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Crystallographic report: Synthesis and biological evaluation of novel azanonaboranes as potential agents for boron neutron capture therapy
Author(s) -
ElZaria Mohamed E.
Publication year - 2005
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.786
Subject(s) - chemistry , spermidine , polyamine , spermine , boron , in vivo , in vitro , diamine , lewis lung carcinoma , nuclear chemistry , stereochemistry , radiochemistry , cancer , organic chemistry , biochemistry , enzyme , medicine , metastasis , microbiology and biotechnology , biology
A number of (hydroxyalkylamine)‐ N ‐(aminoalkyl)azanonaborane(11) derivatives have been synthesized to provide azanonaboranes with different hydrophilic functional groups for use in the treatment of cancer by boron neutron capture therapy (BNCT). The exo‐diamine group of (aminoalkylamine)‐ N ‐(aminoalkyl)azanonaborane(11) {H 2 N(CH 2 ) m H 2 NB 8 H 11 NH(CH 2 ) m NH 2 , where m = 4–6} can be substituted by amino alcohol ligands {HO(CH 2 ) n NH 2 , where n = 3 and 4} to give azanonaboranes containing free amino and hydroxy groups: (3‐hydroxypropylamine)‐ N ‐(aminobutyl)azanonaborane(11) {HO(CH 2 ) 3 H 2 NB 8 H 11 NH(CH 2 ) 4 NH 2 }, 1 ; (4‐hydroxybutylamine)‐ N ‐ (aminobutyl)azanonaborane(11) {HO(CH 2 ) 4 H 2 NB 8 H 11 NH(CH 2 ) 4 NH 2 }, 2 ; (3‐hydroxypropylamine)‐ N ‐ (aminopentyl)azanonaborane(11) {HO(CH 2 ) 3 H 2 NB 8 H 11 NH(CH 2 ) 5 NH 2 }, 3 ; (4‐hydroxypropylamine)‐ N ‐(aminopentyl)azanonaborane(11) {HO(CH 2 ) 4 H 2 NB 8 H 11 NH(CH 2 ) 5 NH 2 }, 4 ; (3‐hydroxypropylamine)‐ N ‐(aminohexyl)azanonaborane(11) {HO(CH 2 ) 3 H 2 NB 8 H 11 NH(CH 2 ) 6 NH 2 }, 5 . The in vitro toxicity test using Chinese hamster‐V79 cells showed that compounds 1 – 3 were less toxic (LD 50 value of ∼2.3, 1.7 and 1.4 m M , respectively) than spermine and spermidine (LD 50 value of ∼0.88 and 0.66 m M , respectively). In vivo distribution experiments of these compounds in Lewis lung carcinoma and B16 melanoma tumor‐bearing mice showed that boron can be found in tumor tissue. The compounds prepared can be considered as a new class of boron containing polyamine compounds that may be useful for boron neutron capture therapy of tumors. Copyright © 2005 John Wiley & Sons, Ltd.