Efficient synthesis of amino acids capped gold nanoparticles from easily reducible aryldiazonium tetrachloroaurate(III) salts for cellular uptake study

Amino Acids. 2020 Jul;52(6-7):941-953. doi: 10.1007/s00726-020-02862-z. Epub 2020 Jun 30.

Abstract

Biomimetic synthesis of gold nanoparticles (GNPs) is critical in biomedical applications. Gold bioconjugates were fabricated by capping the water-dispersible gold-carbon nanoparticles with tyrosine, tryptophan and cysteine amino acids. Incubation of the water-soluble and easily reducible aryldiazonium gold(III) salt [HOOC-4-C6H4N≡N]AuCl4 with amino acids at room temperature formed a purple color over a few minutes with tryptophan and tyrosine and over two hours with cysteine. Rarely that cysteine is capable of reducing gold(III) precursors; however, a cysteine capped gold bioconjugate was synthesized and characterized in this study. Capping GNPs with amino acids was confirmed by high resolution transmission electron microscopy (TEM) and agarose gel electrophoresis. Depending on the amino acid, synthesized particles size was 27.2 ± 5.4 nm, 14.6 ± 7.7 nm and 8.6 ± 2.6 nm for tyrosine, tryptophan and cysteine, respectively. The amino acids capped GNPs showed negligible cytotoxicity to human dermal normal fibroblast cell lines. The highly water dispersible bioconjugates were studied for in vitro cellular uptake by HeLa cancer cells using confocal laser scan microscopy (CLSM) after being labelled with FITC (GNPs-COOH-FITC) and the nuclei were counter stained with DAPI fluorescent dyes. The biomimetic route for the synthesis of the amino acids reduced gold-carbon nanoparticles will benefit the applications in biomedical devices and biosensors.

Keywords: Amino acids; Biocompatibility; Cellular uptake; Diazonium salts; Gold-carbon nanoparticles.

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry*
  • Chlorides / chemical synthesis
  • Chlorides / chemistry*
  • Cysteine / chemistry
  • Electrophoresis, Agar Gel
  • Gold Compounds / chemical synthesis
  • Gold Compounds / chemistry*
  • HeLa Cells
  • Humans
  • Metal Nanoparticles / chemistry*
  • Tryptophan / chemistry
  • Tyrosine / chemistry

Substances

  • Amino Acids
  • Chlorides
  • Gold Compounds
  • Tyrosine
  • Tryptophan
  • gold tetrachloride, acid
  • Cysteine