Luminescent alkynyl-gold(I) coumarin derivatives and their biological activity

Julia Arcau, Vincent Andermark, Elisabet Aguilo, Albert Gandioso, Artur Jorge Carneiro Moro, Mario Cetina, J. C. Lima, Kari Rissanen, Ingo Ott, Laura Rodriguez

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

The synthesis and characterization of three propynyloxycoumarins are reported in this work together with the formation of three different series of gold(I) organometallic complexes. Neutral complexes are constituted by water soluble phosphines (PTA and DAPTA) which confer water solubility to them. The X-ray crystal structure of 7-(prop-2-in-1-yloxy)-1-benzopyran-2-one and its corresponding dialkynyl complex is also shown and the formation of rectangular dimers for the gold derivative in the solid state can be observed. A detailed analysis of the absorption and emission spectra of both ligands and complexes allows us to attribute the luminescent behaviour to the coumarin organic ligand. Moreover, the presence of the gold(I) metal atom seems to be responsible for an increase of coumarin phosphorescence emission. The biological activity of the complexes showed that the anionic complexes triggered strong cytotoxic effects in two different cell lines whereas the neutral gold alkynyl complexes led to lower effects against tumor cell growth. Thioredoxin reductase (TrxR) inhibition was very strong in the case of the neutral complexes (IC50 values below 0.1 mu M) but moderate for the anionic complexes (IC50 values above 0.8 mu M).
Original languageEnglish
Pages (from-to)4426-4436
JournalDalton Transactions
Volume43
Issue number11
DOIs
Publication statusPublished - 21 Mar 2014

Fingerprint

Coumarins
Gold
Inhibitory Concentration 50
Phosphines
Thioredoxin-Disulfide Reductase
Ligands
Water
Solubility
Metals
X-Rays
Cell Line
Growth
Neoplasms
coumarin

Keywords

  • THIOREDOXIN REDUCTASE INHIBITION
  • GOLD(I) COMPLEXES
  • PHOTOPHYSICAL PROPERTIES
  • ANTITUMOR-ACTIVITY
  • AGENTS
  • MECHANISMS
  • CRYSTAL
  • CITOTOXICITY
  • SYSTEMS
  • PROTEIN

Cite this

Arcau, J., Andermark, V., Aguilo, E., Gandioso, A., Moro, A. J. C., Cetina, M., ... Rodriguez, L. (2014). Luminescent alkynyl-gold(I) coumarin derivatives and their biological activity. Dalton Transactions, 43(11), 4426-4436. https://doi.org/10.1039/c3dt52594e
Arcau, Julia ; Andermark, Vincent ; Aguilo, Elisabet ; Gandioso, Albert ; Moro, Artur Jorge Carneiro ; Cetina, Mario ; Lima, J. C. ; Rissanen, Kari ; Ott, Ingo ; Rodriguez, Laura. / Luminescent alkynyl-gold(I) coumarin derivatives and their biological activity. In: Dalton Transactions. 2014 ; Vol. 43, No. 11. pp. 4426-4436.
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abstract = "The synthesis and characterization of three propynyloxycoumarins are reported in this work together with the formation of three different series of gold(I) organometallic complexes. Neutral complexes are constituted by water soluble phosphines (PTA and DAPTA) which confer water solubility to them. The X-ray crystal structure of 7-(prop-2-in-1-yloxy)-1-benzopyran-2-one and its corresponding dialkynyl complex is also shown and the formation of rectangular dimers for the gold derivative in the solid state can be observed. A detailed analysis of the absorption and emission spectra of both ligands and complexes allows us to attribute the luminescent behaviour to the coumarin organic ligand. Moreover, the presence of the gold(I) metal atom seems to be responsible for an increase of coumarin phosphorescence emission. The biological activity of the complexes showed that the anionic complexes triggered strong cytotoxic effects in two different cell lines whereas the neutral gold alkynyl complexes led to lower effects against tumor cell growth. Thioredoxin reductase (TrxR) inhibition was very strong in the case of the neutral complexes (IC50 values below 0.1 mu M) but moderate for the anionic complexes (IC50 values above 0.8 mu M).",
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author = "Julia Arcau and Vincent Andermark and Elisabet Aguilo and Albert Gandioso and Moro, {Artur Jorge Carneiro} and Mario Cetina and Lima, {J. C.} and Kari Rissanen and Ingo Ott and Laura Rodriguez",
note = "The support and sponsorship provided by COST Actions CM1005 and CM1105 are acknowledged. Authors are also grateful to the Ministerio de Ciencia e Innovacion of Spain (project CTQ2012-31335), Fundacao para a Ciencia e Tecnologia of Portugal (PTDC/QUI-QUI/112597/2009; PEst-C/EQB/LA0006/2011), Deutsche Forschungsgemeinschaft (DFG, grant OT 338/7-1) and Academy of Finland (KR, grant no. 265328 and 263256). A. M. thanks FCT for a post-doctoral grant (SFRH/BPD/69210/2010).",
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Arcau, J, Andermark, V, Aguilo, E, Gandioso, A, Moro, AJC, Cetina, M, Lima, JC, Rissanen, K, Ott, I & Rodriguez, L 2014, 'Luminescent alkynyl-gold(I) coumarin derivatives and their biological activity', Dalton Transactions, vol. 43, no. 11, pp. 4426-4436. https://doi.org/10.1039/c3dt52594e

Luminescent alkynyl-gold(I) coumarin derivatives and their biological activity. / Arcau, Julia; Andermark, Vincent; Aguilo, Elisabet; Gandioso, Albert; Moro, Artur Jorge Carneiro; Cetina, Mario; Lima, J. C.; Rissanen, Kari; Ott, Ingo; Rodriguez, Laura.

In: Dalton Transactions, Vol. 43, No. 11, 21.03.2014, p. 4426-4436.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Luminescent alkynyl-gold(I) coumarin derivatives and their biological activity

AU - Arcau, Julia

AU - Andermark, Vincent

AU - Aguilo, Elisabet

AU - Gandioso, Albert

AU - Moro, Artur Jorge Carneiro

AU - Cetina, Mario

AU - Lima, J. C.

AU - Rissanen, Kari

AU - Ott, Ingo

AU - Rodriguez, Laura

N1 - The support and sponsorship provided by COST Actions CM1005 and CM1105 are acknowledged. Authors are also grateful to the Ministerio de Ciencia e Innovacion of Spain (project CTQ2012-31335), Fundacao para a Ciencia e Tecnologia of Portugal (PTDC/QUI-QUI/112597/2009; PEst-C/EQB/LA0006/2011), Deutsche Forschungsgemeinschaft (DFG, grant OT 338/7-1) and Academy of Finland (KR, grant no. 265328 and 263256). A. M. thanks FCT for a post-doctoral grant (SFRH/BPD/69210/2010).

PY - 2014/3/21

Y1 - 2014/3/21

N2 - The synthesis and characterization of three propynyloxycoumarins are reported in this work together with the formation of three different series of gold(I) organometallic complexes. Neutral complexes are constituted by water soluble phosphines (PTA and DAPTA) which confer water solubility to them. The X-ray crystal structure of 7-(prop-2-in-1-yloxy)-1-benzopyran-2-one and its corresponding dialkynyl complex is also shown and the formation of rectangular dimers for the gold derivative in the solid state can be observed. A detailed analysis of the absorption and emission spectra of both ligands and complexes allows us to attribute the luminescent behaviour to the coumarin organic ligand. Moreover, the presence of the gold(I) metal atom seems to be responsible for an increase of coumarin phosphorescence emission. The biological activity of the complexes showed that the anionic complexes triggered strong cytotoxic effects in two different cell lines whereas the neutral gold alkynyl complexes led to lower effects against tumor cell growth. Thioredoxin reductase (TrxR) inhibition was very strong in the case of the neutral complexes (IC50 values below 0.1 mu M) but moderate for the anionic complexes (IC50 values above 0.8 mu M).

AB - The synthesis and characterization of three propynyloxycoumarins are reported in this work together with the formation of three different series of gold(I) organometallic complexes. Neutral complexes are constituted by water soluble phosphines (PTA and DAPTA) which confer water solubility to them. The X-ray crystal structure of 7-(prop-2-in-1-yloxy)-1-benzopyran-2-one and its corresponding dialkynyl complex is also shown and the formation of rectangular dimers for the gold derivative in the solid state can be observed. A detailed analysis of the absorption and emission spectra of both ligands and complexes allows us to attribute the luminescent behaviour to the coumarin organic ligand. Moreover, the presence of the gold(I) metal atom seems to be responsible for an increase of coumarin phosphorescence emission. The biological activity of the complexes showed that the anionic complexes triggered strong cytotoxic effects in two different cell lines whereas the neutral gold alkynyl complexes led to lower effects against tumor cell growth. Thioredoxin reductase (TrxR) inhibition was very strong in the case of the neutral complexes (IC50 values below 0.1 mu M) but moderate for the anionic complexes (IC50 values above 0.8 mu M).

KW - THIOREDOXIN REDUCTASE INHIBITION

KW - GOLD(I) COMPLEXES

KW - PHOTOPHYSICAL PROPERTIES

KW - ANTITUMOR-ACTIVITY

KW - AGENTS

KW - MECHANISMS

KW - CRYSTAL

KW - CITOTOXICITY

KW - SYSTEMS

KW - PROTEIN

U2 - 10.1039/c3dt52594e

DO - 10.1039/c3dt52594e

M3 - Article

VL - 43

SP - 4426

EP - 4436

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9226

IS - 11

ER -

Arcau J, Andermark V, Aguilo E, Gandioso A, Moro AJC, Cetina M et al. Luminescent alkynyl-gold(I) coumarin derivatives and their biological activity. Dalton Transactions. 2014 Mar 21;43(11):4426-4436. https://doi.org/10.1039/c3dt52594e