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Iminium salt benzochlorins: structure-activity relationship studies

D Skalkos¹, J A Hampton, R W Keck

¹Department of Chemistry, University of Toledo, OH 43606.

Photochemistry and Photobiology

|February 1, 1994

Summary

Copper(II) octaethylbenzochlorin iminium salt (CDS1) shows photodynamic action without singlet oxygen production. The study identified copper within the aromatic ring and an iminium group at the meso position as crucial for this effect in urothelial tumor treatment.

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Area of Science:

Photodynamic therapy
Organic chemistry
Medicinal chemistry

Background:

Copper(II) octaethylbenzochlorin iminium salt (CDS1) is a novel photosensitizer.
Its photodynamic action is effective despite lacking singlet oxygen production, fluorescence, and having a short triplet state lifetime (<20 ns).

Purpose of the Study:

To synthesize and evaluate octaethylbenzochlorin derivatives.
To identify the specific structural features responsible for the photodynamic effect of these photosensitizers.

Main Methods:

Synthesis of various octaethylbenzochlorin derivatives.
Photodynamic action studies using N-(4-[5-nitro-2-furyl]-2-thiazolyl)formamide-induced urothelial tumor models.

Main Results:

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The copper(II) octaethylbenzochlorin iminium salt (CDS1) demonstrated photodynamic efficacy.

Photodynamic action was observed to be dependent on specific structural elements.

Conclusions:

The presence of copper within the aromatic ring is essential for photodynamic action.
An iminium group at the meso position is also required for the observed photodynamic effect.