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Supramolecular Complexation in Biological Media: NMR Study on Inclusion of an Anionic Tetraarylporphyrin into a Per‐O‐Methylated β‐Cyclodextrin Cavity in Serum,Blood, and Urine
Authors:Hiroaki Kitagishi  Mai Saito  Qiyue Mao  Akiko Kiriyama  Shigeru Negi  Koji Kano
Abstract:The supramolecular complexation of 5,10,15,20‐tetrakis(4‐sulfonatophenyl)porphyrin (TPPS) with heptakis(2,3,6‐tri‐O‐methyl)‐β‐cyclodextrin (TMCD) has been known to be highly specific in aqueous media. In this study, we have used NMR spectroscopy to reveal that this supramolecular system also works even in biologically crowded media such as serum, blood, and urine. A 13C‐labeled heptakis(2,3,6‐tri‐O‐methyl‐13C)‐β‐cyclodextrin (13C‐TMCD) was synthesized and studied using one‐dimensional (1D) HMQC spectroscopy in serum and blood. The 1D HMQC spectrum of 13C‐TMCD showed clear signals due to the 2‐, 3‐, and 6‐O13CH3 groups, whose chemical shifts changed upon addition of TPPS due to quantitative formation of the 13C‐TMCD/TPPS=2/1 inclusion complex in such biological media. The 1H NMR signals of non‐isotope‐labeled TPPS included by 13C‐TMCD were detected using the 13C‐filtered ROESY technique. A pharmacokinetic study of 13C‐TMCD and its complex with TPPS was carried out in mice using the 1D HMQC method. The results indicated that (1) 1D HMQC is an effective technique for monitoring the inclusion phenomena of 13C‐labeled cyclodextrin in biological media and (2) the intermolecular interaction between 13C‐TMCD and TPPS is highly selective even in contaminated media like blood, serum, and urine.
Keywords:biological media  cyclodextrin  NMR  porphyrin  supramolecular chemistry
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