Synonym
IM-54; IM 54; IM54;
IUPAC/Chemical Name
1-Methyl-3-(1-methyl-1H-indol-3-yl)-4-(pentylamino)-1H-pyrrole-2,5-dione
InChi Key
SGLOMINNEBLJFF-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H23N3O2/c1-4-5-8-11-20-17-16(18(23)22(3)19(17)24)14-12-21(2)15-10-7-6-9-13(14)15/h6-7,9-10,12,20H,4-5,8,11H2,1-3H3
SMILES Code
O=C(C(C1=CN(C)C2=C1C=CC=C2)=C3NCCCCC)N(C)C3=O
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
>2 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
2934.99.9001
Biological target:
IM-54 is a selective inhibitor of oxidative stress-induced necrosis. IM-54 shows potent inhibitory activity against H2O2-induced necrosis. IM-54 acts as a potential cardioprotective agent and biological tool for investigating the molecular mechanisms of cell death.
In vitro activity:
IM-54 inhibited necrosis induced by oxidative stress (TBHP and H2O2), whereas Z-VAD did not.
Reference: ACS Med Chem Lett. 2018 Jan 29;9(3):182-187. https://pubmed.ncbi.nlm.nih.gov/29541357/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
50.0 |
153.65 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
325.41
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.
| 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 |
Formulation protocol:
1. Dodo K, Shimizu T, Sasamori J, Aihara K, Terayama N, Nakao S, Iuchi K, Takahashi M, Sodeoka M. Indolylmaleimide Derivative IM-17 Shows Cardioprotective Effects in Ischemia-Reperfusion Injury. ACS Med Chem Lett. 2018 Jan 29;9(3):182-187. doi: 10.1021/acsmedchemlett.7b00454. PMID: 29541357; PMCID: PMC5846036.
2. Alshangiti AM, Tuboly E, Hegarty SV, McCarthy CM, Sullivan AM, O'Keeffe GW. 4-Hydroxychalcone Induces Cell Death via Oxidative Stress in MYCN-Amplified Human Neuroblastoma Cells. Oxid Med Cell Longev. 2019 Dec 5;2019:1670759. doi: 10.1155/2019/1670759. PMID: 31885773; PMCID: PMC6915131.
In vitro protocol:
1. Dodo K, Shimizu T, Sasamori J, Aihara K, Terayama N, Nakao S, Iuchi K, Takahashi M, Sodeoka M. Indolylmaleimide Derivative IM-17 Shows Cardioprotective Effects in Ischemia-Reperfusion Injury. ACS Med Chem Lett. 2018 Jan 29;9(3):182-187. doi: 10.1021/acsmedchemlett.7b00454. PMID: 29541357; PMCID: PMC5846036.
2. Alshangiti AM, Tuboly E, Hegarty SV, McCarthy CM, Sullivan AM, O'Keeffe GW. 4-Hydroxychalcone Induces Cell Death via Oxidative Stress in MYCN-Amplified Human Neuroblastoma Cells. Oxid Med Cell Longev. 2019 Dec 5;2019:1670759. doi: 10.1155/2019/1670759. PMID: 31885773; PMCID: PMC6915131.
1: Dodo K, Shimizu T, Sasamori J, Aihara K, Terayama N, Nakao S, Iuchi K, Takahashi M, Sodeoka M. Indolylmaleimide Derivative IM-17 Shows Cardioprotective Effects in Ischemia-Reperfusion Injury. ACS Med Chem Lett. 2018 Jan 29;9(3):182-187. doi: 10.1021/acsmedchemlett.7b00454. eCollection 2018 Mar 8. PubMed PMID: 29541357; PubMed Central PMCID: PMC5846036.
2: Dodo K, Hayamizu K, Shimizu T, Sodeoka M. Structure-Activity Relationship Study of 3-Amino-2-indolyllactam Derivatives: Development of Inhibitors of Oxidative Stress-Induced Necrosis. Chem Pharm Bull (Tokyo). 2016;64(7):886-98. doi: 10.1248/cpb.c16-00259. PubMed PMID: 27373644.
3: Zeng F, Sherry JP, Bols NC. Evaluating the toxic potential of benzothiazoles with the rainbow trout cell lines, RTgill-W1 and RTL-W1. Chemosphere. 2016 Jul;155:308-318. doi: 10.1016/j.chemosphere.2016.04.079. Epub 2016 Apr 29. PubMed PMID: 27131451.
4: Zeng F, Sherry JP, Bols NC. Use of the rainbow trout cell lines, RTgill-W1 and RTL-W1 to evaluate the toxic potential of benzotriazoles. Ecotoxicol Environ Saf. 2016 Feb;124:315-323. doi: 10.1016/j.ecoenv.2015.11.003. Epub 2015 Nov 13. PubMed PMID: 26584462.
5: de Araujo CB, Russo LC, Castro LM, Forti FL, do Monte ER, Rioli V, Gozzo FC, Colquhoun A, Ferro ES. A novel intracellular peptide derived from g1/s cyclin d2 induces cell death. J Biol Chem. 2014 Jun 13;289(24):16711-26. doi: 10.1074/jbc.M113.537118. Epub 2014 Apr 24. PubMed PMID: 24764300; PubMed Central PMCID: PMC4059116.
6: Li FC, Yen JC, Chan SH, Chang AY. Bioenergetics failure and oxidative stress in brain stem mediates cardiovascular collapse associated with fatal methamphetamine intoxication. PLoS One. 2012;7(1):e30589. doi: 10.1371/journal.pone.0030589. Epub 2012 Jan 19. PubMed PMID: 22276218; PubMed Central PMCID: PMC3261925.
7: Sodeoka M, Dodo K. Development of selective inhibitors of necrosis. Chem Rec. 2010 Oct;10(5):308-14. doi: 10.1002/tcr.201000031. Review. PubMed PMID: 20848666.
8: Dodo K, Katoh M, Shimizu T, Takahashi M, Sodeoka M. Inhibition of hydrogen peroxide-induced necrotic cell death with 3-amino-2-indolylmaleimide derivatives. Bioorg Med Chem Lett. 2005 Jun 15;15(12):3114-8. PubMed PMID: 15878276.
