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New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their "Click" Chemistry Reactions for the Conjugation with closo-Dodecaborate Anion.

ABSTRACT: Novel fluorescent 7-methoxy- and 7-(diethylamino)-coumarins modified with azido-group on the side chain have been synthesized. Their photophysical properties and single crystals structure characteristics have been studied. In order to demonstrate the possibilities of fluorescent labeling, obtained coumarins have been tested with closo-dodecaborate derivative bearing terminal alkynyl group. CuI catalyzed Huisgen 1,3-dipolar cycloaddition reaction has led to fluorescent conjugates formation. The absorption-emission spectra of the formed conjugates have been presented. The antiproliferative activity and uptake of compounds against several human cell lines were evaluated.

SUBMITTER: Laskova J

PROVIDER: S-EPMC9738631 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their "Click" Chemistry Reactions for the Conjugation with closo-Dodecaborate Anion.

Laskova Julia J Serdyukov Alexander A Kosenko Irina I Ananyev Ivan I Titova Ekaterina E Druzina Anna A Sivaev Igor I Antonets Anastasia A AA Nazarov Alexey A AA Bregadze Vladimir I VI

Molecules (Basel, Switzerland) 20221205 23

Novel fluorescent 7-methoxy- and 7-(diethylamino)-coumarins modified with azido-group on the side chain have been synthesized. Their photophysical properties and single crystals structure characteristics have been studied. In order to demonstrate the possibilities of fluorescent labeling, obtained coumarins have been tested with closo-dodecaborate derivative bearing terminal alkynyl group. CuI catalyzed Huisgen 1,3-dipolar cycloaddition reaction has led to fluorescent conjugate ...[more]

PMID: 36500667

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Project description:In vivo deastatination has been a major problem in the development of reagents for therapeutic applications of the alpha-particle emitting radionuclide (211)At. Our prior studies demonstrated that the use of a closo-decaborate(2-) ([closo-B(10)H(9)R](2-)) moiety for (211)At labeling of biomolecules provides conjugates that are stable to in vivo deastatination. In this investigation, the closo-decaborate(2-) moiety was compared with the structurally similar closo-dodecaborate(2-) ([closo-B(12)H(11)R](2-)) to determine if one has more favorable properties than the other for use in pendant groups as (211)At labeling molecules. To determine the differences, two sets of structurally identical molecules, with the exception that they contained either a closo-decaborate(2-) or a closo-dodecaborate(2-) moiety, were compared with regard to their synthesis, radiohalogenation, stability to in vivo deastatination and tissue distribution. Quite different rates of reaction were noted in the synthetic steps for the two closo-borate(2-) moieties, but ultimately the yields were similar, making these differences of little importance. Differences in radiohalogenation rates were also noted between the two closo-borate(2-) moieties, with the more electrophilic closo-decaborate(2-) reacting more rapidly. This resulted in somewhat higher yields of astatinated closo-decaborate(2-) derivatives (84% vs 53%), but both cage moieties gave good radioiodination yields (e.g., 79-96%). Importantly, both closo-borate(2-) cage moieties were shown to have high stability to in vivo deastatination. The largest differences between pairs of compounds containing the structurally similar boron cage moieties were in their in vivo tissue distributions. For example, [Et(3)NH](2)B(12)H(10)I-CONHpropyl, [(125)I]2b had high concentrations in kidney (1 h, 19.8%ID/g; 4 h, 26.5%ID/g), whereas [Et(3)NH](2)B(10)H(8)I-CONHpropyl, [(125)I]1e had much lower concentrations in kidney (1 h, 6.6%ID/g; 4 h, 0.27%ID/g). Interestingly, when another salt of the closo-decaborate(2-), [nBu(4)N](2)B(10)H(8)I-CONHpropyl, [(125)I]1b, was evaluated, the route of excretion appeared to be hepatobiliary rather than renal. Identical biotin derivatives containing the two closo-borate(2-) cage moieties had similar tissue distributions, except the closo-decaborate(2-) derivative had lower concentrations in kidney (1 h, 19.9%ID/g; 4 h, 24.4%ID/g vs 1 h, 38.9%ID/g; 4 h, 40.6%ID/g). In summary, the higher reactivity, faster tissue clearance, and lower kidney concentrations make the closo-decaborate(2-) more favorable for further studies using them in reactive groups for (211)At labeling of biomolecules.

Dataset Information

New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their "Click" Chemistry Reactions for the Conjugation with closo-Dodecaborate Anion.

Publications

New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their "Click" Chemistry Reactions for the Conjugation with <i>closo</i>-Dodecaborate Anion.

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