All

What are you looking for?

All
Projects
Results
Organizations

Quick search

  • Projects supported by TA ČR
  • Excellent projects
  • Projects with the highest public support
  • Current projects

Smart search

  • That is how I find a specific +word
  • That is how I leave the -word out of the results
  • “That is how I can find the whole phrase”

Lupane and 18a-oleanane derivatives substituted in the position 2, their cytotoxicity and influence on cancer cells

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F16%3A33160885" target="_blank" >RIV/61989592:15310/16:33160885 - isvavai.cz</a>

  • Alternative codes found

    RIV/61989592:15110/16:33160885

  • Result on the web

    <a href="http://www.sciencedirect.com/science/article/pii/S0223523416304251" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0223523416304251</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1016/j.ejmech.2016.05.029" target="_blank" >10.1016/j.ejmech.2016.05.029</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Lupane and 18a-oleanane derivatives substituted in the position 2, their cytotoxicity and influence on cancer cells

  • Original language description

    Lupane derivatives containing an electronegative substituent in the position 2 of the skeleton are often cytotoxic, however, the most active compounds are not selective enough. To further study the influence of a substituent in the position 2 in lupane and 18a-oleanane derivatives on their biological properties, we prepared a set of 38 triterpenoid compounds, 19 of them new, most of them substituted in the position 2. From betulin, we obtained 2-bromo dihydrobetulonic acid and 2-bromo allobetulon and their substitutions yielded derivatives with various substituents in the position 2 such as amines, amides, thiols, and thioethers. Nitration of allobetulon and dihydrobetulonic acid gave 2-nitro and 2,2-dinitro derivatives. Fifteen derivatives had IC50 < 50 mM on a chemosensitive CCRF-CEM (acute lymphoblastic leukemia) cell line and were tested on another seven cancer cell lines including resistant and two noncancer lines. 2-Amino allobetulin had IC50 4.6 mM and caused significant block of the tumor cells in S and slightly in G2/M transition and caused strong inhibition of DNA and RNA synthesis at 5 IC50. 2-Amino allobetulin is the most active derivative of 18a-oleanane skeletal type prepared in our research group to date.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

  • CEP classification

    CC - Organic chemistry

  • OECD FORD branch

Result continuities

  • Project

    Result was created during the realization of more than one project. More information in the Projects tab.

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Others

  • Publication year

    2016

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    European Journal of Medicinal Chemistry

  • ISSN

    0223-5234

  • e-ISSN

  • Volume of the periodical

    121

  • Issue of the periodical within the volume

    OCT

  • Country of publishing house

    FR - FRANCE

  • Number of pages

    12

  • Pages from-to

    120-131

  • UT code for WoS article

    000382269700011

  • EID of the result in the Scopus database