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Functionalization of carboxylated multiwall nanotubes with imidazole derivatives and their toxicity investigations.

Azizian J, Tahermansouri H, Biazar E, Heidari S, Khoei DC - Int J Nanomedicine (2010)

Bottom Line: Imidazoles and their derivatives are compounds with chemotherapeutic applications.These functionalizations were chosen due to -NH(2) and NHCO active sites in MWNT-amide for future application.Cellular results did not show any toxicity change in modified samples from that of the reference samples.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Science and Research branch, Islamic Azad University, Ponak, Tehran, Iran. j-azizian@cc.sbu.ac.ir

ABSTRACT
Imidazoles and their derivatives are compounds with chemotherapeutic applications. In this study, we investigated the chemical functionalization of carboxylated multiwalled carbon nanotubes (MWNT-COOH) by 1,2-phenylendiamine. Multiwalled nanotube (MWNT)-benzimidazole was obtained by an MWNT-amide reaction with POCl(3) after 72 hours, which was confirmed by Fourier transform infrared, scanning electron microscopy, thermal gravimetric analysis, and elemental analysis. These functionalizations were chosen due to -NH(2) and NHCO active sites in MWNT-amide for future application. Toxicity assays with fibroblast cells and MTT test for measurement of viable cell numbers were also performed. Cellular results did not show any toxicity change in modified samples from that of the reference samples.

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Fourier transform spectra (after baseline correction) of functionalized carbon nanotubes. 1. carboxylated multiwalled carbon nanotubes, 2. multiwalled amide nanotubes, and 3. multiwalled benzimidazole nanotubes.
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f2-ijn-5-907: Fourier transform spectra (after baseline correction) of functionalized carbon nanotubes. 1. carboxylated multiwalled carbon nanotubes, 2. multiwalled amide nanotubes, and 3. multiwalled benzimidazole nanotubes.

Mentions: Figure 2 shows the FT-IR spectrum of the modified MWNTs. In spectrum 1, the band at around 1550 cm corresponds to the stretching mode of the C = C double bond that forms the framework of the carbon nanotube sidewall.24,25 The peak at 1730 and 1045 cm apparently corresponds to the stretching modes of the carboxylic acid groups.26 The two bands at 2800–2950 cm which are seen in all spectra are attributed to CH stretching of MWNT–COOH defects. In spectrum 2, the new strong peaks at 3200–3500 can be assigned to the N-H, NH2, and OH stretching modes. The carbonyl peak in the spectrum 2 shift to 1654 cm (as compared with 1730 cm in spectrum 1) is a result of amide C ( = O) NH linkage formation. The other peak at around 1610 cm can be assigned to the NH2 scissoring mode27 in 2 that over-laps with the C = C mode. The peaks at around 1520–1590, 1400–1480, 1200–1350, and 1100 cm correspond to C = C stretching nanotubes, aromatic ring modes, and C-N and C-O stretching modes, respectively. In spectra 3, the peaks of the amide group disappear and three peaks at around 1580, 620, and 1150 cm appear which can be assigned to imidazole ring stretching.28 The two peaks at 1710 and 1700 cm in spectra 2 and 3, respectively, can be related to residual carboxylic acids on the nanotube. Thus, FT-IR spectra confirmed that MWNT–COOH had been successfully modified by an aromatic amine.


Functionalization of carboxylated multiwall nanotubes with imidazole derivatives and their toxicity investigations.

Azizian J, Tahermansouri H, Biazar E, Heidari S, Khoei DC - Int J Nanomedicine (2010)

Fourier transform spectra (after baseline correction) of functionalized carbon nanotubes. 1. carboxylated multiwalled carbon nanotubes, 2. multiwalled amide nanotubes, and 3. multiwalled benzimidazole nanotubes.
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC2990384&req=5

f2-ijn-5-907: Fourier transform spectra (after baseline correction) of functionalized carbon nanotubes. 1. carboxylated multiwalled carbon nanotubes, 2. multiwalled amide nanotubes, and 3. multiwalled benzimidazole nanotubes.
Mentions: Figure 2 shows the FT-IR spectrum of the modified MWNTs. In spectrum 1, the band at around 1550 cm corresponds to the stretching mode of the C = C double bond that forms the framework of the carbon nanotube sidewall.24,25 The peak at 1730 and 1045 cm apparently corresponds to the stretching modes of the carboxylic acid groups.26 The two bands at 2800–2950 cm which are seen in all spectra are attributed to CH stretching of MWNT–COOH defects. In spectrum 2, the new strong peaks at 3200–3500 can be assigned to the N-H, NH2, and OH stretching modes. The carbonyl peak in the spectrum 2 shift to 1654 cm (as compared with 1730 cm in spectrum 1) is a result of amide C ( = O) NH linkage formation. The other peak at around 1610 cm can be assigned to the NH2 scissoring mode27 in 2 that over-laps with the C = C mode. The peaks at around 1520–1590, 1400–1480, 1200–1350, and 1100 cm correspond to C = C stretching nanotubes, aromatic ring modes, and C-N and C-O stretching modes, respectively. In spectra 3, the peaks of the amide group disappear and three peaks at around 1580, 620, and 1150 cm appear which can be assigned to imidazole ring stretching.28 The two peaks at 1710 and 1700 cm in spectra 2 and 3, respectively, can be related to residual carboxylic acids on the nanotube. Thus, FT-IR spectra confirmed that MWNT–COOH had been successfully modified by an aromatic amine.

Bottom Line: Imidazoles and their derivatives are compounds with chemotherapeutic applications.These functionalizations were chosen due to -NH(2) and NHCO active sites in MWNT-amide for future application.Cellular results did not show any toxicity change in modified samples from that of the reference samples.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Science and Research branch, Islamic Azad University, Ponak, Tehran, Iran. j-azizian@cc.sbu.ac.ir

ABSTRACT
Imidazoles and their derivatives are compounds with chemotherapeutic applications. In this study, we investigated the chemical functionalization of carboxylated multiwalled carbon nanotubes (MWNT-COOH) by 1,2-phenylendiamine. Multiwalled nanotube (MWNT)-benzimidazole was obtained by an MWNT-amide reaction with POCl(3) after 72 hours, which was confirmed by Fourier transform infrared, scanning electron microscopy, thermal gravimetric analysis, and elemental analysis. These functionalizations were chosen due to -NH(2) and NHCO active sites in MWNT-amide for future application. Toxicity assays with fibroblast cells and MTT test for measurement of viable cell numbers were also performed. Cellular results did not show any toxicity change in modified samples from that of the reference samples.

Show MeSH
Related in: MedlinePlus