Chrysomycin A
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| Category | Antibiotics |
| Catalog number | BBF-04096 |
| CAS | 82196-88-1 |
| Molecular Weight | 508.51 |
| Molecular Formula | C28H28O9 |
| Purity | >99% by HPLC |
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Description
Chrysomycin A is a C-glycoside antitumor antibiotic isolated from Streptomyces, and it is an inhibitor of the catalytic activity of human topoisomerase II. It has effective antibacterial, antifungal, antiviral and antitumor activities. It may act as a light-activated cross-linking agent between DNA and histones.
Specification
| Synonyms | Chrysomycin V; Virenomycin V; Albacarcin V |
| Storage | Store at -20°C |
| IUPAC Name | 8-ethenyl-1-hydroxy-10,12-dimethoxy-4-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-4,6-dimethyloxan-2-yl]naphtho[1,2-c]isochromen-6-one |
| Canonical SMILES | CC1C(C(C(C(O1)C2=C3C(=C(C=C2)O)C(=CC4=C3OC(=O)C5=C4C(=CC(=C5)C=C)OC)OC)O)(C)O)O |
| InChI | InChI=1S/C28H28O9/c1-6-13-9-16-20(18(10-13)34-4)15-11-19(35-5)22-17(29)8-7-14(21(22)23(15)37-27(16)32)24-26(31)28(3,33)25(30)12(2)36-24/h6-12,24-26,29-31,33H,1H2,2-5H3/t12-,24+,25+,26+,28-/m1/s1 Computed by InChI 1.0.5 (PubChem release 201 |
| InChI Key | OMDANBMKOUVKAG-WZNMFJNZSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Yellow Lyophilisate |
| Antibiotic Activity Spectrum | Fungi; Viruses; parasites |
| Boiling Point | 799.7°C at 760 mmHg |
| Density | 1.405 g/cm3 |
| Solubility | Soluble in DMF, DMSO |
Reference Reading
1. Chrysomycin A inhibits the topoisomerase I of Mycobacterium tuberculosis
G R Jijimole, Aravind Madhavan, Ramakrishnan Ajay Kumar, Azger Dusthackeer, Lekshmi K Edison, Ranjit Ramachandran, Balaji Muralikrishnan J Antibiot (Tokyo) . 2022 Apr;75(4):226-235. doi: 10.1038/s41429-022-00503-z.
Novel anti-tuberculosis drugs are essential to manage drug-resistant tuberculosis, caused by Mycobacterium tuberculosis. We recently reported the antimycobacterial activity of chrysomycin A in vitro and in infected macrophages. In this study, we report that it inhibits the growth of drug-resistant clinical strains of M. tuberculosis and acts in synergy with anti-TB drugs such as ethambutol, ciprofloxacin, and novobiocin. In pursuit of its mechanism of action, it was found that chrysomycin A is bactericidal and exerts this activity by interacting with DNA at specific sequences and by inhibiting the topoisomerase I activity of M. tuberculosis. It also exhibits weak inhibition of the DNA gyrase enzyme of the pathogen.
2. Formulation of Chrysomycin A Cream for the Treatment of Skin Infections
Yuteng Chu, Xiaojie Yu, Yue Cai, Haohua Liu, Hong Wang, Huawei Zhang, Fuhang Song, Xuanrong Sun Molecules . 2022 Jul 19;27(14):4613. doi: 10.3390/molecules27144613.
Chrysomycin A, a compound derived from marine microorganisms, proved to have a specific great in vitro inhibitory effect on methicillin-resistantStaphylococcus aureus(MRSA). It exhibits high safety for the skin, as well as a better therapeutic effect than the current clinical drug, vancomycin. Nevertheless, its poor water solubility highly limits the application and reduces the bioavailability. In view of this, we developed a cream of chrysomycin A (CA) to enhance the solubility for the treatment of skin infection, while avoiding the possible toxicity caused by systemic administration. A comprehensive orthogonal evaluation system composed of appearance, spreading ability, and stability was established to find the optimal formula under experimental conditions. The final product was odorless and easy to be spread, with a lustrous, smooth surface. The particle size of the product met Chinese Pharmacopoeia specifications and the entire cream showed long-term stability in destructive tests. The in vitro and in vivo studies indicated that CA cream had a similar anti-MRSA activity to commercially available mupirocin, showing its potential as an efficacious topical delivery system for skin infections treatment.
3. Mechanochemical preparation of chrysomycin A self-micelle solid dispersion with improved solubility and enhanced oral bioavailability
Xin Gao, Zhuomin Xu, Dehui Xie, Yue Cai, Hong Wang, Shanshan Zheng, Yulu Hong, Qiuqin Zhang, Jiani Xiang, Fuxing Song, Huawei Zhang, Xuanrong Sun J Nanobiotechnology . 2021 May 31;19(1):164. doi: 10.1186/s12951-021-00911-7.
Background:Chrysomycin A (CA) has been reported as numerous excellent biological activities, such as antineoplastic and antibacterial. Though, poor solubility of CA limited its application in medical field. Due to good amphiphilicity and potential anticancer effect of disodium glycyrrhizin (Na2GA) as an excipient, an amorphous solid dispersion (Na2GA/CA-BM) consisting of CA and Na2GA was prepared in the present study by mechanochemical technology (roll mill ML-007, zirconium balls, 30 rpm, 2.5 h) to improve the solubility and oral bioavailability of CA. Then, Na2GA/CA-BM was self-assembled to micelles in water. The interaction of CA and Na2GA in solid state were investigated by X-ray diffraction studies, polarized light microscopy, and scanning electron microscope. Meanwhile, the properties of the sample solution were analyzed by dynamic light scattering and transmission electron. Furthermore, the oral bioavailability and antitumor ability of Na2GA/CA-BM in vivo were tested, providing a theoretical basis for future application of CA on cancer therapy.Results:CA encapsulated by Na2GA was self-assembled to nano-micelles in water. The average diameter of nano-micelle was 131.6 nm, and zeta potential was - 11.7 mV. Three physicochemical detections showed that CA was transformed from crystal into amorphous form after treated with ball milling and the solubility increased by 50 times. Na2GA/CA-BM showed a significant increase of the bioavailability about two time that of free CA. Compared with free CA, the in-vivo antitumor studies also exhibited that Na2GA/CA-BM had an excellent inhibition of tumor growth.Conclusions:Na2GA/CA-BM nanoparticles (131.6 nm, - 11.7 mV) prepared by simple and low-cost mechanochemical technology can improve oral bioavailability and antitumor efficacy of CA in vivo, suggesting a potential formulation for efficient anticancer treatment.
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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 ╳
