Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, IN 46556, USA.
Molecules. 2022 Aug 25;27(17):5440. doi: 10.3390/molecules27175440.
Two new azobenzene heptamethine cyanine conjugates exist as dispersed monomeric molecules in methanol solution and exhibit near-infrared (NIR) cyanine absorption and fluorescence. Both conjugates form non-emissive cyanine H-aggregates in water, but the addition of cucurbit[7]uril (CB7) induces dye deaggregation and a large increase in cyanine NIR fluorescence emission intensity. CB7 encapsulates the protonated azonium tautomer of the 4-(,-dimethylamino)azobenzene component of each azobenzene-cyanine conjugate and produces a distinctive new absorption band at 534 nm. The complex is quite hydrophilic, which suggests that CB7 can be used as a supramolecular additive to solubilize this new family of NIR azobenzene-cyanine conjugates for future biomedical applications. Since many azobenzene compounds are themselves potential drug candidates or theranostic agents, it should be possible to formulate many of them as CB7 inclusion complexes with improved solubility, stability, and pharmaceutical profile.
两种新的偶氮苯七甲川菁染料以分散的单体分子形式存在于甲醇溶液中，具有近红外（NIR）菁染料的吸收和荧光。两种化合物在水中形成非发光的菁 H 聚集体，但加入葫芦[7]脲（CB7）会导致染料解聚，并使菁染料 NIR 荧光发射强度大大增加。CB7 包封每个偶氮苯-菁染料缀合物中 4-（，-二甲基氨基）偶氮苯部分的质子化重氮互变异构体，并在 534nm 处产生独特的新吸收带。该配合物具有很好的亲水性，这表明 CB7 可以用作超分子添加剂，用于溶解这一系列新的近红外偶氮苯-菁染料，用于未来的生物医学应用。由于许多偶氮苯化合物本身就是潜在的药物候选物或治疗诊断试剂，因此有可能将它们中的许多制成 CB7 包合物，以提高其溶解度、稳定性和药物特性。
