Computational modeling of curcumin-based fluorescent probe molecules

  • Vardhan Satalkar
  • Theo A. Rusmore
  • Elizabeth Phillips
  • Xiaoliang Pan
  • Enrico Benassi
  • Qin Wu
  • Chongzhao RanEmail author
  • Yihan ShaoEmail author
Regular Article


In recent years, a series of curcumin analogs have been designed as fluorescent probes for detecting and imaging \({\text {A}}\beta\) peptide aggregates and reactive oxygen species (ROS) in Alzheimer’s disease (AD) brains. In order to gain a better understanding of the photophysical properties of these probe molecules, a systematical computational investigation was performed using the time-dependent density functional theory (TDDFT) calculations. Computed absorption and emission wavelengths well reproduced the spectral shifts among the curcumin analogs. In particular, for a recently proposed pair of probe molecules, CRANAD-5 and CRANAD-61, for sensing ROS in preclinical studies of AD brains, their emission wavelength difference was found to arise from a delocalization of the lowest unoccupied molecular orbital of CRANAD-61 from the curcuminoid backbone to the oxalate moiety. Overall, this study reaffirms the value of employing TDDFT calculations to assist the design of new curcumin-based fluorescence probes for AD research.


Fluorescence Alzheimer’s disease TDDFT 



Y.S. acknowledges financial support from Department of Energy Grant No. DE-SC0011297 and from the University of Oklahoma start-up fund. C.R. is supported by NIH Grant No. R01AG055413. Y.S. greatly appreciates insightful comments from Dr. Roland Lindh. Computational resources and services used in this work were provided by the OU Supercomputing Center for Education and Research (OSCER) and the Center of Functional Nanomaterials (CFN). CFN is a U.S. DOE Office of Science Facility, at the Brookhaven National Laboratory under Contract No. DE-SC0012704.

Supplementary material

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© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of Chemistry and BiochemistryUniversity of OklahomaNormanUSA
  2. 2.Stephenson School of Biomedical EngineeringUniversity of OklahomaNormanUSA
  3. 3.School of Science and TechnologyNazarbayev UniversityAstanaKazakhstan
  4. 4.Novosibirsk State UniversityNovosibirskRussia
  5. 5.Center for Functional NanomaterialsBrookhaven National LaboratoryUptonUSA
  6. 6.Molecular Imaging Laboratory, Athinoula A. Martinos Center for Biomedical ImagingMassachusetts General Hospital and Harvard Medical SchoolBostonUSA

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