Aloisi Adriano, Franchet Adrien, Ferrandon Dominique, Bianco Alberto, Ménard-Moyon Cécilia
University of Strasbourg, CNRS, Immunology, Immunopathology and Therapeutic Chemistry, UPR 3572, 67000 Strasbourg, France.
CNRS, M3I UPR 9022, Université de Strasbourg, Strasbourg, France.
Bioorg Med Chem Lett. 2018 Aug 15;28(15):2631-2635. doi: 10.1016/j.bmcl.2018.06.036. Epub 2018 Jun 19.
Fipronil is a phenyl pyrazole molecule widely used across the world as both insecticide and veterinary drug. The main goal of this work was to synthesize a fluorescently labeled fipronil derivative for cellular imaging without affecting its intrinsic properties. We selected fluorescein as fluorescent probe and we investigated different strategies for stable chemical ligation between both entities, such as thiourea and direct peptide bond. While thiourea bond displayed low stability, direct peptide bond was difficult to achieve due to problems of steric hindrance. The best result was obtained by conjugation using click chemistry, which allowed to obtain fipronil stably labeled with the fluorescent probe.
氟虫腈是一种苯基吡唑分子，在全球广泛用作杀虫剂和兽药。这项工作的主要目标是合成一种荧光标记的氟虫腈衍生物用于细胞成像，同时不影响其固有特性。我们选择荧光素作为荧光探针，并研究了两种实体之间稳定化学连接的不同策略，如硫脲和直接肽键。虽然硫脲键稳定性较低，但由于空间位阻问题，直接肽键难以实现。通过点击化学进行共轭获得了最佳结果，这使得能够获得用荧光探针稳定标记的氟虫腈。
