Title:
GUANIDINYLATED AMINOGLYCOSIDE -LIPID CONJUGATES
Document Type and Number:
WIPO Patent Application WO/2012/004684
Kind Code:
A3
Abstract:
Guanadinylated aminoglycoside-lipid conjugates are prepared. Such conjugates may comprise an aminoglycoside such as an aminoglyucoside antibiotic like neomycin or kanamycin, at least one guanidino group attached to a primary or secondary carbon atom of the aminoglyucoside group and at least one lipid group attached through a bond or a linker to a branched carbon atom of the aminoglycoside. These conjugates exhibit improve antibacterial activity and may be used in conjunction with another antibiotic.
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Inventors:
SCHWEIZER FRANK (CA)
SMRITILEKHA BERA (CA)
ZHANEL GEORGE (CA)
SMRITILEKHA BERA (CA)
ZHANEL GEORGE (CA)
Application Number:
PCT/IB2011/002534
Publication Date:
April 26, 2012
Filing Date:
March 04, 2011
Export Citation:
Assignee:
UNIV MANITOBA (CA)
SCHWEIZER FRANK (CA)
SMRITILEKHA BERA (CA)
ZHANEL GEORGE (CA)
SCHWEIZER FRANK (CA)
SMRITILEKHA BERA (CA)
ZHANEL GEORGE (CA)
International Classes:
A61K47/48; A61P31/04; C07H15/12; C07H15/18
Domestic Patent References:
| WO2010004433A2 | 2010-01-14 |
Foreign References:
| US20030054556A1 | 2003-03-20 | |||
| US6525182B1 | 2003-02-25 |
Other References:
BERA ET AL.: "Antibacterial activity of guanidinylated neomycin B- and kanamycin A-derived amphiphilic lipid conjugates", J. ANTIMICROB. CHEMOTHER., vol. 65, 23 March 2010 (2010-03-23), pages 1224 - 1227, XP055056231
SAINLOS ET AL.: "Kanamycin A-derived cationic lipids as vectors for gene transfection", CHEMBIOCHEM, vol. 6, 2005, pages 1023 - 1033, XP002479876
BELMONT ET AL.: "Aminoglycoside-derived cationic lipids as efficient vectors for gene transfection in vitro and in vivo", J. GENE MED., vol. 4, 2002, pages 517 - 526, XP008012289
BERA ET AL.: "Design, synthesis, and antibacterial activities of neomycin-lipid conjugates: Polycationic lipids with potent gram-positive activity", J. MED. CHEM., vol. 51, 2008, pages 6160 - 6164, XP008123388
LUEDTKE ET AL.: "Guanidinoglycosides: A novel family ofRNA ligands", J. AM. CHEM. SOC., vol. 122, 2000, pages 12035 - 12036, XP002965969
LUEDTKE ET AL.: "Cellular uptake of aminoglycosides, guanidinoglycosides, and poly-arginine", J. AM. CHEM. SOC., vol. 125, 2003, pages 12374 - 12375, XP055107228
BAKER ET AL.: "Synthesis and anti-HIV activity of guanidinoglycosides", J. ORG. CHEM., vol. 65, 2000, pages 9054 - 90-58, XP002370083
ELSON-SCHWAB ET AL.: "Guanidinylated neomycin delivers large, bioactive cargo inot cells through a heparan sulfate-dependent pathway", J. BIOL. CHEM., vol. 282, no. 18, 2007, pages 13585 - 13591, XP055107229
SAINLOS ET AL.: "Kanamycin A-derived cationic lipids as vectors for gene transfection", CHEMBIOCHEM, vol. 6, 2005, pages 1023 - 1033, XP002479876
BELMONT ET AL.: "Aminoglycoside-derived cationic lipids as efficient vectors for gene transfection in vitro and in vivo", J. GENE MED., vol. 4, 2002, pages 517 - 526, XP008012289
BERA ET AL.: "Design, synthesis, and antibacterial activities of neomycin-lipid conjugates: Polycationic lipids with potent gram-positive activity", J. MED. CHEM., vol. 51, 2008, pages 6160 - 6164, XP008123388
LUEDTKE ET AL.: "Guanidinoglycosides: A novel family ofRNA ligands", J. AM. CHEM. SOC., vol. 122, 2000, pages 12035 - 12036, XP002965969
LUEDTKE ET AL.: "Cellular uptake of aminoglycosides, guanidinoglycosides, and poly-arginine", J. AM. CHEM. SOC., vol. 125, 2003, pages 12374 - 12375, XP055107228
BAKER ET AL.: "Synthesis and anti-HIV activity of guanidinoglycosides", J. ORG. CHEM., vol. 65, 2000, pages 9054 - 90-58, XP002370083
ELSON-SCHWAB ET AL.: "Guanidinylated neomycin delivers large, bioactive cargo inot cells through a heparan sulfate-dependent pathway", J. BIOL. CHEM., vol. 282, no. 18, 2007, pages 13585 - 13591, XP055107229
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