N-(all-trans-Retinoyloxy)-succinimide | 65646-64-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-(all-trans-Retinoyloxy)-succinimide
• 英文别名: succinimidyl all-trans-retinoate；N-succinimidyl all-trans-retinoate；(2,5-dioxopyrrolidin-1-yl) (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate
• CAS: 65646-64-2
• 化学式: C₂₄H₃₁NO₄
• 分子量: 397.514
• InChiKey: RUHGNRBGUUGLPD-LYKFAKFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(all-trans-Retinoyloxy)-succinimide 、 3-氨基丙酸甲酯盐酸盐 在 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 以90%的产率得到methyl N-(all-trans-retinoyl)-β-alaninate
  参考文献：
  名称：

  全反式维甲酸和较短的多烯链类似物与氨基酸的缀合物对前列腺癌细胞生长的影响

  摘要：

  在本工作中，通过将酸性类维生素A的琥珀酰亚胺基活性酯与适当保护的氨基酸或肽偶联，合成了一系列氨基酸与全反式维甲酸（ATRA）和较短的多烯链类似物的共轭物。通过脱保护，并检查其对人前列腺癌LNCaP细胞活力的可能影响。与ATRA相反，所有带有极性侧链氨基酸的结合物对LNCaP细胞的增殖均无抑制作用，而带有亲脂性侧链的α-氨基酸（例如7）或线性氨基酸（例如9）的结合物，显着降低了前列腺癌LNCaP细胞的数量。有趣的是，尽管ATRA的作用是RARα依赖性的，但其活性类似物的作用并未受到选择性RARα拮抗剂的抑制。细胞周期分析显示对细胞周期没有影响，而膜联蛋白V-碘化丙啶染色的定量分析表明，ATRA及其类似物均不影响LNCaP细胞凋亡或坏死。这些结果表明，化合物7和9是潜在有用的试剂，需要进一步的临床前开发以治疗前列腺癌。

  DOI：

  10.1016/j.ejmech.2009.03.029
• 作为产物：
  描述：

  丁二酰亚胺 、 维A酸 在 N,N'-二环己基碳二亚胺 作用下， 生成 N-(all-trans-Retinoyloxy)-succinimide
  参考文献：
  名称：

  Preparation and characterization of micelles of oligomeric chitosan linked to all-trans retinoic acid

  摘要：

  New amphiphilic chitosan derivatives of all trans retinoic acid-chitosan (RA-chitosan) with different molar feeding ratios of all trans retinoic acid (ATRA) were synthesized. The degree of ATRA substitution ranged from 8.72% to 18.78%. The RA-chitosan formed micelles with an average size of 142.14-208.4 nm, and zeta potential 01 +27.25 to 34.48 mV. The critical association concentration (CAC) was found to range from 1.3 x 10(-2) to 2.13 x 10(-2) mg ml(-1). Upon evaluation, the RA-chitosan shows no significant cytotoxicity on Hela and HepG2 cells. Analysis of micelles loaded with ATRA revealed that the size of micelles decreased by increasing loaded drug content while zeta potential did not change. ATRA was released slowly over 3-day period, and drug content had no effect on the release rate. These phenomena make RA-chitosan micelles as a candidate for drug carrier. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carbpol.2011.08.093

文献信息

• Nanoformulated Single‐Stranded RNA‐Based Adjuvant with a Coordinative Amphiphile as an Effective Stabilizer: Inducing Humoral Immune Response by Activation of Antigen‐Presenting Cells
  作者：Hyo‐Jung Park、Eun‐Kyoung Bang、Jung Joo Hong、Sang‐Myeong Lee、Hae Li Ko、Hye Won Kwak、Hyelim Park、Kyung Won Kang、Rhoon‐Ho Kim、Seung Rok Ryu、Green Kim、Hanseul Oh、Hye‐Jung Kim、Kyuri Lee、Minjeong Kim、Soo Young Kim、Jae‐Ouk Kim、Karim El‐Baz、Hyukjin Lee、Manki Song、Dae Gwin Jeong、Gyochang Keum、Jae‐Hwan Nam

  DOI：10.1002/anie.202002979

  日期：2020.7.6

  nanoparticles with a coordinative amphiphile, containing a zinc/dipicolylamine complex moiety as a coordinative phosphate binder, as a stabilizer for RNA‐based adjuvants. The nanoformulated ssRNA adjuvant was resistant to enzymatic degradation in vitro and in vivo, and that with a coordinative amphiphile bearing an oleyl group (CA‐O ) was approximately 100 nm, promoted effective recognition, and improved activation

  作为TLR7 / 8的激动剂，单链RNA（ssRNA）是安全且很有前途的佐剂，不会引起脱靶效应或先天性免疫过度激活。但是，低稳定性会阻止它们产生足够的免疫反应。这项研究评估了the麻痹病毒基因间区域内部核糖体进入位点衍生的ssRNA的佐剂作用，配制成纳米级配位两亲物的纳米粒子，其中含有锌/二甲基吡啶胺复合物部分作为配位磷酸盐粘合剂，作为基于RNA的佐剂的稳定剂。纳米级ssRNA佐剂对体内和体外的酶降解具有抵抗力，并且与带有油基的配位两亲物（CA‐O）约为100 nm，可促进有效识别并改善抗原呈递细胞的激活，从而在单次免疫后可更好地诱导中和抗体。因此，CA‐O可能会提高基于ssRNA的佐剂的功效，证明可满足病原体暴发期间对疫苗的紧急需求。
• TRACEABLE RETINOID ACID FOR IMAGING, DISEASE PREVENTION AND THERAPY
  申请人：Ke Shi

  公开号：US20120244079A1

  公开（公告）日：2012-09-27

  The present invention provides nonradioactive NIR optical imaging agents based up on the structure of retinoid acid derivatives. The nonradioactive NIR optical imaging agent has been evaluated at the cellular level by confocal microscopy, and in vivo in a whole animal using a various xenograft models. The specific uptake of this agent in human cancer cells and multiple xenograft models demonstrate that nonradioactive near infrared dye labeled retinoid metabolites and/or analogs are useful for early stage cancer studies and diagnoses. Also, the present invention provides that nonradioactive near infrared dye labeled retinoid metabolites and/or analogs are useful for visualization of drug redistribution within the body which is useful in determining the optimal biological dose. Ultimately, the visualization data can be used as an analytical tool to reduce any systemic toxicity.

  本发明提供了基于视黄酸衍生物结构的非放射性近红外光学成像剂。该非放射性近红外光学成像剂已通过共聚焦显微镜在细胞水平上进行评估，并在整个动物体内利用各种异种移植模型进行评估。该成像剂在人类癌细胞和多个异种移植模型中的特异摄取表明，非放射性近红外染料标记的视黄酸代谢物和/或类似物对于早期癌症研究和诊断是有用的。此外，本发明还提供，非放射性近红外染料标记的视黄酸代谢物和/或类似物对于可视化药物在体内重新分配是有用的，这有助于确定最佳生物剂量。最终，可视化数据可用作分析工具，以减少任何全身毒性。
• Compounds for modulating TRPV3 function
  申请人：Chong Jayhong A.

  公开号：US20090018147A1

  公开（公告）日：2009-01-15

  The present application relates to compounds and methods for treating pain and other conditions related to TRPV3.

  本申请涉及化合物和用于治疗与TRPV3相关的疼痛和其他疾病的方法。
• Compounds for Modulating TRPV3 Function
  申请人：Chong Jayhong A.

  公开号：US20110151559A1

  公开（公告）日：2011-06-23

  The present application relates to compounds and methods for treating pain and other conditions related to TRPV3.

  本申请涉及化合物和治疗与TRPV3相关的疼痛和其他疾病的方法。
• 신규한 화합물 및 이를 함유하는 신경 손상, 신경 질환, 또는 발달 장애에 대한 신경세포의 증식 촉진, 분화, 및/또는 재생을 통한 치료 또는 예방용 약제학적 조성물
  申请人：(주)미래바이오팜

  公开号：KR102362962B1

  公开（公告）日：2022-02-16

  본 발명은 하기 화학식 1의 화합물, 및 이를 함유하는 신경 세포의 증식 촉진, 분화 및/또는 신경 재생을 통한 신경 손상, 신경 질환, 또는 발달 장애의 치료 또는 예방용 약제학적 조성물에 관한 것이다. 따라서, 본 발명은 치매를 비롯한 퇴행성 뇌질환 또는 신경 세포 손상에 따른 뇌신경 질환과 발달 장애 및 다양한 종류의 퇴행성 신경 질환, 허혈성 신경질환 또는 신경손상 질환의 치료제와 학습능력 향상제 및 인지기능 개선제로 매우 유용하게 사용될 수 있다. [화학식 1] 상기 화학식 1 에서, R1 내지 R3은 각각 독립적으로, 수소, 선형 또는 분지형의 (C1-C10)알킬이거나, 임의 결합을 형성하기 위한 전자쌍을 나타내고, A 는 *-(CH2)n-A1-*를 나타내고, n 은 0 내지 5 중 임의 정수를 나타내고, A1 은 *-COO-*, *-CO-*, *-NR4-*, *-CH2-*, *-CONH-*, 또는 *-O-*를 나타내고, Linker는 *-L1-NHCO-L2-*, *-L1-O-R-O-L2-*, *-L1-CH2-L2-*, *-L1-NR5-L2-*, 또는 *-L1-COO-L2-* 를 나타내고, L1 은 선형 또는 분지형의 (C1-C30)알킬을 나타내고, L2 는 단일 결합, 또는 선형 또는 분지형의 (C1-C30)알킬을 나타내고, R 은 선형 또는 분지형의 (C1-C20)알킬을 나타내고, R4 및 R5는, 각각 독립적으로, 수소 또는 선형 또는 분지형의 (C1-C10)알킬을 나타내고, B 는 레티노산(retinoic acid)에서 유래된 부분을 나타낸다.

  本发明涉及化学式1的化合物，以及含有该化合物的药物组合物，其促进神经细胞增殖、分化和/或神经再生，用于治疗或预防神经损伤、神经疾病或发育障碍。因此，本发明可用作治疗退行性脑疾病或神经细胞损伤导致的脑神经疾病、发育障碍和各种类型的退行性神经疾病、缺血性神经疾病或神经损伤疾病的药物，以及用于提高学习能力和改善认知功能的药物。 在化学式1中，R1至R3各自独立地表示氢、线性或支链的（C1-C10）烷基或表示形成电子对的任意键；A表示*-(CH2)n-A1-*，其中n表示0至5之间的任意整数，A1表示*-COO-*、*-CO-*、*-NR4-*、*-CH2-*、*-CONH-*或*-O-*；Linker表示*-L1-NHCO-L2-*、*-L1-O-R-O-L2-*、*-L1-CH2-L2-*、*-L1-NR5-L2-*或*-L1-COO-L2-*；L1表示线性或支链的（C1-C30）烷基，L2表示单键或线性或支链的（C1-C30）烷基；R表示线性或支链的（C1-C20）烷基；R4和R5各自独立地表示氢或线性或支链的（C1-C10）烷基；B表示来自视黄醛(retinoic acid)的部分。