Total syntheses of three copper (II) tetracarboranylphenylporphyrins containing 40 or 80 boron atoms and their biological properties in EMT-6 tumor-bearing mice

Wu, Haitao; Micca, Peggy L.; Makar, Michael; Miura, Michiko

doi:10.1016/j.bmc.2006.04.010

Cited by 18 publications

(8 citation statements)

References 34 publications

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“…Chlorophylls serve mainly as light harvesting complexes in plants and photosynthetic bacteria − elements in molecular logic circuits, , or effective sensitizers in anticancer treatments as photodynamic (PDT), photothermic (PTT), or boron neutron capture therapies (BNCT). − In most applications, the porphyrin derivatives serve as light-harvesting molecules. Therefore, a thorough understanding of its photophysical and photochemical processes are of fundamental interest.…”

Section: Introductionmentioning

confidence: 99%

Near-Infrared Excitation of the Q Band in Free Base and Zinc Tetratolyl-porphyrins

et al. 2008

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The photophysics of 5,10,15,20-tetra-p-tolyl-21H,23H-porphyrin (TTP-H2) and 5,10,15,20-tetra-p-tolyl-porphyrinato zinc II (ZnTTP) have been investigated by means of pump-probe and transient anisotropy experiments. After excitation to the Q band, the molecules were probed by NIR pulses in the range between 950 and 1350 nm in order to study states of gerade symmetry in the vicinity of the Soret band. Examination of transient spectra and anisotropy delivered the first direct observation and the excitation energies of the two lowest so-called dark states. The experimental results were compared with predictions from theoretical calculations.

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Section: Introductionmentioning

confidence: 99%

Near-Infrared Excitation of the Q Band in Free Base and Zinc Tetratolyl-porphyrins

et al. 2008

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“…[1][2][3][4][5][6] Recently, these molecules have been derivatized with boron containing functions for possible use in boron neutron capture therapy (BNCT). [3][4][5] All of these therapies require a "bullet", that is, light or neutrons, and an active compound, such as a strong neutron or light absorber, preferentially located inside malignant cells. 6 Here we describe a new poly(carboranylalkylthio)porphyrazine, (H 2 HECASPz, Figure 1), synthesized with the purpose to contribute to this issue.…”

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confidence: 99%

Synthesis and Liposome Insertion of a New Poly(carboranylalkylthio)porphyrazine to Improve Potentiality in Multiple-Approach Cancer Therapy

et al. 2007

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Liposome insertion of a newly synthesized octa-carboranylhexylthio-porphyrazine (H2HECASPz) with potentiality in anticancer multiple therapy was described at molecular and supramolecular level. Host−guest interactions between H2HECASPz and the liposome constituents were established and were confirmed by DFT calculations. An approach for the design of new porphyrin-like molecules to be carried by liposome is presented

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“…Mannose is absorbed through the intestine, metabolized, and cleanly washed out within 4 h without affecting glucose concentrations [22]. This is a key point, as other artificial boron-containing compounds with much higher tumor to normal tissue retention ratios carried risks of pulmonary and splenic embolism, liver dysfunction, and severe renal dysfunction in preliminary animal biodistribution and toxicity studies [61][62][63]. In contrast, our compound caused no decrease in mice weight while liver and kidney specimens were free from embolisms and showed no particular toxic effect.…”

Section: Discussionmentioning

confidence: 99%

Evaluation of a Novel Boron-Containing α-d-Mannopyranoside for BNCT

Tsurubuchi

Shirakawa

Kurosawa

et al. 2020

Cells

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Boron neutron capture therapy (BNCT) is a unique anticancer technology that has demonstrated its efficacy in numerous phase I/II clinical trials with boronophenylalanine (BPA) and sodium borocaptate (BSH) used as 10B delivery agents. However, continuous drug administration at high concentrations is needed to maintain sufficient 10B concentration within tumors. To address the issue of 10B accumulation and retention in tumor tissue, we developed MMT1242, a novel boron-containing α-d-mannopyranoside. We evaluated the uptake, intracellular distribution, and retention of MMT1242 in cultured cells and analyzed biodistribution, tumor-to-normal tissue ratio and toxicity in vivo. Fluorescence imaging using nitrobenzoxadiazole (NBD)-labeled MMT1242 and inductively coupled mass spectrometry (ICP-MS) were performed. The effectiveness of BNCT using MMT1242 was assessed in animal irradiation studies at the Kyoto University Research Reactor. MMT1242 showed a high uptake and broad intracellular distribution in vitro, longer tumor retention compared to BSH and BPA, and adequate tumor-to-normal tissue accumulation ratio and low toxicity in vivo. A neutron irradiation study with MMT1242 in a subcutaneous murine tumor model revealed a significant tumor inhibiting effect if injected 24 h before irradiation. We therefore report that 10B-MMT1242 is a candidate for further clinical BNCT studies.

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Total syntheses of three copper (II) tetracarboranylphenylporphyrins containing 40 or 80 boron atoms and their biological properties in EMT-6 tumor-bearing mice

Cited by 18 publications

References 34 publications

Near-Infrared Excitation of the Q Band in Free Base and Zinc Tetratolyl-porphyrins

Near-Infrared Excitation of the Q Band in Free Base and Zinc Tetratolyl-porphyrins

Synthesis and Liposome Insertion of a New Poly(carboranylalkylthio)porphyrazine to Improve Potentiality in Multiple-Approach Cancer Therapy

Evaluation of a Novel Boron-Containing α-d-Mannopyranoside for BNCT

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