ArticleBioorganic & medicinal chemistry2013
Synthesis and cellular studies of polyamine conjugates of a mercaptomethyl-carboranylporphyrin.
Article in Bioorganic & medicinal chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Synthesis and Functional Properties of Fluorinated Phosphonate-Substituted Porphyrins: Excellent Photosensitizers and Robust Precursors for Photoactive Langmuir-Schaefer Films.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Article
- Targeting the organelle for radiosensitization in cancer radiotherapy.Asian journal of pharmaceutical sciences · 2024Review
- Synthesis of new representatives of ABeilstein journal of organic chemistry · 2024Article
- Multicomponent Molecular Systems Based on Porphyrins, 1,3,5-Triazine and Carboranes: Synthesis and Characterization.Molecules (Basel, Switzerland) · 2022Article
- Design, Synthesis, and Biological Evaluation of Boron-Containing Macrocyclic Polyamines and Their Zinc(II) Complexes for Boron Neutron Capture Therapy.Journal of medicinal chemistry · 2021Article
- Arylation Chemistry for Bioconjugation.Angewandte Chemie (International ed. in English) · 2019Review
- Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics.Organic & biomolecular chemistry · 2016Review
- Synthesis and properties of a series of carboranyl-BODIPYs.Journal of organometallic chemistry · 2015Article
- Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics.Chemical reviews · 2015Review
- Synthesis and in vitro evaluation of BBB permeability, tumor cell uptake, and cytotoxicity of a series of carboranylporphyrin conjugates.Journal of medicinal chemistry · 2014Article
- Synthesis and transformations of 5-chloro-2,2'-dipyrrins and their boron complexes, 8-chloro-BODIPYs.Chemistry (Weinheim an der Bergstrasse, Germany) · 2014Article
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Authors and funding
2 authors.
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Abstract
Seven polyamine conjugates of a tri(p-carboranylmethylthio)tetrafluorophenylporphyrin were prepared in high yields by sequential substitution of the p-phenyl fluoride of tetrakis(pentafluorophenyl)porphyrin (TPPF), and investigated as boron delivery agents for boron neutron capture therapy (BNCT). The polyamines used were derivatives of the natural-occurring spermine with different lengths of the carbon chains, terminal primary amine groups and, in two of the conjugates, additional aminoethyl moieties. A tri(polyethylene glycol) conjugate was also synthesized for comparison purposes. The polyamine conjugates showed low dark cytotoxicity (IC(50) >400 μM) and low phototoxicity (IC(50) >40 μM at 1.5 J/cm(2)). All polyamine conjugates, with one exception, showed higher uptake into human glioma T98G cells (up to 12-fold) than the PEG conjugate, and localized preferentially in the cell ER, Golgi and the lysosomes. Our results show that spermine derivatives can serve as effective carriers of boronated porphyrins for the BNCT of tumors.
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