PMID: 11606130Oct 19, 2001Paper

N-Benzylpolyamines as vectors of boron and fluorine for cancer therapy and imaging: synthesis and biological evaluation

Journal of Medicinal Chemistry
B MartinJean-Guy Delcros

Abstract

Cancer cells have high-affinity polyamine uptake systems with a low stringency for structural features. Putrescine, spermidine, and spermine have, therefore, been considered as potential vectors for the selective accumulation in tumors of therapeutically or diagnostically useful structures and elements. We envisaged N-benzyl derivatives of the polyamines as vectors of (10)B and (18)F for boron neutron capture therapy (BNCT) and tumor imaging by positron emission tomography (PET), respectively. In the present work, the synthesis, transport characteristics, DNA-binding properties, and cytotoxicity of several N-benzyl derivatives of putrescine and spermidine are described. The fluorinated spermidine derivative N-(3-[(4-aminobutyl)amino]propyl)[(4-fluorophenyl)methyl]amine (N(1)-4-Fbz-spd) may be useful for PET because of its high accumulation in cancer cells via the polyamine transport system. Among the boron-containing benzyl polyamines, N-(4-aminobutyl)([4-(dihydroxyboryl)phenyl]methyl)amine (4-Bbz-put) and N-(3-[(4-aminobutyl)amino]propyl)([4-(dihydroxyboryl)phenyl]methyl)amine (N(1)-4-Bbz-spd) should be suitable for BNCT, because their accumulation in B16 melanoma cells was more efficient than that of borocaptate and boropheny...Continue Reading

References

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Citations

Oct 10, 2002·Bioorganic & Medicinal Chemistry Letters·Emerson T SilvaEdson L S Lima
Apr 17, 2008·The Journal of Organic Chemistry·Gary A Molander, David J Cooper
Apr 15, 2004·Biochemical Pharmacology·François GaboriauGérard Lescoat
Nov 23, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Simin S HosseiniLouis M Rendina
Jun 3, 2005·Clinical Cancer Research : an Official Journal of the American Association for Cancer Research·Rolf F BarthThomas E Blue
Oct 12, 2010·Journal of Medicinal Chemistry·Sophie TomasiJean-Guy Delcros
Nov 20, 2004·The Journal of Organic Chemistry·George W Kabalka, Min-Liang Yao

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