 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C13H14N2O3 |
| Exact Mass | 246.1 |
| CAS # | 81307-24-6 |
| PubChem CID | 149913 |
| Appearance | Typically exists as solid at room temperature |
| Density | 1.43g/cm3 |
| Boiling Point | 520.5ºC at 760 mmHg |
| Flash Point | 268.6ºC |
| Index of Refraction | 1.675 |
| LogP | 1.094 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Heavy Atom Count | 18 |
| Complexity | 371 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | COC1=C(C=C2C(=C1)C(=O)N3CCCC3C=N2)O |
| InChi Key | LQDGLTOVYOUCRG-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C13H14N2O3/c1-18-12-5-9-10(6-11(12)16)14-7-8-3-2-4-15(8)13(9)17/h5-8,16H,2-4H2,1H3 |
| Chemical Name | 3-hydroxy-2-methoxy-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one |
| 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 | Antibiotic DC 81 demonstrates cytotoxicity at IC50 values of 4.4 μM, 18.5 μM, 31.0 μM, and 41.5 μM for the human melanoma cell lines B16, A375, A2058, and RPMI7951, respectively[1][2]. Through its electrophilic carbinolamine functionality at N10–C11, the antibiotic DC 81 demonstrates its biological action by covalently attaching to the N2 of guanine in the minor groove of DNA[1]. Apoptosis dependent on mitochondria is induced by the antibiotic DC 81 (4 μM, 24 h)[2]. |
| ln Vivo | In tumor-bearing animals, Antibiotic DC 81 (0–10 mg/kg, ip, at days 4, 7, 10, and 13 following tumor cell injection) reduces the tumor burden; however, Antibiotic DC 81 at 10 mg/kg severely affects liver and heart muscle function[2]. |
| Cell Assay |
Apoptosis Analysis[2] Cell Types: B16 melanoma cells Tested Concentrations: 4 μM Incubation Duration: 24 h Experimental Results: Induced mitochondria dependent apoptosis. |
| Animal Protocol |
Animal/Disease Models: Female C57BL/6 mice (8-12 weeks old, B16 cells were injected into the tail veins of mice)[2] Doses: 0.1, 1, 10 mg/kg Route of Administration: ip, at day 4, 7, 10, 13 after tumor cell injection Experimental Results: Substantially diminished the tumor burden by 20% at 1 mg/kg. DC- 81 at 10 mg/kg induced an 8-10-fold increase of GPT and a 6-8-fold increase in CPK, which indicated severe impaired liver function and muscle damage. Did not impair significant renal function as demonstrated by serum creatinine. |
| References |
[1]. Biological evaluation of an antibiotic DC-81-indole conjugate agent in human melanoma cell lines. Kaohsiung J Med Sci. 2003 Jan;19(1):6-12. [2]. Pyrrolo[2,1-c][1,4]benzodiazepine and indole conjugate (IN6CPBD) has better efficacy and superior safety than the mother compound DC-81 in suppressing the growth of established melanoma in vivo. Chem Biol Interact. 2009 Aug 14;180(3):360-7. |
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.) |