Conjugates of ferrocene with biological compounds. Coordination to gold complexes and antitumoral properties

Gimeno, M. Concepción; Goitia, Helen; Laguna, Antonio; Luque, M. Elvira; Villacampa, M. Dolores; Sepúlveda, Catarina; Meireles, Margarida

doi:10.1016/j.jinorgbio.2011.07.015

Cited by 61 publications

(48 citation statements)

References 57 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[40,41] We found that complexes 7b and 8 readily formed mono selenol adducts with substitution of the chloro or phosphane ligands, respectively,w hereas the biscarbene complex 10 did not (see the Supporting Information). [14,20,44] The effect of complexes 8 and 10 on the ROS levels in 518A2 melanoma cells was investigated by the nitroblue tetrazolium chloride (NBT) test (Figure5A). PARP-1 has also been identified recently as at arget for gold complexes as well as for heteronuclear iron-gold complexes.…”

Section: Thioredoxin Reductasementioning

confidence: 99%

“…[14] Ah ost of antitumoral ferrocened erivatives have been published, including conjugates with peptides, benzotriazoles, nucleobases, estrogen receptor modulators, and fungal cytotoxins like illudin M. [15][16][17][18][19] There are also reports on gold complexes conjugated to ferrocenew ith distinct anticancer activities against variousc ancerc ell lines. [11,20] In the present paper,w er eport the synthesisa nd structure-dependent anticancer properties in vitro and in vivo of new carbene complexes of gold(I) featuring ferrocenyl-coupled imidazol-2-ylidene ligands.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Ferrocenyl‐Coupled N‐Heterocyclic Carbene Complexes of Gold(I): A Successful Approach to Multinuclear Anticancer Drugs

Muenzner

Biersack

Albrecht

et al. 2016

Chemistry A European J

View full text Add to dashboard Cite

Four gold(I) carbene complexes featuring 4-ferrocenyl-substituted imidazol-2-ylidene ligands were investigated for antiproliferative and antivascular properties. They were active against a panel of seven cancer cell lines, including multidrug-resistant ones, with low micromolar or nanomolar IC (72 h) values, according to their lipophilicity and cellular uptake. The delocalized lipophilic cationic complexes 8 and 10 acted by increasing the reactive oxygen species in two ways: through a genuine ferrocene effect and by inhibiting the thioredoxin reductase. Both complexes gave rise to a reorganization of the F-actin cytoskeleton in endothelial and melanoma cells, associated with a G1 phase cell cycle arrest and a retarded cell migration. They proved antiangiogenic in tube formation assays with endothelial cells and vascular-disruptive on real blood vessels in the chorioallantoic membrane of chicken eggs. Biscarbene complex 10 was also tolerated well by mice where it led to a volume reduction of xenograft tumors by up to 80 %.

show abstract

Section: Thioredoxin Reductasementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ferrocenyl‐Coupled N‐Heterocyclic Carbene Complexes of Gold(I): A Successful Approach to Multinuclear Anticancer Drugs

Muenzner

Biersack

Albrecht

et al. 2016

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…In addition, a number of gold conjugates derived from amino acids or peptides have been reported. As examples, N‐heterocyclic carbene (NHC)–gold complexes,, conjugates of ferrocene coordinated to gold(I) derivatives, gold(III) dithiocarbamates,, gold(I) azides, and gold(I) thiolates, with only one example of a chloro–gold–phosphane found in the recent literature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Gold(I) Derivatives Bearing Alkylated 1,3,5‐Triaza‐7‐phosphaadamantane as Selective Anticancer Metallodrugs

et al. 2016

View full text Add to dashboard Cite

The alkylation of one of the nitrogen atoms of the molecule 1,3,5,triaza‐7‐phosphaadamantane (PTA) with para‐substituted benzylic units and the l‐phenylalanine methyl ester moiety are reported. The crystalline structures of the two alkylated PTA species [PTA‐CH2‐p‐COOH‐C6H4]Br (1a) and [PTA‐CH2‐p‐CH2COOH‐C6H4]Br (2) reveal the presence of interactions between the bromide anion and the OH group of the acid moiety. Bis‐phosphane derivatives were prepared by the alkylation of two PTA molecules with a dibromide salt to afford more water‐soluble species. The corresponding mono‐ and dinuclear chloro‐, thiocyanato‐ and pentafluorophenyl gold(I) derivatives are described. Most of the new complexes have been tested as anticancer agents, exhibiting higher cytotoxicity than cisplatin against human colon cancer cell lines. Some of them display low cytotoxicity towards differentiated cells (non‐carcinogenic), as determined from viability studies, thereby demonstrating a significant specificity in this type of cancer.

show abstract

“…Some ferrocene derivatives have shown antibacterial, antifungal, herbicidal and antitumor activities [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]. On the other hand, their ferrocenium salts are relatively scarce.…”

Section: Introductionmentioning

confidence: 99%

Oxidation of ferrocene by thiocyanic acid in the presence of ammonium oxalate

Ruslin

Yamin

2014

AIP Conference Proceedings

View full text Add to dashboard Cite

Abstract.A flake-like crystalline salt was obtained from the reaction of ferrocene, oxalic acid and ammonium thiocyanate in ethanol The elemental analysis and spectroscopic data were in agreement with the preliminary X-ray molecular structure. The compound consists of four ferrocenium moieties and a counter anion consisting of two (tetraisothiocyanato)iron(III) linked by an oxalato bridging group in such a way that both iron central atoms adopt octahedral geometries.

show abstract

Conjugates of ferrocene with biological compounds. Coordination to gold complexes and antitumoral properties

Cited by 61 publications

References 57 publications

Ferrocenyl‐Coupled N‐Heterocyclic Carbene Complexes of Gold(I): A Successful Approach to Multinuclear Anticancer Drugs

Ferrocenyl‐Coupled N‐Heterocyclic Carbene Complexes of Gold(I): A Successful Approach to Multinuclear Anticancer Drugs

Synthesis of Gold(I) Derivatives Bearing Alkylated 1,3,5‐Triaza‐7‐phosphaadamantane as Selective Anticancer Metallodrugs

Oxidation of ferrocene by thiocyanic acid in the presence of ammonium oxalate

Contact Info

Product

Resources

About