A new Phenol Red-modified porphyrin as efficient protein photocleaving agent.
Protein affinity is of importance for porphyrins in their application in photodynamic therapy (PDT). A new Phenol Red-modified porphyrin (R-TPP) was designed and synthesized to fully take advantage of the binding character of Phenol Red towards protein. Detailed comparisons of absorption spectra, fluorescence spectra, n-octanol/water partition coefficients, (1)O(2) quantum yields, as well as protein photocleaving abilities between R-TPP and its parent porphyrin Br-TPP clearly demonstrate the benefits stemming from the modification of Phenol Red. On one hand, the presence of Phenol Red moiety greatly enhances the binding affinity of R-TPP towards model proteins (bovine serum albumin and hen egg lysozyme), and therefore improves the availability of (1)O(2). On the other hand, the presence of Phenol Red moiety provides R-TPP with amphiphilic character, and therefore restricts aggregation and favors the generation of (1)O(2). As a result, R-TPP photocleaves proteins efficiently, showing promising application potential in PDT.
Jiang
Guo-Yu
GY
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, PR China.
Lei
Wan-Hua
WH
Zhou
Qian-Xiong
QX
Hou
Yuan-Jun
YJ
Wang
Xue-Song
XS
Zhang
Bao-Wen
BW
D000818:Animals; D002417:Cattle; D002645:Chickens; D009113:Muramidase / Q000378:metabolism; D010637:Phenolsulfonphthalein / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010778:Photochemotherapy; D010782:Photolysis; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011485:Protein Binding; D011506:Proteins / Q000378:metabolism*; D012710:Serum Albumin, Bovine / Q000378:metabolism
D017319:Photosensitizing Agents; D011166:Porphyrins; D011506:Proteins; D012710:Serum Albumin, Bovine; D009113:Muramidase; D010637:Phenolsulfonphthalein