Towards dual photodynamic and antiangiogenic agents: design and synthesis of a phthalocyanine-chalcone conjugate
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A phthalocyanine–chalcone conjugate has been designed to combine the vascular disrupting effect of chalcones with the photodynamic effect of phthalocyanines. This potential dual photodynamic and antiangiogenic agent was obtained by the condensation of a tetrahydroxylated non-peripherally substituted Zn(II) phthalocyanine with an amino chalcone converted into the corresponding activated isocyanate. The conjugate was fully characterized.Keywords:
Chalcone
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A phthalocyanine–chalcone conjugate has been designed to combine the vascular disrupting effect of chalcones with the photodynamic effect of phthalocyanines. This potential dual photodynamic and antiangiogenic agent was obtained by the condensation of a tetrahydroxylated non-peripherally substituted Zn(II) phthalocyanine with an amino chalcone converted into the corresponding activated isocyanate. The conjugate was fully characterized.
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Conjugate
Isocyanate
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Diethylzinc
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Photodynamic therapy (PDT) is a light based therapy used to ablate tumors. As practiced in oncology a photosensitizing agent is applied and then activated by a specific wavelength and energy of light. This light energy in the presence of oxygen will lead to the creation of the photodynamic reaction which is cyto and vasculo toxic. This paper will review the mechanisms of action of PDT and how they may be manipulated to improve clinical outcome in cancer patients.
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Photodynamic therapy is a new and effective technique for cancer treatment,and 5-aminolevulinic acid photodynamic therapy is demonstrated to be more safe and effective than other photodynamic therapy.The treatment indication has been enlarged in recent years.This article reviewed the advances of 5-aminolevulinic acid photodynamic therapy in dermatology and venerology.
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The present work emphasizes on the synthesis of a series of 4,5-disubstituted isoxazole derivatives of α,β-chalcone ditosylates which were synthesized by the reaction of α,β-chalcone ditosylates with hydroxylamine hydrochloride. Various α,β-chalcone ditosylates were prepared by the reaction of respective chalcones with hydroxyl (tosyloxy)iodobenzene.The synthesized compounds were characterized and subsequently evaluated for anti-inflammatory and antioxidant properties.
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A phthalocyanine-chalcone conjugate was previously reported to retain the full photodynamic activity of the phthalocyanine and a slightly lowered antivascular effect of the chalcone. Assuming that it was due to an insufficient release of the chalcone, we described here several grafting modes applied to the preparation of phthalocyanine-chalcone conjugates.
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Photodynamic therapy (PDT) kills cancer cells by converting tumour oxygen into reactive singlet oxygen ((1)O2) using a photosensitizer. However, pre-existing hypoxia in tumours and oxygen consumption during PDT can result in an inadequate oxygen supply, which in turn hampers photodynamic efficacy. Here to overcome this problem, we create oxygen self-enriching photodynamic therapy (Oxy-PDT) by loading a photosensitizer into perfluorocarbon nanodroplets. Because of the higher oxygen capacity and longer (1)O2 lifetime of perfluorocarbon, the photodynamic effect of the loaded photosensitizer is significantly enhanced, as demonstrated by the accelerated generation of (1)O2 and elevated cytotoxicity. Following direct injection into tumours, in vivo studies reveal tumour growth inhibition in the Oxy-PDT-treated mice. In addition, a single-dose intravenous injection of Oxy-PDT into tumour-bearing mice significantly inhibits tumour growth, whereas traditional PDT has no effect. Oxy-PDT may enable the enhancement of existing clinical PDT and future PDT design.
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The drug resistance condition of P . falciparum pose a major challenge in the fight against malaria. This prompts a comprehensive research in an effort to discover new drug candidates. Therefore, chalcone was modified into 24 new compounds, including indolyl-benzodioxyl-chalcone, pyrrolyl-benzodioxyl-chalcone, and thiophenyl-benzodioxyl-chalcone in the course of this study. Moreover, these compounds are commercial malaria mediciations screened for their inhibitory activity using molecular docking simulations. Subsequent results of combined indolyl-benzodioxyl-chalcone and Pf DHFR-TS showed the intrinsic indolyl components produced stronger interactions referenced to pyrrolyl-benzodioxyl-chalcone, thiophenyl-benzodioxyl-chalcone, and chloroguanide. Under these circumstances, intense Pf DHFR-TS-indolyl-benzodioxyl-chalcone complex was produced with lower binding affinity values (-7.32 to -8.43 kcal/mole) referenced to Pf DHFR-TS-pyrrolyl-benzodioxyl-chalcone (-6.38 to -6.68 kcal/mole), Pf DHFR-TS-Thiophenyl-benzodioxyl-chalcone (-6.47 to -6.52 kcal/mole), and Pf DHFR-TS-chloroguanide (-6.75 kcal/mole). Furthermore, the hydrogen bond interactions developed by indolyl-benzodioxyl-chalcone (7-10) are observably similar to standard chloroguanide compounds and WR99210. These compounds also possess a binding affinity similar to WR99210 (native ligand) and are expected to be potentially anti-malarial candidates.
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