4EGI-1
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MedKoo CAT#: 563209

CAS#: 315706-13-9

Description: 4EGI-1 is an inhibitor of eIF4E:eIF4G interaction that acts by preventing eIF4E binding to eIF4G.


Chemical Structure

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4EGI-1
CAS# 315706-13-9

Theoretical Analysis

MedKoo Cat#: 563209
Name: 4EGI-1
CAS#: 315706-13-9
Chemical Formula: C18H12Cl2N4O4S
Exact Mass: 449.9956
Molecular Weight: 451.27
Elemental Analysis: C, 47.91; H, 2.68; Cl, 15.71; N, 12.42; O, 14.18; S, 7.10

Price and Availability

Size Price Availability Quantity
5.0mg USD 290.0 2 Weeks
10.0mg USD 470.0 2 Weeks
25.0mg USD 760.0 2 Weeks
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Synonym: 4EGI-1; 4EGI1; 4EGI1; 4 EGI1; 4-EGI1; 4 EGI 1; 4-EGI-1;

IUPAC/Chemical Name: alpha-[2-[4-(3,4-Dichlorophenyl)-2-thiazolyl]hydrazinylidene]-2-nitro-benzenepropanoic acid

InChi Key: KFRKRECSIYXARE-HYARGMPZSA-N

InChi Code: InChI=1S/C18H12Cl2N4O4S/c19-12-6-5-10(7-13(12)20)15-9-29-18(21-15)23-22-14(17(25)26)8-11-3-1-2-4-16(11)24(27)28/h1-7,9H,8H2,(H,21,23)(H,25,26)/b22-14+

SMILES Code: O=C(O)/C(CC1=CC=CC=C1[N+]([O-])=O)=N/NC2=NC(C3=CC=C(Cl)C(Cl)=C3)=CS2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 451.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Frolinger T, Smith C, Cobo CF, Sims S, Brathwaite J, de Boer S, Huang J, Pasinetti GM. Dietary polyphenols promote resilience against sleep deprivation-induced cognitive impairment by activating protein translation. FASEB J. 2018 Apr 27:fj201800030R. doi: 10.1096/fj.201800030R. [Epub ahead of print] PubMed PMID: 29702026.

2: Harris BRE, Wang D, Zhang Y, Ferrari M, Okon A, Cleary MP, Wagner CR, Yang DQ. Induction of the p53 Tumor Suppressor in Cancer Cells through Inhibition of Cap-Dependent Translation. Mol Cell Biol. 2018 Apr 30;38(10). pii: e00367-17. doi: 10.1128/MCB.00367-17. Print 2018 May 15. PubMed PMID: 29483299; PubMed Central PMCID: PMC5954198.

3: De A, Jacobson BA, Peterson MS, Jay-Dixon J, Kratzke MG, Sadiq AA, Patel MR, Kratzke RA. 4EGI-1 represses cap-dependent translation and regulates genome-wide translation in malignant pleural mesothelioma. Invest New Drugs. 2018 Apr;36(2):217-229. doi: 10.1007/s10637-017-0535-z. Epub 2017 Nov 8. PubMed PMID: 29116477.

4: Santini E, Huynh TN, Longo F, Koo SY, Mojica E, D'Andrea L, Bagni C, Klann E. Reducing eIF4E-eIF4G interactions restores the balance between protein synthesis and actin dynamics in fragile X syndrome model mice. Sci Signal. 2017 Nov 7;10(504). pii: eaan0665. doi: 10.1126/scisignal.aan0665. PubMed PMID: 29114037; PubMed Central PMCID: PMC5858943.

5: Jacobson BA, Sadiq AA, Tang S, Jay-Dixon J, Patel MR, Drees J, Sorenson BS, Russell SJ, Kratzke RA. Cap-dependent translational control of oncolytic measles virus infection in malignant mesothelioma. Oncotarget. 2017 Jun 27;8(38):63096-63109. doi: 10.18632/oncotarget.18656. eCollection 2017 Sep 8. PubMed PMID: 28968974; PubMed Central PMCID: PMC5609906.

6: Marques-Ramos A, Candeias MM, Menezes J, Lacerda R, Willcocks M, Teixeira A, Locker N, Romão L. Cap-independent translation ensures mTOR expression and function upon protein synthesis inhibition. RNA. 2017 Nov;23(11):1712-1728. doi: 10.1261/rna.063040.117. Epub 2017 Aug 18. PubMed PMID: 28821580; PubMed Central PMCID: PMC5648038.

7: Sekiyama N, Boeszoermenyi A, Arthanari H, Wagner G, Léger-Abraham M. (1)H, (13)C, and (15)N backbone chemical shift assignments of 4E-BP1(44-87) and 4E-BP1(44-87) bound to eIF4E. Biomol NMR Assign. 2017 Oct;11(2):187-191. doi: 10.1007/s12104-017-9744-9. Epub 2017 Jun 6. PubMed PMID: 28589219; PubMed Central PMCID: PMC5693643.

8: Yoo HS, Lee K, Na K, Zhang YX, Lim HJ, Yi T, Song SU, Jeon MS. Mesenchymal stromal cells inhibit CD25 expression via the mTOR pathway to potentiate T-cell suppression. Cell Death Dis. 2017 Feb 23;8(2):e2632. doi: 10.1038/cddis.2017.45. PubMed PMID: 28230853; PubMed Central PMCID: PMC5386489.

9: Ostroff LE, Botsford B, Gindina S, Cowansage KK, LeDoux JE, Klann E, Hoeffer C. Accumulation of Polyribosomes in Dendritic Spine Heads, But Not Bases and Necks, during Memory Consolidation Depends on Cap-Dependent Translation Initiation. J Neurosci. 2017 Feb 15;37(7):1862-1872. doi: 10.1523/JNEUROSCI.3301-16.2017. Epub 2017 Jan 13. PubMed PMID: 28087764; PubMed Central PMCID: PMC5320614.

10: Wu M, Zhang C, Li XJ, Liu Q, Wanggou S. Anti-Cancer Effect of Cap-Translation Inhibitor 4EGI-1 in Human Glioma U87 Cells: Involvement of Mitochondrial Dysfunction and ER Stress. Cell Physiol Biochem. 2016;40(5):1013-1028. Epub 2016 Dec 12. PubMed PMID: 27941351.

11: Kerr LT, Donoghue JF, Wilding AL, Johns TG. Axitinib Has Antiangiogenic and Antitumorigenic Activity in Myxoid Liposarcoma. Sarcoma. 2016;2016:3484673. Epub 2016 Oct 16. PubMed PMID: 27822137; PubMed Central PMCID: PMC5086398.

12: Chen B, Zhao J, Zhang S, Zhang Y, Huang Z. HPIP promotes gastric cancer cell proliferation through activation of cap-dependent translation. Oncol Rep. 2016 Dec;36(6):3664-3672. doi: 10.3892/or.2016.5157. Epub 2016 Oct 11. PubMed PMID: 27748944.

13: Dabbah M, Attar-Schneider O, Zismanov V, Tartakover Matalon S, Lishner M, Drucker L. Multiple myeloma cells promote migration of bone marrow mesenchymal stem cells by altering their translation initiation. J Leukoc Biol. 2016 Oct;100(4):761-770. Epub 2016 Jun 6. PubMed PMID: 27272311.

14: Salvi N, Papadopoulos E, Blackledge M, Wagner G. The Role of Dynamics and Allostery in the Inhibition of the eIF4E/eIF4G Translation Initiation Factor Complex. Angew Chem Int Ed Engl. 2016 Jun 13;55(25):7176-9. doi: 10.1002/anie.201603254. Epub 2016 May 10. PubMed PMID: 27162083; PubMed Central PMCID: PMC5022372.

15: Sato A, Ueno H, Takase A, Ando A, Sekine Y, Yano T. Cytotoxicity Induced by a Redox-silent Analog of Tocotrienol in Human Mesothelioma H2452 Cell Line via Suppression of Cap-dependent Protein Translation. Anticancer Res. 2016 Apr;36(4):1527-33. PubMed PMID: 27069128.

16: Wang W, Li J, Wen Q, Luo J, Chu S, Chen L, Qing Z, Xie G, Xu L, Alnemah MM, Li M, Fan S, Zhang H. 4EGI-1 induces apoptosis and enhances radiotherapy sensitivity in nasopharyngeal carcinoma cells via DR5 induction on 4E-BP1 dephosphorylation. Oncotarget. 2016 Apr 19;7(16):21728-41. doi: 10.18632/oncotarget.7824. PubMed PMID: 26942880; PubMed Central PMCID: PMC5008318.

17: Yang X, Dong QF, Li LW, Huo JL, Li PQ, Fei Z, Zhen HN. The cap-translation inhibitor 4EGI-1 induces mitochondrial dysfunction via regulation of mitochondrial dynamic proteins in human glioma U251 cells. Neurochem Int. 2015 Nov;90:98-106. doi: 10.1016/j.neuint.2015.07.019. Epub 2015 Jul 26. PubMed PMID: 26220902.

18: Sekiyama N, Arthanari H, Papadopoulos E, Rodriguez-Mias RA, Wagner G, Léger-Abraham M. Molecular mechanism of the dual activity of 4EGI-1: Dissociating eIF4G from eIF4E but stabilizing the binding of unphosphorylated 4E-BP1. Proc Natl Acad Sci U S A. 2015 Jul 28;112(30):E4036-45. doi: 10.1073/pnas.1512118112. Epub 2015 Jul 13. PubMed PMID: 26170285; PubMed Central PMCID: PMC4522750.

19: Basmadjian C, Malka-Mahieu H, Desaubry L. Revision of the Synthesis and Pharmacological Activity of a Reported Translation Inhibitor. Anticancer Agents Med Chem. 2015;15(10):1305-7. PubMed PMID: 26032964.

20: Girardi T, De Keersmaecker K. T-ALL: ALL a matter of Translation? Haematologica. 2015 Mar;100(3):293-5. doi: 10.3324/haematol.2014.118562. PubMed PMID: 25740104; PubMed Central PMCID: PMC4349265.

4EGI-1

5.0mg / USD 290.0