CA2794217A1 - Thiosulfonate compound, reversible cationization agent for protein and/or peptide, and method for solubilization - Google Patents

Thiosulfonate compound, reversible cationization agent for protein and/or peptide, and method for solubilization Download PDF

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Publication number
CA2794217A1
CA2794217A1 CA2794217A CA2794217A CA2794217A1 CA 2794217 A1 CA2794217 A1 CA 2794217A1 CA 2794217 A CA2794217 A CA 2794217A CA 2794217 A CA2794217 A CA 2794217A CA 2794217 A1 CA2794217 A1 CA 2794217A1
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CA
Canada
Prior art keywords
protein
peptide
thiosulfonate compound
solubilization
compound according
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
CA2794217A
Other languages
French (fr)
Other versions
CA2794217C (en
Inventor
Junichiro Futami
Hidenori Yamada
Go Kyuragi
Keiichiro Yagi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Okayama University NUC
Original Assignee
Okayama University NUC
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 Okayama University NUC filed Critical Okayama University NUC
Publication of CA2794217A1 publication Critical patent/CA2794217A1/en
Application granted granted Critical
Publication of CA2794217C publication Critical patent/CA2794217C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/04—Thiosulfonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/14—Extraction; Separation; Purification
    • C07K1/145—Extraction; Separation; Purification by extraction or solubilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K2/00—Peptides of undefined number of amino acids; Derivatives thereof

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Analytical Chemistry (AREA)
  • Peptides Or Proteins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

The object of the present invention is to provide a novel thiosulfonate compound, a reversible cationization agent for protein and/or peptide, which can reversibly cationize a wider range of proteins and peptides with high stability of quality and accuracy and which are useful for a high degree of purification and recovery, as well as, a method for solubilization for protein and/or peptide using the agent.
The present invention is a thiosulfonate compound having three or more cations derived from a quaternary ammonium group within one molecule.

Claims (10)

  1. Claim 1. A thiosulfonate compound having within one molecule three or more cations derived from a quaternary ammonium group.
  2. Claim 2. The thiosulfonate compound according to claim 1, represented by the following general formula (1):
    [Chem. 1]

    (wherein R1 is identical or different from one another and represents an alkylene group having 2 to 20 carbons; R2 represents a lower alkyl group; and n is an integer of 3 to 10).
  3. Claim 3. The thiosulfonate compound according to claim 2, wherein R1 in the general formula (1) is a linear alkylene group having 2 to 6 carbons.
  4. Claim 4. The thiosulfonate compound according to claim 3, wherein the R1 is a propylene group.
  5. Claim 5. The thiosulfonate compound according to any of claims 2 to 4, wherein n in the general formula (1) is 3.
  6. Claim 6. The thiosulfonate compound according to any of claims 2 to 5, wherein R2 in the general formula (1) is a methyl group.
  7. Claim 7. A reversible cationization agent for reversibly-cationizing a protein and/or a peptide, the reversible cationization agent containing the thiosulfonate compound according to any of claims 1 to 6.
  8. Claim 8. A method for protein and/or peptide solubilization using the reversible cationization agent according to claim 7.
  9. Claim 9. The method for protein and/or peptide solubilization according to claim 8, wherein the protein and/or the peptide are denatured protein and/or peptide.
  10. Claim 10. A method for solubilization for solubilizing a mixture of denatured total protein extracted from a cultured cell and/or a living tissue in a physiological salt solution, the solubilization method using the reversible cationization agent according to claim 7.
CA2794217A 2010-03-25 2011-03-24 Thiosulfonate compound, reversible cationization agent for protein and/or peptide, and method for solubilization Expired - Fee Related CA2794217C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2010070804 2010-03-25
JP2010-070804 2010-03-25
PCT/JP2011/057238 WO2011118731A1 (en) 2010-03-25 2011-03-24 Thiosulfonate compound, reversibly cationizing agent for proteins and/or peptides, and method for solubilization

Publications (2)

Publication Number Publication Date
CA2794217A1 true CA2794217A1 (en) 2011-09-29
CA2794217C CA2794217C (en) 2018-01-02

Family

ID=44673276

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2794217A Expired - Fee Related CA2794217C (en) 2010-03-25 2011-03-24 Thiosulfonate compound, reversible cationization agent for protein and/or peptide, and method for solubilization

Country Status (5)

Country Link
US (1) US8653240B2 (en)
EP (1) EP2551263B1 (en)
JP (1) JP5713006B2 (en)
CA (1) CA2794217C (en)
WO (1) WO2011118731A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2833143A4 (en) * 2012-03-30 2015-11-11 Medinet Co Ltd Method for producing reagent for antibody detection and use thereof

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1156386A (en) * 1997-08-08 1999-03-02 Sumitomo Pharmaceut Co Ltd Regeneration of recombinant bdnf
JP2004049214A (en) 2001-11-29 2004-02-19 Nippon Shokubai Co Ltd Method for introducing protein or peptide into cell
JP2005120017A (en) 2003-10-16 2005-05-12 Nippon Shokubai Co Ltd Method for intracellularly introducing denatured protein formed by reversible cationization and activating the same
JP2007314526A (en) * 2006-04-27 2007-12-06 Ai Bio Chips:Kk Membrane protein solubilizing agent and membrane protein solubilizing method
WO2008001888A1 (en) 2006-06-30 2008-01-03 National University Corporation Hokkaido University Method for pre-treatment of serum for analysis of sugar chain
JP5097412B2 (en) 2006-10-13 2012-12-12 株式会社日本触媒 Protein intracellular introduction agent

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2833143A4 (en) * 2012-03-30 2015-11-11 Medinet Co Ltd Method for producing reagent for antibody detection and use thereof
AU2013240942B2 (en) * 2012-03-30 2018-07-05 Junichiro Futami Method for producing reagent for antibody detection and use thereof

Also Published As

Publication number Publication date
WO2011118731A1 (en) 2011-09-29
US8653240B2 (en) 2014-02-18
US20130096278A1 (en) 2013-04-18
CA2794217C (en) 2018-01-02
EP2551263A4 (en) 2015-08-12
JPWO2011118731A1 (en) 2013-07-04
JP5713006B2 (en) 2015-05-07
EP2551263B1 (en) 2017-07-12
EP2551263A1 (en) 2013-01-30

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Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20160120

MKLA Lapsed

Effective date: 20200831