Na-苄氧羰基Nim-Dnp-L-组氨酸 | 63013-46-7

• 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
• 中文名称: Na-苄氧羰基Nim-Dnp-L-组氨酸
• 英文名称: Z-His(Dnp)-OH
• 英文别名: N^α-benzyloxycarbonyl-1-(2,4-dinitro-phenyl)-histidine；(S)-2-(((Benzyloxy)carbonyl)amino)-3-(1-(2,4-dinitrophenyl)-1H-imidazol-4-yl)propanoic acid；(2S)-3-[1-(2,4-dinitrophenyl)imidazol-4-yl]-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 63013-46-7
• 化学式: C₂₀H₁₇N₅O₈
• 分子量: 455.384
• InChiKey: GHVOUAVUVLSUDB-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  185
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Na-苄氧羰基Nim-Dnp-L-组氨酸 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (S)-4-[1-(2,4-dinitro-phenyl)-1H-imidazol-4-ylmethyl]-oxazolidine-2,5-dione
  参考文献：
  名称：

  Rational Design of Multifunctional Polymeric Nanoparticles Based on Poly(l-histidine) and d-α-Vitamin E Succinate for Reversing Tumor Multidrug Resistance

  摘要：

  NPs在MCF-/ADR细胞中表现出比MPEG-PLH-VES NPs更明显的细胞毒性。在MCF-7/ADR肿瘤移植小鼠体内成像研究中，由于生物素介导的主动靶向效应，MPEG-PLH-VES/B NPs比MPEG-PLH-VES NPs更有效地在肿瘤部位聚集。与体外结果一致，DOX-loaded MPEG-PLH-VES/B NPs在MCF-/ADR细胞中表现出比MPEG-PLH-VES NPs更明显的细胞毒性。在MCF-7/ADR肿瘤移植小鼠体内成像研究中，由于生物素介导的主动靶向效应，MPEG-PLH-VES/B NPs比MPEG-PLH-VES NPs更有效地在肿瘤部位聚集。与体外结果一致，DOX-loaded MPEG-PLH-VES/B NPs在MCF-/ADR细胞中表现出比MPEG-PLH-VES NPs更明显的细胞毒性。在MCF-7/ADR肿瘤移植小鼠体内成像研究中，由于生物素介导的主动靶向效应，MPEG-PLH-VES/B NPs比MPEG-PLH-VES NPs更有效地在肿瘤部位聚集。与体外结果一致，DOX-loaded MPEG-PLH-VES/B NPs在MCF-/ADR细胞中表现出比MPEG-PLH-VES NPs

  DOI：

  10.1021/acs.biomac.8b00213

文献信息

• Dendritic polypeptide-based nanocarriers for the delivery of therapeutic agents
  申请人：Rutgers, The State University of New Jersey

  公开号：US09943606B2

  公开（公告）日：2018-04-17

  Dendritic polypeptides useful for the delivery of therapeutic agents into cells are disclosed, together with their methods of preparation. These dendritic polypeptides serve as carriers of drugs, siRNA, aptamers and plasmid DNA in the treatment of various diseases, including cancer.

  揭示了用于将治疗剂传递到细胞中的树突多肽，以及它们的制备方法。这些树突多肽可作为药物、siRNA、aptamers和质粒DNA的载体，在治疗各种疾病，包括癌症方面发挥作用。
• ——
  作者：ZAXARIEV S. G.、 STOEV S. B.、 SIRAKOV L. M.、 LOZEVA S. M.、 VIDENOV G. I.、 +

  DOI：——

  日期：——
• ZAKHARIEV, S. G.;STOEV, S. B.;SIRAKOV, L. M.;LOSEVA, S. M.;VIDENOV, G. T.+, DOKL. BOLG. AN, 41,(1988) N 9, S. 69-72
  作者：ZAKHARIEV, S. G.、STOEV, S. B.、SIRAKOV, L. M.、LOSEVA, S. M.、VIDENOV, G. T.+

  DOI：——

  日期：——
• Shaltiel,S. et al., Israel Journal of Chemistry, 1972, vol. 10, p. 627 - 633
  作者：Shaltiel,S. et al.

  DOI：——

  日期：——
• Rational Design of Multifunctional Polymeric Nanoparticles Based on Poly(<scp>l</scp>-histidine) and d-α-Vitamin E Succinate for Reversing Tumor Multidrug Resistance
  作者：Zhen Li、Qixian Chen、Yan Qi、Zhihao Liu、Tangna Hao、Xiaoxin Sun、Mingxi Qiao、Xiaodong Ma、Ting Xu、Xiuli Zhao、Chunrong Yang、Dawei Chen

  DOI：10.1021/acs.biomac.8b00213

  日期：2018.7.9

  A multifunctional nanoparticulate system composed of methoxy poly(ethylene glycol)-poly(l-histidine)-d-α-vitamin E succinate (MPEG-PLH-VES) copolymers for encapsulation of doxorubicin (DOX) was elaborated with the aim of circumventing the multidrug resistance (MDR) in breast cancer treatment. The MPEG-PLH-VES nanoparticles (NPs) were subsequently functionalized with biotin motif for targeted drug delivery. The MPEG-PLH-VES copolymer exerts no obvious effect on the P-gp expression level of MCF-7/ADR but exhibited a significant influence on the loss of mitochondrial membrane potential, the reduction of intracellular ATP level, and the inhibition of P-gp ATPase activity of MCF-7/ADR cells. The constructed MPEG-PLH-VES NPs exhibited an acidic pH-induced increase on particle size in aqueous solution. The DOX-encapsulated MPEG-PLH-VES/biotin-PEG-VES (MPEG-PLH-VES/B) NPs were characterized to possess high drug encapsulation efficiency of approximate 90%, an average particle size of approximately 130 nm, and a pH-responsive drug release profile in acidic milieu. Confocal laser scanning microscopy (CLSM) investigations revealed that the DOX-loaded NPs resulted in an effective delivery of DOX into MCF-/ADR cells and a notable carrier-facilitated escape from endolysosomal entrapment. Pertaining to the in vitro cytotoxicity evaluation, the DOX-loaded MPEG-PLH-VES/B NPs resulted in more pronounced cytotoxicity to MCF-/ADR cells compared with DOX-loaded MPEG-PLH-VES NPs and free DOX solution. In vivo imaging study in MCF-7/ADR tumor-engrafted mice exhibited that the MPEG-PLH-VES/B NPs accumulated at the tumor site more effectively than MPEG-PLH-VES NPs due to the biotin-mediated active targeting effect. In accordance with the in vitro results, DOX-loaded MPEG-PLH-VES/B NPs showed the strongest inhibitory effect against the MCF-7/ADR xenografted tumors with negligible systemic toxicity, as evidenced by the histological analysis and change of body weight. The multifunctional MPEG-PLH-VES/B nanoparticulate system has been demonstrated to provide a promising strategy for efficient delivery of DOX into MCF-7/ADR cancerous cells and reversing MDR.

  NPs在MCF-/ADR细胞中表现出比MPEG-PLH-VES NPs更明显的细胞毒性。在MCF-7/ADR肿瘤移植小鼠体内成像研究中，由于生物素介导的主动靶向效应，MPEG-PLH-VES/B NPs比MPEG-PLH-VES NPs更有效地在肿瘤部位聚集。与体外结果一致，DOX-loaded MPEG-PLH-VES/B NPs在MCF-/ADR细胞中表现出比MPEG-PLH-VES NPs更明显的细胞毒性。在MCF-7/ADR肿瘤移植小鼠体内成像研究中，由于生物素介导的主动靶向效应，MPEG-PLH-VES/B NPs比MPEG-PLH-VES NPs更有效地在肿瘤部位聚集。与体外结果一致，DOX-loaded MPEG-PLH-VES/B NPs在MCF-/ADR细胞中表现出比MPEG-PLH-VES NPs更明显的细胞毒性。在MCF-7/ADR肿瘤移植小鼠体内成像研究中，由于生物素介导的主动靶向效应，MPEG-PLH-VES/B NPs比MPEG-PLH-VES NPs更有效地在肿瘤部位聚集。与体外结果一致，DOX-loaded MPEG-PLH-VES/B NPs在MCF-/ADR细胞中表现出比MPEG-PLH-VES NPs