Synthesis and characterization of three novel amphiphilic aminated hypocrellins as photodynamic therapeutic agents.

Photochem Photobiol

Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, Peoples' Republic of China.

Published: October 2003

AI Article Synopsis

  • Researchers developed three new 2-amino-2-demethoxy-hypocrellins to enhance their amphiphilicity and red light absorption for potential phototherapeutic use.
  • The structures of these compounds were confirmed using techniques like NMR, infrared, and mass spectrometry, indicating successful synthesis.
  • These new derivatives demonstrated significant absorption in the 600-900 nm range and improved amphiphilicity along with the ability to generate reactive oxygen species when exposed to light, highlighting their potential for photodynamic therapy.

Article Abstract

To improve the amphiphilicities and red absorption of the hypocrellins, three novel 2-amino-2-demethoxy-hypocrellins were synthesized by the mild reactions of hypocrellin B with 4-(2-amino-ethyl)morpholine, N,N-dimethylethylenediamine and 1-(2-amino-ethyl)piperazine, respectively. The structures of these derivatives were characterized with proton nuclear magnetic resonance, infrared and mass spectra (MS). The ultraviolet-visible absorption and fluorescence spectra of the derivatives were measured and the new amino-substituted hypocrellins showed strong absorption in the domain of the phototherapeutic window (600-900 nm). Their amphiphilicities evaluated via the partition coefficients between n-octanol and phosphate-buffered saline buffer improved remarkably. Electron paramagnetic resonance spin-trapping measurements were used to investigate the photodynamic action of the three compounds in the presence of oxygen. Singlet oxygen (1O2) and superoxide anion radical (O2.-) generated by illuminating the hypocrellin derivatives in aerobic solution were observed.

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http://dx.doi.org/10.1562/0031-8655(2003)078<0411:sacotn>2.0.co;2DOI Listing

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