Title:
OLIGONUCLEOTIDE HAVING NON-NATURAL NUCLEOTIDE AT 5'-TERMINAL THEREOF
Document Type and Number:
WIPO Patent Application WO/2015/133491
Kind Code:
A1
Abstract:
Provided are: an oligonucleotide having, at 5'-terminal thereof, a nucleotide or nucleoside residue represented by formula (I) {wherein X1 represents an oxygen atom or the like; R1 represents formula (IIA) (wherein R5A represents a halogen atom or the like; and R6A represents a hydrogen atom or the like), formula (IVA) (wherein Y3A represents a nitrogen atom or the like; and Y4A represents CH or the like) or the like; R2 represents a hydrogen atom, a hydroxy group, a halogen atom or a lower alkoxy group which may have a substituent; and R3 represents a hydrogen atom or formula (VI) (wherein n2 represents 1, 2 or 3)}, wherein the nucleotide or nucleoside residue is bound to an adjacent nucleotide residue through an oxygen atom that is located at position-3 in the nucleotide or nucleoside residue; and others.
Inventors:
SHINOHARA FUMIKAZU (JP)
MAKINO ASANA (JP)
YAMAMOTO JUNICHIRO (JP)
NAKAJIMA TAKAHIRO (JP)
OASHI TAIJI (JP)
SUZUKI MICHIHIKO (JP)
SAITO JUN-ICHI (JP)
NISHIKAWA TOMOYUKI (JP)
NAKOJI MASAYOSHI (JP)
TAKAHASHI YUICHI (JP)
KOUDA YASUO (JP)
MAKINO ASANA (JP)
YAMAMOTO JUNICHIRO (JP)
NAKAJIMA TAKAHIRO (JP)
OASHI TAIJI (JP)
SUZUKI MICHIHIKO (JP)
SAITO JUN-ICHI (JP)
NISHIKAWA TOMOYUKI (JP)
NAKOJI MASAYOSHI (JP)
TAKAHASHI YUICHI (JP)
KOUDA YASUO (JP)
Application Number:
PCT/JP2015/056249
Publication Date:
September 11, 2015
Filing Date:
March 03, 2015
Export Citation:
Assignee:
KYOWA HAKKO KIRIN CO LTD (JP)
International Classes:
C07H19/16; A61K31/7076; A61K31/713; A61K48/00; A61P43/00; C07H19/167; C07H19/173; C07H19/20; C12N15/113
Domestic Patent References:
| WO2013090186A1 | 2013-06-20 | |||
| WO2014034934A1 | 2014-03-06 |
Foreign References:
| US5906918A | 1999-05-25 | |||
| JPS5363399A | 1978-06-06 |
Other References:
LIU, J. ET AL.: "Synthesis of photoactive DNA: incorporation of 8-bromo-2'- deoxyadenosine into synthetic oligodeoxynu", TETRAHEDRON LETT., vol. 33, no. 30, 1992, pages 4265 - 4268, XP028085721, ISSN: 0040-4039
SHIBUTANI, S. ET AL.: "Translesional synthesis on DNA templates containing 8-oxo-7,8- dihydrodeoxyadenosine.", BIOCHEMISTRY, vol. 32, no. 17, 1993, pages 4615 - 4621, XP055223093, ISSN: 0060-2960
BERES, J. ET AL.: "Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3", J. MED. CHEM., vol. 29, no. 4, 1986, pages 488 - 493, XP055223094
MICHEL, J. ET AL.: "Triplex stability of oligodeoxynucleotides containing substituted quinazoline-2,4-(1H,3H)-dione.", TETRAHEDRON, vol. 53, no. 25, 1997, pages 8457 - 8478, XP004105778, ISSN: 0040-4020
TOR, Y. ET AL.: "Designing new isomorphic fluorescent nucleobase analogues: the thieno[3,2-d]pyrimidine core.", TETRAHEDRON, vol. 63, no. 17, 2007, pages 3608 - 3614, XP005929593, ISSN: 0040-4020
SEITZ, H. ET AL.: "A 5'-uridine amplifies miRNA/miRNA* asymmetryin Drosophila by promoting RNA-inducedsilencing complex", SILENCE, vol. 2, no. 4, 2011, pages 1 - 10, XP055223097, ISSN: 1758-907x
FRANK, F. ET AL.: "Structural basis for 5'- nucleotide base-specific recognition of guide RNA by human AG02.", NATURE, vol. 465, no. 7299, 2010, pages 818 - 822, XP055223099, ISSN: 0028-0836
PEACOCK, H. ET AL.: "Chemical modification of siRNA bases to probe and enhance RNA interference.", J. ORG. CHEM., vol. 76, no. 18, 2011, pages 7295 - 7300, XP055087444, ISSN: 0022-3263
DELEAVEY, G.F. ET AL.: "Designing chemically modified oligonucleotides for targeted gene silencing.", CHEM. BIOL., vol. 19, no. 8, 24 August 2012 (2012-08-24), pages 937 - 954, XP055107150, ISSN: 1074-5521
LIMA, W.F. ET AL.: "Binding and cleavage specificities of human Argonaute2.", J. BIOL. CHEM., vol. 284, no. 38, 2009, pages 26017 - 26028, XP055223101, ISSN: 0021-9258
SHIBUTANI, S. ET AL.: "Translesional synthesis on DNA templates containing 8-oxo-7,8- dihydrodeoxyadenosine.", BIOCHEMISTRY, vol. 32, no. 17, 1993, pages 4615 - 4621, XP055223093, ISSN: 0060-2960
BERES, J. ET AL.: "Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3", J. MED. CHEM., vol. 29, no. 4, 1986, pages 488 - 493, XP055223094
MICHEL, J. ET AL.: "Triplex stability of oligodeoxynucleotides containing substituted quinazoline-2,4-(1H,3H)-dione.", TETRAHEDRON, vol. 53, no. 25, 1997, pages 8457 - 8478, XP004105778, ISSN: 0040-4020
TOR, Y. ET AL.: "Designing new isomorphic fluorescent nucleobase analogues: the thieno[3,2-d]pyrimidine core.", TETRAHEDRON, vol. 63, no. 17, 2007, pages 3608 - 3614, XP005929593, ISSN: 0040-4020
SEITZ, H. ET AL.: "A 5'-uridine amplifies miRNA/miRNA* asymmetryin Drosophila by promoting RNA-inducedsilencing complex", SILENCE, vol. 2, no. 4, 2011, pages 1 - 10, XP055223097, ISSN: 1758-907x
FRANK, F. ET AL.: "Structural basis for 5'- nucleotide base-specific recognition of guide RNA by human AG02.", NATURE, vol. 465, no. 7299, 2010, pages 818 - 822, XP055223099, ISSN: 0028-0836
PEACOCK, H. ET AL.: "Chemical modification of siRNA bases to probe and enhance RNA interference.", J. ORG. CHEM., vol. 76, no. 18, 2011, pages 7295 - 7300, XP055087444, ISSN: 0022-3263
DELEAVEY, G.F. ET AL.: "Designing chemically modified oligonucleotides for targeted gene silencing.", CHEM. BIOL., vol. 19, no. 8, 24 August 2012 (2012-08-24), pages 937 - 954, XP055107150, ISSN: 1074-5521
LIMA, W.F. ET AL.: "Binding and cleavage specificities of human Argonaute2.", J. BIOL. CHEM., vol. 284, no. 38, 2009, pages 26017 - 26028, XP055223101, ISSN: 0021-9258
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