ISRIB (trans-isoMer)

ChemicalBook > CAS DataBase List > ISRIB (trans-isoMer)

Product Name: ISRIB (trans-isoMer)
CAS No.: 1597403-47-8
Chemical Name: ISRIB (trans-isoMer)
Synonyms: CS-1768;Trans-ISRIB;ISRIB - trans-ISRIB;ISRIS(trans-isomer);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)-;Acetamide, N,N'-trans-1,4-cyclohexanediylbis[2-(4-chlorophenoxy)-
CBNumber: CB72714669
Molecular Formula: C22H24Cl2N2O4
Formula Weight: 451.34
MOL File: 1597403-47-8.mol

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ISRIB (trans-isoMer) Property

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)
color: White to off-white

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0843
Product name: ISRIB
Purity: ≥98%(HPLC)
Packaging: 5mg
Price: $118
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML0843
Product name: ISRIB
Purity: ≥98% (HPLC)
Packaging: 25MG
Price: $478
Updated: 2024/03/01

Cayman Chemical

Product number: 16258
Product name: trans-ISRIB
Purity: ≥95%
Packaging: 5mg
Price: $81
Updated: 2024/03/01

Cayman Chemical

Product number: 16258
Product name: trans-ISRIB
Purity: ≥95%
Packaging: 10mg
Price: $152
Updated: 2024/03/01

Cayman Chemical

Product number: 16258
Product name: trans-ISRIB
Purity: ≥95%
Packaging: 25mg
Price: $356
Updated: 2024/03/01

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ISRIB (trans-isoMer) Chemical Properties,Usage,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

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ISRIB (trans-isoMer) Suppliers

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View Lastest Price from ISRIB (trans-isoMer) manufacturers

Shanghai UCHEM Inc.

Product: ISRIB (trans-isomer) 1597403-47-8
Price: US $496.00/g
Min. Order: 1g
Purity: 0.98
Supply Ability: 1kg
Release date: 2023-11-17

Wuhan Nutra Biotechnology Co.,Ltd

Product: ISRIB (trans-isomer) 1597403-47-8
Price: US $100.00-40.00/G
Min. Order: 1G
Purity: 98%+
Supply Ability: 10kgs
Release date: 2022-05-28

Wuhan Nutra Biotechnology Co.,Ltd

Product: trans ISRIB 1597403-47-8
Price: US $100.00-60.00/box
Min. Order: 100box
Purity: 98%+
Supply Ability: 10kgs
Release date: 2022-06-21

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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)

Acetamide, N,N'-trans-1,4-cyclohexanediylbis[2-(4-chlorophenoxy)-

ISRIS(trans-isomer)

1597403-47-8

API

Inhibitors

research chem