(S)-2-{4-[(2-Amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-4-(2-mercapto-ethylcarbamoyl)-butyric acid | 153999-73-6

• 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: (S)-2-{4-[(2-Amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-4-(2-mercapto-ethylcarbamoyl)-butyric acid
• 英文别名: Folate-SH；(2S)-2-[[4-[(2-amino-4-oxo-3H-pteridin-6-yl)methylamino]benzoyl]amino]-5-oxo-5-(2-sulfanylethylamino)pentanoic acid
• CAS: 153999-73-6
• 化学式: C₂₁H₂₄N₈O₅S
• 分子量: 500.538
• InChiKey: OQPOZRPSSKDVCO-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  202
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,2'-二硫二吡啶 、 四乙基碳酸氢铵 、 (S)-2-{4-[(2-Amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-4-(2-mercapto-ethylcarbamoyl)-butyric acid 以 二甲基亚砜 为溶剂， 反应 18.0h， 生成 (S)-2-{4-[(2-Amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-4-[2-(pyridin-2-yldisulfanyl)-ethylcarbamoyl]-butyratetetraethyl-ammonium;
  参考文献：
  名称：

  An efficient synthesis of the ribozyme–folate conjugate

  摘要：

  gamma-Cysteamine modified folic acid was synthesized by reductive alkylation of N-2-Bu-i-6-formylpterin with suitably protected cysteaminyl-L-glutamyl-p-aminobenzoic acid, followed by deprotection. Following activation with 2,2'-dipyridyl disulfide, this synthon was conjugated to the 5'-end of 5'-thiol modified ribozyme to afford target ribozyme-folate conjugate in a good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00837-7
• 作为产物：
  描述：

  芴甲氧羰基-L-谷氨酸 1-叔丁酯 在 哌啶 、 吡啶硼烷 、 三异丙基硅烷 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 甲胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 生成 (S)-2-{4-[(2-Amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-4-(2-mercapto-ethylcarbamoyl)-butyric acid
  参考文献：
  名称：

  An efficient synthesis of the ribozyme–folate conjugate

  摘要：

  gamma-Cysteamine modified folic acid was synthesized by reductive alkylation of N-2-Bu-i-6-formylpterin with suitably protected cysteaminyl-L-glutamyl-p-aminobenzoic acid, followed by deprotection. Following activation with 2,2'-dipyridyl disulfide, this synthon was conjugated to the 5'-end of 5'-thiol modified ribozyme to afford target ribozyme-folate conjugate in a good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00837-7

文献信息

• 一种基于酰胺化的叶酸巯基衍生物的制备方法
  申请人：青岛大学

  公开号：CN107722011A

  公开（公告）日：2018-02-23

  本发明公开了一种基于酰胺化的叶酸巯基衍生物的制备方法，1)利用氧化剂双氧水将含有胺基和巯基双官能团的化合物氧化成含有S‑S键的二硫物，两端带有胺基基团，为下一步的酰胺化反应奠定基础，所述双氧水优选浓度为30％的双氧水；2)在步骤1)产物二硫物中加入催化剂与吸水剂，二硫物上的胺基与叶酸发生酰胺化反应，得到含有二硫键的叶酸衍生物；3)在步骤2)产物中加入还原剂将叶酸衍生物中的二硫键断裂，得到末端含有巯基的目标产物。采用4‑二甲氨基吡啶(DMAP)为催化剂、N,N'‑二环己基碳二亚胺(DCC)为吸水剂，反应速度快，整个反应流程时间大大缩短，生产效率大为提高。
• siRNA-hydrophilic polymer conjugates for intracellular delivery of siRNA and method thereof
  申请人：Jeong Hoon Ji

  公开号：US20070287681A1

  公开（公告）日：2007-12-13

  The present invention is related to hybrid conjugates formed by covalently bonding siRNA (small interfering RNA) molecules to hydrophilic polymers for improving stability of the siRNA molecules effective for delivering the siRNA in vivo, and polyelectrolyte complex micelles formed by ionic interactions between the conjugates and multifunctional cationic compounds. The siRNA-hydrophilic polymer conjugates and polyelectrolyte complex micelles derived therefrom can be used for improving stability of the siRNA molecules in vivo. Consequently, the delivery of siRNA molecules for therapeutic applications into cells can be facilitated, and the siRNA is still active even though a small dose of the siRNA is used.

  本发明涉及一种混合共轭物，其通过共价键结合siRNA（小干扰RNA）分子和亲水性聚合物以提高siRNA分子的稳定性，以在体内传递siRNA，以及通过共价键结合siRNA和多功能阳离子化合物形成的聚电解质复合微粒之间的离子相互作用形成的聚电解质复合微粒。由siRNA-亲水性聚合物共轭物和由此得到的聚电解质复合微粒可以用于提高体内siRNA分子的稳定性。因此，可以促进将siRNA分子用于治疗应用并将其传递到细胞中，即使使用小剂量的siRNA，siRNA仍然是活性的。
• SiRNA-hydrophilic polymer conjugates for intracellular delivery of siRNA and method thereof
  申请人：Jeong Ji Hoon

  公开号：US08969543B2

  公开（公告）日：2015-03-03

  The present invention is related to hybrid conjugates formed by covalently bonding siRNA (small interfering RNA) molecules to hydrophilic polymers for improving stability of the siRNA molecules effective for delivering the siRNA in vivo, and polyelectrolyte complex micelles formed by ionic interactions between the conjugates and multifunctional cationic compounds. The siRNA-hydrophilic polymer conjugates and polyelectrolyte complex micelles derived therefrom can be used for improving stability of the siRNA molecules in vivo. Consequently, the delivery of siRNA molecules for therapeutic applications into cells can be facilitated, and the siRNA is still active even though a small dose of the siRNA is used.

  本发明涉及将小干扰RNA（siRNA）分子与亲水性聚合物共价键合形成的杂交共轭物，用于提高siRNA分子在体内的稳定性，以及由共轭物与多功能阳离子化合物之间的离子相互作用形成的聚电解质复合胶束。由siRNA-亲水性聚合物共轭物和由此派生的聚电解质复合胶束可以用于提高siRNA分子在体内的稳定性。因此，可以促进治疗应用中将siRNA分子输送到细胞中，并且即使使用小剂量的siRNA，siRNA仍然活性。
• COMPOUNDS AND METHODS USEFUL IN BRACHYTHERAPY
  申请人：North Carolina State University

  公开号：US20200376130A1

  公开（公告）日：2020-12-03

  Compounds and methods are described herein that are useful in brachytherapy. A compound of the present invention may comprise: a cancer cell targeting agent (e.g., transferrin); a protecting group; a cross-linking moiety; and an enzyme (e.g., a protein, ribozyme, abzyme, or abiological catalyst). Compounds and methods of the present invention may be used for localizing a radioactive compound and/or for creating a self-amplifying response.
• An efficient synthesis of the ribozyme–folate conjugate
  作者：Jasenka Matulic-Adamic、Mark Sanseverino、Leonid Beigelman

  DOI：10.1016/s0040-4039(02)00837-7

  日期：2002.6

  gamma-Cysteamine modified folic acid was synthesized by reductive alkylation of N-2-Bu-i-6-formylpterin with suitably protected cysteaminyl-L-glutamyl-p-aminobenzoic acid, followed by deprotection. Following activation with 2,2'-dipyridyl disulfide, this synthon was conjugated to the 5'-end of 5'-thiol modified ribozyme to afford target ribozyme-folate conjugate in a good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.