Indocyanine green MS/MS investigations using femtosecond laser-pulse photodissociation and collision-induced dissociation

Abstract

The dissociation reactions of indocyanine green (also known as cardiogreen) have been studied in a Fourier-transform ion-cyclotron resonance mass spectrometer by the application of unimolecular, collision-induced dissociation and photodissociation using femtosecond laser pulses. Ions were prepared by electrospray ionization (ESI) in various solvents. Depending on the properties of the solvent mixture, the mono sodiated molecule could be measured through cation exchange in various compositions. Using a mixture of methanol/water/formic acid as solvent, protonated ions, formed by exchange of sodium, are predominantly observed. A mixture of isopropanol/formic acid leads to the addition of a further sodium cation to the molecule yielding an intense bi-sodiated ion signal. The photodissociation of the stored ions was achieved using pulses at a wavelength of 790 nm and approximately 150 fs pulse duration. The results show that only fs-photodissociation leads to the fragmentation of the different molecular structures, while in case of sodiated indocyanine green collision induced dissociation fails completely to observe any fragments. In all other investigated ion structures, the collision-induced-dissociation spectra show unspecified and little intense spectra. It is shown that fs-photodissociation mass spectrometry is the only method that leads to substance specific fragmentation for this sample. Furthermore, indocyanine green is known to form aggregation products. In the ion-cyclotron resonance experiment, the reactions of a dimeric cluster were also investigated. The necessary condition and the interference of the fragmentations with those of the monomer are discussed.

Keywords

Indocyanine green cardiogreen photodissociation collision-induced dissociation Fourier-transform ion cyclotron resonance mass spectrometry

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References

Brodbelt

. Photodissociation mass spectrometry: new tools for characterization of biological molecules. Chem Soc Rev 2014; 43: 2757–2783. DOI: 10.1039/C3CS60444F.

Johnson

Carlson

. Collision-induced dissociation mass spectrometry: a powerful tool for natural product structure elucidation. Anal Chem 2015; 87: 10668–10678. DOI: 10.1021/acs.analchem.5b01543.

Laskin

Futrell

. Activation of large ions in FT-ICR mass spectrometry. Mass Spectrom Rev 2005; 24: 135–167. DOI:10.1002/mas.20012.

Julian

. Ultraviolet photodissociation: developments towards applications for mass-spectrometry-based proteomics. Angewandte Chemie 2009; 48: 7130–7137. DOI: 10.1002/anie.200900613.

Gross

. Mass spectrometry: a textbook, Berlin Heidelberg: Springer-Verlag, 2011. ISBN: 978-3-642-42346-8, DOI: 10.1007/978-3-642-10711-5.

Peters

Grotemeyer

. Fragmentation of xanthene dyes by laser activation and collision-induced dissociatioon a high-resolution Fourier transform ion cyclotron resonance mass spectrometer. Rapid Commun MassSpectrom 2011; 25: 1169–1172. DOI:10.1002/rcm.4972.

Gernert

Grotemeyer

. Photodissociation at various wavelengths: fragmentation studies of oxazine 170 using nanosecond laser pulses. Eur J Mass Spectrom 2015; 21: 599–608. DOI: 10.1255/ejms.1368.

Peters

Clemen

Grotemeyer

. Fragmentation of deuterated rhodamine B derivates by laser and collisional activation in an FT-ICR mass spectrometer. Anal Bioanal Chem 2013; 405: 7061–7069. DOI: 10.1007/s00216-013-7078-8.

Clemen

Gernert

Peters

et al.

Fragmentation reactions of labeled and unlabeled rhodamine B in a high resolution Fourier transform ion cyclotron resonance mass spectrometer. Eur J Mass Spectrom 2013; 19: 135–139. DOI: 10.1255/ejms.1216.

10.

Alander

Kaartinen

Laakso

et al.

A review of indocyanine green fluorescent imaging in surgery. Int J Biomed Imag 2012, pp. 940585. DOI:10.1155/2012/940585.

11.

Lauterburg

Sautter

Preisig

et al.

Hepatic functional deterioration after portacaval shunt in the rat. Gastroenterology 1976; 71: 221–227. DOI: 10.1016/S0016-5085(76)80191-6.

12.

Martisiene

Macianskiene

Treinys

et al.

Voltage-sensitive fluorescence of indocyanine green in the heart. Biophys J 2016; 110: 723–732. DOI: 10.1016/j.bpj/2015.12.021.

13.

McNally

Gillings

BRD

Dawes

. Dye-assisted diode laser ablation of carious enamel and dentine. Aus Dental J 1999; 44: 169–175. DOI: 10.1111/j.1834-7819.1999.tb00218.x.

14.

Luo

Zhang

. Combination of near infrared light-activated photodynamic therapy mediated by indocyanine green with etoposide to treat non-small-cell lung cancer. Cancers 2017; 9: 63. DOI: 10.3390/cancers9060063.

15.

Philip

Penzkofer

Bäumler

et al.

Absorption and fluorescence spectroscopic investigation of indocyanine green. J Photochem Photobiol A: Chem 1996; 96: 137–148. DOI: 10.1016/1010-6030(95)04292-X.

16.

Lee

Berezin

Henary

et al.

Fluorescence lifetime properties of near-infrared cyanine dyes in relation to their structures. J Photochem Photobiol A: Chem 2008; 200: 438–444. DOI: 10.1016/j.jphotochem.2008.09.008.

17.

Landman

MLJ

Kwant

Mook

et al.

Light-absorbing properties, stability and spectral stabilization of indocyanine green. J Appl Physiol 1976; 40: 575–589.

18.

Prahl S. Oregon Medical Laser Center, omlc.ogi.edu/spectra/icg/ (accessed 17 November 2017).

19.

Igarashi

Kamisaka

Maezawa

et al.

Degration and metabolism of indocyanine green: high-pressure liquid chromatographic analysis. Bull Tokyo Med Dent Univ 1990; 37: 59–69.

20.

Chen

Fancher

Ruan

et al.

A liquid chromatography tandem mass spectrometry method for the quantification of indocyanine green in dog plasma and bile. J Pharm Biomedical Anal 2008; 47: 351–359. DOI: 10.1016/j.jpba.2008.01.007.

21.

Peters J. Fragmentierungsverhalten von Rhodamin-Farbstoffen unter Stoß- und Laser-Aktivierung im FT-ICR-Massenspektrometer. PhD Thesis, University Kiel, Kiel, 2015.

22.

Boles

Coates

Berden

et al.

Experimental and theoretical investigations of infrared multiple photon dissociation spectra of glutamine complexes with Zn²⁺ and Cd²⁺. J Phys Chem B 2015; 119: 11607–11617. DOI: 10.1021/acs.jpcb.5b06528.

23.

Dunbar

. BIRD (blackbody infrared radiative dissociation): evolution, principles, and applications. Mass Spectrom Rev 2004; 23: 127–158. DOI: 10.1002/mas.10074.

24.

Mitrofanov E, Muskat T and Grotemeyer J. unpublished results (paper in preparation).

25.

Turećek

McLafferty

. Interpretation of mass spectra Mill Valley, USA: University Science Books. ISBN: 978-0935702255.

26.

Kim

McLafferty

. Efficiency of collisional activation of gaseous organic ions. J Am Chem Soc 1978; 100: 3279–3282.

27.

McLafferty

. Tandem mass spectrometry, Chichester, UK: John Wiley, 1983. ISBN 471 865 974.

28.

Sheil

Guilhaus

Derrick

. Collision-activated decomposition of peptides by Fourier transform ion cyclotron resonance spectrometry. J Mass Spectrom 1990; 25: 671–680. DOI: 10.1002/oms.1210251209.

29.

Susa

Mortensen

Williams

. Effects of cations on protein and peptide charging in electrospray ionization from aqueous solutions. J Am Soc Mass Spectrom 2014; 25: 918–927. DOI: 10.1007/s13361-014-0864-5.

30.

Caetano

Ramalho

Vieira

et al.

Bonding, structure, and stability of [(Na)n(Phe)m]n+ clusters: some surprising results from an experimental and theoretical investigation in gas phase. J Chem 2013. Article ID 362894: 8. DOI: 10.1155/2013/362894.