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Insulin-like Growth Factor 1 Analogs Clicked in the C Domain: Chemical Synthesis and Biological Activities

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00484559" target="_blank" >RIV/61388963:_____/17:00484559 - isvavai.cz</a>

  • Result on the web

    <a href="http://pubs.acs.org/doi/full/10.1021/acs.jmedchem.7b01331" target="_blank" >http://pubs.acs.org/doi/full/10.1021/acs.jmedchem.7b01331</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1021/acs.jmedchem.7b01331" target="_blank" >10.1021/acs.jmedchem.7b01331</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Insulin-like Growth Factor 1 Analogs Clicked in the C Domain: Chemical Synthesis and Biological Activities

  • Original language description

    Human insulin-like growth factor 1 (IGF-1) is a 70 amino acid protein hormone, with key impact on growth, development, and lifespan. The physiological and clinical importance of IGF-1 prompted challenging chemical and biological trials toward the development of its analogs as molecular tools for the IGF-1 receptor (IGF1-R) studies and as new therapeutics. Here, we report a new method for the total chemical synthesis of IGF-1 analogs, which entails the solid-phase synthesis of two IGF-1 precursor chains that is followed by the CuI-catalyzed azidealkyne cycloaddition ligation and by biomimetic formation of a native pattern of disulfides. The connection of the two IGF-1 precursor chains by the triazole-containing moieties, and variation of its neighboring sequences (Arg36 and Arg37), was tolerated in IGF-1R binding and its activation. These new synthetic IGF-1 analogs are unique examples of disulfide bonds rich proteins with intra main-chain triazole links. The methodology reported here also presents a convenient synthetic platform for the design and production of new analogs of this important human hormone with non-standard protein modifications.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10608 - Biochemistry and molecular biology

Result continuities

  • Project

  • Continuities

    I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2017

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Journal of Medicinal Chemistry

  • ISSN

    0022-2623

  • e-ISSN

  • Volume of the periodical

    60

  • Issue of the periodical within the volume

    24

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    13

  • Pages from-to

    10105-10117

  • UT code for WoS article

    000419263400013

  • EID of the result in the Scopus database

    2-s2.0-85037601863