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Fluorescent Guanidinium-Azacarbazole for Oxoanion Binding in Water
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-08-02 , DOI: 10.1021/acs.joc.3c00982
Lindsey O Calabretta 1 , Yana D Petri 1 , Ronald T Raines 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-08-02 , DOI: 10.1021/acs.joc.3c00982
Lindsey O Calabretta 1 , Yana D Petri 1 , Ronald T Raines 1
Affiliation
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Oxoanions such as carboxylates, phosphates, and sulfates play important roles in both chemistry and biology and are abundant on the cell surface. We report on the synthesis and properties of a rationally designed guanidinium-containing oxoanion binder, 1-guanidino-8-amino-2,7-diazacarbazole (GADAC). GADAC binds to a carboxylate, phosphate, and sulfate in pure water with affinities of 3.6 × 104, 1.1 × 103, and 4.2 × 103 M–1, respectively. Like 2-azacarbazole, which is a natural product that enables scorpions to fluoresce, GADAC is fluorescent in water (λabs = 356 nm, λem = 403 nm, ε = 13,400 M–1 cm–1). The quantum yield of GADAC is pH-sensitive, increasing from Φ = 0.12 at pH 7.4 to Φ = 0.53 at pH 4.0 as a result of the protonation of the aminopyridine moiety. The uptake of GADAC into live human melanoma cells is detectable in the DAPI channel at low micromolar concentrations. Its properties make GADAC a promising candidate for applications in oxoanion binding and fluorescence labeling in biological (e.g., the delivery of cargo into cells) and other contexts.
中文翻译:
荧光胍-氮杂咔唑用于水中氧阴离子结合
含氧阴离子,如羧酸根、磷酸根和硫酸根,在化学和生物学中发挥着重要作用,并且在细胞表面大量存在。我们报告了合理设计的含胍含氧阴离子结合剂 1-胍基-8-氨基-2,7-二氮杂咔唑 (GADAC) 的合成和性能。GADAC 在纯水中与羧酸盐、磷酸盐和硫酸盐结合,亲和力分别为 3.6 × 10 4、1.1 × 10 3和 4.2 × 10 3 M –1。与 2-氮杂咔唑(一种能使蝎子发出荧光的天然产物)一样,GADAC 在水中也会发出荧光(λabs = 356 nm,λ em = 403 nm,ε = 13,400 M –1 cm –1)。GADAC 的量子产率对 pH 值敏感,由于氨基吡啶部分的质子化,从 pH 7.4 时的 Φ = 0.12 增加到 pH 4.0 时的 Φ = 0.53。在低微摩尔浓度的 DAPI 通道中可以检测到活人黑色素瘤细胞对 GADAC 的摄取。其特性使 GADAC 成为生物(例如,将货物递送到细胞中)和其他环境中的含氧阴离子结合和荧光标记应用的有前途的候选者。
更新日期:2023-08-03
中文翻译:
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荧光胍-氮杂咔唑用于水中氧阴离子结合
含氧阴离子,如羧酸根、磷酸根和硫酸根,在化学和生物学中发挥着重要作用,并且在细胞表面大量存在。我们报告了合理设计的含胍含氧阴离子结合剂 1-胍基-8-氨基-2,7-二氮杂咔唑 (GADAC) 的合成和性能。GADAC 在纯水中与羧酸盐、磷酸盐和硫酸盐结合,亲和力分别为 3.6 × 10 4、1.1 × 10 3和 4.2 × 10 3 M –1。与 2-氮杂咔唑(一种能使蝎子发出荧光的天然产物)一样,GADAC 在水中也会发出荧光(λabs = 356 nm,λ em = 403 nm,ε = 13,400 M –1 cm –1)。GADAC 的量子产率对 pH 值敏感,由于氨基吡啶部分的质子化,从 pH 7.4 时的 Φ = 0.12 增加到 pH 4.0 时的 Φ = 0.53。在低微摩尔浓度的 DAPI 通道中可以检测到活人黑色素瘤细胞对 GADAC 的摄取。其特性使 GADAC 成为生物(例如,将货物递送到细胞中)和其他环境中的含氧阴离子结合和荧光标记应用的有前途的候选者。