Selective fluorescence turn-off detection of lysine by a curcumin derivative with real sample analysis

Raja Lavanya; Selvam Poovarasan; Venkatesan Srinivasadesikan; Ming chang Lin; Vediappen Padmini

doi:10.1016/j.jphotochem.2023.115008

Selective fluorescence turn-off detection of lysine by a curcumin derivative with real sample analysis

Raja Lavanya, Selvam Poovarasan, Venkatesan Srinivasadesikan, Ming chang Lin, Vediappen Padmini^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

A curcumin-based fluorescence sensor DPT [(2Z,4E,6E)-7-(4-(dimethylamino)phenyl)-3-hydroxy-1-phenylhepta-2,4,6-trien-1-one] was synthesized by a simple synthetic method. The DPT fluorescence sensor selectively detects lysine (Lys) in the presence of other amino acids and metal ions. The lower detection limit of DPT in 94 nM and the binding constant in 5.6 × 10⁷ M⁻¹ in DMSO/H₂O (1:9) medium. The binding mechanism involves intramolecular charge transfer (ICT) as confirmed by DFT studies. In addition, DPT and lysine show 1:1 binding stoichiometry. The interaction has been confirmed with ¹H NMR. Lysine has been detected in blood and urine samples using real sample analysis.

Original language	English
Article number	115008
Journal	Journal of Photochemistry and Photobiology A: Chemistry
Volume	444
DOIs	https://doi.org/10.1016/j.jphotochem.2023.115008
State	Published - 1 Oct 2023

Keywords

Curcumin
DFT studies and real samples
Fluorescence sensor
ICT
Lysine

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10.1016/j.jphotochem.2023.115008

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title = "Selective fluorescence turn-off detection of lysine by a curcumin derivative with real sample analysis",

abstract = "A curcumin-based fluorescence sensor DPT [(2Z,4E,6E)-7-(4-(dimethylamino)phenyl)-3-hydroxy-1-phenylhepta-2,4,6-trien-1-one] was synthesized by a simple synthetic method. The DPT fluorescence sensor selectively detects lysine (Lys) in the presence of other amino acids and metal ions. The lower detection limit of DPT in 94 nM and the binding constant in 5.6 × 107 M−1 in DMSO/H2O (1:9) medium. The binding mechanism involves intramolecular charge transfer (ICT) as confirmed by DFT studies. In addition, DPT and lysine show 1:1 binding stoichiometry. The interaction has been confirmed with 1H NMR. Lysine has been detected in blood and urine samples using real sample analysis.",

keywords = "Curcumin, DFT studies and real samples, Fluorescence sensor, ICT, Lysine",

author = "Raja Lavanya and Selvam Poovarasan and Venkatesan Srinivasadesikan and Lin, {Ming chang} and Vediappen Padmini",

note = "Publisher Copyright: {\textcopyright} 2023 Elsevier B.V.",

year = "2023",

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doi = "10.1016/j.jphotochem.2023.115008",

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T1 - Selective fluorescence turn-off detection of lysine by a curcumin derivative with real sample analysis

AU - Lavanya, Raja

AU - Poovarasan, Selvam

AU - Srinivasadesikan, Venkatesan

AU - Lin, Ming chang

AU - Padmini, Vediappen

PY - 2023/10/1

Y1 - 2023/10/1

N2 - A curcumin-based fluorescence sensor DPT [(2Z,4E,6E)-7-(4-(dimethylamino)phenyl)-3-hydroxy-1-phenylhepta-2,4,6-trien-1-one] was synthesized by a simple synthetic method. The DPT fluorescence sensor selectively detects lysine (Lys) in the presence of other amino acids and metal ions. The lower detection limit of DPT in 94 nM and the binding constant in 5.6 × 107 M−1 in DMSO/H2O (1:9) medium. The binding mechanism involves intramolecular charge transfer (ICT) as confirmed by DFT studies. In addition, DPT and lysine show 1:1 binding stoichiometry. The interaction has been confirmed with 1H NMR. Lysine has been detected in blood and urine samples using real sample analysis.

AB - A curcumin-based fluorescence sensor DPT [(2Z,4E,6E)-7-(4-(dimethylamino)phenyl)-3-hydroxy-1-phenylhepta-2,4,6-trien-1-one] was synthesized by a simple synthetic method. The DPT fluorescence sensor selectively detects lysine (Lys) in the presence of other amino acids and metal ions. The lower detection limit of DPT in 94 nM and the binding constant in 5.6 × 107 M−1 in DMSO/H2O (1:9) medium. The binding mechanism involves intramolecular charge transfer (ICT) as confirmed by DFT studies. In addition, DPT and lysine show 1:1 binding stoichiometry. The interaction has been confirmed with 1H NMR. Lysine has been detected in blood and urine samples using real sample analysis.

KW - Curcumin

KW - DFT studies and real samples

KW - Fluorescence sensor

KW - ICT

KW - Lysine

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U2 - 10.1016/j.jphotochem.2023.115008

DO - 10.1016/j.jphotochem.2023.115008

M3 - Article

AN - SCOPUS:85172177644

SN - 1010-6030

VL - 444

JO - Journal of Photochemistry and Photobiology A: Chemistry

JF - Journal of Photochemistry and Photobiology A: Chemistry

M1 - 115008

ER -

Selective fluorescence turn-off detection of lysine by a curcumin derivative with real sample analysis

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Keywords

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