Physicochemical Properties
| Molecular Formula | C57H67N7O9 |
| Molecular Weight | 994.18 |
| Exact Mass | 993.5 |
| CAS # | 2714510-72-0 |
| PubChem CID | 165412462 |
| Appearance | Typically exists as solid at room temperature |
| LogP | 6.4 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 14 |
| Rotatable Bond Count | 16 |
| Heavy Atom Count | 73 |
| Complexity | 1710 |
| Defined Atom Stereocenter Count | 5 |
| SMILES | CCN1C2=C(C=C(C=C2)C3=NC(=C(N3C4=CC=C(C=C4)OCCOCCOC5(O[C@H]6[C@@H]([C@H]([C@@H](O[C@H]6O5)CO)O)O)C)C7=CC=C(C=C7)N8CCN(CC8)C)C9=CC=C(C=C9)N2CCN(CC2)C)C2=CC=CC=C21 |
| InChi Key | JQFKPFVLERGHMD-BHDRTPEQSA-N |
| InChi Code | InChI=1S/C57H67N7O9/c1-5-63-47-9-7-6-8-45(47)46-36-40(14-23-48(46)63)55-58-50(38-10-15-41(16-11-38)61-28-24-59(3)25-29-61)51(39-12-17-42(18-13-39)62-30-26-60(4)27-31-62)64(55)43-19-21-44(22-20-43)69-34-32-68-33-35-70-57(2)72-54-53(67)52(66)49(37-65)71-56(54)73-57/h6-23,36,49,52-54,56,65-67H,5,24-35,37H2,1-4H3/t49-,52-,53+,54-,56-,57?/m0/s1 |
| Chemical Name | (3aS,5S,6R,7R,7aS)-2-[2-[2-[4-[2-(9-ethylcarbazol-3-yl)-4,5-bis[4-(4-methylpiperazin-1-yl)phenyl]imidazol-1-yl]phenoxy]ethoxy]ethoxy]-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-6,7-diol |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | IC50: 5.0 μM (HepG2); 3.9 μM (MDA-MB-231); ＞100 μM (HBL-100)[1] |
| ln Vitro | Anticancer agent 84 exhibits cytotoxicity in normal cells (HBL-100) and cancer cells (HepG2, MDA-MB-231) with IC50 values of >100 μM, 3.9 μM, and 5.0 μM, respectively[1]. Good c -MYC G4 binding and stability capabilities are demonstrated by anticancer drug 84[1]. Targeting the promoter G4, anticancer drug 84 inhibits c-MYC transcription, causing c-MYC-dependent cancer cell death in triple-negative breast cancer cells MDA-MB-23.[1]. The three proteins' (NM23-H2, BLM, and DHX36) binding to c-MYC G4 is strongly disrupted by anticancer drug 84 (2 μM), with IC50 values of 0.16 μM, 2.3 μM, and 7.0 μM, respectively[1]. 84 (0–5 μM) affects TNBC c-MYC-related processes, such as invasion, apoptosis, cell cycle, and proliferation[1]. |
| ln Vivo | In the MDAMB-231 mouse xenograft model, anticancer drug 84 (ip; 2.5 mg/kg; daily; for 24 days) effectively reduces tumor development along with c-MYC downregulation[1]. |
| Cell Assay |
Western Blot Analysis[1] Cell Types: MDA-MB-231 cells Tested Concentrations: 1.25, 2.5, 5 μM Incubation Duration: 48 h Experimental Results: diminished the mRNA levels of c-MYC. Cell Cycle Analysis[1] Cell Types: MDA-MB-231 cells Tested Concentrations: 1.25, 2.5, 5 μM Incubation Duration: 24 h Experimental Results: Could arrest MDA-MB-231 cells at the Sub G0 phase. Apoptosis Analysis[1] Cell Types: MDA-MB-231 cells Tested Concentrations: 1.25, 2.5, 5 μM Incubation Duration: 24 h Experimental Results: Induced early apoptosis and necrosis in MDA-MB-231 cells. RT-PCR[1] Cell Types: MDA-MB-231 cells Tested Concentrations: 1.25, 2.5 μM Incubation Duration: 24 h Experimental Results: demonstrated relatively weak effects on other genes and suppressed c-MYC transcription by targeting c-MYC G4. Cell Cytotoxicity Assay[1] Cell Types: MDA-MB-231 cells Tested Concentrations: Incubation Duration: 48 h Experimental Results: Displayed good cytotoxicity against various cancer cells, including MDA-MB-231, MCF-7, HepG2, and SiHa and displayed less cytotoxicity against normal HBL-100 and NCM460 cells. Cell Proliferation Assay[1] Cell Types: MDA-MB-231 cells Tested Concentrations: 1.25, 2.5, 5 μM Incubation Duration: 10 days Experimental Results: Exhibits good antiproliferative activity. Cell Invasion Assay[1] Cell Types: MDA-MB-231 cells Tested Concentrations: 1.25, 2.5, 5 μM Incubation Duration: 24 h Experimental Results: Obviously diminished the invasion with an IC50 value of 1.7 μM. |
| Animal Protocol |
Animal/Disease Models: BALB/C-nu/nu (nude) mice(female, five-week-aged, 10−12 g)[1] Doses: 2.5 mg/kg Route of Administration: intraperitoneally (ip), daily, for 24 days Experimental Results: demonstrated potent antitumor activity and could act as a c-MYC repressor in vivo. |
| References |
[1]. Design, Synthesis, and Evaluation of New Sugar-Substituted Imidazole Derivatives as Selective c-MYC Transcription Repressors Targeting the Promoter G-Quadruplex. J Med Chem. 2022 Sep 19. |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.0059 mL | 5.0293 mL | 10.0585 mL | |
| 5 mM | 0.2012 mL | 1.0059 mL | 2.0117 mL | |
| 10 mM | 0.1006 mL | 0.5029 mL | 1.0059 mL |