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

Research output: Contribution to journalArticle

8 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)85-89
Number of pages5
JournalJournal of Electroanalytical Chemistry
Volume610
Issue number1
DOIs
Publication statusPublished - 2007 Nov 15

Fingerprint

Alkaloids
Fluorides
Anions
Negative ions
Fluorescence
Ions
Dimethyl sulfoxide
Quantum yield
Berberine
DNA
Substitution reactions
Nitrogen
Atoms
Dimethyl Sulfoxide
hydroxide ion

Keywords

  • Alkaloid
  • Anion
  • Berberine
  • Fluorescence enhancement
  • Fluoride
  • Palmatine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemical Engineering(all)
  • Electrochemistry

Cite this

Fluorescence enhancement for alkaloids by anions : Spectroscopic and electrochemical characterizations. / Chung, Yu Ling; Hong, Ruey Ding; Wu, Hsiao Wen; Hung, Wei Hsiu; Lai, Lee Jene; Wang, Chong Mou.

In: Journal of Electroanalytical Chemistry, Vol. 610, No. 1, 15.11.2007, p. 85-89.

Research output: Contribution to journalArticle

@article{c9dd1ca637ed4dbf94d0980c3bc044eb,
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}",
year = "2007",
month = "11",
day = "15",
doi = "10.1016/j.jelechem.2007.07.003",
language = "English",
volume = "610",
pages = "85--89",
journal = "Journal of Electroanalytical Chemistry",
issn = "1572-6657",
publisher = "Elsevier BV",
number = "1",

}

TY - JOUR

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

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

UR - http://www.scopus.com/inward/record.url?scp=35748977637&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=35748977637&partnerID=8YFLogxK

U2 - 10.1016/j.jelechem.2007.07.003

DO - 10.1016/j.jelechem.2007.07.003

M3 - Article

AN - SCOPUS:35748977637

VL - 610

SP - 85

EP - 89

JO - Journal of Electroanalytical Chemistry

JF - Journal of Electroanalytical Chemistry

SN - 1572-6657

IS - 1

ER -