N3-KK(palmitoyl)-NH2 | 1258942-79-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N3-KK(palmitoyl)-NH2
• 英文别名: N3-(CH2)3-CONH-KK(palmitoyl)-CONH2
• CAS: 1258942-79-8
• 化学式: C₃₂H₆₂N₈O₄
• 分子量: 622.895
• InChiKey: OGIWGHHIYSLCDA-NSOVKSMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  44.0
• 可旋转键数：
  31.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  205.17
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N3-KK(palmitoyl)-NH2 、 2-propargyloxy-4,6-bis(4-bisnitrobenzyl phosphate)pyrimidine 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Organelle-Specific Detection of Phosphatase Activities with Two-Photon Fluorogenic Probes in Cells and Tissues

  摘要：

  Two-photon fluorescence microscopy (TPFM) provides key advantages over conventional fluorescence imaging techniques, namely, increased penetration depth, lower tissue autofluorescence and self-absorption, and reduced photodamage and photobleaching and therefore is particularly useful for imaging deep tissues and animals. Enzyme-detecting, small molecule probes provide powerful alternatives over conventional fluorescent protein (FP) based methods in bioimaging, primarily due to their favorable photophysical properties, cell permeability, and chemical tractability. In this article, we report the first fluorogenic, small molecule reporter system (Y2/Y1) capable of imaging endogenous phosphatase activities in both live mammalian cells and Drosophila brains. The one and two photon excited photophysical properties of the system were thoroughly investigated, thus confirming the system was indeed a suitable Turn-ON fluorescence pair for TPFM. To our knowledge, this is the first enzyme reporting two-photon fluorescence bioimaging system which was designed exclusively from a centrosymmetric dye possessing desirable two-photon properties. By conjugation of our reporter system to different cell penetrating peptides (CPPs), we were able to achieve organelle- and tumor cell specific imaging of phosphatase activities with good spatial and temporal resolution. The diffusion problem typically associated with most small molecule imaging probes was effectively abrogated. We further demonstrated this novel two photon system could be used for imaging endogenous phosphatase activities in Drosophila brains with a detection depth of >100 mu m.

  DOI：

  10.1021/ja3036256
• 作为产物：
  描述：

  4-叠氮丁酸 、 棕榈酸 、 Fmoc-N'-甲基三苯甲基-L-赖氨酸 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 N3-KK(palmitoyl)-NH2
  参考文献：
  名称：

  Organelle-Specific Detection of Phosphatase Activities with Two-Photon Fluorogenic Probes in Cells and Tissues

  摘要：

  Two-photon fluorescence microscopy (TPFM) provides key advantages over conventional fluorescence imaging techniques, namely, increased penetration depth, lower tissue autofluorescence and self-absorption, and reduced photodamage and photobleaching and therefore is particularly useful for imaging deep tissues and animals. Enzyme-detecting, small molecule probes provide powerful alternatives over conventional fluorescent protein (FP) based methods in bioimaging, primarily due to their favorable photophysical properties, cell permeability, and chemical tractability. In this article, we report the first fluorogenic, small molecule reporter system (Y2/Y1) capable of imaging endogenous phosphatase activities in both live mammalian cells and Drosophila brains. The one and two photon excited photophysical properties of the system were thoroughly investigated, thus confirming the system was indeed a suitable Turn-ON fluorescence pair for TPFM. To our knowledge, this is the first enzyme reporting two-photon fluorescence bioimaging system which was designed exclusively from a centrosymmetric dye possessing desirable two-photon properties. By conjugation of our reporter system to different cell penetrating peptides (CPPs), we were able to achieve organelle- and tumor cell specific imaging of phosphatase activities with good spatial and temporal resolution. The diffusion problem typically associated with most small molecule imaging probes was effectively abrogated. We further demonstrated this novel two photon system could be used for imaging endogenous phosphatase activities in Drosophila brains with a detection depth of >100 mu m.

  DOI：

  10.1021/ja3036256

文献信息

• “Click” synthesis of small molecule–peptide conjugates for organelle-specific delivery and inhibition of lysosomal cysteine proteases
  作者：Yuhui Loh、Haibin Shi、Mingyu Hu、Shao Q. Yao

  DOI：10.1039/c0cc03738a

  日期：——

  A click chemistry approach for the synthesis of small molecule inhibitor–peptide conjugates to achieve organelle-specific delivery has been developed. Biological testing showed that the inhibitor–Tat conjugate was successfully delivered to the lysosomes, leading to potent inhibition of lysosomal cysteine proteases in cultured cells.

  已经开发了一种点击化学方法，用于合成小分子抑制剂-肽 conjugates，以实现细胞器特异性递送。生物测试表明，抑制剂-Tat 结合物成功递送到溶酶体，导致在培养细胞中对溶酶体半胱氨酸蛋白酶的强效抑制。