A multifunctional β-cyclodextrin-conjugate photodelivering nitric oxide with fluorescence reporting

Gábor Benkovics, Marta Perez-Lloret, Damien Afonso, András Darcsi, S. Béni, Éva Fenyvesi, Milo Malanga, Salvatore Sortino

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

This contribution reports the design, synthesis and photochemical properties of a novel cationic, water soluble, β-cyclodextrin (βCD) conjugate integrating an anthracene moiety and a nitroaniline derivative within the primary side of the βCD scaffold. Photoinduced energy transfer between the anthracene and the nitroaniline chromophores effectively suppresses the fluorescence of the anthracene unit. Excitation with visible light triggers the release of nitric oxide (NO) from the nitroaniline chromophore, accompanied to the concomitant revival of the anthracene fluorescence, which acts as an optical reporter for detecting the amount of the NO released. Furthermore, the anthracene moiety photogenerates singlet oxygen (1O2) sequentially to NO release. The conjugate is also able to accommodate hydrophobic guests within the βCD cavity, as proven by using naphthalene as a model compound. In view of the key role NO and 1O2 play as anticancer and antibacterial species, the present βCD derivative represents an intriguing candidate for further studies in biopharmaceutical research addressed to multimodal therapeutic applications.

Original languageEnglish
Pages (from-to)614-620
Number of pages7
JournalInternational Journal of Pharmaceutics
Volume531
Issue number2
DOIs
Publication statusPublished - Oct 15 2017

Fingerprint

Cyclodextrins
Nitric Oxide
Fluorescence
Singlet Oxygen
Energy Transfer
anthracene
Light
Water
Research
nitroaniline

Keywords

  • Cyclodextrin
  • Fluorescence
  • Light
  • Nitric oxide
  • Singlet oxygen

ASJC Scopus subject areas

  • Pharmaceutical Science

Cite this

A multifunctional β-cyclodextrin-conjugate photodelivering nitric oxide with fluorescence reporting. / Benkovics, Gábor; Perez-Lloret, Marta; Afonso, Damien; Darcsi, András; Béni, S.; Fenyvesi, Éva; Malanga, Milo; Sortino, Salvatore.

In: International Journal of Pharmaceutics, Vol. 531, No. 2, 15.10.2017, p. 614-620.

Research output: Contribution to journalArticle

Benkovics, G, Perez-Lloret, M, Afonso, D, Darcsi, A, Béni, S, Fenyvesi, É, Malanga, M & Sortino, S 2017, 'A multifunctional β-cyclodextrin-conjugate photodelivering nitric oxide with fluorescence reporting', International Journal of Pharmaceutics, vol. 531, no. 2, pp. 614-620. https://doi.org/10.1016/j.ijpharm.2017.05.023
Benkovics, Gábor ; Perez-Lloret, Marta ; Afonso, Damien ; Darcsi, András ; Béni, S. ; Fenyvesi, Éva ; Malanga, Milo ; Sortino, Salvatore. / A multifunctional β-cyclodextrin-conjugate photodelivering nitric oxide with fluorescence reporting. In: International Journal of Pharmaceutics. 2017 ; Vol. 531, No. 2. pp. 614-620.
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