TY - JOUR
T1 - Colorimetric/fluorogenic detection of thiols by N-fused porphyrin in water
AU - Ikawa, Yoshiya
AU - Touden, Satoshi
AU - Katsumata, Sho
AU - Furuta, Hiroyuki
N1 - Funding Information:
This work was supported by Grants-in-Aid on Innovative Areas (No. 25104518 to Y.I. and 23108715 to H.F.), for Challenging Exploratory Research (No. 23655159 to Y.I.), and for Scientific Research (B) (No. 23310161 to Y.I.) from the Ministry of Education, Culture, Sports, Science and Technology of Japan.
PY - 2013/11/1
Y1 - 2013/11/1
N2 - 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.
AB - 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.
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U2 - 10.1016/j.bmc.2013.08.037
DO - 10.1016/j.bmc.2013.08.037
M3 - Article
C2 - 24051075
AN - SCOPUS:84885181889
SN - 0968-0896
VL - 21
SP - 6501
EP - 6505
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 21
ER -