| 1431607-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1431607-81-6
• 化学式: C₂₆H₄₃NO₄S₄
• 分子量: 561.896
• InChiKey: MVHPWKVOXDQJRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.27
• 重原子数：
  35.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Dual Stimuli-Responsive Poly(N-isopropylacrylamide)-b-poly(l-histidine) Chimeric Materials for the Controlled Delivery of Doxorubicin into Liver Carcinoma

  摘要：

  A series of dual stimuli responsive synthetic polymer bioconjugate chimeric materials, poly(N-isopropylacrylamide)(ss)-block-poly(L-histidine)(n) [p(NIPAM)(ss)-b-p(His)(n)] (n = 50, 75, 100, 125), have been synthesized by employing reversible addition-fragmentation chain transfer polymerization of NIPAM, followed by ring-opening polymerization of alpha-amino acid N-carboxyanhydrides. The dual stimuli responsive properties of the resulting biocompatiable and membrenolytic p(NIPAM)(ss)-b-p(His)(n) polymers are investigated for their use as a stimuli responsive drug carrier for tumor targeting. Highly uniform self-assembled micelles (similar to 55 nm) fabricated by p(NIPAM)(ss)-b-p(His)(n) polymers display sharp thermal and pH responses in aqueous media. An anticancer drug, doxorubicin (Dox), is effectively encapsulated in the micelles and the controlled Dox release is investigated in different temperature and pH conditions. Antitumor effect of the released Dox is also assessed using the HepG2 human hepatocellular carcinoma cell lines. Dox molecules released from the [p(NIPAM)(ss)-b-p(His)(n)] micelles remain biologically active and have stimuli responsive capability to kill cancer cells. The self-assembling ability of these hybrid materials into uniform micelles and their efficiency to encapsulate Dox makes them a promising drug carrier to cancer cells. The new chimeric materials thus display tunable properties that can make them useful for a molecular switching device and controlled drug delivery applications needing responses to temperature and pH for the improvement of cancer chemotherapy.

  DOI：

  10.1021/bm400089m

文献信息

• Chimeric poly(N-isopropylacrylamide)-b-poly(3,4-dihydroxy-L-phenylalanine) nanocarriers for temperature/pH dual-stimuli-responsive theranostic application
  作者：Rimesh Augustine、Dae-Kyoung Kim、Su Hyeon Jeon、Tae Wook Lee、Nagendra Kalva、Jae Ho Kim、Il Kim

  DOI：10.1016/j.reactfunctpolym.2020.104595

  日期：2020.7

  A series of poly(N-isopropylacrylamide)(60)-block-poly(3,4-dihydroxy-L-phenylalanine)(n) (p(NIPAM)(60)-b-p (DOPA)(n)) (n = 30, 50, 75, 100) copolymers have been prepared by combining reversible addition fragmentation chain transfer polymerization with ring opening polymerization of N-carboxyanhydride alpha-amino acid using N-heterocyclic carbene as an organocatalyst. The copolymers form spherical nanoparticles with an average diameter of similar to 100 nm by self-assembly. Doxorubicin (Dox) is encapsulated in the spherical nanocarriers with a drug loading efficiency of 44.2%. The iron(III) ions are coordinated to the copolymer matrix via catechol moieties in p (DOPA) units, resulting in temperature/pH dual-stimuli-responsive nanocarriers. The microstructures and Dox loading procedure can be predicted using a dissipative particle dynamics simulation. Cellular uptake and theranostic anticancer activity studies reveal that the nanocarriers release encapsulated Dox preferentially in cancer cells in response to morphological changes induced by variations in temperature and pH. Both cell internalization and cytotoxicity in A2780 ovarian cancer cells and in vivo biodistribution studies demonstrate that the Dox-loaded nanocarriers fabricated by p(NIPAM)-b-p(DOPA) copolymers can be a promising candidate for cancer therapy.