Pharmacokinetics, Pharmacodynamics and Drug Metabolism, Merck & Co., Inc., Rahway, NJ, 07065, USA.
J Am Soc Mass Spectrom. 2019 Sep;30(9):1779-1789. doi: 10.1007/s13361-019-02257-9. Epub 2019 Jun 27.
Peptides represent a promising modality for the design of novel therapeutics that can potentially modulate traditionally non-druggable targets. Cell-penetrating peptides (CPPs) and antimicrobial peptides (AMPs) are two large families that are being explored extensively as drug delivery vehicles, imaging reagents, or therapeutic treatments for various diseases. Many CPPs and AMPs are cationic among which a significant portion is extremely basic and hydrophilic (e.g., nona-arginine). Despite their attractive therapeutic potential, it remains challenging to directly analyze and quantify these super cationic peptides from biological matrices due to their poor chromatographic behavior and MS response. Herein, we describe a generic method that combines solid phase extraction and LC-MS/MS for analysis of these peptides. As demonstrated, using a dozen strongly basic peptides, low μM concentration of perfluoropentanoic acid (PFPeA) in the mobile phase enabled excellent compound chromatographic retention, thus avoiding co-elution with solvent front ion suppressants. PFPeA also had a charge reduction effect that allowed the selection of parent/ion fragment pairs in the higher m/z region to further reduce potential low molecular weight interferences. When the method was coupled to the optimized sample extraction process, we routinely achieved low digit ng/ml sensitivity for peptides in plasma/tissue. The method allowed an efficient evaluation of plasma stability of CPPs/AMPs without fluorescence derivatization or other tagging methods. Importantly, using the widely studied HIV-TAT CPP as an example, the method enabled us to directly assess its pharmacokinetics and tissue distribution in preclinical animal models.
肽代表了一类有前途的新型治疗药物设计模式,这些药物可能调节传统上不可成药的靶标。细胞穿透肽(CPP)和抗菌肽(AMP)是两个正在被广泛探索的大家族,它们被用作药物递送载体、成像试剂或治疗各种疾病的治疗方法。许多 CPP 和 AMP 是阳离子的,其中很大一部分是非常碱性和亲水性的(例如,九聚精氨酸)。尽管它们具有诱人的治疗潜力,但由于其较差的色谱行为和 MS 响应,直接从生物基质中分析和定量这些超阳离子肽仍然具有挑战性。本文描述了一种通用方法,该方法结合固相萃取和 LC-MS/MS 用于分析这些肽。如所证明的,使用十几个强碱性肽,流动相中低 μM 浓度的全氟戊酸(PFPeA)可实现化合物的出色色谱保留,从而避免与溶剂前沿离子抑制剂共洗脱。PFPeA 还具有电荷还原作用,可选择较高 m/z 区域中的母/离子碎片对,以进一步减少潜在的低分子量干扰。当该方法与优化的样品提取过程结合使用时,我们能够在血浆/组织中常规实现低至数字 ng/ml 的肽灵敏度。该方法允许在不进行荧光衍生化或其他标记方法的情况下,对 CPP/AMP 的血浆稳定性进行有效评估。重要的是,以广泛研究的 HIV-TAT CPP 为例,该方法使我们能够直接评估其在临床前动物模型中的药代动力学和组织分布。