Abstract
A fluorescent analogue of the lipophilic prodrug of antitumor agent methotrexate has been synthesized. The conjugate consists of a residue of rac-1-[13-(Me4-BODIPY-8)tridecanoyl]-2-oleoylglycerol connected to methotrexate by an ester bond via β-Ala-N-carbonylmethylene linker (Me4-BODIPY-8 stands for 4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene-8-yl). The probe is designed for incorporation in the membrane of the liposomal vehicle to study a mechanism of interaction with tumor cells and intracellular traffic.
Abbreviations
- MTX:
-
methotrexate
- MTX-DG:
-
rac-1,2-dioleoylglyceride conjugate of MTX
- DHFR:
-
dihydrofolate reductase
- RFC:
-
reduced folate carrier
- Me4-BODIPY-8, or BDP:
-
4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene-8-yl
- Gro:
-
glycerol
- Ole:
-
oleoyl (9Z-heptadecenyl-17-carbonyl)
- TEA:
-
triethylamine
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Original Russian Text © Yu.V. Vlasenko, A.S. Alekseeva, E.L. Vodovozova, 2014, published in Bioorganicheskaya Khimiya, 2014, Vol. 40, No. 1, pp. 125–128.
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Vlasenko, Y.V., Alekseeva, A.S. & Vodovozova, E.L. Synthesis of a fluorescent analogue of methotrexate lipophilic prodrug. Russ J Bioorg Chem 40, 114–117 (2014). https://doi.org/10.1134/S1068162014010129
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DOI: https://doi.org/10.1134/S1068162014010129