Skip to main content

Advertisement

SpringerLink
Log in

Lipophilic gold(I) complexes with 1,3,4-oxadiazol-2-thione or 1,3-thiazolidine-2-thione moieties: synthesis and their cytotoxic and antimicrobial activities

  • Published:
BioMetals Aims and scope Submit manuscript

A Correction to this article was published on 11 October 2017

This article has been updated

Abstract

Novel lipophilic gold(I) complexes containing 1,3,4-oxadiazol-2-thione or 1,3-thiazolidine-2-thione derivatives were synthesized and characterized by IR, high resolution mass spectrometry, and 1H, 13C 31P NMR. The cytotoxicity of the compounds was evaluated considering cisplatin and/or auranofin as reference in different tumor cell lines: colon cancer (CT26WT), metastatic skin melanoma (B16F10), breast adenocarcinoma (MCF-7), cervical carcinoma (HeLa), glioblastoma (M059 J). Normal human lung fibroblasts (GM07492-A) and kidney normal cell (BHK-21) were also evaluated. The gold(I) complexes were more active than their respective free ligands and cisplatin. Furthermore, antibacterial activity was evaluated against Gram-positive bacteria Staphylococcus aureus ATCC 25213, Staphylococcus epidermidis ATCC 12228 and Gram-negative bacteria Escherichia coli ATCC 11229 and Pseudomonas aeruginosa ATCC 27853 and expressed as the minimum inhibitory concentration (MIC). The complexes exhibited lower MIC values when compared to the ligands and chloramphenicol against Gram-positive bacteria and Gram-negative bacteria. Escherichia coli was sensitive one to the action of gold(I) complexes.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Fig. 1
Fig. 2

Similar content being viewed by others

Change history

  • 11 October 2017

    This article has been corrected. One of the author names was given incorrect. Please find in this erratum the correct author name: “Heloiza Diniz Nicolella” that should be regarded as final by the reader.

Abbreviations

IR:

Infrared

NMR:

Nuclear magnetic resonance

TMS:

Tetramethylsilane

HEPES:

4-(2-Hydroxyethyl)piperazine-1-ethanesulfonic acid, N-(2-hydroxyethyl)piperazine-N′-(2-ethanesulfonic acid)

HMRS (ESI):

High-resolution mass spectra (eletrospray ionization)

FBS:

Fetal bovine serum

MTT:

Methylthiazolyldiphenyl-tetrazolium bromide

HAM-F10:

Nutrient mixture F-10

DMEM:

Dulbecco’s Modified Eagle’s Medium

XTT:

2,3-Bis(2-methoxy-4-nitro-5-sulfophenyl)-2H-tetrazolium-5-carboxanilide

DMSO:

Dimethylsulfoxide

PBS:

Phosphate buffer saline

RPMI 1640:

Roswell Park Memorial Institute 1640 medium

TTC:

2,3,5-Triphenyltetrazolium chloride

References

  • Baenziger NC, Bennett WE, Soborofe DM (1976) Chloro(triphenylphosphine)gold(I). Acta Crystallogr Sect B 32:962–963

    Article  Google Scholar 

  • Bakhtiar R, Ochiai E-I (1999) Pharmacological applications of inorganic complexes. Gen Pharmacol 32:525–540

    Article  CAS  PubMed  Google Scholar 

  • Benedek TG (2004) The history of gold therapy for tuberculosis. J Hist Med Allied Sci 59:50–89

    Article  PubMed  Google Scholar 

  • Chaves JDS, Neumann F, Francisco TM, Correa CC, Lopes MTP, Silva H, Fontes APS, de Almeida MV (2014) Synthesis and cytotoxic activity of gold(I) complexes containing phosphines and 3-benzyl-1,3-thiazolidine-2-thione or 5-phenyl-1,3,4-oxadiazole-2-thione as ligands. Inorg Chim Acta 414:85–90

    Article  CAS  Google Scholar 

  • Chaves JDS, Damasceno JL, Paula MCF, de OliveiraPF Azevedo GC, Matos RC, Lourenço MCS, Tavares DC, Silva H, Fontes APS, de Almeida MV (2015) Synthesis, characterization, cytotoxic and antitubercular activities of new gold(I) and gold(III) complexes containing ligands derived from carbohydrates. Biometals 28:845–860

    Article  CAS  PubMed  Google Scholar 

  • Chaves JDS, Tunes LG, Franco CHJ, FranciscoTM Correa CC, Murta SMF, Monte-Neto RL, Silva H, Fontes APS, de Almeida MV (2017) Novel gold(I) complexes with 5-phenyl-1,3,4-oxadiazole-2-thione and phosphine as potential anticancer and antileishmanial agents. Eur J Med Chem 127:727–739

    Article  CAS  PubMed  Google Scholar 

  • Clinical and Laboratory Standards Institute (CLSI) (2015) Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically (M07-A10), 10th edn. CLSI, Wayne

    Google Scholar 

  • Coimbra ES, de Almeida MV, Junior CO, Taveira AF, da Costa CF, de Almeida AC, Reis EF, da Silva AD (2010) Synthesis and antileishmanial activity of lipidic amino alcohols. Chem Biol Drug Des 75:233–235

    Article  CAS  PubMed  Google Scholar 

  • de Almeida AM, Nascimento T, Ferreira BS, de Castro PP, Silva VL, Diniz CG, Le Hyaric M (2013) Synthesis and antimicrobial activity of novel amphiphilic aromatic amino alcohols. Bioorg Med Chem Lett 23:2883–2887

    Article  PubMed  Google Scholar 

  • de Souza SM, Delle Monache F, Smania A Jr (2005) Antibacterial activity of coumarins. Z Nat C 60:693–700

    Google Scholar 

  • Ferreira BDS, de Almeida AM, Nascimento TC, de Castro PP, Silva VL, Diniz CG, Le Hyaric M (2014) Synthesis and biological evaluation of a new series of N-acyldiamines as potential antibacterial and antifungal agents. Bioorg Med Chem Lett 24:4626–4629

    Article  CAS  PubMed  Google Scholar 

  • Garcia A, Machado RC, Grazul RM, Lopes MTP, Correa CC, dos Santos HF, de Almeida MV, Silva H (2016) Novel antitumor adamantane-azole gold(I) complexes as potential inhibitors of thioredoxin reductase. JBIC J Biol Inorg Chem 21:275–292

    Article  CAS  PubMed  Google Scholar 

  • Lucas SJ, Lord RM, Basri AM, Allison SJ, Phillips RM, Blacker AJ, McGowan PC (2016) Increasing anti-cancer activity with longer tether lengths of group 9 Cp* complexes. Dalton Trans 45:6812–6815

    Article  CAS  PubMed  Google Scholar 

  • Manjunatha K, Poojary B, Lobo PL, Fernandes J, Kumari NS (2010) Synthesis and biological evaluation of some 1,3,4-oxadiazole derivatives. Eur J Med Chem 45:5225–5233

    Article  CAS  PubMed  Google Scholar 

  • Medici S, Peana M, Nurchi VM, Lachowicz JI, Crisponi G, Zoroddu MA (2015) Noble metals in medicine: latest advances. Coord Chem Rev 284:329–350

    Article  CAS  Google Scholar 

  • Mirabelli CK, Johnson RK, Sung CM, Faucette L, Muirhead K, Crooke ST (1985) Evaluation of the in vivo antitumor activity and in vitro cytotoxic properties of auranofin, a coordinated gold compound, in murine tumor models. Cancer Res 45:32–39

    CAS  PubMed  Google Scholar 

  • Ott I (2009) On the medicinal chemistry of gold complexes as anticancer drugs. Coord Chem Rev 253:1670–1681

    Article  CAS  Google Scholar 

  • Reis EFC, Júnior COR, Alves LL, Ferreira AP, De Almeida MV (2008) Synthesis and immunosuppressive activity of lipophilic amino alcohols and diamines. Chem Biol Drug Des 72:596–598

    Article  CAS  PubMed  Google Scholar 

  • Rosenberg B, Vancamp L, Trosko JE, Mansour VH (1969) Platinum compounds: a new class of potent antitumour agents. Nature 222:385–386

    Article  CAS  PubMed  Google Scholar 

  • Shi J-C, Chen L-J, Huang X-Y, Wu D-X, Kang B-S (1997) Chiral phosphine ligands derived from sugars 10. Syntheses, structure, characterization, and antitumor activity of the gold(I) complexes with sugar-substructure phosphine ligands. J Organomet Chem 535:17–23

    Article  CAS  Google Scholar 

  • Thangamani S, Mohammad H, Abushahba MFN, Sobreira TJP, Hedrick VE, Paul LN, Seleem MN (2016) Antibacterial activity and mechanism of action of auranofin against multi-drug resistant bacterial pathogens. Sci Rep 6:22571

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgements

The authors wish to thank CAPES, CNPq and FAPEMIG for financial supports and fellowships. This work is a collaboration research project of members of the Rede Mineira de Química (RQ-MG) supported by FAPEMIG (Project: CEX- RED-0010/14).

Author information

Authors and Affiliations

  1. Department of Chemistry, Federal University of Juiz de Fora, Campus Martelos, Juiz de Fora, MG, 36036-900, Brazil

    Angelina Maria de Almeida, Bruno Assis de Oliveira, Pedro Pôssa de Castro, Camille Carvalho de Mendonça & Mauro Vieira de Almeida

  2. Department of Research on Natural Products, University of Franca, Franca, SP, 14406-600, Brazil

    Ricardo Andrade Furtado, Heloiza Diniz Nicolella & Denise Crispim Tavares

  3. Department of Parasitology, Microbiology and Immunology, Federal University of Juiz de Fora, Campus Martelos, Juiz de Fora, MG, 36036-900, Brazil

    Vânia Lúcia da Silva & Cláudio Galuppo Diniz

  4. Department of Chemistry, Federal University of Minas Gerais, Campus Pampulha, Belo Horizonte, MG, 31270-901, Brazil

    Heveline Silva

Authors
  1. Angelina Maria de Almeida
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Bruno Assis de Oliveira
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pedro Pôssa de Castro
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Camille Carvalho de Mendonça
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ricardo Andrade Furtado
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Heloiza Diniz Nicolella
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Vânia Lúcia da Silva
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Cláudio Galuppo Diniz
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Denise Crispim Tavares
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Heveline Silva
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Mauro Vieira de Almeida
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mauro Vieira de Almeida.

Additional information

This article has been corrected. One of the author names was given incorrect. The corrected author name is: “Heloiza Diniz Nicolella” and should be regarded as final by the reader.

A correction to this article is available online at https://doi.org/10.1007/s10534-017-0049-3.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

de Almeida, A.M., de Oliveira, B.A., de Castro, P.P. et al. Lipophilic gold(I) complexes with 1,3,4-oxadiazol-2-thione or 1,3-thiazolidine-2-thione moieties: synthesis and their cytotoxic and antimicrobial activities. Biometals 30, 841–857 (2017). https://doi.org/10.1007/s10534-017-0046-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10534-017-0046-6

Keywords

Search

Navigation