In modern medical clinics, photodynamic therapy (PDT) using the photosensitizer has become an efficient technology for the diagnosis and treatment of cancer with lower toxicity and side effects. The photosensitizer plays a vital role to generate singlet oxygen as well as fluorescence which makes it useful for both imaging and therapy. In this regard, chlorin e6 and its derivatives have been revealed as an effective photosensitizer in PDT for the treatment of pancreatic cancer. As a part of ongoing studies of Ce6, novel series of chlorin e6-curcumin (ce6-cur) conjugates were synthesized. All prepared compounds were characterized by UV, 1H NMR, 13C NMR, and LC-MS. These Ce6-cur conjugates showed good physicochemical properties and higher singlet oxygen generation. Further, the synthesized compounds were also investigated against pancreatic cancer cell lines AsPC-1, MIA-PaCa-2, and PANC-1 in vitro and melanoma cancer model in vivo. The cellular uptake study was carried out in the aforementioned cell lines using fluorescence-activated cell sorting (FACS). Among the synthesized compounds, compound C displayed the best PDT effectiveness as displayed by cell permeability and cell viability (IC50: 0.22, 0.36, and 0.18µM) test in AsPC-1, MIA PaCa-2, and PANC-1 respectively. Moreover, treatment with compound C upregulated the protein expression of apoptotic proteins cytochrome C while down-regulated anti-apoptotic protein, Bcl2. Apart from in vitro tests, compound C also showed good effects in vivo melanoma tumor model in mice. Thus compound C can be a promising photosensitizer for the treatment of pancreatic cancer.

Synthesis of novel chlorin e6-curcumin derivatives and their photodynamic therapy against pancreatic carcinoma

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ACS Fall 2022

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