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Analytical Studies on Photochemical Behavior of Phototoxic Substances; Effect of Detergent Additives on Singlet Oxygen Generation

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Abstract

Purpose

Monitoring of reactive oxygen species (ROS) generation from photoirradiated compounds would be effective for the prediction of the phototoxic potential. The aim of this investigation was to clarify the possible role of biomimetic vehicle systems on the photochemical properties of phototoxic compounds, focusing on the singlet oxygen generation.

Materials and Methods

Nine phototoxic and one non-phototoxic compounds (200 μM), dissolved in Tween 20, sodium laurate, or sodium dodecyl sulfate (SDS) micellar solution, were exposed to UVA/B light (250 W/m2), and singlet oxygen generation was monitored by RNO bleaching methodology. Photochemical properties of photosensitizers were also evaluated by UV measurement, and the interaction of photosensitizers with surfactant micelles was assessed by Z-potential and NMR spectroscopic analyses.

Results

All phototoxic compounds tended to generate singlet oxygen under light exposure in the all micellar solutions tested. There appeared to be some differences in photoreactivity of both cationic and anionic photosensitizers among the micelles tested, whereas ROS data on anthracene, dissolved in three micellar solutions, were found to be quite similar. Photosensitizers exhibited no significant changes in UV spectral patterns among the dissolving micellar solutions. Addition of cationic photosensitizer at the final concentration of 100 μM into 100 mM SDS solution resulted in the 20 mV increase of zeta potential and transition of NMR spectral pattern, which would reflect the electrostatic interaction with anionic micelles.

Conclusion

Based on the data obtained, the photoreactivity of photosensitizing molecules, especially cationic and anionic photosensitizers, strongly depends on the physicochemical properties of the microenvironment.

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Abbreviations

DNA:

deoxyribonucleic acid

DMSO:

dimethyl sulfoxide

NMR:

nuclear magnetic resonance

NRU:

neutral red uptake

NSAIDs:

non-steroidal anti-inflammatory drugs

ROS:

reactive oxygen species

SDS:

sodium dodecyl sulfate

UV:

ultraviolet

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Acknowledgement

We are grateful to Ms. Satsuki Segawa for her excellent technical assistance throughout this work.

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Author notes

  1. Satomi Onoue

    Present address: Department of Pharmacokinetics and Pharmacodynamics, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan

Authors and Affiliations

  1. Analytical Research and Development, Pfizer Global Research and Development, Nagoya Laboratories, Pfizer Japan Inc., 5-2 Taketoyo, Aichi, 470-2393, Japan

    Satomi Onoue, Yukinori Yamauchi, Naoko Igarashi & Yoshiko Tsuda

  2. Pharmaceutical Research and Development, Pfizer Global Research and Development, Nagoya Laboratories, Pfizer Japan Inc., 5-2 Taketoyo, Aichi, 470-2393, Japan

    Takashi Kojima

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  1. Satomi Onoue
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  2. Yukinori Yamauchi
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  4. Naoko Igarashi
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  5. Yoshiko Tsuda
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Correspondence to Satomi Onoue.

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Onoue, S., Yamauchi, Y., Kojima, T. et al. Analytical Studies on Photochemical Behavior of Phototoxic Substances; Effect of Detergent Additives on Singlet Oxygen Generation. Pharm Res 25, 861–868 (2008). https://doi.org/10.1007/s11095-007-9383-4

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  • DOI: https://doi.org/10.1007/s11095-007-9383-4

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