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Type: Artigo de periódico
Title: Gold(i)-phosphine-n-heterocycles: Biological Activity And Specific (ligand) Interactions On The C-terminal Hivncp7 Zinc Finger.
Author: Abbehausen, Camilla
Peterson, Erica J
de Paiva, Raphael E F
Corbi, Pedro P
Formiga, André L B
Qu, Yun
Farrell, Nicholas P
Abstract: The syntheses and the characterization by chemical analysis, (1)H and (31)P NMR spectroscopy, and mass spectrometry of a series of linear triphenylphosphine gold(I) complexes with substituted N-heterocycle ligands (L), [(PPh3)Au(I)(L)](+), is reported. The reaction of [(PPh3)Au(L)](+) (L = Cl(-) or substituted N- heterocyclic pyridine) with the C-terminal (Cys3His) finger of HIVNCp7 shows evidence by mass spectrometry (ESI-MS) and (31)P NMR spectroscopy of a long-lived {(PPh3)Au}-S-peptide species resulting from displacement of the chloride or pyridine ligand by zinc-bound cysteine with concomitant displacement of Zn(2+). In contrast, reactions with the Cys2His2 finger-3 of the Sp1 transcription factor shows significantly reduced intensities of {(PPh3)Au} adducts. The results suggest the possibility of systematic (electronic, steric) variations of carrier group PR3 and leaving group L as well as the nature of the zinc finger in modulation of biological activity. The cytotoxicity, cell cycle signaling effects, and cellular accumulation of the series are also reported. All compounds display cytotoxicity in the micromolar range upon 96 h continuous exposure to human tumor cells. The results may have relevance for the reported inhibition of viral load in simian virus by the gold(I) drug auranofin.
Subject: Cell Line, Tumor
Cell Proliferation
Circular Dichroism
Heterocyclic Compounds
Inhibitory Concentration 50
Magnetic Resonance Spectroscopy
Spectrometry, Mass, Electrospray Ionization
Zinc Fingers
Gag Gene Products, Human Immunodeficiency Virus
Citation: Inorganic Chemistry. v. 52, n. 19, p. 11280-7, 2013-Oct.
Rights: fechado
Identifier DOI: 10.1021/ic401535s
Date Issue: 2013
Appears in Collections:Unicamp - Artigos e Outros Documentos

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