Ramsay Rona R, Majekova Magdalena, Medina Milagros, Valoti Massimo
Biomedical Sciences Research Complex, University of St. Andrews St. Andrews, UK.
Department of Biochemical Pharmacology, Institute of Experimental Pharmacology and Toxicology, Slovak Academy of Sciences Bratislava, Slovakia.
Front Neurosci. 2016 Aug 22;10:375. doi: 10.3389/fnins.2016.00375. eCollection 2016.
HIGHLIGHTS Compounds that interact with multiple targets but minimally with the cytochrome P450 system (CYP) address the many factors leading to neurodegeneration.Acetyl- and Butyryl-cholineEsterases (AChE, BChE) and Monoamine Oxidases A/B (MAO A, MAO B) are targets for Multi-Target Designed Ligands (MTDL).ASS234 is an irreversible inhibitor of MAO A >MAO B and has micromolar potency against the cholinesterases.ASS234 is a poor CYP substrate in human liver, yielding the depropargylated metabolite.SMe1EC2, a stobadine derivative, showed high radical scavenging property, in vitro and in vivo giving protection in head trauma and diabetic damage of endothelium.Control of mitochondrial function and morphology by manipulating fission and fusion is emerging as a target area for therapeutic strategies to decrease the pathological outcome of neurodegenerative diseases. Growing evidence supports the view that neurodegenerative diseases have multiple and common mechanisms in their aetiologies. These multifactorial aspects have changed the broadly common assumption that selective drugs are superior to "dirty drugs" for use in therapy. This drives the research in studies of novel compounds that might have multiple action mechanisms. In neurodegeneration, loss of neuronal signaling is a major cause of the symptoms, so preservation of neurotransmitters by inhibiting the breakdown enzymes is a first approach. Acetylcholinesterase (AChE) inhibitors are the drugs preferentially used in AD and that one of these, rivastigmine, is licensed also for PD. Several studies have shown that monoamine oxidase (MAO) B, located mainly in glial cells, increases with age and is elevated in Alzheimer (AD) and Parkinson's Disease's (PD). Deprenyl, a MAO B inhibitor, significantly delays the initiation of levodopa treatment in PD patients. These indications underline that AChE and MAO are considered a necessary part of multi-target designed ligands (MTDL). However, both of these targets are simply symptomatic treatment so if new drugs are to prevent degeneration rather than compensate for loss of neurotransmitters, then oxidative stress and mitochondrial events must also be targeted. MAO inhibitors can protect neurons from apoptosis by mechanisms unrelated to enzyme inhibition. Understanding the involvement of MAO and other proteins in the induction and regulation of the apoptosis in mitochondria will aid progress toward strategies to prevent the loss of neurons. In general, the oxidative stress observed both in PD and AD indicate that antioxidant properties are a desirable part of MTDL molecules. After two or more properties are incorporated into one molecule, the passage from a lead compound to a therapeutic tool is strictly linked to its pharmacokinetic and toxicity. In this context the interaction of any new molecules with cytochrome P450 and other xenobiotic metabolic processes is a crucial point. The present review covers the biochemistry of enzymes targeted in the design of drugs against neurodegeneration and the cytochrome P450-dependent metabolism of MTDLs.
与多个靶点相互作用但与细胞色素P450系统(CYP)相互作用最小的化合物可解决导致神经退行性变的多种因素。乙酰胆碱酯酶和丁酰胆碱酯酶(AChE、BChE)以及单胺氧化酶A/B(MAO A、MAO B)是多靶点设计配体(MTDL)的靶点。ASS234是一种不可逆的MAO A>MAO B抑制剂,对胆碱酯酶具有微摩尔效力。ASS234在人肝脏中是一种不良的CYP底物,可产生去炔丙基代谢物。SMe1EC2是一种司巴丁衍生物,具有高自由基清除特性,在体外和体内对头外伤和糖尿病性内皮损伤均有保护作用。通过操纵分裂和融合来控制线粒体功能和形态正在成为减少神经退行性疾病病理结果的治疗策略的一个目标领域。越来越多的证据支持神经退行性疾病在病因上具有多种共同机制的观点。这些多因素方面改变了广泛存在的一种普遍假设,即选择性药物在治疗中优于“脏药物”。这推动了对可能具有多种作用机制的新型化合物的研究。在神经退行性变中,神经元信号传导的丧失是症状的主要原因,因此通过抑制分解酶来保存神经递质是首要方法。乙酰胆碱酯酶(AChE)抑制剂是优先用于治疗阿尔茨海默病(AD)的药物,其中一种药物卡巴拉汀也被批准用于治疗帕金森病(PD)。多项研究表明,主要位于胶质细胞中的单胺氧化酶(MAO)B随年龄增长而增加,在阿尔茨海默病(AD)和帕金森病(PD)中升高。司来吉兰是一种MAO B抑制剂,可显著延迟PD患者左旋多巴治疗的起始时间。这些迹象表明,AChE和MAO被认为是多靶点设计配体(MTDL)的必要组成部分。然而,这两个靶点都只是对症治疗,因此如果新药要预防神经变性而不是补偿神经递质的丧失,那么氧化应激和线粒体事件也必须成为靶点。MAO抑制剂可通过与酶抑制无关的机制保护神经元免受凋亡。了解MAO和其他蛋白质在诱导和调节线粒体凋亡中的作用将有助于推进预防神经元丧失的策略。一般来说,在PD和AD中观察到的氧化应激表明抗氧化特性是MTDL分子的一个理想组成部分。将两种或更多种特性整合到一个分子中后,从先导化合物到治疗工具的转变与其药代动力学和毒性密切相关。在这种情况下,任何新分子与细胞色素P450和其他外源性代谢过程的相互作用都是一个关键点。本综述涵盖了针对神经退行性疾病设计药物所靶向的酶的生物化学以及MTDL的细胞色素P450依赖性代谢。