Polymyxin derivatives and uses thereof

Details Polymyxin derivatives and uses thereof Polymyxin derivatives and uses thereof

2007-08-10

2010-10-05

Bradley, Christina (Department: 1654)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

Reexamination Certificate

active

07807637

ABSTRACT:
The present invention relates to a polymyxin derivative wherein R1, R2 and R3 are optional and R1, R2, R3, R5, R8 and R9 are cationic or neutral amino acid residues selected so that the total number of positive charges at physiological pH is at least two but no more than three; and to a combination product comprising at least two such derivatives. The invention further relates to a method for treating, alleviating or ameliorating an infection in a subject, caused by a Gram-negative bacterium by administering a therapeutically effective amount of a derivative according to the present invention to said subject; to a method for sensitizing Gram-negative bacteria to an antibacterial agent by administering, simultaneously or sequentially in any order a therapeutically effective amount of said antibacterial agent and a derivative according to the present invention to said subject; to methods for developing novel antibiotics; for reducing the nephrotoxicity, for improving the pharmacokinetic properties of natural polymyxins and octapeptins; and for sensitizing clinically important bacteria to a host defence mechanism complement present in serum. Finally, the invention relates to a process for preparing such polymyxin derivatives.

REFERENCES:
patent: 4510132 (1985-04-01), Vaara
patent: 2004/0082505 (2004-04-01), Ofek et al.
patent: 2006/0004185 (2006-01-01), Leese et al.
patent: 1906699 (1970-02-01), None
patent: 1323362 (1973-07-01), None
patent: 71-15630 (1971-04-01), None
patent: 72-51356 (1982-12-01), None
Shoji et al. (“The Structure of Polymyxin S1 Studies on Antibiotics From theGenus bacillus. XXI” J. Antibiotics, 1977, 12, 1035-1041).
Kato, Toshiyuki et al., The Structure of Octapeptin D (Studies on Antibiotics from theGenus bacillus. XXVIII), The Journal of Antibiotics, vol. 33(2):186-191 (1980).
Shoji, Jun'ichi et al., “Isolation of Octapeptin D (Studies on Antibiotics from theGenus bacillus. XXVII),”The Journal of Antibiotics, vol. 33(2):182-185 (1980).
Chihara, Shiro et al., “Chemical Synthesis, Isolation and Characterization of α-N-Fattyacyl Colistin Nonapeptide with Special Reference to the Correlation between Antimicrobial Activity and Carbon Number of Fattyacyl Moiety,”Agr. Biol. Chem., vol. 38(3):521-529 (1974).
Chihara, Shiro et al., “Enzymatic Degradation of Colistin Isolation and Identification of α-N-Acyl α,γ-Diaminobutyric Acid and Colistin Nonapeptide,”Agr. Biol. Chem., vol. 37(11):2455-2463 (1973).
Kimura, Yukio et al., “Polymyxin B Octapeptide and Polymyxin B Heptapeptide are Potent Outer Membrane Permeability—Increasing Agents,”The Journal of Antibiotics, vol. 45(5):742-749 (1992).
Kurihara, Tozaburo et al., “Studies on the Compounds related to Colistin. IX. On the Chemical Deacylation of Colistin and Colistin Derivatives,”Yakugaku Zasshi, vol. 94(11):1491-1494 (1974).
Potter, Ross et al., “Inhibition of foodborne bacteria by native and modified protamine: importance of electrostatic interactions,”International Journal of Food Microbiology, vol. 103:23-34 (2005).
Sakura, Naoki et al., “The Contribution of theN-Terminal Structure of Polymyxin B Peptides to Antimicrobial and Lipopolysaccharide Binding Activity,”Bull. Chem. Soc. Jpn., vol. 77:1915-1924 (2004).
Srinivasa, B.R. et al., “Chemical Modification of Peptide Antibiotics: Part VI-Biological Activity of Derivatives of Polymyxin B,”Indian Journal of Biochemistry&Biophysics, vol. 14:54-58 (1978).
Srinivasa, B.R. et al., “Deacylation of Polymyxin B by Hydrazine & Solvolysis,”Indian Journal of Biochemistry&Biophysics, vol. 17:298-302 (1980).
Srinivasa, B.R. et al., “Essential Amino Groups of Polymyxin B,”Indian Journal of Biochemistry&Biophysics, vol. 17:112-118 (1980).
Srinivasa, B.R. et al., “The Polymyxins,”Journal of Scientific and Industrial Research, vol. 38:695-709 (1979).
Storm, Daniel R. et al., “Polymyxin and Related Peptide Antibiotics,”Annu. Rev. Biochem., vol. 46:723-763 (1977).
Teuber, Michael, “Preparation of biologically active mono-N-acetyl(14C)-derivatives of the membrane-specific polypeptide antibiotic polymyxin B,”Z. Naturforsch B., vol. 25(1):117 (1970).
Thomas, Celestine J. et al., “Kinetics of the interaction of endotoxin with polymyxin B and its analogs: a surface plasmon resonance analysis,”FEBS Letters, vol. 445:420-424 (1999).
Tsubery, Haim et al., “N-terminal modifications of Polymyxin B nonpeptide and their effect on antibacterial activity,”Peptides, vol. 22:1675-1681 (2001).
Tsubery, Haim et al., “Neopeptide Antibiotics That Function as Opsonins and Membrane-Permeabilizing Agents for Gram-Negative Bacteria,”Antimicrobial Agents and Chemotherapy, vol. 49(8):3122-3128 (2005).
Tsubery, Haim et al., “Structure—Function Studies of Polymyxin B Nonapeptide: Implications to Sensitization of Gram-Negative Bacteria,”J. Med. Chem., vol. 43:3085-3092 (2000).
Tsubery, Haim et al., “The Functional Association of Polymyxin B with Bacterial Lipopolysaccharide Is Sterospecific: Studies on Polymyxin B Nonapeptide,”Biochemistry, vol. 39(39):11837-11844 (2000).
Vaara, Martti, “Agents that Increase the Permeability of the Outer Membrane,”Microbiological Reviews, vol. 56(3):395-411 (1992).
Vaara, Martti et al., “Group of Peptides That Act Synergistically with Hydrophobic Antibiotics against Gram-Negative Enteric Bacteria,”Antimicrobial Agents and Chemotherapy, vol. 40(8):1801-1805 (1996).
Vaara, Martti, “Lipopolysaccharide and the Permeability of the Bacterial Outer Membrane,”Endotoxin in Health and Disease, Chpt. 2, Helmut Brade Ed., pp. 31-38 (1999).
Vaara, Martti et al., “Sensitization of Gram-negative bacteria to antibiotics and complement by a nontoxic oligopeptide,”Nature, vol. 303(5917):526-528 (1983).
Viljanen, Petri et al., “The Outer Membrane Permeability-Increasing Action of Deacylpolymyxins,”The Journal of Antibiotics, vol. 44(5):517-523 (1991).
Zewail, M.A., “Biologically Active Cyclopeptides: Lysine Analogs of Polymyxins Antibiotics M, D, E & B,”Indian Journal of Chemistry, vol. 15B:128-130 (1977).
International Search Report for Application No. PCT/FI2007/050441, dated Nov. 22, 2007.
Clausell, A. et al., “Influence of polymyxins on the structural dynamics ofEscherichia colilipid membranes,”Talanta, vol. 60:225-234 (2003).
de Visser, P.C. et al., “Solid-phase synthesis of polymyxin B1 and analogues via a safety-catch approach,”J. Peptide Res., vol. 61:298-306 (2003).
Okimura, Keiko et al., “Chemical Conversion of Natural Polymyxin B and Colistin to TheirN-Terminal Derivatives,”Bull. Chem. Soc. Jpn., vol. 80(3):543-552 (2007).
Weinstein, Jay et al., “Selective Chemical Modifications of Polymyxin B,”Bioorganic&Medicinal Chemistry Letters, vol. 8:3391-3396 (1998).
European Office Action for Application No. 07803704.1, dated Jul. 21, 2009.
International Search Report for Application No. PCT/FI2009/050093, dated Jul. 24, 2009.

Affiliated with

Also associated with

Rating

Polymyxin derivatives and uses thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Polymyxin derivatives and uses thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Polymyxin derivatives and uses thereof will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4240175