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Issue 7, 2015
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Novel bio-friendly and non-toxic thiocarbohydrate stabilizers of gold nanoparticles

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Abstract

Several bio-friendly carbohydrate disulfides and thiocarbohydrates have been synthesized via the reaction of D-(+)-gluconic acid δ-lactone with aminoalkylthiols, leading to n-gluconamidoalkyldisulfides {di-(2-gluconamidoethyl)disulfide (L1), di(3-gluconamidopropyl)-disulfide (L2), di(4-gluconamidobutyl) disulfide (L3) and (2-gluconamidoethyl)thiol (L4)}. Acetylation of hydroxy groups in L1–L3 and subsequent reduction produced the following disulfides and thiols: acetylated di(2-gluconamidoethyl)disulfide (L5), acetylated di(3-gluconamidopropyl)disulfide (L6), acetylated di(4-gluconamidobutyl)disulfide (L7), acetylated di(2-gluconamidoethyl)thiol (L8), acetylated di(3-gluconamidopropyl)thiol (L9) and acetylated di(4-gluconamidobutyl)thiol (L10). Compounds L1–L10 were characterized by combination of NMR and infrared spectroscopy, microanalysis, mass spectrometry and in a selected case X-ray crystallographic data. These thiocarbohydrate compounds were used to stabilize gold nanoparticles to gold glyconanoparticles (AuNPs) of sizes in the range of ca. 2–9 nm. The thiocrabohydrates are non-toxic toward both cancer and normal cell lines and have IC50 values generally ≥200 μM.

Graphical abstract: Novel bio-friendly and non-toxic thiocarbohydrate stabilizers of gold nanoparticles

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Publication details

The article was received on 03 Feb 2015, accepted on 24 Apr 2015 and first published on 27 Apr 2015


Article type: Paper
DOI: 10.1039/C5NJ00293A
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Citation: New J. Chem., 2015,39, 5249-5258
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    Novel bio-friendly and non-toxic thiocarbohydrate stabilizers of gold nanoparticles

    C. K. Adokoh, C. Obuah, H. H. Kinfe, O. Zinyemba and J. Darkwa, New J. Chem., 2015, 39, 5249
    DOI: 10.1039/C5NJ00293A

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