WO2012004684A3 - Guanidinylated aminoglycoside -lipid conjugates - Google Patents
Guanidinylated aminoglycoside -lipid conjugates Download PDFInfo
- Publication number
- WO2012004684A3 WO2012004684A3 PCT/IB2011/002534 IB2011002534W WO2012004684A3 WO 2012004684 A3 WO2012004684 A3 WO 2012004684A3 IB 2011002534 W IB2011002534 W IB 2011002534W WO 2012004684 A3 WO2012004684 A3 WO 2012004684A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- aminoglycoside
- conjugates
- guanidinylated
- lipid conjugates
- lipid
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/228—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings
- C07H15/23—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings with only two saccharide radicals in the molecule, e.g. ambutyrosin, butyrosin, xylostatin, ribostamycin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/543—Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/554—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound the modifying agent being a steroid plant sterol, glycyrrhetic acid, enoxolone or bile acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Botany (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
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.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2791257A CA2791257A1 (en) | 2010-03-05 | 2011-03-04 | Guanidinylated aminoglycoside-lipid conjugates |
US13/582,823 US20130053337A1 (en) | 2010-03-05 | 2011-03-04 | Guanidinylated aminoglycoside-lipid conjugates |
EP11803210A EP2542265A2 (en) | 2010-03-05 | 2011-03-04 | Guanidinylated aminoglycoside -lipid conjugates |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US31107410P | 2010-03-05 | 2010-03-05 | |
US61/311,074 | 2010-03-05 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2012004684A2 WO2012004684A2 (en) | 2012-01-12 |
WO2012004684A3 true WO2012004684A3 (en) | 2012-04-26 |
Family
ID=45441590
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2011/002534 WO2012004684A2 (en) | 2010-03-05 | 2011-03-04 | Guanidinylated aminoglycoside -lipid conjugates |
Country Status (4)
Country | Link |
---|---|
US (1) | US20130053337A1 (en) |
EP (1) | EP2542265A2 (en) |
CA (1) | CA2791257A1 (en) |
WO (1) | WO2012004684A2 (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2847203A1 (en) * | 2012-02-03 | 2015-03-18 | Selectx Pharmaceuticals, Inc. | 4,6-substituted 2,5-dideoxystreptamine aminoglycoside antibiotics |
WO2013191550A1 (en) | 2012-06-20 | 2013-12-27 | Rijksuniversiteit Groningen | Regioselective diazotation of aminoglycosides |
EP3180364B1 (en) * | 2014-08-12 | 2019-07-17 | The Regents of the University of California | Multifunctional membrane-active aminoglycoside-peptide conjugates |
WO2016161377A1 (en) * | 2015-04-01 | 2016-10-06 | The Regents Of The University Of California | Guanidinoglycoside-mediated liposome-based delivery of therapeutics |
US10449230B2 (en) | 2016-10-06 | 2019-10-22 | The Regents Of The University Of California | Polymyxin derived cell penetrating scaffolds |
WO2018187867A1 (en) * | 2017-04-13 | 2018-10-18 | University Of Manitoba | Amphiphilic conjugates of tobramycin linked to a lysine-based peptoid mimic via a tether |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6525182B1 (en) * | 2000-01-21 | 2003-02-25 | Regents Of The University Of California | Guanidinylation, guanidinoglycosides, uses, and methods of assaying their activity |
US20030054556A1 (en) * | 2001-08-29 | 2003-03-20 | Jean-Marie Lehn | Lipid derivatives of aminoglycosides |
WO2010004433A2 (en) * | 2008-07-09 | 2010-01-14 | University Of Manitoba | Hydrophobically enhanced aminoglycosides |
-
2011
- 2011-03-04 US US13/582,823 patent/US20130053337A1/en not_active Abandoned
- 2011-03-04 CA CA2791257A patent/CA2791257A1/en not_active Abandoned
- 2011-03-04 WO PCT/IB2011/002534 patent/WO2012004684A2/en active Application Filing
- 2011-03-04 EP EP11803210A patent/EP2542265A2/en not_active Withdrawn
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6525182B1 (en) * | 2000-01-21 | 2003-02-25 | Regents Of The University Of California | Guanidinylation, guanidinoglycosides, uses, and methods of assaying their activity |
US20030054556A1 (en) * | 2001-08-29 | 2003-03-20 | Jean-Marie Lehn | Lipid derivatives of aminoglycosides |
WO2010004433A2 (en) * | 2008-07-09 | 2010-01-14 | University Of Manitoba | Hydrophobically enhanced aminoglycosides |
Non-Patent Citations (8)
Title |
---|
BAKER ET AL.: "Synthesis and anti-HIV activity of guanidinoglycosides", J. ORG. CHEM., vol. 65, 2000, pages 9054 - 90-58, XP002370083 * |
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.: "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 * |
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 * |
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 * |
LUEDTKE ET AL.: "Cellular uptake of aminoglycosides, guanidinoglycosides, and poly-arginine", J. AM. CHEM. SOC., vol. 125, 2003, pages 12374 - 12375, XP055107228 * |
LUEDTKE ET AL.: "Guanidinoglycosides: A novel family ofRNA ligands", J. AM. CHEM. SOC., vol. 122, 2000, pages 12035 - 12036, XP002965969 * |
SAINLOS ET AL.: "Kanamycin A-derived cationic lipids as vectors for gene transfection", CHEMBIOCHEM, vol. 6, 2005, pages 1023 - 1033, XP002479876 * |
Also Published As
Publication number | Publication date |
---|---|
CA2791257A1 (en) | 2012-01-12 |
EP2542265A2 (en) | 2013-01-09 |
WO2012004684A2 (en) | 2012-01-12 |
US20130053337A1 (en) | 2013-02-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2011009539A8 (en) | ε-POLYLYSINE CONJUGATES AND USE THEREOF | |
WO2012004684A3 (en) | Guanidinylated aminoglycoside -lipid conjugates | |
WO2011142858A3 (en) | Chlorotoxin variants, conjugates, and methods for their use | |
KR20180085042A (en) | Bismuth-thiols as antiseptics for agricultural, industrial and other uses | |
AU2011278165A8 (en) | Adhesive composition including deacetylated chitosan | |
WO2012061290A3 (en) | Pesticidal compositions and processes related thereto | |
EP3284772B8 (en) | Thioethers, methods for their preparation, and compositions including such thioethers | |
EP2651958A4 (en) | Glycoside blends | |
IL226267A0 (en) | Conjugates of an il-2 moiety and a polymer, compositions comprising the same and uses thereof | |
WO2011154711A8 (en) | Peptide-carrying nanoparticles | |
BRPI0924902A2 (en) | Bacterial strains with high anti-inflammatory activity | |
EP2536798A4 (en) | Binder compositions comprising lignin derivatives | |
WO2013103301A3 (en) | Method for preparing cell targeting conjugates, and the complexes obtained | |
TW201129411A (en) | Ball bat including multiple failure planes | |
WO2012044684A3 (en) | Interferon-beta for use as monotherapy or in combination with other cancer therapies | |
WO2009037592A3 (en) | Triazole-based aminoglycoside-peptide conjugates and methods of use | |
HK1210432A1 (en) | Doxorubicin adjuvants to reduce toxicity and methods for using the same | |
WO2011135580A3 (en) | Pharmaceutical compositions of sirolimus | |
IL209337A (en) | Conjugates of a cholinesterase moiety and a polymer, compositions comprising the same and processes for the preparation of the same | |
WO2011124986A3 (en) | Polyol modified aminoglycoside-lipid conjugates | |
EP2653606A4 (en) | Fiber-treating agent | |
WO2012042540A9 (en) | Anticancer agent | |
WO2009067175A3 (en) | Oligomer-dantrolene conjugates and related compounds | |
WO2012036520A3 (en) | Novel antibiotically active compound and an antibiotic composition comprising the compound | |
WO2012024637A3 (en) | Ethyl pyruvate compositions and methods |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
ENP | Entry into the national phase |
Ref document number: 2791257 Country of ref document: CA |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2011803210 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13582823 Country of ref document: US |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 11803210 Country of ref document: EP Kind code of ref document: A2 |