Synthesis and Properties of Fluorescent cycloSal Nucleotides Based on the Pyrimidine Nucleoside m⁵K and Its 2′,3′‐Dideoxy Analog dm⁵K

Abstract

The synthesis of the fluorescent thymidine nucleoside analog 5-methyl-pyrimidin-2-one nucleoside 1 (m 5 K) and that of its 2Ј,3Ј-dideoxy derivative 2 (dm 5 K) are described. Moreover, the conversion of 1 and 2 into the corresponding 3-methylcycloSal-phosphate triesters 11 and 12 or an enzyme-cleavable prodrug 5-acetoxymethylpropionate-cycloSal-phosphate triester 13, and the fluorescence and hydrolysis proper-

Synthesis and evaluation of thymidine kinase 1-targeting carboranyl pyrimidine nucleoside analogs for boron neutron capture therapy of cancer

“…The reaction was carried at 80°C for 3 days without solvent to produce compounds 25 – 27 in 12–48% yields. Aminolysis was carried out with 3′,5′-TBDMS-protected nucleoside in accordance with a previously reported procedure [39]. …”

“…The reaction of compound 31 [39] with 1-(2-aminoethyl)- closo -1,7-carborane [35], 1-(3-aminopropyl)- closo -1,7-carborane [35], or 1-(4-aminobutyl)- closo -1,7-carborane [35] at 60°C in CH 3 CN overnight gave 32 , 33 , and 34 in 87%, 40%, and 94% yield, respectively. The TBDMS-groups of 32 – 34 were removed by treatment with TBAF in THF for 2 h at room temperature to produce N4-carboranylalkyl-5-methyl-2′-deoxycytidine analogues 35 , 36 , 37 in 86%, 95%, and 97% yield, respectively.…”

“…Other chemicals used for synthesis were purchased from standard commercial vendors. 1-(2-Iodoethyl)- closo -1,7-carborane [35], 1-(3-iodopropyl)- closo -1,7-carborane [35], 1-(4-iodobutyl)- closo -1,7-carborane [35], 1-(2-aminoethyl)- closo -1,7-carborane [35], 1-(3-aminopropyl)- closo -1,7-carborane [35], and 1-(4-aminobutyl)- closo -1,7-carborane [35], as well as compounds 2 [32], 3 [31], 4 [31], 5 [34], 10 [29], 23 [37], and 31 [39] were synthesized according to previously described procedures. Spectroscopic data for compounds 2 – 5 , 10 , and 31 are provided in SM.…”

“…A mixture of compound 31 [39] (52 mg, 0.1 mmol) and aminoalkyl- closo -1,7-carborane [35] (0.3 mmol) in anhydrous CH 3 CN (2 mL) was refluxed overnight. The solvent was evaporated and residue was purified by silica gel column chromatography DCM/acetone (9/1, v/v) as the solvent system to produce a white amorphous solid.…”

Use of Drosophila deoxynucleoside kinase to study mechanism of toxicity and mutagenicity of deoxycytidine analogs in Escherichia coli

“…To quantify dZeb, we used fluorescence properties of this base analog [27]. First, fluorescence intensity of different concentrations of a 26-mer duplex ( Z -duplex) containing a single zebularine base was used create a calibration curve.…”