Department of Chemistry, Brandeis University, 415 South Street, Waltham, Massachusetts 02454, United States.
School of Materials Science and Engineering, Wuhan University of Technology, 122 Luoshi Road, Wuhan, Hubei 430070, China.
J Am Chem Soc. 2021 Sep 29;143(38):15852-15862. doi: 10.1021/jacs.1c07923. Epub 2021 Sep 16.
Tumorigenic risk of undifferentiated human induced pluripotent stem cells (iPSCs), being a major obstacle for clinical application of iPSCs, requires novel approaches for selectively eliminating undifferentiated iPSCs. Here, we show that an l-phosphopentapeptide, upon the dephosphorylation catalyzed by alkaline phosphatase (ALP) overexpressed by iPSCs, rapidly forms intranuclear peptide assemblies made of α-helices to selectively kill iPSCs. The phosphopentapeptide, consisting of four l-leucine residues and a C-terminal l-phosphotyrosine, self-assembles to form micelles/nanoparticles, which transform into peptide nanofibers/nanoribbons after enzymatic dephosphorylation removes the phosphate group from the l-phosphotyrosine. The concentration of ALP and incubation time dictates the morphology of the peptide assemblies. Circular dichroism and FTIR indicate that the l-pentapeptide in the assemblies contains a mixture of an α-helix and aggregated strands. Incubating the l-phosphopentapeptide with human iPSCs results in rapid killing of the iPSCs (=<2 h) due to the significant accumulation of the peptide assemblies in the nuclei of iPSCs. The phosphopentapeptide is innocuous to normal cells (e.g., HEK293 and hematopoietic progenitor cell (HPC)) because normal cells hardly overexpress ALP. Inhibiting ALP, mutating the l-phosphotyrosine from the C-terminal to the middle of the phosphopentapeptides, or replacing l-leucine to d-leucine in the phosphopentapeptide abolishes the intranuclear assemblies of the pentapeptides. Treating the l-phosphopentapeptide with cell lysate of normal cells (e.g., HS-5) confirms the proteolysis of the l-pentapeptide. This work, as the first case of intranuclear assemblies of peptides, not only illustrates the application of enzymatic noncovalent synthesis for selectively targeting nuclei of cells but also may lead to a new way to eliminate other pathological cells that express a high level of certain enzymes.
致瘤风险的未分化的人类诱导多能干细胞(iPSCs),作为一个主要的障碍,为临床应用的 iPSCs,需要新的方法来选择性地消除未分化的 iPSCs。在这里,我们表明,一个 l-磷酸五肽,在去磷酸化的催化下碱性磷酸酶(ALP)表达由 iPSCs,迅速形成核内肽组装的α-螺旋来选择性地杀死 iPSCs。磷酸五肽,由四个 l-亮氨酸残基和一个 C 端 l-磷酸酪氨酸,自组装成胶束/纳米粒子,这转变为肽纳米纤维/纳米带后的酶去磷酸化去除磷酸基团从 l-磷酸酪氨酸。ALP 的浓度和孵育时间决定了肽组装的形态。圆二色性和傅里叶变换红外光谱表明,在组装 l-五肽含有混合物的α-螺旋和聚集链。孵育 l-磷酸五肽与人类 iPSCs 导致快速杀死的 iPSCs(=<2 小时),由于显著积累的肽组装在核 iPSCs。磷酸五肽是无害的正常细胞(如,HEK293 和造血祖细胞(HPC)),因为正常细胞几乎不表达 ALP。抑制 ALP,突变的 l-磷酸酪氨酸从 C 端到中间的磷酸五肽,或取代 l-亮氨酸到 d-亮氨酸在磷酸五肽消除核内组装的五肽。治疗 l-磷酸五肽与细胞裂解液的正常细胞(如,HS-5)证实了蛋白酶解的 l-五肽。这项工作,作为第一个核内组装的肽,不仅说明了应用酶非共价合成有选择性地针对细胞核的细胞,但也可能导致一种新的方法来消除其他病理细胞表达高水平的某些酶。