Chartreusin
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| Category | Antibiotics |
| Catalog number | BBF-00769 |
| CAS | 6377-18-0 |
| Molecular Weight | 640.59 |
| Molecular Formula | C32H32O14 |
| Purity | >99% by HPLC |
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Description
It is produced by the strain of Streptomyces chartreusis. It has the activity of anti-gram-positive bacteria and mycobacterium. Chartreusin is an antitumour antibiotic that binds to GC-rich tracts in DNA, with a clear preference for B-DNA over Z-DNA; inhibits RNA synthesis and causes single-strand scission of DNA via the formation of free radicals; a potent inhibitor of topoisomerase II.
Specification
| Synonyms | Lambdamycin; Antibiotic X-465A; NSC 5159; (1R,2R,3aS,8aR)-1-[(Z)-5-hydroxy-3-(hydroxymethyl)pent-3-enyl]-1-(hydroxymethyl)-2,5-dimethyl-2,3,4,7,8,8a-hexahydroazulene-3a-carbaldehyde; 10-[[6-Deoxy-2-O-(6-deoxy-3-O-methyl-α-D-galactopyranosyl)-β-D-galactopyranosyl]oxy]-6-hydroxy-1-methylbenzo[h][1]benzopyrano[5,4,3-cde][1]benzopyran-5,12-dione |
| Storage | −20 °C under inert atmosphere |
| IUPAC 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 |
| Canonical SMILES | CC1C(C(C(C(O1)OC2=CC=CC3=C2C4=C5C6=C(C=CC(=C6C(=O)O4)C)OC(=O)C5=C3O)OC7C(C(C(C(O7)C)O)OC)O)O)O |
| InChI | 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 |
| InChI Key | PONPPNYZKHNPKZ-RYBWXQSLSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Yellow Flake Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor); mycobacteria |
| Boiling Point | 945.5 °C at 760 mmHg |
| Melting Point | 184-186 °C |
| Density | 1.63 g/cm3 |
| Solubility | Soluble in Ethanol, Pyridine, Acetic acid; Slightly soluble in Chloroform, Methanol, Pyridine |
Reference Reading
1. Synthetic remodeling of the chartreusin pathway to tune antiproliferative and antibacterial activities
Hans-Martin Dahse, Kirstin Scherlach, Christian Hertweck, Tom Bretschneider, Nico Ueberschaar, Helmar Görls, Zhongli Xu, Mikko Metsä-Ketelä J Am Chem Soc . 2013 Nov 20;135(46):17408-16. doi: 10.1021/ja4080024.
Natural products of the benzonaphthopyranone class, such as chartreusin, elsamicin A, gilvocarcin, and polycarcin, represent potent leads for urgently needed anticancer therapeutics and antibiotics. Since synthetic protocols for altering their architectures are limited, we harnessed enzymatic promiscuity to generate a focused library of chartreusin derivatives. Pathway engineering of the chartreusin polyketide synthase, mutational synthesis, and molecular modeling were employed to successfully tailor the structure of chartreusin. For the synthesis of the aglycones, improved synthetic avenues to substituted coumarin building blocks were established. Using an engineered mutant, in total 11 new chartreusin analogs (desmethyl, methyl, ethyl, vinyl, ethynyl, bromo, hydroxy, methoxy, and corresponding (1→2) abeo-chartreusins) were generated and fully characterized. Their biological evaluation revealed an unexpected impact of the ring substituents on antiproliferative and antibacterial activities. Irradiation of vinyl- and ethynyl-substituted derivatives with blue light resulted in an improved antiproliferative potency against a colorectal cancer cell line. In contrast, the replacement of a methyl group by hydrogen caused a drastically decreased cytotoxicity but markedly enhanced antimycobacterial activity. Furthermore, mutasynthesis of bromochartreusin led to the first crystal structure of a chartreusin derivative that is not modified in the glycoside residue. Beyond showcasing the possibility of converting diverse, fully synthetic polyphenolic aglycones into the corresponding glycosides in a whole-cell approach, this work identified new chartreusins with fine-tuned properties as promising candidates for further development as therapeutics.
2. Map of chartreusin and elsamicin binding sites on DNA
J Portugal, X Salas FEBS Lett . 1991 Nov 4;292(1-2):223-8. doi: 10.1016/0014-5793(91)80872-z.
Three DNA restriction fragments designated tyrT, 102-mer and 70-mer, have been used as substrates for footprinting studies using DNase I in the presence of the structurally similar antibiotics chartreusin and elsamicin A. The sequence-selective binding sites of the antibiotics can be mapped in regions which are rich in guanine + cytosine. Chartreusin and elsamicin appear to recognize and bind preferentially to sequences containing a CpG step. Regions containing a TpG step also seem to be a good binding site. The binding of elsamicin to these sites appears to be more concentration-dependent. A comparative analysis is performed of the sizes and locations of the different binding sites, aimed to infer whether the different biological effects of chartreusin and elsamicin A can be correlated to differences in their sequence-selective binding to DNA.
3. Chartreusin: production and microbiological assay
L J Hanka, S A Gerpheide Antimicrob Agents Chemother . 1977 Nov;12(5):571-2. doi: 10.1128/AAC.12.5.571.
Chartreusin was produced in the fermentation liquors of Streptomyces chartreusis at peak concentrations of 200 to 300 mug/ml. The titers could be increased by 200 to 300% or more by incorporating d-fucose, a part of the chartreusin molecule, into the fermentation media. A microbiological assay with Sarcina lutea could detect concentrations of the drug of 0.5 to 1.0 mug/ml.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
