Diverse in vitro and in vivo anti-inflammatory effects of trichlorido-gold(III) complexes with N6-benzyladenine derivatives
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
24584156
DOI
10.1016/j.jinorgbio.2014.02.002
PII: S0162-0134(14)00041-5
Knihovny.cz E-resources
- Keywords
- Adenine derivatives, Anti-inflammatory, Cytotoxicity, Gold(III) complexes, TNF-α,
- MeSH
- Anti-Inflammatory Agents, Non-Steroidal chemical synthesis pharmacology MeSH
- Auranofin pharmacology MeSH
- Benzyl Compounds MeSH
- Chlorides chemistry MeSH
- Edema drug therapy pathology MeSH
- Indomethacin pharmacology MeSH
- Kinetin chemistry MeSH
- Coordination Complexes chemical synthesis pharmacology MeSH
- Rats MeSH
- Humans MeSH
- Ligands MeSH
- Monocytes cytology drug effects MeSH
- Cell Line, Tumor MeSH
- Rats, Wistar MeSH
- Purines MeSH
- Cell Survival drug effects MeSH
- Hindlimb MeSH
- Gold chemistry MeSH
- Animals MeSH
- Check Tag
- Rats MeSH
- Humans MeSH
- Male MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Anti-Inflammatory Agents, Non-Steroidal MeSH
- Auranofin MeSH
- benzylaminopurine MeSH Browser
- Benzyl Compounds MeSH
- Chlorides MeSH
- Indomethacin MeSH
- Kinetin MeSH
- Coordination Complexes MeSH
- Ligands MeSH
- Purines MeSH
- Gold MeSH
A series of gold(III) complexes involving differently substituted derivatives of a plant hormone N6-benzyladenine (HL1-5) is reported. The complexes have the general formula [Au(HL1-5)Cl3]∙nH2O (n=0 for 1, 3-5; and n=1 for 2), where N6-(2-fluorobenzyl)adenine (HL1), N6-(2-chlorobenzyl)adenine (HL2), N6-(3-chlorobenzyl)adenine (HL3), N6-(4-chlorobenzyl)adenine (HL4) and N6-(4-methylbenzyl)adenine (HL5) represent the N9-coordinated ligands. The results of thorough characterization (elemental and thermal analyses, FT-IR, Raman and NMR spectroscopies, ESI+ mass spectrometry, conductivity measurements, DFT calculations) showed that the presented complexes 1-5 involve a central gold(III) atom coordinated in a square-planar geometry by the N9 atom of the purine moiety of HL1-5 and by three chlorido ligands. The complexes (1-5) were studied in vitro for cytotoxicity and anti-inflammatory activity on LPS-activated macrophages (THP-1 cell line), and in vivo for anti-inflammatory effects (1, 2, 5) using the carrageenan-induced hind paw oedema model on rats. Surprisingly, the results on the in vitro level revealed that the complexes show negligible cytotoxicity and anti-inflammatory activity, however, the activity on the in vivo level was found to be significant, fully comparable with the utilized drug Indomethacin, or even better as compared to a gold-containing metallodrug Auranofin.
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