Caerulomycin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00595 |
| CAS | 21802-37-9 |
| Molecular Weight | 229.23 |
| Molecular Formula | C12H11N3O2 |
| Purity | ≥98% by HPLC |
Online Inquiry
Description
Caerulomycin is an antibiotic produced by Streptomyces caerleus and Nocadi-opsis cirriefficiens. It is mainly resistant to Gram-positive bacteria, yeast and mold (weak).
Specification
| Synonyms | Caerulomycin A |
| Storage | Store at -20°C |
| IUPAC Name | (NE)-N-[(4-methoxy-6-pyridin-2-ylpyridin-2-yl)methylidene]hydroxylamine |
| Canonical SMILES | COC1=CC(=NC(=C1)C2=CC=CC=N2)C=NO |
| InChI | InChI=1S/C12H11N3O2/c1-17-10-6-9(8-14-16)15-12(7-10)11-4-2-3-5-13-11/h2-8,16H,1H3/b14-8+ |
| InChI Key | JCTRJRHLGOKMCF-RIYZIHGNSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Colorless Needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; yeast; fungi |
| Boiling Point | 400.4°C at 760 mmHg |
| Melting Point | 169-170°C |
| Density | 1.23 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1. Characterization of Caerulomycin A as a dual-targeting anticancer agent
Shiyong Wu, Weichao Sun, Lingying Tong, Yong Han Eur J Pharmacol . 2022 May 5;922:174914. doi: 10.1016/j.ejphar.2022.174914.
Caerulomycin A (CaeA), isolated from actinomycetes, has a featured 2,2'-bipyridine core structure. Based on the results of in silico drug-protein docking analysis, CaeA shows potential ligands for interacting with both tubulin and DNA topoisomerase I (Topo-1). The result was confirmed by cell-free tubulin polymerization assay and Topo-1 activity assay. In vitro assays also demonstrated that CaeA increases the polymerization of tubulin and increases cell size. In addition, CaeA inhibits cell viability and growth of various cancer cells, yet exhibits low cytotoxicity. CaeA also affects paclitaxel-resistant cancer cells and synergizes the effect with paclitaxel in reducing cancer cell colony formation rate. In vivo experiments confirm the effect of CaeA on reducing tumor size and weight in nude mouse inoculated with tumor cells with no noticeable side effects. Taken together, our data demonstrate that CaeA is a potential potent agent for cancer treatment through tubulin and Topo-1 dual-targeting with little side effects.
2. The Influence of Caerulomycin A on the Intestinal Microbiota in SD Rats
Guodong Cui, Hongwei Zhang, Mengmeng Lan, Weiming Zhu Mar Drugs . 2020 May 22;18(5):277. doi: 10.3390/md18050277.
Caerulomycin A (CRM A) is the first example of natural caerulomycins with a 2,2'-bipyridyl ring core and 6-aldoxime functional group fromStreptomyces caeruleusand recently from marine-derivedActinoalloteichuscyanogriseusWH1-2216-6. Our previous study revealed that CRM A showed anti-tumor activity against human colorectal cancer (CRC) both in vitro and in vivo. Because some intestinal flora can affect the occurrence and development of CRC, the influence of CRM A on the intestinal flora is worthy of study in Sprague-Dawley (SD) rats. The high throughput sequencing of the V3-V4 hypervariable region in bacterial 16S rDNA gene results showed that the CRM A affected the diversity of intestinal flora of the SD rats treated with CRM A for 2, 3 and 4 weeks. Further analysis indicated that the abundance of genera Prevotella_1, Prevotellaceae_UCG-001, and Lactobacillus were increased while the that of genera Alloprevotella and Ruminiclostridium_1 were decreased. For the CRC related intestinal flora, the abundance of generaBacteroides,Fusobacterium,Enterococcus,Escherichia-Shigella,Klebsiella,Streptococcus,Ruminococcus_2,andPeptococcusof SD rats treated with CRM A were decreased, while that of abundance of genera Bifidobacterium, Lactobacillus, Faecalibacterium, Blautia, Oscillibacter, and Clostridium were increased. The results indicated that CRM A could influence the intestinal flora by inhibiting some species of harmful flora and improving the beneficial bacteria in intestinal flora in the SD rats. The results may provide a new idea for revealing the mechanism of the anti-CRC activity of CRM A.
3. Caerulomycin A inhibits Th2 cell activity: a possible role in the management of asthma
Rama Krishna Gurram, Weshely Kujur, Javed N Agrewala, Sudeep K Maurya, Nazia Haleem Sci Rep . 2015 Oct 20;5:15396. doi: 10.1038/srep15396.
We have recently demonstrated that Caerulomycin A induces regulatory T cells differentiation by suppressing Th1 cells activity. The role of regulatory T cells is well established in suppressing the function of Th2 cells. Th2 cells are known to inflict the induction of the activation of asthma. Consequently, in the present study, we monitored the influence of Caerulomycin A in inhibiting the activity of Th2 cells and its impact in recuperating asthma symptoms. Interestingly, we observed that Caerulomycin A significantly suppressed the differentiation of Th2 cells, as evidenced by downregulation in the GATA-3 expression. Further, decline in the levels of IL-4, IL-5 and IL-13 cytokines and IgE was noted in the animals suffering from asthma. Furthermore, we noticed substantial suppression in the inflammatory response and number of eosinophils in the lungs. In essence, this study signifies an important therapeutic role of Caerulomycin A in asthma.
Recommended Products
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
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 ╳
