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

doi:10.1007/s00214-019-2415-4

Title: Computational modeling of curcumin-based fluorescent probe molecules

Journal Article · 23 January 2019 · Theoretical Chemistry Accounts

DOI: https://doi.org/10.1007/s00214-019-2415-4 · OSTI ID:1496576

Satalkar, Vardhan ^[1]; Rusmore, Theo A. ^[1]; Phillips, Elizabeth ^[1]; Pan, Xiaoliang ^[1]; Benassi, Enrico ^[2];

^[3]; Ran, Chongzhao ^[4];

^[1]

Univ. of Oklahoma, Norman, OK (United States)
Nazarbayev Univ., Astana (Kazakhstan); Novosibirsk State Univ., Novosibirsk (Russia)
Brookhaven National Lab. (BNL), Upton, NY (United States)
Massachusetts General Hospital and Harvard Medical School, Boston, MA (United States)

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.

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Research Organization:: Brookhaven National Laboratory (BNL), Upton, NY (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: SC0012704

OSTI ID:: 1496576

Report Number(s):: BNL--211293-2019-JAAM

Journal Information:: Theoretical Chemistry Accounts, Journal Name: Theoretical Chemistry Accounts Journal Issue: 2 Vol. 138; ISSN 1432-881X

Publisher:: SpringerCopyright Statement

Country of Publication:: United States

Language:: English

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