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DNA–drug dimers: Drugs based on the phenothiazine scaffold have a wide variety of therapeutic applications and are also used as DNA photosensitizers. Highly cooperative formation of a 2:1 complex was revealed by electrospray mass spectrometry experiments, and a structural model is proposed. This bisphenothiazine scaffold can therefore be exploited for future design of new minor groove binding agents having photosensitizing properties.