Synthesis and EPR-spectroscopic characterization of the perchlorotriarylmethyl tricarboxylic acid radical (PTMTC) and its13C labelled analogue (13C-PTMTC)

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2017
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Elewa, Marwa
Maltar-Strmečki, Nadica
Said, Mohamed M.
El Shihawy, Hosam A.
El-Sadek, Mohamed
Frank, Juliane
Drescher, Simon
Mäder, Karsten
Hinderberger, Dariush
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10.1039/c6cp07200c
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Physical chemistry chemical physics : PCCP ; 19 (2017), 9. - pp. 6688-6697. - ISSN 1463-9076. - eISSN 1463-9084
Abstract
A hydrophilic tris(tetrachlorotriaryl)methyl (tetrachloro-TAM) radical labelled 50% with13C at the central carbon atom was prepared. The mixture of isotopologue radicals was characterised by continuous wave and pulsed X-band electron paramagnetic spectroscopy (EPS). For the pharmaceutical and medical applications planned, the quantitative influence of oxygen, viscosity, temperature and pH on EPR line widths was studied in aqueous buffer, DMSO, water-methanol and water-glycerol mixtures. Under in vivo conditions, pH can be disregarded. There is a clear oxygen dependence of the width of the12C isotopologue single EPR line in aqueous solutions while changes in rotational motion (viscosity) are observable only in the doublet lines of the central carbon of the13C isotopologue. The tetrachloro-TAM proved to be very stable as a solid. Its thermal decay was determined quantitatively by thermal annealing. Towards ascorbic acid as a reducing agent and towards an oocyte cell extract it had a half-life of approx. 60 and 10 min. Thus for in vivo applications, 50%13C tetrachloro-TAMs are suitable for selective and simultaneous oxygen and macroviscosity measurements in a formulation, e.g. nanocapsules.
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ISO 690ELEWA, Marwa, Nadica MALTAR-STRMEČKI, Mohamed M. SAID, Hosam A. EL SHIHAWY, Mohamed EL-SADEK, Juliane FRANK, Simon DRESCHER, Malte DRESCHER, Karsten MÄDER, Dariush HINDERBERGER, 2017. Synthesis and EPR-spectroscopic characterization of the perchlorotriarylmethyl tricarboxylic acid radical (PTMTC) and its13C labelled analogue (13C-PTMTC). In: Physical chemistry chemical physics : PCCP. 19(9), pp. 6688-6697. ISSN 1463-9076. eISSN 1463-9084. Available under: doi: 10.1039/c6cp07200c
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@article{Elewa2017Synth-41744,
  year={2017},
  doi={10.1039/c6cp07200c},
  title={Synthesis and EPR-spectroscopic characterization of the perchlorotriarylmethyl tricarboxylic acid radical (PTMTC) and its<sup>13</sup>C labelled analogue (<sup>13</sup>C-PTMTC)},
  number={9},
  volume={19},
  issn={1463-9076},
  journal={Physical chemistry chemical physics : PCCP},
  pages={6688--6697},
  author={Elewa, Marwa and Maltar-Strmečki, Nadica and Said, Mohamed M. and El Shihawy, Hosam A. and El-Sadek, Mohamed and Frank, Juliane and Drescher, Simon and Drescher, Malte and Mäder, Karsten and Hinderberger, Dariush}
}
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