ISRIB (trans-isoMer)

 化学構造式
1597403-47-8
CAS番号.
1597403-47-8
化学名:
别名:
英語名:
ISRIB (trans-isoMer)
英語别名:
Trans-ISRIB;CS-1768;RMA-330;ISRIB - trans-ISRIB;ISRIS(trans-isomer);ISRIB (trans-isoMer);ISR Inhibitor, ISRIB;ISRIB (trans-isomer), >98%;ISRIB (trans-isoMer) USP/EP/BP;N,N'-trans-1,4-cyclohexanediylbis[2-(4-chlorophenoxy)acetamide]
CBNumber:
CB72714669
化学式:
C22H24Cl2N2O4
分子量:
451.34
MOL File:
1597403-47-8.mol
MSDS File:
SDS

ISRIB (trans-isoMer) 物理性質

沸点 :
719.0±60.0 °C(Predicted)
比重(密度) :
1.33±0.1 g/cm3(Predicted)
貯蔵温度 :
2-8°C
溶解性:
insoluble in EtOH; insoluble in H2O; insoluble in EtOH; ≥8.96 mg/mL in DMSO with gentle warming
外見 :
solid
酸解離定数(Pka):
13.63±0.40(Predicted)
色:
White to off-white
InChIKey:
HJGMCDHQPXTGAV-IYARVYRRSA-N
SMILES:
[C@@H]1(NC(=O)COC2=CC=C(Cl)C=C2)CC[C@@H](NC(=O)COC2=CC=C(Cl)C=C2)CC1

安全性情報

WGK Germany  WGK 3
ストレージクラス 11 - Combustible Solids

ISRIB (trans-isoMer) 価格 もっと(9)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01TOC5284
trans-ISRIB
1597403-47-8 10mg ¥54000 2024-03-01 購入
富士フイルム和光純薬株式会社(wako) W01TOC5284
trans-ISRIB
1597403-47-8 50mg ¥225000 2024-03-01 購入
富士フイルム和光純薬株式会社(wako) W01COBQJ-4746
Isrib
1597403-47-8 5g ¥1070000 2024-03-01 購入
富士フイルム和光純薬株式会社(wako) W01TRCI926000
ISRIB
1597403-47-8 100mg ¥57900 2024-03-01 購入
富士フイルム和光純薬株式会社(wako) W01TRCI926000
ISRIB
1597403-47-8 250mg ¥124800 2024-03-01 購入

ISRIB (trans-isoMer) 化学特性,用途語,生産方法

説明

ISRIB (trans-isomer), the trans-isomer of ISRIB, is a potent and selective PERK inhibitor with IC50 of 5 nM and does not have global effects on translation, transcription, or mRNA stability in non-stressed cells.

使用

trans-ISRIB is an integrated stress response (ISR) inhibitor; reverses the effects of eIF2α phosphorylation (IC50 = 5 nM) and restores cell translation capacity. Acts downstream of PERK, targeting interactions between eIF2α kinases and elF2B. Blocks ATF4 production without altering the IRE1 or ATF6 responses in vitro. Displays memory enhancement in hippocampus-dependent spatial and fear-associated learning in rodents. trans-ISRIB promotes survival of pluripotent stem cells in culture when used in combination with Chroman-1, emricasan, and polyamines, a combination known as CEPT. When used as part of the CEPT cocktail, trans-ISRIB improves survival of differentiated cells following cryopreservation. Brain penetrant.

生物学の機能

ISRIB (trans-isomer) is a potent inhibitor of the integrated stress response (ISR).
Integrated stress response (ISR) is activated by diverse cellular conditions and rapidly reduces overall protein synthesis while enhancing translation of specific transcripts that support adaptive stress responses. The ISR is mediated by diverse stress-sensing kinases that phosphorylating serine 51 in eukaryotic translation initiation factor alpha (eIF2α).
ISRIB (trans-isomer) is a potent ISR inhibitor. ISRIB reversed the effects of eIF2α phosphorylation with IC50 value of 5 nM. ISRIB inhibited production of endogenous ATF4 (a cAMP element binding transcription factor). In mouse embryonic fibroblasts (MEFs), ISRIB reversed the increase in the 80S monosomes at the expense of polyribosomes induced by endoplasmic reticulum (ER) stress. In ER-stressed cells, ISRIB reduced cell survival. In stressed cells, ISRIB restored mRNA translation and inhibited stress granule (SG) formation induced by eIF2α phosphorylation. ISRIB inhibited the interaction between eIF2B and eIF2 that located at the core of the ISR. Also, ISRIB was an activator of eIF2B and stabilized activated eIF2B dimers.
In mice, ISRIB significantly increased hippocampus-dependent spatial and fear-associated learning.

生物活性

ISRIB, a drug that inhibits the integrated stress response (ISR), imparts resistance to the cells against the downstream effects of eukaryotic initiation factor 2 (eIF2)α phosphorylation such as activating transcription factor 4 (ATF4) and eukaryotic translation initiation factor 4E (eIF4E)-binding protein 1 (4E-BP1) induction. This potent and selective inhibitor of ISR can penetrate the blood-brain barrier and prevent cells from adapting to the endoplasmic reticulum (ER) stress. By inhibiting the PERK signaling pathway, ISRIB can effectively reverse the effects of eIF2a phosphorylation and restore the cells' translation capacity, resulting in enhanced cognitive memory in rodents.

参考文献

[1]. Sidrauski C, Acosta-Alvear D, Khoutorsky A, et al. Pharmacological brake-release of mRNA translation enhances cognitive memory. Elife, 2013, 2: e00498.
[2]. Sidrauski C, McGeachy AM, Ingolia NT, et al. The small molecule ISRIB reverses the effects of eIF2α phosphorylation on translation and stress granule assembly. Elife, 2015, 4.
[3]. Sekine Y, Zyryanova A, Crespillo-Casado A, et al. Stress responses. Mutations in a translation initiation factor identify the target of a memory-enhancing compound. Science, 2015, 348(6238): 1027-1030.
[4]. Sidrauski C, Tsai JC, Kampmann M, et al. Pharmacological dimerization and activation of the exchange factor eIF2B antagonizes the integrated stress response. Elife, 2015, 4: e07314.

ISRIB (trans-isoMer) 上流と下流の製品情報

原材料

準備製品


ISRIB (trans-isoMer) 生産企業

Global( 172)Suppliers
名前 電話番号 電子メール 国籍 製品カタログ 優位度
Tianjin Kailiqi Biotechnology Co., Ltd. 15076683720
klq@cw-bio.com China 9778 55
TR Pharma & Tech Co., Ltd. 0531-88633905 15863156350
jntryy@hotmail.com China 45 55
InvivoChem 13549236410
sales@invivochem.cn China 6745 58
Hangzhou Sinoda Pharmaceutical Technology Co. LTD 0571-87213919 17306812703
3007955328@qq.com China 7446 58
Yichang Chanod Biomedical Technology Co,LTD 0717-6855399 15377615856
sales@chanodpharm.com China 71 58
Nanjing Chemlin Chemical Co., Ltd 025-83697070 13770331960
info@chemlin.com.cn China 16307 64
Dalian Meilun Biotech Co., Ltd. 0411-62910999 13889544652
sales@meilune.com China 4765 58
Haoyuan Chemexpress Co., Ltd. 021-58950125
info@chemexpress.com China 7545 61
Nanjing Dulai Biotechnology Co., Ltd. 025-84699383-8003;025-846993838003-8003 18013301590
njduly@126.com China 3293 55
Guangzhou Isun Pharmaceutical Co., Ltd 020-39119399 18927568969
isunpharm@qq.com China 4773 55

  スペクトルデータ(1HNMR)


1597403-47-8()キーワード:


  • 1597403-47-8
  • ISRIB (trans-isoMer)
  • trans-N,N'-(cyclohexane-1,4-diyl)bis(2-(4-chlorophenoxy)acetamide)
  • N,N'-((1r,4r)-cyclohexane-1,4-diyl)bis(2-(4-chlorophenoxy)acetamide) ISRIB(trans-isomer)
  • Acetamide, N,N'-trans-1,4-cyclohexanediylbis[2-(4-chlorophenoxy)-
  • N,N'-trans-1,4-cyclohexanediylbis[2-(4-chlorophenoxy)acetamide]
  • CS-1768
  • ISRIB - trans-ISRIB
  • ISRIB (trans-isomer), >98%
  • ISRIB (trans-isoMer) USP/EP/BP
  • N,N'-(trans-cyclohexane-1,4-diyl)bis(2-(4-chlorophenoxy)acetamide)
  • ISRIB/N,N'-trans-1,4-Cyclohexanediylbis[2-(4-chlorophenoxy)acetamide
  • ISRIS(trans-isomer)
  • ISR Inhibitor, ISRIB
  • RMA-330
  • Trans-ISRIB
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