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Title: Computational modeling of curcumin-based fluorescent probe molecules

Abstract

In recent years, a series of curcumin analogs have been designed as fluorescent probes for detecting and imaging Aβ 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. Altogether, this study reaffirms the value of employing TDDFT calculations to assist the design of new curcumin-based fluorescence probes for AD research.

Authors:
 [1];  [1];  [1];  [1];  [2]; ORCiD logo [3];  [4]; ORCiD logo [1]
  1. Univ. of Oklahoma, Norman, OK (United States)
  2. Nazarbayev Univ., Astana (Kazakhstan); Novosibirsk State Univ., Novosibirsk (Russia)
  3. Brookhaven National Lab. (BNL), Upton, NY (United States)
  4. Massachusetts General Hospital and Harvard Medical School, Boston, MA (United States)
Publication Date:
Research Org.:
Brookhaven National Lab. (BNL), Upton, NY (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1496576
Report Number(s):
BNL-211293-2019-JAAM
Journal ID: ISSN 1432-881X
Grant/Contract Number:  
SC0012704
Resource Type:
Accepted Manuscript
Journal Name:
Theoretical Chemistry Accounts
Additional Journal Information:
Journal Volume: 138; Journal Issue: 2; Journal ID: ISSN 1432-881X
Publisher:
Springer
Country of Publication:
United States
Language:
English
Subject:
77 NANOSCIENCE AND NANOTECHNOLOGY; Fluorescence; Alzheimer’s disease; TDDFT

Citation Formats

Satalkar, Vardhan, Rusmore, Theo A., Phillips, Elizabeth, Pan, Xiaoliang, Benassi, Enrico, Wu, Qin, Ran, Chongzhao, and Shao, Yihan. Computational modeling of curcumin-based fluorescent probe molecules. United States: N. p., 2019. Web. doi: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. United States. doi:10.1007/s00214-019-2415-4.
Satalkar, Vardhan, Rusmore, Theo A., Phillips, Elizabeth, Pan, Xiaoliang, Benassi, Enrico, Wu, Qin, Ran, Chongzhao, and Shao, Yihan. Wed . "Computational modeling of curcumin-based fluorescent probe molecules". United States. doi:10.1007/s00214-019-2415-4. https://www.osti.gov/servlets/purl/1496576.
@article{osti_1496576,
title = {Computational modeling of curcumin-based fluorescent probe molecules},
author = {Satalkar, Vardhan and Rusmore, Theo A. and Phillips, Elizabeth and Pan, Xiaoliang and Benassi, Enrico and Wu, Qin and Ran, Chongzhao and Shao, Yihan},
abstractNote = {In recent years, a series of curcumin analogs have been designed as fluorescent probes for detecting and imaging Aβ 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. Altogether, this study reaffirms the value of employing TDDFT calculations to assist the design of new curcumin-based fluorescence probes for AD research.},
doi = {10.1007/s00214-019-2415-4},
journal = {Theoretical Chemistry Accounts},
number = 2,
volume = 138,
place = {United States},
year = {2019},
month = {1}
}

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