Abstract
Photodynamic therapy (PDT) has attracted widespread attention due to its potential in the treatment of various cancers. Porphyrinic pyropheophorbide-a (PPa) has been shown to be a potent photosensitizer in PDT experiments. In this paper, a C-31,131 bisphenylhydrazone modified methyl pyropheophorbide-a (BPHM) was designed and synthesized with the consideration that phenylhydrazone structure may extend absorption wavelength of methyl pyro-pheophorbide-a (Mppa), and make the photosensitizer potential in deep tumor treatment. The synthesis, spectral properties and in vitro photodynamic therapy (PDT) against human HeLa cervical cancer cell line was studied. Methyl thiazolyl tetrazolium (MTT) assay showed the title compound could achieve strong inhibition of cervical cancer cell viability under visible light (675 nm, 25 J/cm2). Cell uptake experiments were performed on HeLa cells. Morphological changes were examined and analyzed by fluorescent inverted microscope. In addition, the mechanism of the photochemical processes of PDT was investigated, which showed that the formation of singlet oxygen after treatment with PDT played a moderate important role.
Highlights
Cancer has been seriously threatening human health for a long period
methyl pyro-pheophorbide-a (Mppa) was hydrolyzed by hydrobromic acid in acetic acid, oxidized by N(t-Pr)3 RuO4 to obtain C-31,131 -dicarbonyl product (3), which reacted with p-CF3 -phenylhydrazine under reflux conditions to obtain the end-product C-31,131 -Bisphenylhydrazone modified methyl pyropheophorbide-a (BPHM, 4)
human cervical cancer cell line (HeLa) cells were used to concentrations of BPHMactivity and Mppa were analyzed by Methyl thiazolyl tetrazolium (MTT) The assay
Summary
Cancer has been seriously threatening human health for a long period. Diagnosis and treatment of cancer has become the most pressing concern in contemporary society. Because the photosensitizer may be excited by appropriate wavelength of light, it passes on the excess energy to surrounding molecular oxygen, resulting in the generation of reactive oxygen species (ROS) [7]. An ideal photosensitizer should have high efficiency in generating ROS within the aerobic tissues and have characteristics of low dark toxicity, targeted aggregation and long wavelength absorption (>600 nm) [8]. It is widely acknowledged that increasing the π-conjugation extending from the porphyrin core can lead to enhanced absorption properties [24] In this present study, we made a modification on C-3, C-13 of Mppa by p-CF3 -phenylhydrazine to produce a new chlorin-based compound to develop photosensitizers in PDT. The photochemical processes mechanism of PDT was investigated by using specific quenching agent sodium azide (SA) and D-mannitol (DM) [27,28], respectively
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