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(12) United States Patent (10) Patent No.: US 7,504,381 B2 Mor Et Al

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(12) United States Patent (10) Patent No.: US 7,504,381 B2 Mor Et Al USOO7504381 B2 (12) United States Patent (10) Patent No.: US 7,504,381 B2 Mor et al. (45) Date of Patent: Mar. 17, 2009 (54) ANTIMICROBIAL AGENTS Tossi et al. "Amphipathic, Alpha-Helical Antimicrobial Peptides'. Biopolymers, 55(1): 4-30, 2000. Abstract, Table 1, p. 7-8, Table II, p. (75) Inventors: Amram Mor, Haifa (IL); Inna 13. Radzishevsky, Haifa (IL) Huang "Peptide-Lipid Interactions and Mechanisms of Antimicro bial Peptides”, Novartis Found Symposium, 225: 188-200, 1999. (73) Assignee: Technion Research & Development Discussion 200-206. Epand et al. “Mechanisms for the Modulation of Membrane Bilayer Foundation Ltd., Haifa (IL) Properties by Amphipathic Helical Peptides'. Biopolymers, 37(5): 319-338, 1995. Abstract. (*) Notice: Subject to any disclaimer, the term of this Ono et al. “Design and Synthesis of Basic Peptides Having patent is extended or adjusted under 35 Amphipathic Beta-Structure and Their Interaction With U.S.C. 154(b) by 153 days. Phospholipid Membranes'. Biochimica et Biophysica Acta (BBA) Biomembranes, 1022(2): 237-244, 1990. Abstract. (21) Appl. No.: 11/234,183 Aarbiou et al. “Human Neutrophil Defensins Induce Lung Epithelial Cell Proliferation. In Vitro”, Journal of Leukocyte Biology, 72: 167 (22) Filed: Sep. 26, 2005 174, 2002. Acar “Consequences of Bacterial Resistance to Antibiotics in Medi (65) Prior Publication Data cal Practice'. Clinical Infectious Diseases, 24(Suppl. 1): S17-S18. 1997. US 2006/OO74O21 A1 Apr. 6, 2006 Alan et al. “Expression of A Magainin-Type Antimicrobial Peptide Gene (MSI-99) in Tomato Enhances Resistance to Bacterial Speck Related U.S. Application Data Disease'. Plant Cell Reports, 22:388-396, 2004. (60) Provisional application No. 60/612,778, filed on Sep. National Nosocomial Infections Surveillance “National Nosocomial Infections Surveillance (NNIS) Report, Data Summary From Oct. 27, 2004. 1986-Apr. 1996, Isued May 1996. A Report From the National Nosocomial Infections Surveillance (NNIS) System', AJIC, Ameri (51) Int. Cl. can Journal of Infection Control, 24:380-388, 1996. A6 IK 38/08 (2006.01) National Nosocomial Infections Surveillance “National Nosocomial A6 IK 38/10 (2006.01) Infections Surveillance (NNIS) System Report, Data Summary From C07K 7/06 (2006.01) Jan. 1990-May 1999, Issued Jun. 1999', AJIC, American Journal of C07K 7/08 (2006.01) Infection Control, 27: 520-532, 1999. (52) U.S. Cl. ............................. 514/14: 514/15: 514/16; Ammar et al. “Dermaseptin, A Peptide Antibiotic, Stimulates 530/326; 530/327: 530/329; 530/332 Microbicidal Activities of Polymorphonuclear Leukocytes'. Bio (58) Field of Classification Search ........... ... None chemical and Biophysical Research Communications, 247: 870-875, See application file for complete search history. 1998. Andreau et al. "Animal Antimicrobial Peptides: An Overview”. (56) References Cited Biopolymers, 47: 415-433, 1998. Appendini et al. "Antimicrobial Activity of A 14-Residue Synthetic U.S. PATENT DOCUMENTS Peptide Against Foodborne Microorganisms”, Journal of Food Pro tection, 63(7): 889-893, 2000. 5,965,525 A * 10/1999 Burkhardt et al. ............. 514/11 Avrahami et al. “Conjugation of a Magainin Analogue With 6,127,337 A * 10/2000 Konishi et al. ....... Lipophilic Acids Controls Hydrophobicity, Solution Assembly, and 6,548,048 B1 * 4/2003 Cuthbertson et al. ....... 424,952 Cell Selectivity”. Biochemistry, 41: 2254-2263, 2002. 6,566,324 B2 5, 2003 Nadel et al. 6,571,790 B1 6, 2003 Weinstein (Continued) 6,637,430 B1 10/2003 Voges et al. 6,652,323 B2 11/2003 Yanda Primary Examiner Jeffrey E. Russel 2003/0036628 A1 2/2003 Zhelva et al. ............... 530/327 2003/0171539 A1* 9/2003 Quentin et al. .............. 530,329 (57) ABSTRACT 2005/01 18678 A1* 6/2005 Mayo ........................ 435/69.1 A novel class of antimicrobial polymeric agents, which FOREIGN PATENT DOCUMENTS include a plurality of amino acid residues, such as positively WO WO98, 185O1 A2 * 5, 1998 charged amino acid residues, and at least one hydrophobic WO WO98,25953 6, 1998 residue linking there between. Such as an omega-amino-fatty WO WOO3,035677 1, 2003 acid residue designed to exert antimicrobial activity while being stable, non-toxic and avoiding development of resis tance thereto and a process of preparing same are disclosed. OTHER PUBLICATIONS Further disclosed are pharmaceutical compositions contain Doyle et al. Synthesis of Potential Anti-HIV GP120 Inhibitors. Using ing same and a method of treating medical conditions asso A Lysine Template. Journal of Enzyme Inhibition and Medicinal ciated with pathological microorganisms, a medical device, Chemistry, 2002, vol. 17, No. 3, pp. 175-182.* an imaging probe and a food preservative utilizing same. Stark et al. “Cationic Hydrophobic Peptides With Antimicrobial Further disclosed are conjugates of an amino acid residue and Activity”. Antimicrobial Agents and Chemotherapy, 46(11): 3585 a hydrophobic moiety residue and a process of preparing 3590, 2002. Abstract, Table 2, p. 3587, p. 3586, Lines 17-22. Haynie et al. "Antimicrobial Activities of Amphiphilic Peptides SaC. Covalently Bonded to A Water-Insoluble Resin'. Antimicrobial Agents and Chemotherapy, 39(2): 301-307, 1995. Abstract, Table 1. 6 Claims, 8 Drawing Sheets p. 303. (8 of 8 Drawing Sheet(s) Filed in Color) US 7,504,381 B2 Page 2 OTHER PUBLICATIONS Devine et al. “Cationic Peptides: Distribution and Mechanisms of Resistance'. Current Pharmaceutical Design, 8: 703-714, 2002. Avrahamietal. “Effect of Multiple Aliphatic Amino Acids Substitu Elsbach et al. “Role of the Bactericidal/Peremeability-Increasing tions on the Structure, Function, and Mode of Action of Protein in Host Defence'. Current Opinion in Immunology, 10: Diastereomeric Membrane Active Peptides'. Biochemistry, 40: 45-49, 1998. 12591-12603, 2001. Baker et al. "Anticancer Efficacy of Magainin2 and Analogue Epand “Biophysical Studies of Lipopeptide-Membrane Interac Peptides”, Cancer Research, 53: 3052-3057, 1993. tions'. Biopolymers, 43: 15-24, 1997. Balaban et al. "A Chimeric Peptide Composed of A Dermaseptin Epand et al. “Diversity of Antimicrobial Peptides and Their Derivative and An RNA III-Inhibiting Peptide Prevents Graft-Asso Mechansims of Action'. Biochimica et Biophysica Acta, 1462: ciated Infections by Antibiotic-Resistant Staphylococci'. Antimicro 11-28, 1999. bial Agents and Chemotherapy, 48(7): 2544-2550, 2004. Fahrner et al. “Solution Structure of Protegrin-1, A Broad-Spectrum Bassarello et al. “Tolaasins A. E. Five New Lipodepsipeptides Pro Antimicrobial Peptide From Porcine Leukocytes', Chemistry & duced by Pseudomonas Tolaasi'. Journal of Natural Products, 67: Biology, 3:543-550, 1996. 811-816, 2004. Fritig et al. "Antimicrobial Proteins in Induced Plant Defense”. Cur Belaid et al. “In Vitro Antiviral Activity of Dermaseptins Against rent Opinion in Immunology, 10: 16-22, 1998. Herpes Simplex Virus Type 1", Journal of Medical Virology, 66: Gaidukov et al. "Analysis of Membrane-Binding Properties of 229-234, 2002. Dermaseptin Analogues: Relationships Between Binding and Blazyk et al. “A Novel Linear Amphipathic Beta-Sheet Cationic Cytotoxicity”, Biochemistry, 42: 12866-12874, 2003. Antimicrobial Peptide With Enhanced Selectivity for Bacterial Gallo et al. "Antimicrobial Peptides: An Emerging Concept in Cuta Lipids”. The Journal of Biological Chemistry, 276(30): 27899 neous Biology”, Journal ofInvestigative Dermatology, 111: 739-743, 27906, 2001. 1998. Blondelle et al. “Combinatorial Libraries: A Tool to Design Antimi crobial and Antifungal PeptideAnalogues Having Lytic Specificities Gennaro et al. "Pro-Rich Antimicrobial Peptides From Animals: for Structure-Activity Relationship Studies'. Biopolymers, 55: Structure, Biological Functions and Mechanism of Action'. Current 74-87, 2000. Pharmaceutical Design, 8: 763-778, 2002. Boman "Antibacterial Peptides: Basic Facts and Emerging Con Ghosh et al. “Selective Cytotoxicity of Dermaseptin S3 Toward cepts”, Journal of Internal Medicine, 254: 197-215, 2003. Intraerythrocytic Plasmodium Falciparum and the Underlying Brand et al. “Dermaseptins From Phyllomedusa Oreades and Phyl Molecular Basis'. The Journal of Biological Chemistry, 272(50): lomedusa Distincta. Anti-Tryponasoma Cruzi Activity Without 31609-31616, 1997. Cytotoxicity to Mammalian Cells'. The Journal of Biological Chem Giacomettietal. "In-Vitro Activity and Killing Effect of Polycationic istry, 277(51): 49332-49340, 2002. Peptides on Methicillin-Resistant Stapholoccus Aureus and Interac Brogden et al. "Antimicrobial Peptides in Animals and Their Role in tions With Clinically Used Antibiotics', Diagnostic Microbiology Host Defences”, International Journal of Antimicrobial Agents, 22: and Infectious Disease, 38: 115-118, 2000. 465-478, 2003. Giacometti et al. "Antiendotoxin Acitivity of Antimicrobial Peptides Bruletal. “Preservative Agents in Foods. Mode of Action and Micro and Glycopeptides”, Journal of Chemotherapy, 15(2): 129-133, bial Resistance Mechanisms’. International Journal of Food 2003. Microbiology, 50: 1-17, 1999. Gough et al. "Antiendotoxin Activity of Cationic Peptide Antimicro Chapple et al. “Structure-Function Relationship of Antibacterial bial Agents'. Infection and Immunity, 64(12): 4922-4927, 1996. Synthetic Peptides Homologous to A Helical Surface Region on Gudmundsson et al. “Neutrophil Antibacterial Peptides, Human Lactoferrin Against Escherichia coliSerotype O 111'. Infec Multifunctional Effector Molecules in the Mammalian Immune Sys tion and Immunity, 66(6): 2434-2440, 1998. tem”, Journal of Immunological Methods,
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