Collect. Czech. Chem. Commun.
2007, 72, 1707-1716
https://doi.org/10.1135/cccc20071707
Boronated Conjugates of Protohemin IX with L-Amino Acids: Synthesis and Antitumor Activity
Valentina A. Olshevskayaa,*, Arina N. Savchenkoa, Alexander Yu. Gorshkovb, Valentina N. Luzginab, Victor V. Tatarskii, Jr.c, Elena G. Kononovaa, Chan Seong Cheongd, Valery N. Kalinina and Alexander A. Shtilc
a Laboratory of Fine Organic Synthesis, A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation
b Laboratory of Chemistry and Technology of Biological Active Compounds, M. V. Lomonosov Moscow State Academy of Fine Chemical Technology, 119571 Moscow, Russian Federation
c Laboratory of Tumor Cell Death, N. N. Blokhin Cancer Center, 115478, Moscow, Russian Federation
d Life Sciences Division, Korea Institute of Science and Technology, 130-650 Seoul, Korea
Abstract
We report the synthesis of novel conjugates of protohemin IX with neutral and anionic boron polyhedra and L-amino acids. The amino acids are linked to the porphyrin macrocycle via the amide or ester bond. The serine containing boronated protohemin was the most cytotoxic for K562 human leukemia cell line. This compound interacted with double-stranded DNA in vitro and caused apoptosis of tumor cells including those that are resistant to several chemotherapeutic drugs.
Keywords: Protohemin IX; L-Amino acids; Cytotoxicity; DNA fragmentation; Antitumor drugs.
References: 17 live references.
