<i>N</i>-Methylpyridylporphyrin tailed with folate conjugate as a potential lysosomal-targeted photosensitizer: Synthesis, DNA interaction, singlet oxygen and subcellular localization

Zhao, Yimei; Lu, Qianqian; Yao, Si; Su, Huifang; Liu, Hongjian; Wang, Zejiang; Wu, Fengshou; Wang, Kai

doi:10.1142/s1088424619500445

Cited by 3 publications

(4 citation statements)

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“…Another interesting application of NMR is the investigation of the modulation of the PS-quencher unit, which promotes the PDT development, by assessing their interactions with DNA [ 150 , 151 ]. For instance, Hirakawa et al synthesized a series of water-soluble porphyrin derivatives that target DNA: meso -anthryl-tris( p -pyridyl)porphyrin (AnTPyP) [ 152 ], meso -pyrenyl-tris( N -methyl- p -pyridinio)porphyrin (PyTMPyP) [ 153 ], meso -(9-anthryl)-tris( N -methyl- p -pyridinio)porphyrin (AnTMPyP) [ 154 ], meso -(naphthyl)-tris( N -methyl- p -pyridinio)porphyrin (NapTMPyP), and TMPyP [ 155 ].…”

Section: Applications To Study Porphyrin–macromolecule Interactionmentioning

confidence: 99%

Probing the Interactions of Porphyrins with Macromolecules Using NMR Spectroscopy Techniques

2021

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Porphyrinic compounds are widespread in nature and play key roles in biological processes such as oxygen transport in blood, enzymatic redox reactions or photosynthesis. In addition, both naturally derived as well as synthetic porphyrinic compounds are extensively explored for biomedical and technical applications such as photodynamic therapy (PDT) or photovoltaic systems, respectively. Their unique electronic structures and photophysical properties make this class of compounds so interesting for the multiple functions encountered. It is therefore not surprising that optical methods are typically the prevalent analytical tool applied in characterization and processes involving porphyrinic compounds. However, a wealth of complementary information can be obtained from NMR spectroscopic techniques. Based on the advantage of providing structural and dynamic information with atomic resolution simultaneously, NMR spectroscopy is a powerful method for studying molecular interactions between porphyrinic compounds and macromolecules. Such interactions are of special interest in medical applications of porphyrinic photosensitizers that are mostly combined with macromolecular carrier systems. The macromolecular surrounding typically stabilizes the encapsulated drug and may also modify its physical properties. Moreover, the interaction with macromolecular physiological components needs to be explored to understand and control mechanisms of action and therapeutic efficacy. This review focuses on such non-covalent interactions of porphyrinic drugs with synthetic polymers as well as with biomolecules such as phospholipids or proteins. A brief introduction into various NMR spectroscopic techniques is given including chemical shift perturbation methods, NOE enhancement spectroscopy, relaxation time measurements and diffusion-ordered spectroscopy. How these NMR tools are used to address porphyrin–macromolecule interactions with respect to their function in biomedical applications is the central point of the current review.

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Section: Applications To Study Porphyrin–macromolecule Interactionmentioning

confidence: 99%

Probing the Interactions of Porphyrins with Macromolecules Using NMR Spectroscopy Techniques

2021

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“…Cells of various types of tumours are characterized by active expression of folate receptors (FRs) and are able to accumulate folic acid and its derivatives [26][27][28][29]. Modification of xenobiotics [30][31][32][33][34][35], liposomes [36][37][38][39][40], and nanoparticles [41][42][43][44][45][46] using folic acid is a common way to obtain targeted agents for the tumour treatment and imaging.…”

Section: Of 14mentioning

confidence: 99%

Carborane-Containing Folic Acid bis-Amides: Synthesis and In Vitro Evaluation of Novel Promising Agents for Boron Delivery to Tumour Cells

Gruzdev

Telegina

Левит

et al. 2022

IJMS

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The design of highly selective low-toxic, low-molecular weight agents for boron delivery to tumour cells is of decisive importance for the development of boron neutron capture therapy (BNCT), a modern efficient combined method for cancer treatment. In this work, we developed a simple method for the preparation of new closo- and nido-carborane-containing folic acid bis-amides containing 18–20 boron atoms per molecule. Folic acid derivatives containing nido-carborane residues were characterised by high water solubility, low cytotoxicity, and demonstrated a good ability to deliver boron to tumour cells in in vitro experiments (up to 7.0 µg B/106 cells in the case of U87 MG human glioblastoma cells). The results obtained demonstrate the high potential of folic acid–nido-carborane conjugates as boron delivery agents to tumour cells for application in BNCT.

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“…It plays a significant role in understanding the mechanism of the interaction between the ligand being studied and the corresponding biological target that can be represented by a specific DNA sequence or by specific protein binding sites. It should be noted that DNA is not a typical target for PS; however, in the case of photosensitizers modified with various DNA-targeted ligands, the interaction of such molecules with DNA was identified [35].…”

Section: Dockingmentioning

confidence: 99%

“…The results of calculations on the energies of ligand-targeted bonds are presented in the summary plot below (Figure 2). target for PS; however, in the case of photosensitizers modified with various DNA-targeted ligands, the interaction of such molecules with DNA was identified [35].…”

Section: Dockingmentioning

confidence: 99%

Tin Carboxylate Complexes of Natural Bacteriochlorin for Combined Photodynamic and Chemotherapy of Cancer è

Tikhonov

Ostroverkhov

Suvorov

et al. 2021

IJMS

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Photodynamic therapy (PDT) is currently one of the most promising methods of cancer treatment. However, this method has some limitations, including a small depth of penetration into biological tissues, the low selectivity of accumulation, and hypoxia of the tumor tissues. These disadvantages can be overcome by combining PDT with other methods of treatment, such as radiation therapy, neutron capture therapy, chemotherapy, etc. In this work, potential drugs were obtained for the first time, the molecules of which contain both photodynamic and chemotherapeutic pharmacophores. A derivative of natural bacteriochlorophyll a with a tin IV complex, which has chemotherapeutic activity, acts as an agent for PDT. This work presents an original method for obtaining agents of combined action, the structure of which is confirmed by various physicochemical methods of analysis. The method of molecular modeling was used to investigate the binding of the proposed drugs to DNA. In vitro biological tests were carried out on several lines of tumor cells: Hela, A549, S37, MCF7, and PC-3. It was shown that the proposed conjugates of binary action for some cell lines had a dark cytotoxicity that was significantly higher (8–10 times) than the corresponding metal complexes of amino acids, which was explained by the targeted chemotherapeutic action of the tin (IV) complex due to chlorin. The greatest increase in efficiency relative to the initial dipropoxy-BPI was found for the conjugate with lysine as a chelator of the tin cation relative to cell lines, with the following results: S-37 increased 3-fold, MCF-7 3-fold, and Hela 2.4-fold. The intracellular distribution of the obtained agents was also studied by confocal microscopy and showed a diffuse granular distribution with predominant accumulation in the near nuclear region.

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N-Methylpyridylporphyrin tailed with folate conjugate as a potential lysosomal-targeted photosensitizer: Synthesis, DNA interaction, singlet oxygen and subcellular localization

Cited by 3 publications

References 20 publications

Probing the Interactions of Porphyrins with Macromolecules Using NMR Spectroscopy Techniques

Probing the Interactions of Porphyrins with Macromolecules Using NMR Spectroscopy Techniques

Carborane-Containing Folic Acid bis-Amides: Synthesis and In Vitro Evaluation of Novel Promising Agents for Boron Delivery to Tumour Cells

Tin Carboxylate Complexes of Natural Bacteriochlorin for Combined Photodynamic and Chemotherapy of Cancer è

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