WO2011053065A3 - 카테콜 폴리에틸렌글리콜 유도체와 단백질 또는 펩타이드의 접합체 및 이의 제조방법 - Google Patents

카테콜 폴리에틸렌글리콜 유도체와 단백질 또는 펩타이드의 접합체 및 이의 제조방법 Download PDF

Info

Publication number
WO2011053065A3
WO2011053065A3 PCT/KR2010/007567 KR2010007567W WO2011053065A3 WO 2011053065 A3 WO2011053065 A3 WO 2011053065A3 KR 2010007567 W KR2010007567 W KR 2010007567W WO 2011053065 A3 WO2011053065 A3 WO 2011053065A3
Authority
WO
WIPO (PCT)
Prior art keywords
protein
polyethylene glycol
conjugates
catechol
present
Prior art date
Application number
PCT/KR2010/007567
Other languages
English (en)
French (fr)
Other versions
WO2011053065A9 (ko
WO2011053065A2 (ko
Inventor
이해신
이혁진
박태관
송인택
이문수
Original Assignee
한국과학기술원
(주) 이노테라피
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 한국과학기술원, (주) 이노테라피 filed Critical 한국과학기술원
Priority to US13/133,166 priority Critical patent/US8604127B2/en
Priority to ES10827149.5T priority patent/ES2617713T3/es
Priority to EP10827149.5A priority patent/EP2495258B1/en
Priority to JP2012536696A priority patent/JP5657011B2/ja
Publication of WO2011053065A2 publication Critical patent/WO2011053065A2/ko
Publication of WO2011053065A9 publication Critical patent/WO2011053065A9/ko
Publication of WO2011053065A3 publication Critical patent/WO2011053065A3/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K19/00—Hybrid peptides, i.e. peptides covalently bound to nucleic acids, or non-covalently bound protein-protein complexes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/59—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
    • A61K47/60—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
    • 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
    • C07K1/13—Labelling of peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

본 발명은 카테콜을 갖는 폴리에틸렌글리콜 유도체를 이용하여 단백질 또는 펩타이드의 특정부위인 N-말단에 폴리에틸렌글리콜 유도체를 단일접합시킨 단백질- 또는 펩타이드-카테콜 폴리에틸렌글리콜 유도체의 접합체 및 이의 제조방법에 관한 것이다. 본 발명에 따르면, 카테콜-PEG 유도체가 단백질 또는 펩타이드의 특정부위인 N 말단 아민 그룹에 위치특이적이면서도 단일 분자로 결합하여, 균일한 폴리에틸렌글리콜 단백질- 또는 펩타이드-접합체를 높은 수율로 수득할 수 있다. 수득된 접합체는 종래기술에 비하여 단백질 자체의 화학적 변형이 없으면서도 단백질 활성도 저해를 최소화할 수 있어 접합체의 약학적 효과가 뛰어나며, 그 균질성에 의해 제조 공정을 단순화 시킬 수 있으며, 또한 생체 내에서의 생물학적 약효성이 균일하게 예측되고, 가수분해에 강하여 생체 내 지속시간이 길어지므로, 단백질 약물의 체내 약효 및 안정성을 증진시키는 효과가 있다.
PCT/KR2010/007567 2009-10-29 2010-10-29 카테콜 폴리에틸렌글리콜 유도체와 단백질 또는 펩타이드의 접합체 및 이의 제조방법 WO2011053065A2 (ko)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US13/133,166 US8604127B2 (en) 2009-10-29 2010-10-29 Conjugate of catechol-modified polyethylene glycol with protein or peptide and preparation method thereof
ES10827149.5T ES2617713T3 (es) 2009-10-29 2010-10-29 Conjugados de derivado de polietilenglicol, catecol y proteína o péptido, y procedimiento de preparación de los mismos
EP10827149.5A EP2495258B1 (en) 2009-10-29 2010-10-29 Catechol polyethylene glycol derivative and protein or peptide conjugates, and method for preparing same
JP2012536696A JP5657011B2 (ja) 2009-10-29 2010-10-29 カテコールポリエチレングリコール誘導体と蛋白質またはペプチドの接合体、及びこれの製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2009-0103662 2009-10-29
KR20090103662 2009-10-29

Publications (3)

Publication Number Publication Date
WO2011053065A2 WO2011053065A2 (ko) 2011-05-05
WO2011053065A9 WO2011053065A9 (ko) 2011-08-25
WO2011053065A3 true WO2011053065A3 (ko) 2011-10-27

Family

ID=43922888

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2010/007567 WO2011053065A2 (ko) 2009-10-29 2010-10-29 카테콜 폴리에틸렌글리콜 유도체와 단백질 또는 펩타이드의 접합체 및 이의 제조방법

Country Status (5)

Country Link
US (1) US8604127B2 (ko)
EP (1) EP2495258B1 (ko)
JP (1) JP5657011B2 (ko)
ES (1) ES2617713T3 (ko)
WO (1) WO2011053065A2 (ko)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10046058B2 (en) * 2014-12-02 2018-08-14 Rezolute, Inc. Use of hydrophobic organic acids to increase hydrophobicity of proteins and protein conjugates
CN104877982B (zh) * 2015-05-11 2019-08-30 香港大学深圳研究院 制备肽/蛋白缀合物的方法和试剂
CN105017390B (zh) * 2015-06-29 2018-02-23 广东海纳川生物科技股份有限公司 抗菌肽His6K及其应用
EP3652316A4 (en) 2017-07-11 2021-04-07 Synthorx, Inc. INTEGRATION OF NON-NATURAL NUCLEOTIDES AND METHOD FOR THEREFORE
TWI757528B (zh) 2017-08-03 2022-03-11 美商欣爍克斯公司 用於增生及感染性疾病治療之細胞激素結合物
BR112021014415A2 (pt) 2019-02-06 2021-09-21 Synthorx, Inc. Conjugados de il-2 e métodos de uso dos mesmos
CN109939272B (zh) * 2019-03-21 2020-08-11 西南交通大学 一种抗凝血材料及其制备方法
CN111053917B (zh) * 2019-12-31 2022-06-07 哈尔滨工业大学 一种基于蛋白质的智能高效抗菌剂的制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4585585A (en) * 1984-03-07 1986-04-29 University Of Connecticut Research & Development Corporation Decapeptides produced from bioadhesive polyphenolic proteins
WO2003008376A2 (en) * 2001-07-20 2003-01-30 Northwestern University Adhesive dopa-containing polymers and related methods of use
US20090093610A1 (en) * 2005-08-24 2009-04-09 Marcus Textor Catechol Functionalized Polymers and Method for Preparing Them

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100345214B1 (ko) * 1999-08-17 2002-07-25 이강춘 생체적합성 고분자가 수식된 펩타이드의 비점막 전달
BRPI0818288A2 (pt) * 2007-10-09 2015-04-14 Polytherics Ltd Proteínas conjugadas e peptídeos.
US20100137903A1 (en) * 2008-09-26 2010-06-03 Nerites Corporation Bioadhesive constructs

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4585585A (en) * 1984-03-07 1986-04-29 University Of Connecticut Research & Development Corporation Decapeptides produced from bioadhesive polyphenolic proteins
WO2003008376A2 (en) * 2001-07-20 2003-01-30 Northwestern University Adhesive dopa-containing polymers and related methods of use
US20090093610A1 (en) * 2005-08-24 2009-04-09 Marcus Textor Catechol Functionalized Polymers and Method for Preparing Them

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP2495258A4 *

Also Published As

Publication number Publication date
EP2495258B1 (en) 2016-12-07
WO2011053065A9 (ko) 2011-08-25
US20120208258A1 (en) 2012-08-16
US8604127B2 (en) 2013-12-10
JP2013509402A (ja) 2013-03-14
JP5657011B2 (ja) 2015-01-21
EP2495258A4 (en) 2015-10-07
WO2011053065A2 (ko) 2011-05-05
ES2617713T3 (es) 2017-06-19
EP2495258A2 (en) 2012-09-05

Similar Documents

Publication Publication Date Title
WO2011053065A3 (ko) 카테콜 폴리에틸렌글리콜 유도체와 단백질 또는 펩타이드의 접합체 및 이의 제조방법
EP2810661A3 (en) Disulfide-linked polyethyleneglycol/peptide conjugates for the transfection of nucleic acids
AU2016219654A1 (en) Crystallization method and bioavailability
NZ621868A (en) Growth hormone polypeptides and methods of making and using same
EP2583976A3 (en) Peptide vaccines with SEQ ID NO: 210, 196, 202, 213, 214, 214 or 223 for cancers expressing tumor-associated antigens
TW200642700A (en) Chemically defined stabiliser
WO2012006376A3 (en) Virion-like delivery particles for self-replicating rna molecules
WO2012135805A3 (en) Delivery and formulation of engineered nucleic acids
WO2009151708A3 (en) Peptide analogs of alpha-melanocyte stimulating hormone
WO2011122921A3 (en) An insulin conjugate using an immunoglobulin fragment
WO2009115531A3 (en) Yopm as delivery vehicle for cargo molecules and as biological therapeutic for immunomodulation of inflammatory reactions
WO2012142320A8 (en) Compositions and methods for preventing or treating diseases, conditions, or processes characterized by aberrant fibroblast proliferation and extracellular matrix deposition
WO2011131896A3 (fr) Derives peptidiques, leur preparation et leurs utilisations comme vecteurs
WO2010107256A3 (en) Method for preparing a site-specific physiologically active polypeptide conjugate
NO20055209D0 (no) Peptabody for cancerbehandling
WO2012083302A3 (en) Compositions and methods for the treatment or prevention of human adenovirus-36 infection
UA100127C2 (ru) Пептид cdh3 и лекарственное средство, содержащее его
WO2011071280A3 (ko) 세포내 타겟 결합용 바이포달 펩타이드 바인더
WO2009064366A3 (en) Methods and compositions for protein labeling using lipoic acid ligases
EP2269625A3 (en) Protective proteins of S. agalactiae, combinations thereof and methods of using the same
WO2010057275A8 (en) Cyclic peptides and uses thereof
WO2009093246A3 (en) Clusterin derived peptide
CN101716343A (zh) 一种单克隆抗体的冻干制剂
WO2009148955A3 (en) Multi-arm amines and uses thereof
WO2011036619A3 (en) Two step ultrasound protocol for drug delivery

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10827149

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 13133166

Country of ref document: US

REEP Request for entry into the european phase

Ref document number: 2010827149

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2010827149

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2012536696

Country of ref document: JP