Research output: Contribution to journal › Article › peer-review
Nido-Carborane Derivatives of (S)-Ornithine and (S)-Lysine as Potential Boron Delivery Agents : Synthesis and In Vitro Evaluation. / Gruzdev, Dmitry A; Levit, Galina L; Musiyak, Vera V et al.
In: International Journal of Molecular Sciences, Vol. 26, No. 17, 8560, 03.09.2025.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - Nido-Carborane Derivatives of (S)-Ornithine and (S)-Lysine as Potential Boron Delivery Agents
T2 - Synthesis and In Vitro Evaluation
AU - Gruzdev, Dmitry A
AU - Levit, Galina L
AU - Musiyak, Vera V
AU - Telegina, Angelina A
AU - Ganebnykh, Ilya N
AU - Ezhikova, Marina A
AU - Kodess, Mikhail I
AU - Solovieva, Olga I
AU - Gusel'nikova, Tatiana Y
AU - Razumov, Ivan A
AU - Krasnov, Victor P
N1 - This research was financially supported by the Ministry of Science and Higher Education of the Russian Federation (theme no. 124020200038-6 in part of the compounds synthesis and no. 124020500023-9 in part of in vitro evaluation).
PY - 2025/9/3
Y1 - 2025/9/3
N2 - Derivatives of natural amino acids are selectively absorbed by many types of tumour cells. This makes the use of amino acids, especially polyfunctional ones, attractive as a basis in the design of low-toxicity agents for targeted boron delivery for boron neutron capture therapy (BNCT) of tumours. We synthesized a series of new (S)-ornithine and (S)-lysine derivatives containing a 7,8-dicarba-nido-undecaborane (nido-carborane) residue attached to the amino group in the side chain or alpha position. The MTT assay demonstrated moderate cytotoxicity of the lysine and ornithine derivatives containing a nido-carborane residue in the side chain. It has been found that sodium salt of Nε-(nido-carboran-7-yl)acetyl-(S)-lysine is capable of accumulation by MDA-MB-231 (human breast carcinoma) and SK-Mel 28 (human melanoma) cell lines, providing a boron concentration of up to 0.67 µg/106 cells in in vitro experiments. This (S)-lysine derivative containing a nido-carborane residue in the side chain can be considered as a promising compound for in-depth study in vivo experiments aimed at designing an efficient boron delivery agent for BNCT.
AB - Derivatives of natural amino acids are selectively absorbed by many types of tumour cells. This makes the use of amino acids, especially polyfunctional ones, attractive as a basis in the design of low-toxicity agents for targeted boron delivery for boron neutron capture therapy (BNCT) of tumours. We synthesized a series of new (S)-ornithine and (S)-lysine derivatives containing a 7,8-dicarba-nido-undecaborane (nido-carborane) residue attached to the amino group in the side chain or alpha position. The MTT assay demonstrated moderate cytotoxicity of the lysine and ornithine derivatives containing a nido-carborane residue in the side chain. It has been found that sodium salt of Nε-(nido-carboran-7-yl)acetyl-(S)-lysine is capable of accumulation by MDA-MB-231 (human breast carcinoma) and SK-Mel 28 (human melanoma) cell lines, providing a boron concentration of up to 0.67 µg/106 cells in in vitro experiments. This (S)-lysine derivative containing a nido-carborane residue in the side chain can be considered as a promising compound for in-depth study in vivo experiments aimed at designing an efficient boron delivery agent for BNCT.
KW - Humans
KW - Lysine/chemistry
KW - Cell Line, Tumor
KW - Ornithine/chemistry
KW - Boron Neutron Capture Therapy/methods
KW - Boron/chemistry
KW - Boron Compounds/chemistry
KW - Boranes/chemistry
KW - Cell Survival/drug effects
UR - https://www.scopus.com/pages/publications/105015894456
U2 - 10.3390/ijms26178560
DO - 10.3390/ijms26178560
M3 - Article
C2 - 40943478
VL - 26
JO - International Journal of Molecular Sciences
JF - International Journal of Molecular Sciences
SN - 1661-6596
IS - 17
M1 - 8560
ER -
ID: 69753741