1,8-Naphthalimide Derivative Dyes with Large Stokes Shifts for Targeting Live-Cell Mitochondria.
An ideal fluorescent dye for staining cell organelles should have multiple properties including specificity, stability, biocompatibility, and a large Stokes shift. Tunable photophysical properties enable 1,8-naphthalimide to serve as an excellent fluorophore in biomedical applications. Many naphthalimide derivatives have been developed into drugs, sensors, and other dyes. In this study, a series of 1,8-naphthalimide derivatives targeting live cell mitochondria were synthesized. Among these probes, Mt-4 was characterized as the best one, with highly specific mitochondrial localization, low cytotoxicity, and a large Stokes shift. More importantly, Mt-4 stood out as a potential mitochondrial dye for living-cell experiments involving induced mitochondrial stress arising from the treatments because Mt-4 shows enhanced fluorescence in mitochondrial stress situations.
Center for Biosignatures Discovery Automation, Biodesign Institute, Arizona State University, 1001 S. McAlister Ave., P. O. Box 876501, Tempe, AZ, 85287, USA.
Liqiang
L
Zhang
Center for Biosignatures Discovery Automation, Biodesign Institute, Arizona State University, 1001 S. McAlister Ave., P. O. Box 876501, Tempe, AZ, 85287, USA.
Fengyu
F
Su
Center for Biosignatures Discovery Automation, Biodesign Institute, Arizona State University, 1001 S. McAlister Ave., P. O. Box 876501, Tempe, AZ, 85287, USA.
Xiangxing
X
Kong
Center for Biosignatures Discovery Automation, Biodesign Institute, Arizona State University, 1001 S. McAlister Ave., P. O. Box 876501, Tempe, AZ, 85287, USA.
Fred
F
Lee
Center for Biosignatures Discovery Automation, Biodesign Institute, Arizona State University, 1001 S. McAlister Ave., P. O. Box 876501, Tempe, AZ, 85287, USA.
Steven
S
Sher
Center for Biosignatures Discovery Automation, Biodesign Institute, Arizona State University, 1001 S. McAlister Ave., P. O. Box 876501, Tempe, AZ, 85287, USA.
Kevin
K
Day
Center for Biosignatures Discovery Automation, Biodesign Institute, Arizona State University, 1001 S. McAlister Ave., P. O. Box 876501, Tempe, AZ, 85287, USA. tianyq@sustc.edu.cn.|Department of Materials Science and Engineering, South University of Science and Technology of China, 1088, Xueyuan Rd., Xili, Nanshan District, Shenzhen, Guangdong, 518055, P. R. China. tianyq@sustc.edu.cn.
Yanqing
Y
Tian
Center for Biosignatures Discovery Automation, Biodesign Institute, Arizona State University, 1001 S. McAlister Ave., P. O. Box 876501, Tempe, AZ, 85287, USA. deirdre.meldrum@asu.edu.
Deirdre R
DR
Meldrum
D002470:Cell Survival; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D008928:Mitochondria / Q000378:metabolism*; D015394:Molecular Structure; D053644:Naphthalimides / Q000737:chemistry*
D005456:Fluorescent Dyes; D053644:Naphthalimides
Stokes shifts; fluorescent probes; imaging agents; mitochondria; naphthalimide; single live cells