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ISRIB (trans-isoMer)

CAS No.
1597403-47-8
Chemical Name:
ISRIB (trans-isoMer)
Synonyms
CS-1768;Trans-ISRIB;ISRIB - trans-ISRIB;ISRIB (trans-isoMer);ISRIB (trans-isomer), >98%;ISRIB (trans-isoMer) USP/EP/BP;N,N'-trans-1,4-cyclohexanediylbis[2-(4-chlorophenoxy)acetamide];Acetamide, N,N'-trans-1,4-cyclohexanediylbis[2-(4-chlorophenoxy)-;N,N'-(trans-cyclohexane-1,4-diyl)bis(2-(4-chlorophenoxy)acetamide);trans-N,N'-(cyclohexane-1,4-diyl)bis(2-(4-chlorophenoxy)acetamide)
CBNumber:
CB72714669
Molecular Formula:
C22H24Cl2N2O4
Molecular Weight:
451.34
MDL Number:
MFCD27952932
MOL File:
1597403-47-8.mol
MSDS File:
SDS
Last updated:2023-11-17 18:01:30

ISRIB (trans-isoMer) Properties

Boiling point 719.0±60.0 °C(Predicted)
Density 1.33±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility insoluble in EtOH; insoluble in H2O; insoluble in EtOH; ≥8.96 mg/mL in DMSO with gentle warming
form solid
pka 13.63±0.40(Predicted)

ISRIB (trans-isoMer) price More Price(19)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML0843 ISRIB ≥98%(HPLC) 1597403-47-8 5mg $118 2024-03-01 Buy
Sigma-Aldrich SML0843 ISRIB ≥98% (HPLC) 1597403-47-8 25MG $478 2024-03-01 Buy
Cayman Chemical 16258 trans-ISRIB ≥95% 1597403-47-8 5mg $81 2024-03-01 Buy
Cayman Chemical 16258 trans-ISRIB ≥95% 1597403-47-8 10mg $152 2024-03-01 Buy
Cayman Chemical 16258 trans-ISRIB ≥95% 1597403-47-8 25mg $356 2024-03-01 Buy
Product number Packaging Price Buy
SML0843 5mg $118 Buy
SML0843 25MG $478 Buy
16258 5mg $81 Buy
16258 10mg $152 Buy
16258 25mg $356 Buy

ISRIB (trans-isoMer) Chemical Properties,Uses,Production

Description

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.

Uses

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.

Uses

ISRIB (integrated stress response inhibitor, 1597403-47-8) has been used as an inhibitor of integrated stress response.

Biological Functions

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.

Biological Activity

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.

storage

Store at +4°C

References

[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) Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 124)Suppliers
Supplier Tel Email Country ProdList Advantage
Wuhan Nutra Biotechnology Co.,Ltd
+8617786394783 nutrabiotech@outlook.com China 300 58
career henan chemical co
+86-0371-86658258 15093356674; factory@coreychem.com China 29826 58
Shanghai UCHEM Inc.
+862156762820 +86-13564624040 sales@myuchem.com China 6710 58
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714 fandachem@gmail.com China 9348 55
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795 ivan@atkchemical.com China 32480 60
Hubei Jusheng Technology Co.,Ltd.
18871490254 linda@hubeijusheng.com CHINA 28180 58
BOC Sciences
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HANGZHOU CLAP TECHNOLOGY CO.,LTD
86-571-88216897,88216896 13588875226 sales@hzclap.com CHINA 6313 58
Dideu Industries Group Limited
+86-29-89586680 +86-15129568250 1026@dideu.com China 29220 58
Zhejiang J&C Biological Technology Co.,Limited
+1-2135480471 +1-2135480471 sales@sarms4muscle.com China 10523 58

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View Lastest Price from ISRIB (trans-isoMer) manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
ISRIB (trans-isomer) pictures 2024-02-23 ISRIB (trans-isomer)
1597403-47-8
US $496.00 / g 1g 0.98 1kg Shanghai UCHEM Inc.
trans ISRIB pictures 2021-12-14 trans ISRIB
1597403-47-8
US $100.00-60.00 / box 100box 98%+ 10kgs Wuhan Nutra Biotechnology Co.,Ltd
ISRIB (trans-isomer) pictures 2021-10-08 ISRIB (trans-isomer)
1597403-47-8
US $100.00-40.00 / G 1G 98%+ 10kgs Wuhan Nutra Biotechnology Co.,Ltd
  • trans ISRIB pictures
  • trans ISRIB
    1597403-47-8
  • US $100.00-60.00 / box
  • 98%+
  • Wuhan Nutra Biotechnology Co.,Ltd

ISRIB (trans-isoMer) Spectrum

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) Trans-ISRIB 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 N,N'-(trans-cyclohexane-1,4-diyl)bis(2-(4-chlorophenoxy)acetamide) 1597403-47-8 API Inhibitors research chem