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WazaGaY: An Innovative Aza-BODIPY-Derived Near-Infrared Fluorescent Probe for Enhanced Tumor Imaging
Journal of Medicinal Chemistry ( IF 6.8 ) Pub Date : 2024-09-17 , DOI: 10.1021/acs.jmedchem.4c01435 Mohamed Bendellaa 1 , Charlotte Cave 2 , Amélie Godard 2 , Fabien Dalonneau 1 , Annika Sickinger 3 , Christine Goze 2 , Olivier Maury 3 , Pierre Le Gendre 2 , Ewen Bodio 2, 4, 5 , Benoit Busser 1, 5, 6 , Lucie Sancey 1
Journal of Medicinal Chemistry ( IF 6.8 ) Pub Date : 2024-09-17 , DOI: 10.1021/acs.jmedchem.4c01435 Mohamed Bendellaa 1 , Charlotte Cave 2 , Amélie Godard 2 , Fabien Dalonneau 1 , Annika Sickinger 3 , Christine Goze 2 , Olivier Maury 3 , Pierre Le Gendre 2 , Ewen Bodio 2, 4, 5 , Benoit Busser 1, 5, 6 , Lucie Sancey 1
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Aza-BODIPYs represent a class of fluorophores in which the π-conjugated system is rigidified and stabilized by a boron atom. A promising strategy to enhance their fluorescence properties involves replacing the boron atom with a metal ion. Here, we describe the synthesis and characterization of a water-soluble derivative where the metal is a gallium(III) ion, termed WazaGaY (water-soluble aza-GaDIPY). Water solubility is ensured by two ammonium substituents, inducing a bathochromic shift and a significant increase in quantum yield compared to that of the dimethylamino analog. The cellular behavior of WazaGaY-1 was observed across different tumor cells. In vivo, the distribution and safety profiles were determined, and tumor uptake was assessed in various tumor types. Following intravenous injection, WazaGaY-1 enabled clear discrimination of tumors engrafted subcutaneously in mice with high tumor-to-muscle ratios (ranging from 7 to 20), even in the absence of specific conjugation. Its potential as a contrast agent for fluorescence-guided surgery was confirmed.
中文翻译：
WazaGaY：一种用于增强肿瘤成像的创新型 Aza-BODIPY 衍生的近红外荧光探针
Aza-BODIPYs 代表一类荧光团，其中 π 偶联系统由硼原子刚性化和稳定化。增强其荧光特性的一种有前途的策略是用金属离子取代硼原子。在这里，我们描述了一种水溶性衍生物的合成和表征，其中金属是镓 （III） 离子，称为 WazaGaY（水溶性 aza-GaDIPY）。两个铵态取代基确保了水溶性，与二甲基氨基类似物相比，诱导了浴变色偏移和量子产率的显著增加。在不同的肿瘤细胞中观察到 WazaGaY-1 的细胞行为。在体内，确定了分布和安全性特征，并评估了各种肿瘤类型的肿瘤摄取。静脉注射后，WazaGaY-1 能够清楚地区分肿瘤与肌肉比高（范围为 7 到 20）的小鼠皮下移植的肿瘤，即使没有特异性结合。它作为荧光引导手术造影剂的潜力得到证实。
更新日期：2024-09-17
中文翻译：
WazaGaY：一种用于增强肿瘤成像的创新型 Aza-BODIPY 衍生的近红外荧光探针
Aza-BODIPYs 代表一类荧光团，其中 π 偶联系统由硼原子刚性化和稳定化。增强其荧光特性的一种有前途的策略是用金属离子取代硼原子。在这里，我们描述了一种水溶性衍生物的合成和表征，其中金属是镓 （III） 离子，称为 WazaGaY（水溶性 aza-GaDIPY）。两个铵态取代基确保了水溶性，与二甲基氨基类似物相比，诱导了浴变色偏移和量子产率的显著增加。在不同的肿瘤细胞中观察到 WazaGaY-1 的细胞行为。在体内，确定了分布和安全性特征，并评估了各种肿瘤类型的肿瘤摄取。静脉注射后，WazaGaY-1 能够清楚地区分肿瘤与肌肉比高（范围为 7 到 20）的小鼠皮下移植的肿瘤，即使没有特异性结合。它作为荧光引导手术造影剂的潜力得到证实。
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