Image

2. M. Takahashi, N. Minakawa, A. Matsuda

Synthesis and characterization of 2’-modified-4’-thioRNA: a comprehensive comparison of nuclease stability

Nucleic Acids Res. 2009, 37, 1353-1362.

 An external file that holds a picture, illustration, etc.
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3. S. Ogata, M. Takahashi, N. Minakawa, A. Matsuda

Unnatural imidazopyridopyrimidine:naphthyridine base pairs: selective incorporation and extension reaction by Deep Vent (exo–) DNA polymerase

Nucleic Acids Res. 2009, 37, 5602-5609.

 An external file that holds a picture, illustration, etc.
Object name is gkp611f1.jpg

総説・著書

1. 南川 典昭,松田 彰
siRNA分子のデザインとターゲッティング
『がん分子標的治療研究 実践マニュアル』(金芳堂)2009年,pp164–170.

 

2008年以前

原著論文

1. N. Minakawa, Y. Kawano, S. Murata, N. Inoue, A. Matsuda

Oligodeoxynucleotides containing 3-bromo-3-deazaadenine and 7-bromo-7-deazaadenine nucleosides as chemical probes to investigate DNA-protein interaction.

ChemBioChem 2008, 9, 464–470.

 

2. M. Takahashi, S. Daidouji, M. Shiro, N. Minakawa, A. Matsuda

Synthesis and Crystal Structure of 2’-Deoxy-2’-fluoro-4’-thionucleosides: Substrates for the Synthesis on Novel Modified RNAs.

Tetrahedron 2008, 64, 4313-4324.

 

3. A. Matsugami, T. Ohyama, M. Inada, N. Inoue, N. Minakawa, A. Matsuda, M. Katahira

Unxepected A-form formation of 4’-thioDNA in solution, revealed by NMR, and the implications as to the mechanism of nuclease-resistance.

Nucleic Acids Res. 2008, 36, 1805-1812.

 

4. N. Minakawa, M. Sanji, Y. Kato, A. Matsuda

Investigations toward the selection of fully-modified 4’-thioDNA aptamers: Optimization of in vitro transcription steps in the presence of 4’-thioNTPs

Bioorg. Med. Chem. 2008, 16, 9450-9456.

 

5. S. Hoshika, N. Minakawa, A. Shionoya, K. Imada, N. Ogawa, A. Matsuda.

Study of modification pattern–RNAi activity relationships using siRNAs modified with 4’-thioribonucleosides.

ChemBioChem 2007, 8, 2133–2138.

 

6. N. Inoue, A. Shionoya, N. Minakawa, A. Kawakami, N. Ogawa, A. Matsuda

Amplification of 4’-thioDNA in the presence of 4’-thio-dTTP and 4’-thio-dCTP, and 4’-thioDNA-derected transcription in vitro and in cells.

J. Am. Chem. Soc. 2007, 129, 15424–15425.

 

7. N. Minakawa, K. Kuramoto, S. Hikishima, A. Matsuda

Four hydrogen-bonding motifs in oligonucleotides

ARKIVOC 2006, 7, 326–337.

 

8. S. Ichikawa, N. Minakawa, S. Shuto, M. Tanaka, T. Sasaki, A. Matsuda

Synthesis of 3’--carbamoylmethylcytidine (CAMC) and its derivatives as potential antitumor agents

Org. Biomol. Chem. 2006, 4, 1284–1296.

 

9. N. Inoue, N. Minakawa, A. Matsuda

Synthesis and Properties of 4’-ThioDNA: Unexpected RNA-like Behavior of 4’-ThioDNA

Nucleic Acids Res. 2006, 34, 3476–3483.

 

10. S. Hikishima, N. Minakawa, K. Kuramoto, S. Ogata, A. Matsuda

Synthesis and Characterization of Oligodeoxynucleotides Containing Naphthyridine:Imidazopyridopyrimidine Base Pairs on their Sticky Ends. Application to Thermally Stabilized Decoy Molecules.

ChemBioChem 2006, 7, 1970–1975.

 

11. H. Kamiya, C. Cadene-Amaro, L. Dugué, H. Yakushiji, N. Minakawa, A. Matsuda, S. Pochet, Y. Nakabeppu, H. Harashima.

Recognition of Nucleotide Analogs Containing the 7,8-Dihydro-8-oxo Structure by the Human MTH1 Protein.

J. Biochem. 2006, 140, 843–849.

 

12. S. Hikishima, N. Minakawa, K. Kuramoto, Y. Fujisawa, M. Ogawa, A. Matsuda

Synthesis of 1,8-Naphthyridine C-Nucleosides and Their Base-Pairing Properties in Oligodeoxynucleotides: Thermally Stable Naphthyridine:Imidazopyridopyrimidine Base-Pairing Motifs.

Angew. Chem. Int. Ed. 2005, 44, 596–598.

 

13. D. Kaga, N. Minakawa, A. Matsuda

Synthesis of 2’-C-Methyl-4’-thiocytidine: Unexpected Anomerization of the 2’-keto-4’-thionucleoside Precursor.

Nucleosides Nucleotides Nucleic Acids 2005, 24, 1789–1800.

 

14. M. M. Changalov, G. D. Ivanova, M. A. Rangelov, P. Acharya, S. Acharya, N. Minakawa, A. Foldesi, I. B. Stoineva, V. M. Yomtova, C. D. Roussev, A. Matsuda, J. Chattopadhyaya, D. D. Petkov

2’/3’-O-Peptidyl Adenosine as a General Base catalyst of it Own External Peptidyl Transfer: Implications for the Ribosome Catalytic Mechanism.

ChemBioChem 2005, 6, 992–996.

 

15. S. Hoshika, N. Minakawa, H. Kamiya, H. Harashima, A. Matsuda

RNA interference (RNAi) induced by siRNAs modified with 4’-thioribonucleosides in cultured mammalian cells.

FEBS Lett. 2005, 579, 3115–3118.

 

16. Y. Kato, N. Minakawa, Y. Komatsu, H. Kamiya, N. Ogawa, H. Harashima, A. Matsuda

New NTP Analogs: The Synthesis of 4’-ThioUTP and 4’-ThioCTP and Their Utility for SELEX.

Nucleic Acids Res. 2005, 33, 2942–2951.

 

17. N. Inoue, D. Kaga, N. Minakawa, A. Matsuda

Practical Synthesis of 2’-Deoxy-4’-thioribonucleosides: Substrates for the Synthesis of 4’-thioDNA.

J. Org. Chem. 2005, 70, 8597–8600.

 

18. S. Hoshika, N. Minakawa, A. Matsuda

Synthesis and physical and physiological properties of 4’-thioRNA: application to post-modification of RNA aptamer toward NF-B.

Nucleic Acids Res. 2004, 32, 3815–3825.

 

19. N. Minakawa, Y. Kato, K. Uetake, D. Kaga, A. Matsuda

An Improved large scale synthesis of 1,4-anhydro-4-thio-D-ribitol.

Tetrahedron, 2003, 59, 1699–1702.

 

20. A. B. Smith, III, N. Kanoh, H. Ishiyama, N. Minakawa, J. D. Rainier, R. A. Hartz, Y. S. Cho, H. Cui, W. H. Moser

Tremorgenic Indole Alkaloids. The Total Synthesis of (–)-Penitrem D.

J. Am. Chem. Soc., 2003, 125, 8228–8237.

 

21. N. Minakawa, N. Kojima, S. Hikishima, T. Sasaki, A. Kiyosue, N. Atsumi, Y. Ueno, A. Matsuda

New Base Paring Motifs. The Synthesis and Thermal Stability of Oligodeoxynucleotides Containing Imidazopyridopyrimidine Nucleosides with the Ability to Form Four Hydrogen Bonds.

J. Am. Chem. Soc., 2003, 125, 9970–9982.

 

22. N. Minakawa, Y. Ono, A. Matsuda

A Versatile Modification of On-Column Oligodeoxynucleotides Using a Copper-Catalyzed Oxidative Acetylenic Coupling Reaction.

J. Am. Chem. Soc., 2003, 125, 11545–11552.

 

23. M. Tanimoto, H. Kamiya, N. Minakawa, A. Matsuda, H. Harashima

No Enhancement of Nuclear Entry by Direct Conjugation of a Nuclear Localization signal Peptide to Linearized DNA.

Bioconjugate Chem., 2003, 14, 1197–1202.

 

24. S. Shuto, N. Minakawa, S. Niizuma, H-S. Kim, Y. Wataya, A. Matsuda

Alternative Synthesis and Antimalarial Effect of (6'R)-6'-C-Methylneplanocin A, a Potent AdoHcy Hydrolase Inhibitor.

J. Med. Chem., 2002, 45, 748–751.

 

25. J. K. Soukup, N. Minakawa, A. Matsuda, S. A. Strobel

Identification of A-Minor Tertiary Interactions within a Bacterial Group I Intron Active Site by 3-Deazaadenosine Interference Mapping.

Biochemistry, 2002, 41, 10426–10438.

 

26. N. Minakawa, D. Kaga, Y. Kato, K. Endo, M. Tanaka, T. Sasaki, A. Matsuda

Synthesis and structural elucidation of 1-(3-C-ethynyl-4-thio--D-ribofuranosyl)cytosine (4'-thioECyd).

J. Chem. Soc., Perkin Trans. 1, 2002, 2182–2189.

 

27. T. Umino, K. Yoshioka, Y. Saitoh, N. Minakawa, H. Nakata, A. Matsuda

Nucleosides and Nucleotides. 200. Reinvestigation of 5’-N-Ethylcarboxamideadenosine Derivatives: Structure-Activity Relationships for P3 purinoceptor-like protein.

J. Med. Chem., 2001, 44, 208–214.

 

28. K. Shinozuka, R. Ishii-Nozawa, K. Takeuchi, N. Minakawa, A. Matsuda, H. Nakata, M. Kunitomo

Effect of 9-(6,7-Dideoxy--D-allo-hept-5-ynofuranosyl)adenine on Noradrenaline Release from Vascular Sympathetic Nerves.

Clin. Exp. Pharmacol. Physiol., 2001, 28, 312–314.

 

29. M. Fukuoka, S. Shuto, N. Minakawa, Y. Ueno, A. Matsuda

Synthesis and Biological Activities of Cyclic ADP-carbocyclic-ribose and Its Analogs.

Nucleosides, Nucleotides, Nucleic Acids, 2001, 20, 1355–1358.

 

30. P. R. Wyde, D. K. Moore-Poveda, E. DeClercq, J. Neyts, A. Matsuda, N. Minakawa, E. Guzman, B. E. Gilbert

Use of Cotton Rats to Evaluate the Efficacy of Antivirals in Treatment of Measles Virus Infections.

Antimicrob. Agents Chemother., 2000, 44, 1146–1152.

 

31. T. Umino, N. Minakawa, A. Matsuda

Alternative Method to Synthesize 9-(6,7-Dideoxy--D-allo-hept-5-ynofuranosyl)adenine, A Selective and Potent Ligand for P3 Purinoceptor-like Protein: A Stereoselective Reduction Based on Sugar Puckering of the Furanose Ring.

Tetrahedron Lett., 2000, 41, 6419–6423.

 

32. T. Naka, N. Minakawa, H. Abe, D. Kaga, A. Matsuda

The Stereoselective Synthesis of 4’--Thioribonucleosides via the Pummerer Reaction.

J. Am. Chem. Soc., 2000, 122, 7233–7243.

 

33. M. Fukuoka, S. Shuto, N. Minakawa, Y. Ueno, A. Matsuda

An Efficient Synthesis of Cyclic IDP- and Cyclic 8-Bromo-IDP-Carbocyclic-Riboses Using a Modified Hata Condensation Method To Form an Intramolecular Pyrophosphate Linkage as a Key Step. An Entry to a General Method for the Chemical Synthesis of Cyclic ADP-Ribose Analogues.

J. Org. Chem., 2000, 65, 5238–5248.

 

34. N. Kojima, N. Minakawa, A. Matsuda

Studies in the Chemical Conversion of the 4-Carboxamide Group of 5-Amino-1--D-ribofuranosylimidazole-4-carboxamide (AICA-Riboside). Application for the Synthesis of 1-Deazaguanosine.

Tetrahedron, 2000, 56, 7909–7914.

 

35. M. Fukuoka, S. Shuto, N. Minakawa, Y. Ueno, A. Matsuda

Alternative Synthesis of Cyclic IDP-Carbocyclic Ribose. Efficient Cyclization of an 8-Bromo-N1-[5-(phosphoryl)carbocyclic-ribosyl]inosine 5’-Phenylthiophosphate Derivative Mediated by Iodine.

Tetrahedron Lett., 1999, 40, 5361–5364.

 

36. T. Naka, N. Nishizono, N. Minakawa, A. Matsuda

Investigation of the Stereoselective Coupling of Thymine with meso-Thiolane-3,4-diol-1-oxide Derivative via the Pummerer Reaction.

Tetrahedron Lett., 1999, 40, 6297–6300.

 

37. N. Minakawa, N. Kojima, A. Matsuda

Synthesis and Conformational Investigation of Anti-fixed 3-Deaza-3-halopurine Ribonucleosides.

J. Org. Chem., 1999, 64, 7158–7172.

 

38. A. B. Smith, III, N. Kanoh, N. Minakawa, J. D. Rainier, F. R. Blase, R. A. Hartz

Tremorgenic Indole Alkaloids. Studies Directed Towards the Assembly of the A, F and I Rings of Penitrem D: Observation of an Unexpected Stereochemical Outcome.

Org. Lett., 1999, 1, 1263–1266.

 

39. T. Mizutani, H. Inagaki, D. Hayasaka, S. Shuto, N. Minakawa, A. Matsuda, H. kariwa, I. Takashima

Transcriptional control of borna disease virus (BDV) in persistently BDV-infected cells.

Arch. Virol., 1999, 144, 1937–1946.

 

40. N. Minakawa, T. Sasaki, A. Matsuda

Ring-expanded Purine Nucleosides. The synthesis and Cytotoxicity of Imidazo[4,5-c]azepine Nucleosides.

Tetrahedron, 1998, 54, 13517–13528.

 

41. S. Shuto, M. Kanazaki, S. Ichikawa, N. Minakawa, A. Matsuda

Stereo- and Regioselective Introduction of 1- or 2-Hydroxyethyl Group via Intramolecular Radical Cyclization Reaction with a Novel Silicon-Containing Tether. An Efficient Synthesis of 4’-Branched 2’-Deoxyadenosines.

J. Org. Chem., 1998, 63, 746–754.

 

42. A. Matsuda, H. Kosaki, Y. Saitoh, Y. Yoshimura, N. Minakawa, H. Nakata

Nucleosides and Nucleotides. 177. 9-(6,7-Dideoxy--D-allo-hept-5-ynofuranosyl)adenine: A Selective and Potent Ligand for P3 Purinoceptor-like Protein.

J. Med. Chem., 1998, 41, 2676–2678.

 

43. S. Ichikawa, S. Shuto, N. Minakawa, A. Matsuda

Synthesis of 3’--Branched Uridine Derivatives via Intramolecular Reformatsky-type Reaction Promoted by Samarium Diiodide.

J. Org. Chem., 1997, 62, 1368–1375.

 

44. N. Minakawa, N. Kojima, A. Matsuda

Synthesis of 3-Halo-3-deazainosines: Conformational Lock with the Halogen at the 3-Position of the 3-Deazainosine in Anti-conformation.

Heterocycles, 1996, 42, 149–154.

 

45. N. Minakawa, N. Kojima, T. Sasaki, A. Matsuda

Synthesis and Antileukemic Activity of 5-Carbon-substituted 1--D-Ribofuranosylimidazole-4-carboxamides.

Nucleosides Nucleotides, 1996, 15, 251–263.

 

46. N. Minakawa, Y. Sasabuchi, A. Kiyosue, N. Kojima, A. Matsuda

Synthesis of 5-Amino-4-imidazolecarboxamide (AICA) Deoxyribosides from Deoxyinosines and Their Conversion into 3-Deazapurine Derivatives.

Chem. Pharm. Bull., 1996, 44, 288–295.

 

47. N. Minakawa, A. Matsuda, Z. Xia, L. I. Wiebe, E. E. Knaus

Synthesis of [2-2H]-5-Ethynyl-1-(-D-ribofuranosyl)imidazole-4-carboxamide and 5-Ethynyl-1-([5-3H]--D-ribofuranosyl)imidazole-4-carboxamide (EICAR).

J. Labelled Comp. Radiopharm., 1996, 38, 809–824.

 

48. W. Wang, V. V. Papov, N. Minakawa, A. Matsuda, K. Biemann, L. Hedstrom

Inactivation of Inosine 5’-Monophosphate Dehydrogenase by the Antiviral Agent 5-Ethynyl-1--D-ribofuranosylimidazole-4-carboxamide 5’-Monophosphate.

Biochemistry, 1996, 35, 95–101.

 

49. A. E. A. Hassan, N. Nishizono, N. Minakawa, S. Shuto, A. Matsuda

Conversion of (Z)-2’-(Cyanomethylene)-2’-deoxyuridines into their (E)-Isomers via Addition of Thiophenol to the Cyanomethylene Moiety Followed by Oxidative Syn-elimination Reactions.

J. Org. Chem., 1996, 61, 6261–6267.

 

50. A. Ono, N. Haginoya, M. Kiyokawa, N. Minakawa, A. Matsuda

A Novel and Convenient Post-synthetic Modification Method for the Synthesis of Oligodeoxyribonucleotides of 2’-Deoxyuridine.

Bioorg. Med. Chem. Lett., 1994, 4, 361–366.

 

51. M. Aoyagi, N. Minakawa, A. Matsuda

The synthesis of Imidazo[4,5-e][1,4]diazepine Nucleosides from N1-Substituted Inosines.

Nucleosides Nucleotides, 1994, 13, 1535–1549.

 

52. Y. Yamagata, M. Kato, M. Aoyagi, N. Minakawa, A. Matsuda

Conformation of 3-Substituted Purine Nucleoside Studied by X-Ray Crystallography and Theoretical Calculations.

Nucleosides Nucleotides, 1994, 13, 1327–1335.

 

53. N. Minakawa, A. Matsuda

A Convenient Method for the Synthesis of 3-Deazapurine Nucleosides from AICA-riboside.

Tetrahedron Lett., 1993, 34, 661–664.

 

54. M. Aoyagi, N. Minakawa, A. Matsuda

Synthesis of 3-Alkyl-3-deazainosines via Palladium-catalyzed Intramolecular Cyclization: A New Conformational Lock with the Alkyl Group at the 3-Position of the 3-Deazainosine in Anti-conformation.

Tetrahedron Lett., 1993, 34, 103–106.

 

55. N. Minakawa, A. Matsuda

Convenient Synthesis of 3-Deazaadenosine, 3-Deazaguanosine, and 3-Deazainosine via Ring Closure of 5-Ethynyl-1--D-ribofuranosylimidazole-4-carboxamide or –carbonitrile.

Tetrahedron, 1993, 49, 557–570.

 

56. N. Minakawa, T. Sasaki, A. Matsuda

A Transition-state Analogue in Purine Nucleotide Biosynthesis: The Design and Synthesis of an Imidazo[4,5-c]azepine Nucleoside.

Bioorg. Med. Chem. Lett., 1993, 3, 183–186.

 

57. A. Azuma, Y. Nakajima, N. Nishizono, N. Minakawa, A. Suzuki, K. Hanaoka, T. Kobayashi, M. Tanaka, T. Sasaki, A. Matsuda

2’-C-Cyano-2’-deoxy-1--D-arabinofuranosylcytosine and its Derivatives. A New Class of Nucleoside with a Broad Antitumor Spectrum.

J. Med. Chem., 1993, 36, 4183–4189.

 

58. A. Matsuda, A. Dan, N. Minakawa, S. J. Tregear, S. Okazaki, Y. Sugimoto, T. Sasaki

Synthesis of 1-(2-Deoxy-2-isocyano--D-arabinofuranosyl)cytosine and Related Nucleosides as Potential Antitumor Agents.

J. Med. Chem., 1993, 36, 4190–4194.

 

59. N. Minakawa, T. Takeda, T. Sasaki, A. Matsuda, T. Ueda

Synthesis and Antitumor Activity of 5-Ethynyl-1--D-ribofuranosylimidazole-4-carboxamide (EICAR) and Its Derivatives.

J. Med. Chem., 1991, 34, 778–786.

 

60. E. De Clercq, M. Cools, J. Balzarini, R. Snoeck, G. Andrei, M. Hosoya, S. Shigeta, T. Ueda, N. Minakawa, A. Matsuda

Antiviral Activities of 5-Ethynyl-1--D-ribofuranosylimidazole-4-carboxamide and Related Compounds.

Antimicrob. Agents Chemother., 1991, 35, 679–684.

 

61. N. Minakawa, A. Matsuda, T. Ueda, T, Sasaki

Synthesis and Antitumor Activies of 5-Ethynylimidazole-4-carboxamide and –carbonitrile Derivatives.

Nucleosides Nucleotides, 1990, 9. 1067–1078.

 

62. A. Matsuda, N. Minakawa, T. Sasaki, T. Ueda

The Design, Synthesis and Antileukemic Activity of 5-Alkynyl-1--D-ribofuranosylimidazole-4-carboxamide.

Chem. Pharm. Bull., 1988, 36, 2730–2733.

 

総説・著書

1. 南川 典昭,松田 彰
スーパー核酸:4’-チオ核酸の合成から核酸医薬開発に向けた基礎研究の展開
『化学フロンティア19 創薬をめざす有機合成戦略』(化学同人)2007年,pp157–164.

 

 2. 松田 彰,南川 典昭
核酸医薬の創製をめざして
『バイオとナノの融合 II;新生命科学の応用』(北海道大学COE研究成果編集委員会編;北海道大学)2007年,pp187–198.

 

 3. N. Minakawa, S. Hoshika, N. Inoue, Y. Kato, A. Matsuda
4’-Thionucleic Acids; Chemistry, properties and Applications for Developing Functional Oligonucleotides.
Frontiers in Organic Chemistry: Atta-Ur-Rahman, Y. Hayakawa, Eds.; Bentham Science Publishers LTD., 2005, Vol. 1, p79–102.

 

 4. 南川 典昭
RNAi研究において有機化学ができること:その現状と展望
『RNAi法とアンチセンス法;RNAの科学と応用』(関根光雄・多比良和誠編;講談社サイエンティフィック)2005年、pp110–122.

 

 5. S. Shuto, M. Kanazaki, I. Sugimoto, S. Ichikawa, Y. Nagasawa, Y. Ueno, H. Abe, N. Minakawa, M. Sukeda, T. Kodama, M. Nomura, A. Matsuda

Development of New Radical Reactions with a Vinylsilyl Group and Their Application to the Synthesis of Branched-chain Sugar Nucleosides.
Recent Advances in Nucleosides: Chemistry and Chemotherapy: C. K. Chu, Eds.; Elsevier Science B. V., 2002; p21–55.

 

 6. N. Minakawa, A. Matsuda
Mechanism-based Design of Inosine 5’-Monophosphate Dehydrogenase Inhibitors: Synthesis and Biological Activities of 5-Ethynyl-1--D-ribofuranosylimidazole-4-carboxamide (EICAR) and its Derivatives.

Curr. Med. Chem., 1999, 6, 615–628.

 

 7. 南川 典昭 、松田 彰
イノシン5’–一リン酸脱水素酵素阻害剤と生物活性
蛋白質 核酸 酵素、1995年7月増刊号、40巻、p1299–1305

 

 8. A. Matsuda, A. Azuma, Y. Nakajima, K. Takenuki, A. Dan, T. Iino, Y. Yoshimura, N. Minakawa, T, Sasaki
Design of New Types of Antitumor Nucleosides: The Synthesis and Antitumor Activity of 2’-Deoxy-(2’-C-substituted)cytidines.
Nucleosides and Nucleotides as Antitumor and Antiviral Agents: C. K. Chu, D. C. Baker, Eds.; Plenum Publishing Co.: New York, 1993; p1–22.