The syntheses of closo- and nido-carboranylchlorins 4 and 5 from a known carboranylporphyrin are described. Water-soluble nido-carboranylporphyrin 5 was found to have very low dark cytotoxicity (IC50 > 500 microM using a MTT-based assay) but to be toxic in the presence of red light (IC50 = 80 microM at 0.55 J/cm2 light dose). Under the same experimental conditions, carboranylchlorin 5 was taken up by human glioma T98G cells to a significantly higher extent than chlorin e6, a chlorophyll degradation product. The preferred sites of subcellular localization of carboranylchlorin 5 were found to be the cell lysosomes. Our results suggest that carboranylchlorin 5 is a promising new dual sensitizer for the PDT and BNCT treatment of tumors.
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http://dx.doi.org/10.1016/j.bmc.2006.05.026 | DOI Listing |
Front Chem
November 2024
Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Bellaterra, Spain.
Icosahedral boron clusters-based BODIPY dyes represent a cutting-edge class of compounds that merge the unique properties of boron clusters with the exceptional fluorescence characteristics of BODIPY dyes. These kinds of molecules have garnered substantial interest due to their potential applications across various fields, mainly including optoelectronics, bioimaging, and potential use as boron carriers for Boron Neutron Capture Therapy (BNCT). Carborane clusters are known for their exceptional stability, rigid geometry, and 3D-aromaticity, while BODIPY dyes are renowned for their strong absorption, high fluorescence quantum yields, and photostability.
View Article and Find Full Text PDFMolecules
May 2023
Institut de Ciència de Materials de Barcelona, ICMAB-CSIC, 08193 Bellaterra, Spain.
Traditionally, drugs were obtained by extraction from medicinal plants, but more recently also by organic synthesis. Today, medicinal chemistry continues to focus on organic compounds and the majority of commercially available drugs are organic molecules, which can incorporate nitrogen, oxygen, and halogens, as well as carbon and hydrogen. Aromatic organic compounds that play important roles in biochemistry find numerous applications ranging from drug delivery to nanotechnology or biomarkers.
View Article and Find Full Text PDFJ Pers Med
November 2022
Department of Microbiology, Graduate School of Medical Sciences, Kumamoto University, Kumamoto 860-8556, Japan.
In 1979, development of the first polymer drug SMANCS [styrene-co-maleic acid (SMA) copolymer conjugated to neocarzinostatin (NCS)] by Maeda and colleagues was a breakthrough in the cancer field. When SMANCS was administered to mice, drug accumulation in tumors was markedly increased compared with accumulation of the parental drug NCS. This momentous result led to discovery of the enhanced permeability and retention effect (EPR effect) in 1986.
View Article and Find Full Text PDFBioengineering (Basel)
December 2021
Department of Chemistry and Technology of Biologically Active Compounds, Medicinal and Organic Chemistry, Institute of Fine Chemical Technologies, MIREA-Russian Technological University, 86 Vernadsky Avenue, 119571 Moscow, Russia.
To combine the neutron-capturing and photodynamic properties of boron nanoclusters and derivatives of natural chlorins, respectively, in one molecule, conjugate of chlorin e6 methyl ester with cyclen and dioxane and nitrile derivatives of cobalt bis(dicarbollide) were synthesized. The conditions for the purification of compounds by HPLC were selected since the work with natural compounds is complicated by the production of closely related impurities.
View Article and Find Full Text PDFInorg Chem
August 2021
Dipartimento di Chimica, Università degli Studi di Roma Sapienza, P. le A. Moro 5, I-00185 Rome, Italy.
Recent work has been developed on two new classes of neutral porphyrazine complexes of formulas [(PdCl)PyPzM]·HO (PyPz = octakis(2-pyridyl)porphyrazinato anion; M = Mg(HO), Zn, Pd) and [{Pd(CBT)}PyPzM]·HO (M = Mg(HO), Zn; CBT = -carborane-1-thiolate anion). Characterization of all the species has been conducted by IR and UV-visible spectral measurements in a systematic comparison with the corresponding already known mononuclear species [PyPzM] (M = Mg(HO), Zn) and the mono-Pd analogue isolated and presented here for the first time. Comparison includes also the two parent classes of pentanuclear tetrapyrazinoporphyrazines having the more extended π-electron delocalized macrocyclic core PyTPyzPz.
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