Computational modeling of curcumin-based fluorescent probe molecules

Vardhan Satalkar, Theo A. Rusmore, Elizabeth Phillips, Xiaoliang Pan, Enrico Benassi, Qin Wu, Chongzhao Ran, Yihan Shao

Research output: Contribution to journalArticle

Abstract

In recent years, a series of curcumin analogs have been designed as fluorescent probes for detecting and imaging A β 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.

Original languageEnglish
Article number29
JournalTheoretical Chemistry Accounts
Volume138
Issue number2
DOIs
Publication statusPublished - 1 Feb 2019

Fingerprint

Curcumin
Fluorescent Dyes
Molecules
Density functional theory
probes
Reactive Oxygen Species
Brain
brain
molecules
Wavelength
Oxalates
Molecular orbitals
analogs
density functional theory
oxygen
oxalates
Fluorescence
wavelengths
peptides
Imaging techniques

Keywords

  • Alzheimer’s disease
  • Fluorescence
  • TDDFT

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

Computational modeling of curcumin-based fluorescent probe molecules. / Satalkar, Vardhan; Rusmore, Theo A.; Phillips, Elizabeth; Pan, Xiaoliang; Benassi, Enrico; Wu, Qin; Ran, Chongzhao; Shao, Yihan.

In: Theoretical Chemistry Accounts, Vol. 138, No. 2, 29, 01.02.2019.

Research output: Contribution to journalArticle

Satalkar, V, Rusmore, TA, Phillips, E, Pan, X, Benassi, E, Wu, Q, Ran, C & Shao, Y 2019, 'Computational modeling of curcumin-based fluorescent probe molecules', Theoretical Chemistry Accounts, vol. 138, no. 2, 29. https://doi.org/10.1007/s00214-019-2415-4
Satalkar, Vardhan ; Rusmore, Theo A. ; Phillips, Elizabeth ; Pan, Xiaoliang ; Benassi, Enrico ; Wu, Qin ; Ran, Chongzhao ; Shao, Yihan. / Computational modeling of curcumin-based fluorescent probe molecules. In: Theoretical Chemistry Accounts. 2019 ; Vol. 138, No. 2.
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