The host-guest chemistry of proflavine with cucurbit[6,7,8]urils

Sharon Kemp, Nial J. Wheate, Frank H. Stootman, Janice R. Aldrich-Wright

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

The binding of the polyaromatic guest, 3,6-diaminoacridine (Proflavine) to cucurbit[n]uril (CB[n]) where n = 6, 7 and 8 has been studied by fluorescence spectrophotometry and binding constants determined using a least squares fitting method. Titration of CB[8] into a solution of Proflavine results in a 95% decrease in fluorescence up to a CB[8] to Proflavine ratio of 2:1. From the induced fluorescence spectra a binding constant of 1.9 times 107 M- 1 was determined. When Proflavine is titrated into a solution of CB[8] a similar binding constant is calculated (1.3 times 107 M- 1). Titration of CB[6] into a solution of Proflavine yields a decrease in fluorescence of 18-20%, but no binding is observed beyond what is seen within experimental error. Finally, titration of CB[7] into a solution of Proflavine results in an increase in fluorescence (32%) and a blue-shift of the emission wavelength from 509 nm to 485 nm. From the induced fluorescence spectra a binding constant of 1.65 times 107 M- 1 was determined. From 1H NMR it appears that the decrease in fluorescence for Proflavine with CB[6] and CB[8] is due to collisional quenching, whereas the increase in fluorescence with CB[7] may be due to rotational restriction.
LanguageEnglish
Pages475-484
Number of pages9
JournalSupramolecular Chemistry
Volume19
Issue number7
DOIs
Publication statusPublished - 2007

Fingerprint

Proflavine
Fluorescence
Titration
Spectrophotometry
Quenching
Nuclear magnetic resonance
Wavelength

Keywords

  • proflavine
  • DNA intercalator
  • cucurbituril
  • flourescence spectroscopy
  • binding constant
  • 1H NMR

Cite this

Kemp, S., Wheate, N. J., Stootman, F. H., & Aldrich-Wright, J. R. (2007). The host-guest chemistry of proflavine with cucurbit[6,7,8]urils. Supramolecular Chemistry, 19(7), 475-484. https://doi.org/10.1080/10610270601124019
Kemp, Sharon ; Wheate, Nial J. ; Stootman, Frank H. ; Aldrich-Wright, Janice R. / The host-guest chemistry of proflavine with cucurbit[6,7,8]urils. In: Supramolecular Chemistry. 2007 ; Vol. 19, No. 7. pp. 475-484.
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Kemp, S, Wheate, NJ, Stootman, FH & Aldrich-Wright, JR 2007, 'The host-guest chemistry of proflavine with cucurbit[6,7,8]urils' Supramolecular Chemistry, vol. 19, no. 7, pp. 475-484. https://doi.org/10.1080/10610270601124019

The host-guest chemistry of proflavine with cucurbit[6,7,8]urils. / Kemp, Sharon; Wheate, Nial J.; Stootman, Frank H.; Aldrich-Wright, Janice R.

In: Supramolecular Chemistry, Vol. 19, No. 7, 2007, p. 475-484.

Research output: Contribution to journalArticle

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T1 - The host-guest chemistry of proflavine with cucurbit[6,7,8]urils

AU - Kemp, Sharon

AU - Wheate, Nial J.

AU - Stootman, Frank H.

AU - Aldrich-Wright, Janice R.

PY - 2007

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N2 - The binding of the polyaromatic guest, 3,6-diaminoacridine (Proflavine) to cucurbit[n]uril (CB[n]) where n = 6, 7 and 8 has been studied by fluorescence spectrophotometry and binding constants determined using a least squares fitting method. Titration of CB[8] into a solution of Proflavine results in a 95% decrease in fluorescence up to a CB[8] to Proflavine ratio of 2:1. From the induced fluorescence spectra a binding constant of 1.9 times 107 M- 1 was determined. When Proflavine is titrated into a solution of CB[8] a similar binding constant is calculated (1.3 times 107 M- 1). Titration of CB[6] into a solution of Proflavine yields a decrease in fluorescence of 18-20%, but no binding is observed beyond what is seen within experimental error. Finally, titration of CB[7] into a solution of Proflavine results in an increase in fluorescence (32%) and a blue-shift of the emission wavelength from 509 nm to 485 nm. From the induced fluorescence spectra a binding constant of 1.65 times 107 M- 1 was determined. From 1H NMR it appears that the decrease in fluorescence for Proflavine with CB[6] and CB[8] is due to collisional quenching, whereas the increase in fluorescence with CB[7] may be due to rotational restriction.

AB - The binding of the polyaromatic guest, 3,6-diaminoacridine (Proflavine) to cucurbit[n]uril (CB[n]) where n = 6, 7 and 8 has been studied by fluorescence spectrophotometry and binding constants determined using a least squares fitting method. Titration of CB[8] into a solution of Proflavine results in a 95% decrease in fluorescence up to a CB[8] to Proflavine ratio of 2:1. From the induced fluorescence spectra a binding constant of 1.9 times 107 M- 1 was determined. When Proflavine is titrated into a solution of CB[8] a similar binding constant is calculated (1.3 times 107 M- 1). Titration of CB[6] into a solution of Proflavine yields a decrease in fluorescence of 18-20%, but no binding is observed beyond what is seen within experimental error. Finally, titration of CB[7] into a solution of Proflavine results in an increase in fluorescence (32%) and a blue-shift of the emission wavelength from 509 nm to 485 nm. From the induced fluorescence spectra a binding constant of 1.65 times 107 M- 1 was determined. From 1H NMR it appears that the decrease in fluorescence for Proflavine with CB[6] and CB[8] is due to collisional quenching, whereas the increase in fluorescence with CB[7] may be due to rotational restriction.

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KW - DNA intercalator

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KW - flourescence spectroscopy

KW - binding constant

KW - 1H NMR

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