Journal
SCIENCE CHINA-CHEMISTRY
Volume 62, Issue 6, Pages 719-726Publisher
SCIENCE PRESS
DOI: 10.1007/s11426-019-9464-1
Keywords
tandem formation; iron(III) complex; DFT calculation; photodynamic therapy; breast cancer
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Funding
- BAGUI Talent Program and Scholar Program [2014A001]
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University) [CMEMR2017-A04, CMEMR2017-B01]
- National Natural Science Foundation of China [81773775, 21525101]
- Guangxi Natural Science Foundation [2014GXNSFFA118003, 2017GXNSFDA- 198040]
- Centre National de la Recherche Scientifique (France)
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A tandem reaction of pyridin-2-ylmethanamine (L1) with 8-hydroxyquinoline-2-carbaldehyde (HL1) assisted by FeCl3 was observed to give the new nitrogen heterocycle HL3 (HL3=2-(imidazo[1,5-a]pyridin-3-yl)quinolin-8-ol) as its Fe(III) complex, [Fe(L3)Cl-2] (Fel). Electrospray ionization mass spectrometry (ESI-MS) reveals its formation involves three steps: (1) coordination of both HL1 and Ll to Fe, (2) aldehyde-amine coupling, and (3) ring closure. The results of electronic absorption spectroscopy, cyclic voltammetry, and density functional theory (DFT) calculations show the proximity of the optical transition energy to that of the excitation of O-3(2) to O-1(2), which prompted us to explore its application as a photosensitizer for photodynamic therapy (PDT). Photo-toxicity studies show that Fel exhibits the highest anti-proliferation efficiency in human breast cancer MDA-MB-231 cells under light irradiation. Moreover, studies with orthotopic models of breast cancer further expounded the anti-tumor activity of Fe1 with no significant toxicity to other organs and low retention in the body.
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