| Size | Price | Stock | Qty |
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| 1mg |
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| Other Sizes |
| Targets |
Chartreusin is a potent inhibitor of topoisomerase II. It binds to GC-rich tracts in DNA, with a clear preference for B-DNA over Z-DNA. It inhibits RNA synthesis and causes single-strand scission of DNA via the formation of free radicals.
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| ln Vitro |
In vitro, chartreusin inhibits the growth of Gram-positive bacteria such as Staphylococcus aureus, Bacillus subtilis, and Micrococcus luteus. It is active against mycobacteria. Its mechanism involves binding to DNA GC-rich sequences and inhibiting topoisomerase II, leading to DNA damage.
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| ln Vivo |
In vivo, chartreusin has demonstrated antitumor activity. As an antibiotic, it is active against certain Gram-positive bacteria and mycobacteria. Its anticancer activity is related to its ability to inhibit topoisomerase II and induce DNA damage.
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| Enzyme Assay |
Cell-free assays for chartreusin involve studying its binding to DNA. The compound is incubated with various DNA sequences (e.g., GC-rich vs. AT-rich), and its binding affinity is measured using techniques such as gel mobility shift assays, fluorescence spectroscopy, or surface plasmon resonance.
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| Cell Assay |
In vitro cytotoxicity assays are performed using cancer cell lines, and chartreusin's ability to inhibit cell growth is measured using MTT or similar assays. Topoisomerase II inhibition can be assessed by measuring the accumulation of catenated DNA or the relaxation of supercoiled DNA in cell-free or cell-based systems.
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| Animal Protocol |
In vivo efficacy is evaluated in tumor-bearing mouse models. Chartreusin is administered via appropriate routes (e.g., intraperitoneal or intravenous), and tumor growth inhibition is measured. Its antibacterial activity is evaluated in animal models of bacterial infection.
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| ADME/Pharmacokinetics |
Chartreusin (C32H32O14) has a molecular weight of 640.59 g/mol. It is a yellow solid. It is soluble in ethanol, methanol, DMF, and DMSO, and partly miscible with water. It is derived from Streptomyces chartreusis and is stored at 4°C.
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| Toxicity/Toxicokinetics |
The toxicity of chartreusin is related to its mechanism of action as a DNA-binding and topoisomerase II-inhibiting agent. Its effects on rapidly dividing cells, such as bone marrow and gastrointestinal epithelium, may cause myelosuppression and gastrointestinal toxicity. Detailed toxicological data are limited to preclinical studies.
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| References | |
| Additional Infomation |
Chartreusin is a glycoside and benzo[a]chromone. It has been reported that Streptomyces chartreusis contains Chartreusin, and relevant data are available for reference.
Chartreusin is an antitumor antibiotic that binds to GC-rich tracts in DNA, with a clear preference for B-DNA over Z-DNA. It is a potent inhibitor of topoisomerase II. It inhibits RNA synthesis and causes single-strand scission of DNA via the formation of free radicals. It is also known as Antibiotic X 465A and Lambdamycin. |
| Exact Mass |
640.179
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|---|---|
| CAS # |
6377-18-0
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| PubChem CID |
5281394
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.63g/cm3
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| Boiling Point |
945.5ºC at 760 mmHg
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| Flash Point |
307.8ºC
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| Index of Refraction |
1.718
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| LogP |
1.369
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
14
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
46
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| Complexity |
1150
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| Defined Atom Stereocenter Count |
10
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| SMILES |
C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)OC2=CC=CC3=C2C4=C5C6=C(C=CC(=C6C(=O)O4)C)OC(=O)C5=C3O)O[C@@H]7[C@@H]([C@H]([C@H]([C@H](O7)C)O)OC)O)O)O
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| InChi Key |
PONPPNYZKHNPKZ-RYBWXQSLSA-N
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| InChi Code |
InChI=1S/C32H32O14/c1-10-8-9-15-18-16(10)29(38)45-26-17-13(23(35)20(19(18)26)30(39)43-15)6-5-7-14(17)44-32-28(24(36)21(33)11(2)42-32)46-31-25(37)27(40-4)22(34)12(3)41-31/h5-9,11-12,21-22,24-25,27-28,31-37H,1-4H3/t11-,12-,21+,22+,24+,25-,27+,28-,31-,32+/m1/s1
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| Chemical Name |
3-[(2S,3R,4S,5R,6R)-3-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxy-8-hydroxy-15-methyl-11,18-dioxapentacyclo[10.6.2.02,7.09,19.016,20]icosa-1(19),2(7),3,5,8,12(20),13,15-octaene-10,17-dione
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| Synonyms |
Chartreusin NSC-5159 NSC 5159
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| HS Tariff Code |
2934.99.9001
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| 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)
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| 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
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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