Lactimidomycin is a potent glutarimide-based antibiotic isolated from Streptomyces amphibiosporus, acting as a potent inhibitor of eukaryotic translation elongation with anticancer and antiviral activities.
Physicochemical Properties
| Molecular Formula | C26H35NO6 |
| Molecular Weight | 457.5592 |
| Exact Mass | 457.246 |
| CAS # | 134869-15-1 |
| PubChem CID | 11669726 |
| Appearance | White to off-white solid powder |
| Density | 1.115g/cm3 |
| Boiling Point | 704.6ºC at 760mmHg |
| Flash Point | 379.9ºC |
| Vapour Pressure | 6.04E-23mmHg at 25°C |
| Index of Refraction | 1.514 |
| LogP | 3.618 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 33 |
| Complexity | 837 |
| Defined Atom Stereocenter Count | 4 |
| SMILES | C[C@H]1/C=C\C=C\CC/C=C/C(=O)O[C@H]1/C(=C/[C@H](C)C(=O)C[C@@H](CC2CC(=O)NC(=O)C2)O)/C |
| InChi Key | OYOKHBHOTQDIPM-BRHOHSSQSA-N |
| InChi Code | InChI=1S/C26H35NO6/c1-17-10-8-6-4-5-7-9-11-25(32)33-26(17)19(3)12-18(2)22(29)16-21(28)13-20-14-23(30)27-24(31)15-20/h4,6,8-12,17-18,20-21,26,28H,5,7,13-16H2,1-3H3,(H,27,30,31)/b6-4+,10-8-,11-9+,19-12+/t17-,18-,21+,26+/m0/s1 |
| Chemical Name | 4-[(E,2R,5S)-2-hydroxy-5-methyl-7-[(2R,3S,4Z,6E,10E)-3-methyl-12-oxo-1-oxacyclododeca-4,6,10-trien-2-yl]-4-oxooct-6-enyl]piperidine-2,6-dione |
| 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
| ln Vitro | Lactimidomycin (0.01-100 nM; 24 hours; Hs 579T, HCC 1937, HCC 1395, HCC 2218, BT 474, MCF 7, MDA MB231 cells, and MCF 10A) inhibits cell growth with low nanomolar IC50 concentrations, but higher doses are required to inhibit growth of the non-tumorigenic breast cell line MCF10A[1]. Lactimidomycin inhibits DENV2 infectious particle formation at a dose-responsive level (EC90 = 0.4 μM). Cell viability remained unchanged at doses as high as 12.5 µM [2]. Lactimidomycin is a strong DENV2 inhibitor, and its reduction of DENV2 translation reduces the creation of new infectious particles. Lactimidomycin may protect cells against viral cytotoxic effects such as apoptosis, most likely by inhibiting virus protein creation and reproduction [2]. |
| ln Vivo | The administration of lactimidomycin (0.6 mg/kg; intraperitoneal injection; daily; for one month; female nude mice) significantly inhibits the formation of tumors in these mice[1]. |
| Cell Assay |
Cell Proliferation Assay[1] Cell Types: Hs 579T, HCC 1937, HCC 1395, HCC 2218, BT 474, MCF 7, MDA MB231 cells and MCF 10A Tested Concentrations: 0.01-100 nM Incubation Duration: 24 hrs (hours) Experimental Results: Inhibited cell growth with IC50 concentrations in the low nanomolar range. |
| Animal Protocol |
Animal/Disease Models: Female nude mice (6-8 week old) with MDA MB 231 cells[1] Doses: 0.6 mg/kg Route of Administration: intraperitoneal (ip)injection; daily; for one month Experimental Results: Had an appreciable effect on tumor growth in vivo. |
| References |
[1]. Inhibition of eukaryotic translation elongation by cycloheximide and lactimidomycin. Nat Chem Biol. 2010 Mar;6(3):209-217. [2]. Lactimidomycin is a broad-spectrum inhibitor of dengue and other RNA viruses. Antiviral Res. 2016 Apr;128:57-62. |
| Additional Infomation |
Lactimidomycin is a macrolide. Lactimidomycin has been reported in Streptomyces amphibiosporus with data available. |
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 | 2.1855 mL | 10.9275 mL | 21.8551 mL | |
| 5 mM | 0.4371 mL | 2.1855 mL | 4.3710 mL | |
| 10 mM | 0.2186 mL | 1.0928 mL | 2.1855 mL |