Title:
AROMATIC COMPOUND, MODIFICATION CARRIER THAT USES SAME AND IS USED FOR SYNTHESIZING AN OLIGONUCLEOTIDE DERIVATIVE, OLIGONUCLEOTIDE DERIVATIVE, AND OLIGONUCLEOTIDE CONSTRUCT
Document Type and Number:
WIPO Patent Application WO/2011/071078
Kind Code:
A1
Abstract:
Provided is an oligonucleotide derivative, the 3′ end of which is chemically modified with two skeletons selected from among benzene skeletons and pyridine skeletons. Said oligonucleotide derivative can be easily synthesized in a small number of steps. Also provided is an aromatic compound that serves as a precursor for preparing a modification carrier for synthesizing the oligonucleotide derivative. The oligonucleotide derivative and a provided oligonucleotide construct have good cell membrane permeability and excellent nuclease resistance. The aforementioned modification carrier is characterized in that the carrier is chemically modified, via a linker, with the unit represented by structural formula (a) (in which R1 through R6 each independently represent hydrogen or a non-hydrogen substituent, Z1 and Z2 each independently represent CH or nitrogen, and X represents oxygen or sulfur).
Inventors:
KITADE YUKIO (JP)
KITAMURA YOSHIAKI (JP)
KITAMURA YOSHIAKI (JP)
Application Number:
PCT/JP2010/072020
Publication Date:
June 16, 2011
Filing Date:
December 08, 2010
Export Citation:
Assignee:
UNIV GIFU (JP)
KITADE YUKIO (JP)
KITAMURA YOSHIAKI (JP)
KITADE YUKIO (JP)
KITAMURA YOSHIAKI (JP)
International Classes:
C07C275/24; A61K31/7088; A61K31/7105; A61K31/711; A61K31/713; A61K48/00; C07C335/12; C07D213/40; C07F7/10; C07F9/09; C07F9/6558; C07H21/00; C07H21/02; C07H21/04; C12N15/09; C12Q1/68
Other References:
LEUNG, A.N. ET AL.: "Effect of spacer geometry on oxoanion binding by bis- and tetrakis-thiourea hosts", TETRAHEDRON, vol. 64, no. LL, 2008, pages 2530 - 2536, XP022454903, DOI: doi:10.1016/j.tet.2008.01.026
LEE, K.H. ET AL.: "C3-Symmetric metacyclophane- based anion receptors with three thiourea groups as linkers between aromatic groups", TETRAHEDRON LETTERS, vol. 41, no. 32, 2000, pages 6083 - 6087, XP004243519, DOI: doi:10.1016/S0040-4039(00)00966-7
SMITH, J. ET AL.: "Solid and Solution Phase Organic Syntheses of Oligomeric Thioureas", JOURNAL OF ORGANIC CHEMISTRY, vol. 61, no. 25, 1996, pages 8811 - 8818
See also references of EP 2511260A4
J. B. MA.; K. YE; D. J. PATEL., NATURE, vol. 429, 2004, pages 318 - 322
J. J. SONG.; J. LIU.; N. H. TOLIA.; J. SCHNEIDERMAN.; S. K. SMITH.; R. A. MARTIENSSEN.; G. J. HANNON; L. JOSHUA-TOR., NAT. STRUCT. BIOL., vol. 10, 2003, pages 1026 - 1032
K. S. YAN.; S. YAN.; A. FAROOQ.; A. HAN.; L. ZENG; M. M. ZHOU., NATURE., vol. 426, 2003, pages 468 - 474
ZHANG.; F. A. KOLB.; L. JASKIEWICZ.; E. WESTHOF; W. FILIPOWICZ., CELL., vol. 118, 2003, pages 57 - 68
A. LINGEL.; B. SIMON.; E. IZAURRALDE; M. SATTLER., NATURE., vol. 426, 2003, pages 465 - 469
L. BEIGELMAN.; J.A MCSWIGGEN.; K. G. DRAPER ET AL., J BIOLCHEM, vol. 270, 1995, pages 25702 - 25708
S . P. ZINNEN K.DOMENICO.; M. WILSON ET AL., RNA, vol. 8, 2002, pages 214 - 228
S. AGRAWALAND; E. R. KANDIMAILA., CURR. CANCER DRUG TARGETS., vol. 1, 2001, pages 197 - 209
H.HOSHI, FEBS LETTERS, vol. 521, 2002, pages 197 - 199
Y. UENO; T. NAITO; K. KAWADA; A. SHIBATA; HYE-SOOK KIM Y. WATAYA; Y. KIDADE, BIOCHEM BIOPHYS RES COMMUN, vol. 330, 2005, pages 1168 - 1175
LEE, K.H. ET AL.: "C3-Symmetric metacyclophane- based anion receptors with three thiourea groups as linkers between aromatic groups", TETRAHEDRON LETTERS, vol. 41, no. 32, 2000, pages 6083 - 6087, XP004243519, DOI: doi:10.1016/S0040-4039(00)00966-7
SMITH, J. ET AL.: "Solid and Solution Phase Organic Syntheses of Oligomeric Thioureas", JOURNAL OF ORGANIC CHEMISTRY, vol. 61, no. 25, 1996, pages 8811 - 8818
See also references of EP 2511260A4
J. B. MA.; K. YE; D. J. PATEL., NATURE, vol. 429, 2004, pages 318 - 322
J. J. SONG.; J. LIU.; N. H. TOLIA.; J. SCHNEIDERMAN.; S. K. SMITH.; R. A. MARTIENSSEN.; G. J. HANNON; L. JOSHUA-TOR., NAT. STRUCT. BIOL., vol. 10, 2003, pages 1026 - 1032
K. S. YAN.; S. YAN.; A. FAROOQ.; A. HAN.; L. ZENG; M. M. ZHOU., NATURE., vol. 426, 2003, pages 468 - 474
ZHANG.; F. A. KOLB.; L. JASKIEWICZ.; E. WESTHOF; W. FILIPOWICZ., CELL., vol. 118, 2003, pages 57 - 68
A. LINGEL.; B. SIMON.; E. IZAURRALDE; M. SATTLER., NATURE., vol. 426, 2003, pages 465 - 469
L. BEIGELMAN.; J.A MCSWIGGEN.; K. G. DRAPER ET AL., J BIOLCHEM, vol. 270, 1995, pages 25702 - 25708
S . P. ZINNEN K.DOMENICO.; M. WILSON ET AL., RNA, vol. 8, 2002, pages 214 - 228
S. AGRAWALAND; E. R. KANDIMAILA., CURR. CANCER DRUG TARGETS., vol. 1, 2001, pages 197 - 209
H.HOSHI, FEBS LETTERS, vol. 521, 2002, pages 197 - 199
Y. UENO; T. NAITO; K. KAWADA; A. SHIBATA; HYE-SOOK KIM Y. WATAYA; Y. KIDADE, BIOCHEM BIOPHYS RES COMMUN, vol. 330, 2005, pages 1168 - 1175
Attorney, Agent or Firm:
AOYAMA, Yo (JP)
Aoyama Sun (JP)
Aoyama Sun (JP)
Download PDF:
Previous Patent: LIGHT EMITTING ELEMENT AND METHOD FOR MANUFACTURING SAME
Next Patent: SKIN CLEANSING AGENT
Next Patent: SKIN CLEANSING AGENT