8-氨基-肌苷 | 13389-16-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 8-氨基-肌苷
• 英文名称: 8-aminoinosine
• 英文别名: (2R,3R,4S,5R)-2-(8-Amino-6-hydroxy-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol；8-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 13389-16-7
• 化学式: C₁₀H₁₃N₅O₅
• 分子量: 283.244
• InChiKey: OBCXRIVPFSZZSN-UUOKFMHZSA-N

物化性质

• 熔点：
  >215°C (dec.)
• 溶解度：
  DMSO（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  8-benzylaminoinosine 在 palladium on activated charcoal 、 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 120.0h， 以96%的产率得到8-氨基-肌苷
  参考文献：
  名称：

  通过简单的亲水相互作用液相色谱酶法检测发现一种新型人嘌呤核苷磷酸化酶抑制剂

  摘要：

  人嘌呤核苷磷酸化酶（Hs PNP）属于核酸的嘌呤补救途径。由于脱氧鸟苷三磷酸 (dGTP) 的积累，这种酶的遗传缺陷会触发活化的 T 细胞凋亡。因此，人类 PNP 抑制剂的潜在化疗应用包括治疗 T 细胞白血病、自身免疫性疾病和移植组织排斥。在本报告中，我们通过结合实验和计算工具介绍了新型Hs PNP 抑制剂的发现。开发了一种简单、廉价、直接和非放射性的酶法，结合亲水相互作用液相色谱和紫外检测（使用 HILIC 作为洗脱模式的 LC-UV）来筛选HsPNP抑制剂。通过监测 LC-UV 将肌苷 (Ino) 磷酸化为次黄嘌呤 (Hpx) 来评估酶活性。合成并筛选了一个小型的 6 和 8 取代核苷库。最有希望的化合物 8-氨基肌苷 ( 4 )的抑制效力通过K i和 IC 50测定进行量化。的效果HS PNP抑制也评价在体外通过细胞毒性对人T细胞白血病细胞（CCRF-CEM）的研究。还对最有效的化合

  DOI：

  10.1002/cmdc.202000874

文献信息

• Triplex-forming oligonucleotides containing modified purines and their applications
  申请人：Eritja Ramon

  公开号：US20050014164A1

  公开（公告）日：2005-01-20

  This invention presents oligonucleotide derivatives comprising a complementary purine part carrying one or more 8-aminopurines such as 8-aminoadenine, 8-aminoguanine and 8-aminohypoxanthine connected with a linker to an oligonucleotide carrying either GT or GA sequences. These oligonucleotide derivatives bind polypyrimidine sequences complementary (in the antiparallel sense) to the purine part by formation of purine-purine-pyrimidine triple helices. The oligonucleotides carrying 8-aminoguanines described in this invention have better binding properties than unmodified oligonucleotides. This enhancement in stability, coupled with the lack of an acidic pH requirement, makes the oligonucleotides carrying 8-aminopurines effective in applications involving oligonucleotide targeting of single stranded RNA in vitro and in vivo, as well as applications requiring triple helix formation.

  本发明提出了寡核苷酸衍生物，其包含的互补嘌呤部分带有一个或多个 8-氨基嘌呤，如 8-氨基腺嘌呤、8-氨基鸟嘌呤和 8-氨基次黄嘌呤，并与带有 GT 或 GA 序列的寡核苷酸连接。这些寡核苷酸衍生物通过形成嘌呤-嘌呤-嘧啶三螺旋，与嘌呤部分互补（反平行）的多嘧啶序列结合。与未修饰的寡核苷酸相比，本发明所述的含有 8-氨基鸟嘌呤的寡核苷酸具有更好的结合性能。这种稳定性的提高，再加上不需要酸性 pH 值，使得携带 8-氨基嘌呤的寡核苷酸在涉及体外和体内单链 RNA 的寡核苷酸靶向应用以及需要形成三螺旋的应用中非常有效。
• Purine and 8-substituted purine arabinofuranosyl and ribofuranosyl nucleoside derivatives as potential inducers of the differentiation of the Friend erythroleukemia
  作者：Tai Shun Lin、Jia Chong Cheng、Kimiko Ishiguro、Alan C. Sartorelli

  DOI：10.1021/jm00148a018

  日期：1985.10

  Several antimetabolites have been demonstrated to have the capacity to initiate differentiation in vitro of a variety of leukemic cell lines. To explore the structural requirements for this activity, a series of purine and 8-substituted purine arabinofuranosyl and ribofuranosyl nucleoside derivatives were synthesized and tested as inducers of the differentiation of Friend murine erythroleukemia cells. 9-(beta-D-Arabinofuranosyl)hypoxanthine and 6-(hydroxyamino)-9-(beta-D-arabinofuranosyl)purine were effective inducers of maturation, producing 82% and 74% benzidine-positive cells, a measure of the number of cells synthesizing hemoglobin. 6-Mercapto-9-(beta-D-ribofuranosyl)purine and 6-(methylmercapto)-9-(beta-D-ribofuranosyl)purine and their corresponding beta-D-arabinofuranosyl derivatives were also effective initiators of maturation, causing approximately 50% of the cell population to assume a differentiated phenotype.
• METHODS FOR TREATING BLADDER AND URETHRA DYSFUNCTION AND DISEASE
  申请人：University of Pittsburgh - Of the Commonwealth System of Higher Education

  公开号：US20220054494A1

  公开（公告）日：2022-02-24

  Methods of treating bladder or urethra dysfunction or disease in a subject and methods of increasing bladder smooth muscle contractility or increasing bladder wall volume in a subject are disclosed. In some examples, a purine nucleoside phosphorylase (PNPase) inhibitor or purine nucleoside substrate is administered, such as 8-aminoguanine or forodesine.
• [EN] TRIPLEX-FORMING OLIGONUCLEOTIDES CONTAINING MODIFIED PURINES AND THEIR APPLICATIONS<br/>[FR] OLIGONUCLEOTIDES FORMANT UN TRIPLEX CONTENANT DES PURINES MODIFIEES ET APPLICATIONS ASSOCIEES
  申请人：CYGENE LAB INC

  公开号：WO2004037981A2

  公开（公告）日：2004-05-06

  This invention presents oligonucleotide derivatives comprising a complementary purine part carrying one or more 8-aminopurines such as 8-aminoadenine, 8-aminoguanine and 8-aminohypoxanthine connected with a linker to an oligonucleotide carrying either GT or GA sequences. These oligonucleotide derivatives bind polypyrimidine sequences complementary (in the antiparallel sense) to the purine part by formation of purine-purine­pyrimidine triple helices. The oligonucleotides carrying 8-aminoguanines described in this invention have better binding properties than unmodified oligonucleotides. This enhancement in stability, coupled with the lack of an acidic pH requirement, makes the oligonucleotides carrying 8-aminopurines effective in applications involving oligonucleotide targeting of single stranded RNA in vitro and in vivo, as well as applications requiring triple helix formation.
• [EN] METHODS FOR TREATING BLADDER AND URETHRA DYSFUNCTION AND DISEASE<br/>[FR] PROCÉDÉS DE TRAITEMENT D'UN DYSFONCTIONNEMENT ET D'UNE MALADIE DE LA VESSIE ET DE L'URÈTRE
  申请人：UNIV PITTSBURGH COMMONWEALTH SYS HIGHER EDUCATION

  公开号：WO2020186187A1

  公开（公告）日：2020-09-17

  Methods of treating bladder or urethra dysfunction or disease in a subject and methods of increasing bladder smooth muscle contractility or increasing bladder wall volume in a subject are disclosed. In some examples, a purine nucleoside phosphorylase (PNPase) inhibitor or purine nucleoside substrate is administered, such as 8-aminoguanine or forodesine.