Аннотация:In this work, we analyzed the non-covalent binding of water-soluble charged metallophthalocyanines to nanodiamonds with variable surface parameters and identified two conjugation mechanisms. The first mechanism is π-π stacking which leads to the phthalocyanine fluorescence quenching, decrease of singlet oxygen quantum yield and photodynamic efficiency against A431 cells. The second mechanism is realized by electrostatic interactions, with preservation of phthalocyanine fluorescent properties and variable singlet oxygen quantum yield depending on the stoichiometric ratio in the conjugate. In such a case the photodynamic effect was enhanced compared to phthalocyanine in the absence of nanodiamond. Results may be helpful for designing the third generation photosensitizers with nanoparticles that act as a platform for drug delivery.