Apigenin, a flavone abundant in parsley and celery, is known to act on several CNS receptors, but its very poor water solubility (<0.001 mg/mL) impedes its absorption in vivo and prevents clinical use. Herein, apigenin was directly conjugated with glycine, l-phenylalanine, and l-lysine to give the corresponding carbamate derivatives, all of which were much more soluble than apigenin itself (0.017, 0.018, and 0.13 mg/mL, respectively). The Lys-apigenin carbamate 10 had a temporary sedative effect on the mice within 5 min of intraperitoneal administration (single dose of 0.4 mg/g) and could be detected in the mice brain tissues at a concentration of 0.82 μg/g of intact Lys-apigenin carbamate 10 and 0.42 ug/g of apigenin at 1.5 h. This study accomplished the delivery of apigenin across the BBB in a manner that might be applicable to other congeners, which should inform the future development of BBB-crossing flavonoids.

中文翻译：

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芹菜素的可切割l-赖氨酸结合物穿越血脑屏障

芹菜素是一种在欧芹和芹菜中丰富的黄酮，已知可作用于几种中枢神经系统受体，但其极差的水溶性（<0.001 mg / mL）阻碍了其在体内的吸收并阻止了临床使用。在本文中，芹菜素直接与甘氨酸，1-苯丙氨酸和1-赖氨酸偶联，得到相应的氨基甲酸酯衍生物，所有这些衍生物均比芹菜素本身更易溶（分别为0.017、0.018和0.13 mg / mL）。Lys-芹菜素氨基甲酸酯10在腹膜内给药5分钟内（单剂量0.4 mg / g）对小鼠具有暂时的镇静作用，并且可以在小鼠脑组织中以0.82μg/ g的完整Lys-芹菜素氨基甲酸酯10在1.5 h时为0.42 ug / g芹菜素。这项研究以可能适用于其他同源物的方式完成了芹菜素跨BBB的递送，这应该为穿越BBB的类黄酮的未来发展提供信息。