Lack of singlet oxygen formation by photoexcited promazine derivatives in aqueous and ethanolic solutions

Decuyper, J.; Piette, Jacques; Merville, Marie Paule; Calberg-Bacq, Claire-Michelle; Vorst, A. Van de

doi:10.1007/bf01323713

Cited by 12 publications

(2 citation statements)

References 13 publications

(17 reference statements)

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“…We have detected lo2 in ethanol while Decuyper et al (1983) did not. They have estimated the sensitivity of their cholesterol product analysis to be 1.6 pmol of the oxygen-cholesterol adduct per mole of singlet oxygen produced.…”

Section: Discussionmentioning

confidence: 49%

NEAR‐INFRARED DETECTION OF SINGLET MOLECULAR OXYGEN PRODUCED BY PHOTOSENSITIZATION WITH PROMAZINE and CHLORPROMAZINE

Buettner

et al. 1987

Photochem & Photobiology

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A sensitive near‐infrared detection system has been used to study the steady‐state emission of 1O2 at 1268 nra produced by promazine (PZ) and chlorpromazine (CPZ) during photo‐illumination. Singlet molecular oxygen could be detected in a variety of ordinary and perdeuterated organic solvents, but was not detectable in water or deuterium oxide. The emission was enhanced in the perdeuterated organic solvents and could be eliminated by rigorous degassing or by addition of the singlet oxygen scavenger 2,3‐dimethylfuran. Singlet oxygen could not be detected in any of the solvents during irradiation of the sulfoxides of PZ and CPZ. We conclude that in biological systems 1O2 production is not a major pathway to phototoxicity for the sulfoxides, while for the parent phenothiazines the formation of 1O2 is much more likely to be important in nonpolar environments such as cell membranes than in the aqueous parts of the cell.

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Section: Discussionmentioning

confidence: 49%

NEAR‐INFRARED DETECTION OF SINGLET MOLECULAR OXYGEN PRODUCED BY PHOTOSENSITIZATION WITH PROMAZINE and CHLORPROMAZINE

Buettner

et al. 1987

Photochem & Photobiology

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“…Moore(27) has studied a series of phenothiazine tranquilizers in methanol solution and shown that 2,5-dimethylfuran stimulates oxygen uptake in the presence of promethazine, promazine, chlorpromazine, prochlorperazine, trifluperazine and thioridiazine. In contrast, Decuyper and co-workers(28) failed to detect singlet oxygen during the irradiation of ethanol solutions of promazine, triflupromazine, methoxypromazine, and acepromazine using the method of Lion et al (29). Similar results were obtained by the same workers in aqueous solution using cholesterol attached to polystyrene latex beads as the singlet oxygen monitor.…”

mentioning

confidence: 89%

Photoinduced Free Radicals from Chlorpromazine and Related Phenothiazines: Relationship to Phenothiazine-Induced Photosensitization

Chignell¹,

Motten²,

Buettner³

1985

Environmental Health Perspectives

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JSTOR is a not-for-profit service that helps scholars, researchers, and students discover, use, and build upon a wide range of content in a trusted digital archive. We use information technology and tools to increase productivity and facilitate new forms of scholarship. For more information about JSTOR, please contact support@jstor.org.. The National Institute of Environmental Health Sciences (NIEHS) and Brogan & Partners are collaborating with JSTOR to digitize, preserve and extend access to Environmental Health Perspectives.Chlorpromazine and several other related phenothiazines are known to cause both phototoxic and photoallergic reactions in the skin and eyes of patients receiving these drugs. While the detailed mechanisms of photosensitization are not known, it is obvious that the first step must be the absorption of light by the drug, its metabolites, or photoproducts, or possibly an induced endogenous chemical. In this review, the free-radical photochemistry of phenothiazines is described, and the evidence for the involvement of photoinduced free radicals in photosensitization is examined. Upon irradiation chlorpromazine yields a variety of free radicals including the corresponding cation radical (via photoionization), the neutral promazinyl radical and a chlorine atom (CI') (via homolytic cleavage), and a sulfur-centered peroxy radical. The chlorpromazine cation radical is probably responsible for some of the observed in vitro phototoxic effects of this drug. However, it seems unlikely that the cation radical is involved in phototoxicity in vivo, since photoionization only occurs when chlorpromazine is excited into the S2 level (x,, < 280 nm). The promazinyl radical is a more likely candidate for the phototoxic species both in vivo and in vitro. In addition, this radical can react covalently with proteins and other macromolecules to yield antigens which could be responsible for the photoallergic response to chlorpromazine. Neither oxygen-derived radicals nor singlet oxygen (102*), appear to be important in chlorpromazine photosensitization. In contrast, it would seem that promazine-induced phototoxicity may result in part from the generation of superoxide (02').The inability of promazine, which lacks a chlorine atom at the 2-position, to undergo homolytic fission to give the promazinyl radical, probably explains why this drug is much less phototoxic than chlorpromazine both in vivo and in vitro.

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Nanosecond time-resolved resonance Raman and absorption studies of the photochemistry of chlorpromazine and related phenothiazine derivatives

Sarata

Sakai

Takahashi

2000

J. Raman Spectrosc.

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Lack of singlet oxygen formation by photoexcited promazine derivatives in aqueous and ethanolic solutions

Cited by 12 publications

References 13 publications

NEAR‐INFRARED DETECTION OF SINGLET MOLECULAR OXYGEN PRODUCED BY PHOTOSENSITIZATION WITH PROMAZINE and CHLORPROMAZINE

NEAR‐INFRARED DETECTION OF SINGLET MOLECULAR OXYGEN PRODUCED BY PHOTOSENSITIZATION WITH PROMAZINE and CHLORPROMAZINE

Photoinduced Free Radicals from Chlorpromazine and Related Phenothiazines: Relationship to Phenothiazine-Induced Photosensitization

Nanosecond time-resolved resonance Raman and absorption studies of the photochemistry of chlorpromazine and related phenothiazine derivatives

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