WO2015172077A1 - O-acetylated high molecular weight polygalacturonic acids and their use as vi polysaccharide vaccine - Google Patents

O-acetylated high molecular weight polygalacturonic acids and their use as vi polysaccharide vaccine Download PDF

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Publication number
WO2015172077A1
WO2015172077A1 PCT/US2015/029979 US2015029979W WO2015172077A1 WO 2015172077 A1 WO2015172077 A1 WO 2015172077A1 US 2015029979 W US2015029979 W US 2015029979W WO 2015172077 A1 WO2015172077 A1 WO 2015172077A1
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WO
WIPO (PCT)
Prior art keywords
hpga
oac
acceptable salt
pharmaceutically acceptable
molecular weight
Prior art date
Application number
PCT/US2015/029979
Other languages
English (en)
French (fr)
Other versions
WO2015172077A8 (en
Inventor
Yawei Ni
Michael Springer
Original Assignee
Yawei Ni
Michael Springer
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Yawei Ni, Michael Springer filed Critical Yawei Ni
Priority to JP2016566668A priority Critical patent/JP2017514961A/ja
Priority to CN201580023307.6A priority patent/CN106459225A/zh
Priority to CA2946900A priority patent/CA2946900A1/en
Priority to EP15723634.0A priority patent/EP3140324A1/en
Priority to AU2015255693A priority patent/AU2015255693A1/en
Publication of WO2015172077A1 publication Critical patent/WO2015172077A1/en
Publication of WO2015172077A8 publication Critical patent/WO2015172077A8/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0045—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Galacturonans, e.g. methyl ester of (alpha-1,4)-linked D-galacturonic acid units, i.e. pectin, or hydrolysis product of methyl ester of alpha-1,4-linked D-galacturonic acid units, i.e. pectinic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/02—Bacterial antigens
    • A61K39/025—Enterobacteriales, e.g. Enterobacter
    • A61K39/0275—Salmonella
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants

Definitions

  • acetylation can be achieved by other processes, including the one described by Carson and aclay, J. Am. Chem. Soc, 88:1015-1017 (1946).
  • O-acetylation or "G-acetylated” refers to addition of acetyl groups at the C2 and C3 positions of a sugar residue. The maximum degree of O-acetylation (200%) is reached when both the C2 and C3 positions of each sugar residue are acetylated.
  • OAc-HPGA possesses the boosting effect or memory immune response, exhibiting more than a 2-fold rise in antibody titers upon the second immunization, No such boosting effect was observed with the Vi vaccine (Typhim Vi ® ) tested in parallel.
  • the polysaccharide antigens are known to be T-independent and lack the immune memory or boosting effect.
  • the memory or boosting immune response is only achieved with polysaccharide antigens by conjugating them with a protein carrier.
  • OAc- HPGA is highly unique in possessing the boosting effect on its own without any conjugation, which is likely due to its novel chemical properties.
  • the process modified from the Schweiger method, consists of six simple steps (Fig, 2). Compared to the original Schweiger method, it is much simplified by the two distinct properties of GelSite ® - acid gelation and insolubility in water in its acid form.
  • the first step is to convert the substrate or GelSite ® to its acid form from the sodium salt form by rinsing in dilute HCI and then glacial acetic acid.
  • One of the novel properties of GelSite ® is that it gels efficiently at low H, forming strong acid gel beads or strands which can withstand the down-stream steps.
  • the original Schweiger method first prepared calcium precipitates prior to acid wash steps. This is therefore not necessary and eliminated for O-acetylation of GelSite ® .

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Molecular Biology (AREA)
  • Materials Engineering (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biochemistry (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
PCT/US2015/029979 2014-05-08 2015-05-08 O-acetylated high molecular weight polygalacturonic acids and their use as vi polysaccharide vaccine WO2015172077A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2016566668A JP2017514961A (ja) 2014-05-08 2015-05-08 Ｏ−アセチル化高分子ポリガラクツロン酸およびＶｉ多糖類ワクチンとしてのその利用
CN201580023307.6A CN106459225A (zh) 2014-05-08 2015-05-08 O‑乙酰化高分子量聚半乳糖醛酸及其作为Vi多糖疫苗的用途
CA2946900A CA2946900A1 (en) 2014-05-08 2015-05-08 O-acetylated high molecular weight polygalacturonic acids and their use as vi polysaccharide vaccine
EP15723634.0A EP3140324A1 (en) 2014-05-08 2015-05-08 O-acetylated high molecular weight polygalacturonic acids and their use as vi polysaccharide vaccine
AU2015255693A AU2015255693A1 (en) 2014-05-08 2015-05-08 O-acetylated high molecular weight polygalacturonic acids and their use as Vi polysaccharide vaccine

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201461990493P 2014-05-08 2014-05-08
US61/990,493 2014-05-08

Publications (2)

Publication Number Publication Date
WO2015172077A1 true WO2015172077A1 (en) 2015-11-12
WO2015172077A8 WO2015172077A8 (en) 2016-01-28

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2015/029979 WO2015172077A1 (en) 2014-05-08 2015-05-08 O-acetylated high molecular weight polygalacturonic acids and their use as vi polysaccharide vaccine

Country Status (6)

Country Link
EP (1) EP3140324A1 (ja)
JP (1) JP2017514961A (ja)
CN (1) CN106459225A (ja)
AU (1) AU2015255693A1 (ja)
CA (1) CA2946900A1 (ja)
WO (1) WO2015172077A1 (ja)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5929051A (en) 1998-05-13 1999-07-27 Carrington Laboratories, Inc. Aloe pectins
US7691986B2 (en) 1998-05-13 2010-04-06 Nanotherapeutics, Inc. High molecular weight, low methoxyl pectins, and their production and uses

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5929051A (en) 1998-05-13 1999-07-27 Carrington Laboratories, Inc. Aloe pectins
US7691986B2 (en) 1998-05-13 2010-04-06 Nanotherapeutics, Inc. High molecular weight, low methoxyl pectins, and their production and uses
US7705135B2 (en) 1998-05-13 2010-04-27 Nanotherapeutics, Inc. Pharmaceutical compositions comprising aloe pectins, and methods for their production and use

Non-Patent Citations (20)

* Cited by examiner, † Cited by third party
Title
B SZEWCZYK ET AL: "Immunochemical properties of Vi antigen from Salmonella typhi Ty2: presence of two antigenic determinants", INFECTION AND IMMUNITY, vol. 29, no. 2, 1 August 1980 (1980-08-01), pages 539 - 544, XP055206183, ISSN: 0019-9567 *
CARSON; MACLAY, J. AM. CHEM. SOC., vol. 68, 1946, pages 1015 - 1017
GONZALEZ-FERNANDEZ ET AL., VACCINE, vol. 26, 2008, pages 292 - 300
HESTRIN, J. BIOL. CHEM., vol. 180, 1949, pages 249 - 261
JARVIS ET AL., J. BACTERIOL., vol. 94, 1967, pages 1406 - 1410
KOSSACZKA ET AL., INFECT. IMMUN., vol. 67, 1997, pages 5806 - 5810
MARTIN ET AL., J. BACTERIOL., vol. 94, 1967, pages 1411 - 1416
RICHARD G. SCHWEIGER: "Acetyl Pectates and Their Reactivity with Polyvalent Metal Ions 1", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 29, no. 10, 1 October 1964 (1964-10-01), pages 2973 - 2975, XP055205872, ISSN: 0022-3263, DOI: 10.1021/jo01033a041 *
RIJPKEMA ET AL., BIOLOGICALS, vol. 32, 2004, pages 11 - 6
SCHWEIGER, J. ORG. CHEM, vol. 29, 1964, pages 2973 - 2975
SZEWCZYK; TAYLOR, INFECT. IMMUN, vol. 29, 1980, pages 539 - 544
SZEWCZYK; TAYLOR, INFECT. LMMUN., vol. 29, 1980, pages 539 - 544
SZU ET AL., ENZYMOL., vol. 363, 2003, pages 552 - 567
SZU ET AL., INFECT IMMUN., vol. 62, 1994, pages 5545 - 5549
SZU ET AL., INFECT. IMMUN, vol. 59, 1991, pages 4555 - 4561
SZU ET AL., INFECT. IMMUN., vol. 59, 1991, pages 4555 - 4561
SZU ET AL., INFECT. IMMUN., vol. 62, 1994, pages 5545 - 5549
SZU S C ET AL: "Synthesis and Some Immunologic Properties of an O-Acetyl Pectin [Poly(1->4)-.alpha.-D-GalpA]-Protein Conjugate as a Vaccine for Typhoid Fever", INFECTION AND IMMUNITY, AMERICAN SOCIETY FOR MICROBIOLOGY, US, vol. 62, no. 12, 1 December 1994 (1994-12-01), pages 5545 - 5549, XP008120217, ISSN: 0019-9567 *
SZU; BYSTRICKY, ENZYMOL, vol. 363, 2003, pages 552 - 567
WHO EXPERT COMMITTEE ON BIOLOGICAL STANDARDIZATION, 1993

Also Published As

Publication number Publication date
CA2946900A1 (en) 2015-11-12
WO2015172077A8 (en) 2016-01-28
JP2017514961A (ja) 2017-06-08
CN106459225A (zh) 2017-02-22
EP3140324A1 (en) 2017-03-15
AU2015255693A1 (en) 2016-11-03

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