CA2484638A1 - Polyene polyketides and methods of production - Google Patents

Polyene polyketides and methods of production Download PDF

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Publication number
CA2484638A1
CA2484638A1 CA002484638A CA2484638A CA2484638A1 CA 2484638 A1 CA2484638 A1 CA 2484638A1 CA 002484638 A CA002484638 A CA 002484638A CA 2484638 A CA2484638 A CA 2484638A CA 2484638 A1 CA2484638 A1 CA 2484638A1
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CA
Canada
Prior art keywords
compounds
polyene polyketides
production
methods
cultivation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002484638A
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French (fr)
Other versions
CA2484638C (en
Inventor
James B. Mcalpine
Chris M. Farnet
Emmanuel Zazopoulos
Dan Sorensen
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Thallion Pharmaceuticals Inc
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Ecopia Biosciences Inc
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Publication of CA2484638A1 publication Critical patent/CA2484638A1/en
Application granted granted Critical
Publication of CA2484638C publication Critical patent/CA2484638C/en
Expired - Fee Related legal-status Critical Current
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C279/14Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
    • C07H5/06Aminosugars
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/20Bacteria; Culture media therefor
    • C12N1/205Bacterial isolates
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09Recombinant DNA-technology
    • C12N15/11DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
    • C12N15/52Genes encoding for enzymes or proenzymes
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00Preparation of nitrogen-containing organic compounds
    • C12P13/001Amines; Imines
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00Preparation of nitrogen-containing organic compounds
    • C12P13/02Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02Oxygen as only ring hetero atoms
    • C12P17/06Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/16Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing two or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00Preparation of compounds containing saccharide radicals
    • C12P19/44Preparation of O-glycosides, e.g. glucosides
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00Preparation of oxygen-containing organic compounds
    • C12P7/40Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • C12P7/42Hydroxy-carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/06Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12RINDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00Microorganisms ; Processes using microorganisms
    • C12R2001/01Bacteria or Actinomycetales ; using bacteria or Actinomycetales
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00Chemistry: molecular biology and microbiology
    • Y10S435/821Microorganisms used in the destruction of hazardous or toxic waste

Abstract

Novel polyene polyketides, their pharmaceutically acceptable salts, prodrugs and derivatives have been found to have antibiotic activity. One method for obtaining the compounds is by cultivation of Amycolatopsis orientalis ATCC
.TM.
43491 or a mutant or variant such as the strain IDAC-220604-1. Another method for obtaining the compounds is post-biosynthesis chemical modification of the compounds obtained by cultivation. Novel polynucleotide sequences and encoded proteins for the biosynthesis of the polyene polyketides are also presented.
CA002484638A 2003-09-11 2004-09-10 Polyene polyketides and methods of production Expired - Fee Related CA2484638C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US50182103P 2003-09-11 2003-09-11
US60/501,821 2003-09-11
US57492204P 2004-05-28 2004-05-28
US60/574,922 2004-05-28
US58170704P 2004-06-23 2004-06-23
US60/581,707 2004-06-23
PCT/CA2004/001603 WO2005024025A1 (en) 2003-09-11 2004-09-10 Polyene polyketides and methods of production

Publications (2)

Publication Number Publication Date
CA2484638A1 true CA2484638A1 (en) 2005-02-14
CA2484638C CA2484638C (en) 2008-03-25

Family

ID=34198998

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002484638A Expired - Fee Related CA2484638C (en) 2003-09-11 2004-09-10 Polyene polyketides and methods of production

Country Status (4)

Country Link
US (2) US7300921B2 (en)
EP (1) EP1539962A4 (en)
CA (1) CA2484638C (en)
WO (1) WO2005024025A1 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004030371A1 (en) * 2004-06-23 2006-01-19 Dynamit Nobel Gmbh Process for the preparation of gaseous diazoalkanes
GB0805363D0 (en) 2008-03-20 2008-04-30 Sinvent As Novel NRPS-PKS gene cluster and its manipulation and utility
US8865761B1 (en) 2012-08-07 2014-10-21 The University Of Notre Dame Du Lac Regulation of cholesterol homeostasis
US20230106760A1 (en) * 2020-03-17 2023-04-06 The United States Of America,As Represented By The Secretary,Department Of Health And Human Services Antibacterial and antifungal polyketides from environmental amycolatopsis spp
CN116234572A (en) * 2020-04-30 2023-06-06 安驰肿瘤公司 Therapeutic SIRP alpha antibodies
CN114317580A (en) * 2022-01-13 2022-04-12 上海交通大学 Specific gene knockout CRISPR/Cas9 editing plasmid containing double sgRNAs and application thereof

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3854480A (en) 1969-04-01 1974-12-17 Alza Corp Drug-delivery system
US4452775A (en) 1982-12-03 1984-06-05 Syntex (U.S.A.) Inc. Cholesterol matrix delivery system for sustained release of macromolecules
GB8700513D0 (en) * 1987-01-09 1987-02-11 Pfizer Ltd Antibiotics produced by fermentation
US5039660A (en) 1988-03-02 1991-08-13 Endocon, Inc. Partially fused peptide pellet
PT94638A (en) * 1989-07-10 1991-03-20 Bristol Myers Squibb Co BU-3889V ANTIBIOTIC PREPARATION WITH ANTIVIRAL ACTIVITY AND PHARMACEUTICAL COMPOSITIONS CONTAINING IT
AU695814B2 (en) 1993-09-22 1998-08-20 Xoma Corporation Method of treating gram-negative bacterial infection by administration of bactericidal/permeability-increasing (bpi) protein product and antibiotic
JPH09508359A (en) 1994-01-14 1997-08-26 ゾーマ コーポレイション Anti-gram positive bacteriological methods and substances
US5917084A (en) * 1996-07-03 1999-06-29 Millennium Pharmaceuticals, Inc. Antifungal agents
US6670168B1 (en) 1999-10-29 2003-12-30 Kosan Bioscience, Inc. Recombinant Streptomyces hygroscopicus host cells that produce 17-desmethylrapamycin
US6953679B2 (en) * 2000-09-19 2005-10-11 Bristol-Myers Squibb Company Method for the preparation of fused heterocyclic succinimide compounds and analogs thereof
CA2352451C (en) 2001-07-24 2003-04-08 Ecopia Biosciences Inc. High throughput method for discovery of gene clusters
EP1470241A2 (en) 2002-01-24 2004-10-27 Ecopia Biosciences Inc. Method, system and knowledge repository for identifying a secondary metabolite from a microorganism
JP2007525148A (en) * 2003-01-21 2007-09-06 エコピア バイオサイエンシーズ インク Polyene polyketides, methods for their production and use as pharmaceuticals [Related Applications] This application is based on US Provisional Application No. 60 / 441,123, filed Jan. 21, 2003, and US Provisional Application No. 60 / 441,2003. Claims priority to 60 / 494,568, US provisional application 60 / 469,810 filed May 13, 2003 and US provisional application 60 / 491,516 filed August 1, 2003 Is.

Also Published As

Publication number Publication date
US7300921B2 (en) 2007-11-27
US20050215490A1 (en) 2005-09-29
CA2484638C (en) 2008-03-25
WO2005024025A1 (en) 2005-03-17
EP1539962A1 (en) 2005-06-15
EP1539962A4 (en) 2006-12-27
WO2005024025A8 (en) 2005-05-19
US20050176653A1 (en) 2005-08-11

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