Reversible low-light induced photoswitching of crowned spiropyran-DO3A complexed with gadolinium(III) ions

Klaus Kruttwig, Diego R. Yankelevich, Chantal Brueggemann, Chuqiao Tu, Noelle L'Etoile, André Knoesen, Angelique Y. Louie

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Photoswitchable spiropyran has been conjugated to the crowned ring system DO3A, which improves its solubility in dipolar and polar media and stabilizes the merocyanine isomer. Adding the lanthanide ion gadolinium(III) to the macrocyclic ring system leads to a photoresponsive magnetic resonance imaging contrast agent that displays an increased spin-lattice relaxation time (T 1) upon visible light stimulation. In this work, the photoresponse of this photochromic molecule to weak light illumination using blue and green light emitting diodes was investigated, simulating the emission spectra from bioluminescent enzymes. Photon emission rate of the light emitting diodes was changed, from 1.75 × 10 16 photons·s -1 to 2.37 × 10 12 photons·s -1. We observed a consistent visible light-induced isomerization of the merocyanine to the spiropyran form with photon fluxes as low as 2.37 × 1012 photons·s-1 resulting in a relaxivity change of the compound. This demonstrates the potential for use of the described imaging probes in low light level applications such as sensing bioluminescence enzyme activity. The isomerization behavior of gadolinium(III)-ion complexed and non-complexed spiropyran-DO3A was analyzed in water and ethanol solution in response to low light illumination and compared to the emitted photon emission rate from over-expressed Gaussia princeps luciferase.

Original languageEnglish (US)
Pages (from-to)6605-6624
Number of pages20
JournalMolecules
Volume17
Issue number6
DOIs
StatePublished - Jun 2012

Fingerprint

Gadolinium
gadolinium
Ions
Light
Photons
Isomerization
ions
isomerization
Light emitting diodes
Lighting
photons
light emitting diodes
illumination
Bioluminescence
bioluminescence
Imaging techniques
Lanthanoid Series Elements
enzyme activity
Spin-lattice relaxation
rings

Keywords

  • DO3A
  • Light emitting diodes
  • Low light applications
  • Luciferase
  • MRI contrast agent
  • Photochromic molecule
  • Rate constant
  • Spiropyran

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

Kruttwig, K., Yankelevich, D. R., Brueggemann, C., Tu, C., L'Etoile, N., Knoesen, A., & Louie, A. Y. (2012). Reversible low-light induced photoswitching of crowned spiropyran-DO3A complexed with gadolinium(III) ions. Molecules, 17(6), 6605-6624. https://doi.org/10.3390/molecules17066625

Reversible low-light induced photoswitching of crowned spiropyran-DO3A complexed with gadolinium(III) ions. / Kruttwig, Klaus; Yankelevich, Diego R.; Brueggemann, Chantal; Tu, Chuqiao; L'Etoile, Noelle; Knoesen, André; Louie, Angelique Y.

In: Molecules, Vol. 17, No. 6, 06.2012, p. 6605-6624.

Research output: Contribution to journalArticle

Kruttwig, K, Yankelevich, DR, Brueggemann, C, Tu, C, L'Etoile, N, Knoesen, A & Louie, AY 2012, 'Reversible low-light induced photoswitching of crowned spiropyran-DO3A complexed with gadolinium(III) ions', Molecules, vol. 17, no. 6, pp. 6605-6624. https://doi.org/10.3390/molecules17066625
Kruttwig K, Yankelevich DR, Brueggemann C, Tu C, L'Etoile N, Knoesen A et al. Reversible low-light induced photoswitching of crowned spiropyran-DO3A complexed with gadolinium(III) ions. Molecules. 2012 Jun;17(6):6605-6624. https://doi.org/10.3390/molecules17066625
Kruttwig, Klaus ; Yankelevich, Diego R. ; Brueggemann, Chantal ; Tu, Chuqiao ; L'Etoile, Noelle ; Knoesen, André ; Louie, Angelique Y. / Reversible low-light induced photoswitching of crowned spiropyran-DO3A complexed with gadolinium(III) ions. In: Molecules. 2012 ; Vol. 17, No. 6. pp. 6605-6624.
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