Fluorescence enhancement for alkaloids by anions: Spectroscopic and electrochemical characterizations

Yu Ling Chung; Ruey Ding Hong; Hsiao Wen Wu; Wei Hsiu Hung; Lee Jene Lai; Chong Mou Wang

doi:10.1016/j.jelechem.2007.07.003

Fluorescence enhancement for alkaloids by anions: Spectroscopic and electrochemical characterizations

Yu Ling Chung, Ruey Ding Hong, Hsiao Wen Wu, Wei Hsiu Hung^*, Lee Jene Lai, Chong Mou Wang

^*Corresponding author for this work

Department of Chemistry

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

8 Citations (Scopus)

Abstract

Alkaloids such as palmatine and berberine are potential phototoxins, but they exhibit low quantum yields for fluorescence (Φ_F). We found that fluoride and hydroxide ions are promising promoters that enhance their values of Φ_F in aprotic and aqueous solutions. For example, an increase of Φ_F by a factor of 10² was observed when palmatine incorporated 40 equiv TBAF in dimethyl sulfoxide (DMSO). The cause of the enhancement in Φ_F was shown to be the interaction of fluoride and hydroxide ions with the quaternary nitrogen atoms contained in the target alkaloid. The effect of substitution of fluoride with other anions such as Cl^-, Br^-, I^-, PF₆^-, and ClO₄^- is insignificant. In aqueous media, the efficacy of fluoride and hydroxide ions was greatly reduced. Nevertheless, introducing DNA helped restore the effectiveness of fluoride in enhancing the value of Φ_F of alkaloids.

Original language	English
Pages (from-to)	85-89
Number of pages	5
Journal	Journal of Electroanalytical Chemistry
Volume	610
Issue number	1
DOIs	https://doi.org/10.1016/j.jelechem.2007.07.003
Publication status	Published - 2007 Nov 15

Keywords

Alkaloid
Anion
Berberine
Fluorescence enhancement
Fluoride
Palmatine

ASJC Scopus subject areas

Analytical Chemistry
General Chemical Engineering
Electrochemistry

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10.1016/j.jelechem.2007.07.003

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title = "Fluorescence enhancement for alkaloids by anions: Spectroscopic and electrochemical characterizations",

abstract = "Alkaloids such as palmatine and berberine are potential phototoxins, but they exhibit low quantum yields for fluorescence (ΦF). We found that fluoride and hydroxide ions are promising promoters that enhance their values of ΦF in aprotic and aqueous solutions. For example, an increase of ΦF by a factor of 102 was observed when palmatine incorporated 40 equiv TBAF in dimethyl sulfoxide (DMSO). The cause of the enhancement in ΦF was shown to be the interaction of fluoride and hydroxide ions with the quaternary nitrogen atoms contained in the target alkaloid. The effect of substitution of fluoride with other anions such as Cl-, Br-, I-, PF6-, and ClO4- is insignificant. In aqueous media, the efficacy of fluoride and hydroxide ions was greatly reduced. Nevertheless, introducing DNA helped restore the effectiveness of fluoride in enhancing the value of ΦF of alkaloids.",

keywords = "Alkaloid, Anion, Berberine, Fluorescence enhancement, Fluoride, Palmatine",

author = "Chung, {Yu Ling} and Hong, {Ruey Ding} and Wu, {Hsiao Wen} and Hung, {Wei Hsiu} and Lai, {Lee Jene} and Wang, {Chong Mou}",

note = "Funding Information: The National Science Council of Republic of China supported this work under grant number NSC 95-2113-M-003-015.",

year = "2007",

month = nov,

day = "15",

doi = "10.1016/j.jelechem.2007.07.003",

language = "English",

volume = "610",

pages = "85--89",

journal = "Journal of Electroanalytical Chemistry",

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T1 - Fluorescence enhancement for alkaloids by anions

T2 - Spectroscopic and electrochemical characterizations

AU - Chung, Yu Ling

AU - Hong, Ruey Ding

AU - Wu, Hsiao Wen

AU - Hung, Wei Hsiu

AU - Lai, Lee Jene

AU - Wang, Chong Mou

N1 - Funding Information: The National Science Council of Republic of China supported this work under grant number NSC 95-2113-M-003-015.

PY - 2007/11/15

Y1 - 2007/11/15

N2 - Alkaloids such as palmatine and berberine are potential phototoxins, but they exhibit low quantum yields for fluorescence (ΦF). We found that fluoride and hydroxide ions are promising promoters that enhance their values of ΦF in aprotic and aqueous solutions. For example, an increase of ΦF by a factor of 102 was observed when palmatine incorporated 40 equiv TBAF in dimethyl sulfoxide (DMSO). The cause of the enhancement in ΦF was shown to be the interaction of fluoride and hydroxide ions with the quaternary nitrogen atoms contained in the target alkaloid. The effect of substitution of fluoride with other anions such as Cl-, Br-, I-, PF6-, and ClO4- is insignificant. In aqueous media, the efficacy of fluoride and hydroxide ions was greatly reduced. Nevertheless, introducing DNA helped restore the effectiveness of fluoride in enhancing the value of ΦF of alkaloids.

AB - Alkaloids such as palmatine and berberine are potential phototoxins, but they exhibit low quantum yields for fluorescence (ΦF). We found that fluoride and hydroxide ions are promising promoters that enhance their values of ΦF in aprotic and aqueous solutions. For example, an increase of ΦF by a factor of 102 was observed when palmatine incorporated 40 equiv TBAF in dimethyl sulfoxide (DMSO). The cause of the enhancement in ΦF was shown to be the interaction of fluoride and hydroxide ions with the quaternary nitrogen atoms contained in the target alkaloid. The effect of substitution of fluoride with other anions such as Cl-, Br-, I-, PF6-, and ClO4- is insignificant. In aqueous media, the efficacy of fluoride and hydroxide ions was greatly reduced. Nevertheless, introducing DNA helped restore the effectiveness of fluoride in enhancing the value of ΦF of alkaloids.

KW - Alkaloid

KW - Anion

KW - Berberine

KW - Fluorescence enhancement

KW - Fluoride

KW - Palmatine

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JO - Journal of Electroanalytical Chemistry

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Fluorescence enhancement for alkaloids by anions: Spectroscopic and electrochemical characterizations

Abstract

Keywords

ASJC Scopus subject areas

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