Synthesis and comparative photodynamic properties of two isosteric alkyl substituted zinc(II) phthalocyanines

Gauna, Gabriela A.; Marino, Julieta; Vior, María C. García; Roguin, Leonor P.; Awruch, Josefina

doi:10.1016/j.ejmech.2011.09.014

Cited by 38 publications

(24 citation statements)

References 24 publications

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“…Nickel(II) complexes were shown as telomerase and topoisomerase II inhibitors678, inducing cancer cell apoptosis via mitochondrial pathways910. Increasing evidence indicated that zinc(II) complexes exhibited high anticancer activity, such as zinc(II) chelated dihalo-8-quinolinol11, isoquinoline derivatives10, phthalocyanine12, thiosemicarbazone131415, and etc. In addition, Zn(II) complexes of some thiosemicarbazones possess intrinsic fluorescence, which enables the use for fluorescence imaging and further study of their mechanism of action1617 Thus, Zn(II) complexes were shown to have the potential as novel anticancer agents.…”

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confidence: 99%

Oxoaporphine Metal Complexes (CoII, NiII, ZnII) with High Antitumor Activity by Inducing Mitochondria-Mediated Apoptosis and S-phase Arrest in HepG2

Qin

Shen

Chen

et al. 2017

Sci Rep

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Three new oxoaporphine Co(II), Ni(II) and Zn(II) complexes 1–3 have been synthesized and fully characterized. 1–3 have similar mononuclear structures with the metal and ligand ratio of 1:2. 1–3 exhibited higher cytotoxicity than the OD ligand and cisplatin against HepG2, T-24, BEL-7404, MGC80–3 and SK-OV-3/DDP cells, with IC50 value of 0.23−4.31 μM. Interestingly, 0.5 μM 1–3 significantly caused HepG2 arrest at S-phase, which was associated with the up-regulation of p53, p21, p27, Chk1 and Chk2 proteins, and decrease in cyclin A, CDK2, Cdc25A, PCNA proteins. In addition, 1–3 induced HepG2 apoptosis via a caspase-dependent mitochondrion pathway as evidenced by p53 activation, ROS production, Bax up-regulation and Bcl-2 down-regulation, mitochondrial dysfunction, cytochrome c release, caspase activation and PARP cleavage. Furthermore, 3 inhibited tumor growth in HepG2 xenograft model, and displayed more safety profile in vivo than cisplatin.

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confidence: 99%

Oxoaporphine Metal Complexes (CoII, NiII, ZnII) with High Antitumor Activity by Inducing Mitochondria-Mediated Apoptosis and S-phase Arrest in HepG2

Qin

Shen

Chen

et al. 2017

Sci Rep

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“…1.12) [71]. The photodynamic effect and the cellular uptake of both phthalocyanines were evaluated on human nasopharynx KB carcinoma cells.…”

Section: Zinc Phthalocyaninesmentioning

confidence: 99%

Introduction

Lau

2013

Towards Dual and Targeted Cancer Therapy With Novel Phthalocyanine-Based Photosensitizers

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“…5 However, only few phthalocyanines have been synthesized using this strategy. 6,7 We have recently reported the synthesis and photophysical and photobiological studies of four isosteric water-soluble cationic zinc(II) phthalocyanines by using human nasopharynx KB carcinoma cells. Our results showed the efficiency of one of them 2,9(10), 16(17),23(24)-terakis[(2-trimethylammonium)ethylsulfanyl]phthalocyaninatozinc(II) tetraiodide (Pc13), for suitable PDT studies.…”

Section: Introductionmentioning

confidence: 99%

“…In previous studies, we stated that sulfur-linked cationic aliphatic phthalocyanines show a higher bathochromic shift in the order of 10 nm for the Q band than the isosteric oxygen-linked cationic aliphatic phthalocyanines. 6,7 On the other hand, it has been established that several bioactive selenium-based compounds show a large spectra of biological activities. 5,[8][9][10] However, alkylselenium substituted dyes have received less attention than oxygen or sulfur analogous molecules.…”

Section: Introductionmentioning

confidence: 99%