Colorimetric/fluorogenic detection of thiols by N-fused porphyrin in water.
A water-soluble derivative of N-fused porphyrin (NFP) possessing four cationic side-arms (pPyNFP) serves as a unique class of colorimetric/fluorogenic reporters that selectively react with biothiols in aquaous media to afford N-confused porphyrin (NCP) derivatives, while other nucleophilic amino acids were inert under a wide range of pH conditions. Owing to the large difference of the optical properties between NCP and NFP, the transformation enabled selective detection of biothiols in colorimetric/fluorogenic manner, especially in the near-infrared region. To the best our knowledge, this is the first example of porphyrin-based thiol detection systems that use the direct attack of thiol group on the optical reporter.
Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 819-0395, Japan; Center for Molecular Systems (CMS), Kyushu University, Fukuoka 819-0395, Japan; Synthetic Systems Biology Research Center, Kyushu University, Fukuoka 812-8582, Japan.
Yoshiya
Y
Ikawa
Satoshi
S
Touden
Sho
S
Katsumata
Hiroyuki
H
Furuta
D005456:Fluorescent Dyes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D011166:Porphyrins / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013438:Sulfhydryl Compounds / Q000032:analysis*; D014867:Water / Q000737:chemistry*
D005456:Fluorescent Dyes; D011166:Porphyrins; D013438:Sulfhydryl Compounds; D014867:Water
Biothiol; Cysteine; Glutathione; Homocysteine; N-confused porphyrin; N-fused porphyrin; Near-infrared