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(12) United States Patent (10) Patent No.: US 9,018,158 B2 Onsoyen Et Al

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(12) United States Patent (10) Patent No.: US 9,018,158 B2 Onsoyen Et Al US0090181.58B2 (12) United States Patent (10) Patent No.: US 9,018,158 B2 Onsoyen et al. (45) Date of Patent: Apr. 28, 2015 (54) ALGINATE OLIGOMERS FOR USE IN 7,208,141 B2 * 4/2007 Montgomery .................. 424/45 OVERCOMING MULTIDRUG RESISTANCE 22:49 R: R388 al al W . aSOC ea. N BACTERA 7,671,102 B2 3/2010 Gaserod et al. 7,674,837 B2 3, 2010 G d et al. (75) Inventors: Edvar Onsoyen, Sandvika (NO); Rolf 7,758,856 B2 T/2010 it. Myrvold, Sandvika (NO); Arne Dessen, 7,776,839 B2 8/2010 Del Buono et al. Sandvika (NO); David Thomas, Cardiff 2006.8 R 38 8. Melist al. (GB); Timothy Rutland Walsh, Cardiff 2003/0022863 A1 1/2003 Stahlang et al. (GB) 2003/0224070 Al 12/2003 Sweazy et al. 2004/OO73964 A1 4/2004 Ellington et al. (73) Assignee: Algipharma AS, Sandvika (NO) 2004/0224922 A1 1 1/2004 King 2010.0068290 A1 3/2010 Ziegler et al. (*) Notice: Subject to any disclaimer, the term of this 2010/0305062 A1* 12/2010 Onsoyen et al. ................ 514/54 patent is extended or adjusted under 35 U.S.C. 154(b) by 184 days. FOREIGN PATENT DOCUMENTS DE 268865 A1 1, 1987 (21) Appl. No.: 13/376,164 EP O324720 A1 T, 1989 EP O 506,326 A2 9, 1992 (22) PCT Filed: Jun. 3, 2010 EP O590746 A1 4f1994 EP 1234584 A1 8, 2002 (86). PCT No.: PCT/GB2O1 O/OO1097 EP 1714660 A1 10, 2006 EP 1745705 A1 1, 2007 S371 (c)(1), FR T576 M 3/1968 (2), (4) Date: Jan. 26, 2012 GB 1042379 9, 1966 GB 243O881 A 4/2007 (87) PCT Pub. No.: WO2010/139957 JP O5-252970 10, 1993 Continued PCT Pub. Date: Dec. 9, 2010 ( ) OTHER PUBLICATIONS (65) Prior Publication Data Kitamikado, M. et al. 1993 “Bacteriostatic Action of Oligosac US 2012/O122768 A1 May 17, 2012 charides Prepared from Alginate by Enzymatic Degradation” Nippon O O Suisan Gakkaishi Bulletin of the Japanese Society of Scientific (30) Foreign Application Priority Data Fisheries 59: 315-320. Hu, X. et al. 2005 "Antibacterial activity of lyase-depolymerized X. 3. 3. E. - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 9. 35 products of alginate” Journal of Applied Phycology 17: 57-60. O 4. 2009 GB). - - - 097995.3 Office Action in corresponding Chinese Application No. CN CL. 14, (GB) ................................... 200880118093.0 dated Nov. 29, 2012. 51) Int. C Office Action in corresponding Chinese Application No. CN (51) Int. Cl. 20108.0034492.6 dated Oct. 24, 2012. AOIN37/18 (2006.01) Office Action in corresponding Russian Application No. 2010 120766 A6 IK38/04 (2006.01) dated Sep. 26, 2012. A6 IK3I/7048 (2006.01) A 6LX3L/7052 (2006.01) (Continued) A6 IK3I/734 (2006.01) A6 IK 45/06 (2006.01) Primary Examiner — Dirk Bass (52) U.S. Cl. (74) Attorney, Agent, or Firm — Knobbe, Martens, Olson & CPC ......... A6IK3I/7048 (2013.01); A6IK3I/7052 Bear, LLP (2013.01); A61 K3I/734 (2013.01);45/06 (2013.01) A61 K (57) ABSTRACT (58) Field of Classification Search The invention provides a method of overcoming resistance to None at least one antibiotic in a multidrug resistant bacterium, said See application file for complete search history. method comprising contacting said bacterium with an algi nate oligomer together with the antibiotic. The multidrug 56 Refeferences CitedCite reS1Stant bbacterium maVy bbe On an animate Or 1nanimate Sur face and both medical and non-medical uses and methods are U.S. PATENT DOCUMENTS provided. In one aspect the invention provides an alginate 4,225,592 A 9, 1980 Lakatos et al. oligomer for use together with at least one antibiotic in treat 5,166,137 A 11/1992 Otterlei et al. ing a Subject infected, Suspected to be infected, or at risk of 5,169,840 A 12/1992 Otterlei et al. infection, with a multidrug resistant bacterium to overcome 5, 192,362 A 3/1993 Harvey et al. resistance to the antibiotic in said multidrug resistant bacte 5,683,991 A 11/1997 Guggenbichler et al. 6,121441 A 9, 2000 Simensen et al. rium. In another aspect the method can be used to combat 6,339,075 B1 1/2002 King et al. contamination of a site with multidrug resistant bacteria, e.g. 6,395,307 B1 5/2002 Banning et al. for disinfection and cleaning purposes. 6,407.226 B1 6/2002 Simensen et al. 6,641,740 B2 11/2003 Cornelius et al. 41 Claims, No Drawings US 9,018,158 B2 Page 2 (56) References Cited Fernandez-Cuenca, F. etal. 2003 "Invitro activity of Azithromycin in combination with Amikacin, Ceftazidime, Ciprofloxacin or Imipenem against clinical isolates of Acinetobacter baumanni' FOREIGN PATENT DOCUMENTS Chemotherapy 49: 24-26. JP O9208472 8, 1997 Gimmestad, M et al. 2003 “The Pseudomonas fluorescens AIgG JP 2005.145885 11, 2003 Protein, but not its Mannuronan C-5-Epimerase Activity, is needed JP 2008285431 5/2007 for Alginate Polymer Formation” Journal of Bacteriology, KR 20000032630 11, 1998 185(12):3515-3523. WO WO 88,097.94 A1 12, 1988 Gimmestad, M. etal. 2006 “Identification and Characterization of an WO WO91/11205 A1 8, 1991 Azotobacter vinelandii Type I Secretion System Responsible for WO WO 94,09124 A1 4f1994 Export of the AIgE-Type Mannuronan C-5-Epimerases” Journal of WO WO95/18145 A1 7, 1995 Bacteriology, 188(15):5551-5560. WO WO 98.02488 A1 1, 1998 Head, N.E. et al. 2004 “Cross-Sectional Analysis of Clinical and WO WO 98.51342 A1 11, 1998 WO WO 98.51710 A1 11, 1998 Environmental Isolates of Pseudomonas aeruginosa. Biofilm For WO WOO1? 15672 A2 3, 2001 mation, Virulence, and Genome Diversity” Infection and Immunity WO WOO1,66084 A2 9, 2001 72(1): 133-144. WO WO 03/0454.02 A1 6, 2003 Jahr T.G. etal. 1997 "Induction of Tumor Necrosis Factor Production WO WO 03/046199 A2 6, 2003 from Monocytes Stimulated with Mannuronic Acid Polymers and WO WO 2004/O11628 A1 2, 2004 Involvement of Lipopolysaccharide-Binding Protein, CD14, and WO WO 2005/0231.76 A2 3, 2005 Bactericidal/Permeability-increasing Factor” Infection and Immu WO WO 2005/079210 A2 9, 2005 nity 65(1):89-94. WO WO 2006/12O705 A2 11/2006 Kitamikado, M. etal 1992 “Two Types of Bacterial Alginate Lyases” WO WO 2007/039754 A1 4/2007 Appl Environ Microbiol 58(8):2474-2478. WO WO 2007/039760 A2 4/2007 Lasa, I. 2006 “Towards the identification of the common features of WO WO 2008/006658 A1 1, 2008 bacterial biofilm development' International Microbiology, 9:21-28. WO WO 2008/071.407 A2 6, 2008 WO WO 2008/082948 A2 T 2008 McGowan, J.E. Jr. “Resistance in nonfermenting gram-negative bac WO WO 2008,125828 A2 10/2008 teria: multidrug resistance to the maximum” Am J Infection Control WO WO 2009/018060 A1 2, 2009 34: S29-S37. WO WO 2009/032433 A1 3, 2009 Moore, J.E. et al. 2001 "Antibiotic resistance in Burkholderia WO WO 2009/068841 A2 6, 2009 cepacia at two regional cystic fibrosis centres in Northern Ireland: is there a need for synergy testing?”J Antimicrobial Chemotherapy 48: OTHER PUBLICATIONS 315-329. Moskowitz, S.M. et al. 2004 “Clinically Feasible Biofilm Suscepti Alkawash, M.A. et al. 2006 “Alginate lyase enhances antibiotic kill bility Assay for Isolates of Pseudomonas aeruginosa from Patients ing of mucoid Pseudomonas aeruginosa in biofilms' APMIS, with Cystic Fibrosis” Journal of Clinical Microbiology 42(5):1915 114(2): 131-138. 1922. Appleman, M.D. et al. 2000 “In vitro activities of nontraditional Mrsny R.J., et al. 1994 "Addition of a Bacterial Alginate Lyase to antimicrobials against mutiresistant Acinetobacter baumannistrains Purulent CFSputum InVitro Can Result in the Disruption of Alginate isolated in an intensive care unit outbreak” Antimicrobial Agents and and Modification of SputumViscoelasticity” Pulmonary Pharmacol Chemotherapy 44: 1035-1040. ogy, 7:357-366. Araque-Calderon, Y. et al. 2008 "Antibiotic resistance patterns and Murata, Ketal. 1992 “Continuous Depolymerization of Alginates by SDS-PAGE protein profiles of Burkholderia cepacia complex iso a Non-Support Bioreactor System Containing Flocculated Bacterial lates from nosocomial and environmental Sources in Venezuela' Med Cells' Journal of Fermentation and Bioengineering 73(2): 172-174. Sci Monit 14: BR49-55. Otterlei, Metal. 1991 Induction fo Cytokine Production from Human Banning, D. et al. 1997 "Oscillatory and thermorheological charac Monocytes Stimulated with Alginate Journal of Immunotherapy, terization of alginate? mucin mixes' Pharmacy and Pharmacology, 10:286-291 49(Supp. 4) Poster 65. Qiu, D, et al. 2007 "Regulated proteolysis controls mucoid conver Cannon, C. et al. 2006 “Emerging Pulmonary Infections in Cystic sion in Pseudomonas aeruginosa' Proc Natl Acad Sci USA Fibrosis' US Respiratory Disease, pp. 27-29. 104(19):8107-8112. Cuenca, F.F. et al. 2003 “Actividad in vitro de azitromicina frente a Remminghorst, U. etal. 2006 “Bacterial alginates: from biosynthesis aislamientos clinicos de Acinetobacter baumannii' Rev Esp to applications' Biotechnology Letters 28:1701-1712. Quimioterap 16: 204-208. Strugala et al. 2004, “Bioactive Properties of Epimerised Alginates' Dizbay, M. etal. 2009 “Nosocomial Burkholderia cepacia infections Gums and Stabilisers for the Food Industry 12:84-94. in a Turkish university hospital: a five-year Surveillance'J Infect Dev Tang, J.X. et al. 2005 “Anionic poly(amino acid)s dissolve F-actin Ctries 3:273-277. and DNA bundles, enhance DNase activity, and reduce the viscosity Djordjevic, D. et al. 2002 “Microtiter Plate Assay for Assessment of of cystic fibrosis sputum” American Journal of Physiology—Lung, Listeria monocytogenes Biofilm Formation’ Appl Environ Microbiol Cellular and Molecular Physiology 289; L599-L605. 68:2950-2958. Thibault, F.M. et al.
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