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Purity: ≥98%
Caerulomycin A (also known as Cerulomycin, CaeA) is a novel bipyridyl compound that induces generation of T cells, enhances TGF-β-Smad3 protein signaling via suppressing interferon-γ-induced STAT1 signaling. It is also a toxin that inhibits growth of Entamoeba. It has antifungal and antibiotic activity, and can be used in autoimmune diseases. Cytokines play a very important role in the regulation of immune homeostasis. Regulatory T cells (Tregs) responsible for the generation of peripheral tolerance are under the tight regulation of the cytokine milieu. It was observed that Caerulomycin A substantially up-regulated the pool of Tregs, as evidenced by an increased frequency of CD4(+) Foxp3(+) cells. In addition, CaeA significantly suppressed the number of Th1 and Th17 cells, as supported by a decreased percentage of CD4(+)/IFN-γ(+) and CD4(+)/IL-17(+) cells, respectively.
| Targets |
Antifungal;TGF-β-Smad3
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| ln Vitro |
Caerulomycin A (CaeA), in inducing the generation of Tregs. It was observed that CaeA substantially up-regulated the pool of Tregs, as evidenced by an increased frequency of CD4(+) Foxp3(+) cells. In addition, CaeA significantly suppressed the number of Th1 and Th17 cells, as supported by a decreased percentage of CD4(+)/IFN-γ(+) and CD4(+)/IL-17(+) cells, respectively. Furthermore, we established the mechanism and observed that CaeA interfered with IFN-γ-induced STAT1 signaling by augmenting SOCS1 expression. An increase in the TGF-β-mediated Smad3 activity was also noted. Furthermore, CaeA rescued Tregs from IFN-γ-induced inhibition. These results were corroborated by blocking Smad3 activity, which abolished the CaeA-facilitated generation of Tregs. In essence, our results indicate a novel role of CaeA in inducing the generation of Tregs. This finding suggests that CaeA has enough potential to be considered as a potent future drug for the treatment of autoimmunity.[1]
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| Cell Assay |
Th1 and Th17 cells were treated with phorbol 12-myristate 13-acetate (40 nm) and ionomycin (1 μm) for 2 h. To block cytokine secretion, brefeldin A (10 μg/ml) was added. Later, and cells were incubated further for 3 h. Tregs, Th1, and Th17 cells were cultured with different concentrations of CaeA (0–0.15 μm). The modulation in the frequency of Tregs, Th1, and Th17 cells was analyzed by flow cytometry.[1]
A booster dose of bovine collagen type II in incomplete Freund adjuvant was injected on day 21. Later, CaeA (1 and 10 mg/kg body weight) and 0.5% carboxyl methyl cellulose emulsion in water was administered daily for 50 days, and animals were monitored every day for arthritis symptoms. [1] The IFN-γ-mediated STAT1 response was measured by initially incubating CD4 T cells with CaeA (0–0.31 μm) for 24 h, followed by IFN-γ (200 units/ml) stimulation for 30 min. To evaluate the TGF-β-mediated Smad3 response, CD4 T cells were incubated initially with CaeA (0–0.31 μm) for 24 h, followed by IFN-γ (200 units/ml) treatment for 48 h. Later, cells were pulsed with TGF-β (2 ng/ml) for 1 h. [1] CD4 T cells stimulated with anti-CD3 (2 μg/ml) and CD28 (1 μg/ml) Abs were cultured with CaeA (0–0.31 μm) for 72 h. Later, cells were pelleted and resuspended in JC-1 (5,5′,6,6′-tetrachloro-1,1′,3,3′-tetraethylbenzimidazolylcarbocyanine iodide) medium (2.5 μg/ml). The cultures were incubated at room temperature for 15–20 min in the dark. Later, cells were washed with flow cytometry staining buffer (2% FBS in PBS) and acquired immediately using a flow cytometer (FACSCalibur), and then the analysis was done using FACSDiva software. [1] |
| References | |
| Additional Infomation |
Caerulomycin A is a pyridine alkaloid that is 2,2'-bipyridine substituted by a methoxy group at position 4 and a (E)-(hydroxyimino)methyl group at position 6. Isolated from the marine-derived actinomycete Actinoalloteichus cyanogriseus, it exhibits antineoplastic activity. It has a role as an antineoplastic agent, a marine metabolite and a bacterial metabolite. It is an aldoxime, an aromatic ether, a member of bipyridines and a pyridine alkaloid. It derives from a hydride of a 2,2'-bipyridine.
Cerulomycin has been reported in Actinoalloteichus cyanogriseus with data available. |
| Molecular Formula |
C12H11N3O2
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| Molecular Weight |
229.23
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| Exact Mass |
229.085
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| Elemental Analysis |
C, 62.87; H, 4.84; N, 18.33; O, 13.96
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| CAS # |
21802-37-9
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| Related CAS # |
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| PubChem CID |
135514797
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| Appearance |
White to off-white solid powder
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| Density |
1.23g/cm3
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| Boiling Point |
400.4ºC at 760mmHg
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| Flash Point |
195.9ºC
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| LogP |
1.96
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
17
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| Complexity |
260
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| Defined Atom Stereocenter Count |
0
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| SMILES |
COC1=CC(C2=NC=CC=C2)=NC(/C=N/O)=C1
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| InChi Key |
JCTRJRHLGOKMCF-RIYZIHGNSA-N
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| InChi Code |
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+
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| Chemical Name |
(E)-4-methoxy-[2,2'-bipyridine]-6-carbaldehyde oxime
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| Synonyms |
Carulomycin A; AC1NTHG8; AC1N-THG8; AC1N THG8 NSC-114341; NSC114341; NSC 114341; HE185727; HE 185727; HE-185727; Caerulomycin A
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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 |
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| 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) |
DMSO : ~150 mg/mL (~654.34 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.91 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (10.91 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (10.91 mM) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.3624 mL | 21.8122 mL | 43.6243 mL | |
| 5 mM | 0.8725 mL | 4.3624 mL | 8.7249 mL | |
| 10 mM | 0.4362 mL | 2.1812 mL | 4.3624 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
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.
CaeA alone and in conjunction with TGF-β augments the pool of Tregs.J Biol Chem.2014 Jun 20;289(25):17515-28. |
CaeA ameliorated the symptoms of experimental arthritis by generating Tregs.Arthritis-induced mice were treated with CaeA.A, disease progression.J Biol Chem.2014 Jun 20;289(25):17515-28. |
CaeA antagonized the IFN-γ- and IL-6-mediated STAT1 signaling pathway in CD4 T cells by enhancing SOCS1 expression.J Biol Chem.2014 Jun 20;289(25):17515-28. |
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