PREPARATION OF NICOTINOYL AMINO ACID DERIVATIVES BY FMOC-SOLID PHASE SYNTHESIS AND PRELIMINARY STUDIES ON THE DNA-BINDING PROPERTIES OF NICOTINOYL DERIVATIVES

Dongxin Zhao, K. Lu
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Abstract

Three types of nicotinoyl amino acids, i.e., nicotinoyl leucine (NA-Leu), NA-Leu-His, and NA-Tyr-Tyr, were synthesized by Fmoc solid-phase peptide synthesis, purified by reversed-phase HPLC, and characterized by 1H, 13C NMR and ESI-MS. The interactions of nicotinic acid and nicotinoyl derivatives with ctDNA were investigated by fluorescence spectroscopy. NA-Leu-His and NA-Tyr-Tyr exhibited higher affinity for ctDNA compared with free NA, indicating that the imidazolyl of histidine and the phenol group of tyrosine can enhance the embedding interaction of nicotinoyl derivatives into ctDNA. In addition, leucine in the derivatives helped form a special surrounding and spatial structure to interact with ctDNA. The stronger interaction of NA-Tyr-Tyr and NA-Leu-His with ctDNA suggested that the modified nicotinic acid probably erhaps had significant practical value and should be further studied. INTRODUCTION Nicotinic acid (NA) is one of thirteen necessary vitamins, and also is known as vitamin PP (pellegra preventive factor) because it has been identified as the cause of pellegra disease. Niacinamide cannot be directly converted from NA in the body, but both compounds are important components of the co-factors NAD and NADP.1 At present, NA and niacinamide are mainly used as peripheral vasodilators in the 252 HETEROCYCLES, Vol. 92, No. 2, 2016
fmoc -固相合成法制备烟酰氨基酸衍生物及其与dna结合性能的初步研究
采用Fmoc固相肽合成法合成了烟酰亮氨酸(NA-Leu)、NA-Leu- his和NA-Tyr-Tyr三种类型的烟酰氨基酸,采用反相高效液相色谱法纯化,并用1H、13C NMR和ESI-MS对其进行了表征。采用荧光光谱法研究了烟酸及其烟碱衍生物与ctDNA的相互作用。NA- leu - his和NA- tyr - tyr对ctDNA的亲和力高于游离NA,说明组氨酸的咪唑基和酪氨酸的酚基可以增强烟碱衍生物在ctDNA中的包埋作用。此外,衍生物中的亮氨酸有助于形成与ctDNA相互作用的特殊环境和空间结构。NA-Tyr-Tyr和NA-Leu-His与ctDNA有较强的相互作用,表明改性后的烟酸可能具有重要的实用价值,值得进一步研究。烟酸(NA)是人体必需的十三种维生素之一,也被称为维生素PP(小糙皮病预防因子),因为它已被确定为引起小糙皮病的原因。在体内,NA不能直接转化为烟酰胺,但这两种化合物都是辅助因子NAD和NADP.1的重要组成部分。目前,NA和烟酰胺主要作为外周血管扩张剂在《252 HETEROCYCLES》,Vol. 92, No. 2, 2016中使用
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