Synthesis of double-clickable functionalised graphene oxide for biological applications

Kuo-Ching Mei; Noelia  Rubio; Pedro Miguel Coutinho Da Costa; Houmam Kafa; Vincenzo Abbate; Frederic Festy; Sukhvinder S Bansal; Robert C Hider; Khuloud T Al-Jamal

doi:10.1039/c5cc05412e

Synthesis of double-clickable functionalised graphene oxide for biological applications

Kuo-Ching Mei, Noelia Rubio, Pedro Miguel Coutinho Da Costa, Houmam Kafa, Vincenzo Abbate, Frederic Festy, Sukhvinder S Bansal, Robert C Hider, Khuloud T Al-Jamal

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Abstract

Azide- and alkyne-double functionalised graphene oxide (Click(2) GO) was synthesised and characterised with attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR), thermogravimetric analysis (TGA) and Raman spectroscopy. Fourteen-percentage increase in azide content was found, after pre-treatment of GO with meta-chloroperoxybenzoic acid (mCPBA), determined with elemental analysis. No effect on A549 cell viability was found, up to 100 μg mL(-1) and 72 h of incubation, determined with the modified lactate dehydrogenase (mLDH) assay. Two sequential copper(i) catalysed azide-alkyne cycloaddition (CuAAC) reactions were performed to conjugate the propargyl-modified blood-brain barrier targeting peptide Angiopep-2, and a bis-azide polyethylene glycol (MW = 3500), to the Click(2) GO. The final conjugate was characterised with ATR-FTIR and TGA.

Original language	English
Pages (from-to)	14981-14984
Number of pages	4
Journal	Chemical communications (Cambridge, England)
Volume	51
Issue number	81
DOIs	https://doi.org/10.1039/c5cc05412e
Publication status	Published - 7 Aug 2015

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10.1039/c5cc05412eLicence: CC BY

Mei et al Chem Comm 2016Final published version, 2.83 MBLicence: CC BY

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title = "Synthesis of double-clickable functionalised graphene oxide for biological applications",

abstract = "Azide- and alkyne-double functionalised graphene oxide (Click(2) GO) was synthesised and characterised with attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR), thermogravimetric analysis (TGA) and Raman spectroscopy. Fourteen-percentage increase in azide content was found, after pre-treatment of GO with meta-chloroperoxybenzoic acid (mCPBA), determined with elemental analysis. No effect on A549 cell viability was found, up to 100 μg mL(-1) and 72 h of incubation, determined with the modified lactate dehydrogenase (mLDH) assay. Two sequential copper(i) catalysed azide-alkyne cycloaddition (CuAAC) reactions were performed to conjugate the propargyl-modified blood-brain barrier targeting peptide Angiopep-2, and a bis-azide polyethylene glycol (MW = 3500), to the Click(2) GO. The final conjugate was characterised with ATR-FTIR and TGA.",

author = "Kuo-Ching Mei and Noelia Rubio and {Coutinho Da Costa}, {Pedro Miguel} and Houmam Kafa and Vincenzo Abbate and Frederic Festy and Bansal, {Sukhvinder S} and Hider, {Robert C} and Al-Jamal, {Khuloud T}",

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doi = "10.1039/c5cc05412e",

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T1 - Synthesis of double-clickable functionalised graphene oxide for biological applications

AU - Mei, Kuo-Ching

AU - Rubio, Noelia

AU - Coutinho Da Costa, Pedro Miguel

AU - Kafa, Houmam

AU - Abbate, Vincenzo

AU - Festy, Frederic

AU - Bansal, Sukhvinder S

AU - Hider, Robert C

AU - Al-Jamal, Khuloud T

PY - 2015/8/7

Y1 - 2015/8/7

N2 - Azide- and alkyne-double functionalised graphene oxide (Click(2) GO) was synthesised and characterised with attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR), thermogravimetric analysis (TGA) and Raman spectroscopy. Fourteen-percentage increase in azide content was found, after pre-treatment of GO with meta-chloroperoxybenzoic acid (mCPBA), determined with elemental analysis. No effect on A549 cell viability was found, up to 100 μg mL(-1) and 72 h of incubation, determined with the modified lactate dehydrogenase (mLDH) assay. Two sequential copper(i) catalysed azide-alkyne cycloaddition (CuAAC) reactions were performed to conjugate the propargyl-modified blood-brain barrier targeting peptide Angiopep-2, and a bis-azide polyethylene glycol (MW = 3500), to the Click(2) GO. The final conjugate was characterised with ATR-FTIR and TGA.

AB - Azide- and alkyne-double functionalised graphene oxide (Click(2) GO) was synthesised and characterised with attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR), thermogravimetric analysis (TGA) and Raman spectroscopy. Fourteen-percentage increase in azide content was found, after pre-treatment of GO with meta-chloroperoxybenzoic acid (mCPBA), determined with elemental analysis. No effect on A549 cell viability was found, up to 100 μg mL(-1) and 72 h of incubation, determined with the modified lactate dehydrogenase (mLDH) assay. Two sequential copper(i) catalysed azide-alkyne cycloaddition (CuAAC) reactions were performed to conjugate the propargyl-modified blood-brain barrier targeting peptide Angiopep-2, and a bis-azide polyethylene glycol (MW = 3500), to the Click(2) GO. The final conjugate was characterised with ATR-FTIR and TGA.

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DO - 10.1039/c5cc05412e

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SP - 14981

EP - 14984

JO - Chemical communications (Cambridge, England)

JF - Chemical communications (Cambridge, England)

IS - 81

ER -

Synthesis of double-clickable functionalised graphene oxide for biological applications

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