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Purity: ≥98%
Nanchangmycin (Nanchangmycin A) is a polyether antibiotic isolated from Streptomyces nanchangensis NS3226 with similar structure to dianemycin. It is very active against a broad spectrum of harmful nematodes and insects but not for mammals and plants. Nanchangmycin inhibits gram-positive bacteria and can be used as a growth promotant in poultry and to cure coccidiosis in chickens.
| Targets |
Bacteria
Zika virus Nanchangmycin biosynthetic thioesterase (NcmTE) [1] - Zika Virus (ZIKV) (EC50 = 0.5 μM in Vero cells; CC50 = 8.3 μM, SI = 16.6) [2] - Dengue Virus (DENV-2) (EC50 = 0.8 μM in Vero cells; CC50 = 8.3 μM, SI = 10.4) [2] - Yellow Fever Virus (YFV) (EC50 = 0.7 μM in Vero cells; CC50 = 8.3 μM, SI = 11.9) [2] - West Nile Virus (WNV) (EC50 = 0.9 μM in Vero cells; CC50 = 8.3 μM, SI = 9.2) [2] |
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| ln Vitro |
Nanchangmycin can be used to treat chicken coccidiosis and as a growth promoter in poultry. Nanchangmycin is effective against malaria strains that are resistant to drugs[1]. Zika virus (ZIKV) entry was effectively inhibited by nanchangmycin in all tested cell types, including primary cells that are physiologically relevant. All three ZIKV strains are significantly less likely to infect any of the three cell types when nanchangmycin is used. Nanchangmycin exhibits low toxicity within the range of 0.1 to 0.4 μM, where the IC50s for infection fall within this range. Furthermore, nanchangmycin inhibits DENV in a variety of cell types[2].
Catalyzed chain release in nanchangmycin biosynthesis by hydrolyzing the thioester bond between the polyketide chain and acyl carrier protein (ACP) of the nanchangmycin polyketide synthase (PKS) [1] - Exhibited broad-spectrum antiviral activity against flaviviruses (ZIKV, DENV-2, YFV, WNV) in Vero cells, with EC50 values ranging from 0.5 to 0.9 μM [2] - Inhibited ZIKV replication at the post-entry stage: treatment at 2 hours post-infection (hpi) showed similar antiviral efficacy to treatment at 0 hpi, while treatment at 8 hpi (late replication stage) had no significant effect [2] - Reduced ZIKV RNA copy number by ~90% at 1 μM concentration and decreased viral envelope protein (E protein) expression by ~85% as detected by western blot [2] - Did not affect viral attachment or entry into Vero cells, as demonstrated by similar viral RNA levels in cells treated with Nanchangmycin (Nanchangmycin A) at -1 to 0 hpi compared to the vehicle control [2] |
| ln Vivo |
In a ZIKV-infected AG129 mouse model (IFN-α/β and IFN-γ receptor deficient), intraperitoneal administration of Nanchangmycin (Nanchangmycin A) (5 mg/kg, once daily for 5 days) starting at 1 day post-infection (dpi) significantly reduced ZIKV RNA levels in the brain (by ~75%) and spleen (by ~68%) compared to vehicle control [2]
- Improved survival rate of ZIKV-infected AG129 mice: 60% of treated mice survived until 14 dpi, while all vehicle-treated mice died by 10 dpi [2] - Reduced ZIKV-induced neurological symptoms (ataxia, hindlimb paralysis) in treated mice, with clinical score (0-4) decreasing from ~3.2 (vehicle) to ~1.5 (treated) at 7 dpi [2] |
| Enzyme Assay |
NcmTE thioesterase activity assay: Recombinant NcmTE protein was incubated with synthetic thioester substrates (mimicking the nanchangmycin polyketide chain-ACP conjugate) in reaction buffer at 30°C. The reaction was quenched by adding trichloroacetic acid, and the released free acid product was detected by high-performance liquid chromatography (HPLC) with UV detection. Enzyme activity was quantified based on the peak area of the product relative to a standard curve [1]
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| Cell Assay |
Flavivirus antiviral activity assay: Vero cells or HeLa cells were seeded in 96-well plates and cultured overnight. Cells were infected with ZIKV, DENV-2, YFV, or WNV at a multiplicity of infection (MOI) of 0.1. Nanchangmycin (Nanchangmycin A) was added at concentrations ranging from 0.01 to 20 μM immediately after infection (0 hpi) or at specified time points (2, 4, 8 hpi). After 48 hours of incubation, cell viability was measured by MTT assay to determine CC50, and viral load was quantified by qRT-PCR (viral RNA) or plaque assay to calculate EC50 and selectivity index (SI = CC50/EC50) [2]
- ZIKV E protein western blot analysis: HeLa cells infected with ZIKV (MOI = 0.1) were treated with Nanchangmycin (Nanchangmycin A) (0.5-2 μM) for 48 hours. Cells were lysed, and proteins were separated by SDS-PAGE, transferred to PVDF membranes, and probed with anti-ZIKV E protein antibody and anti-β-actin antibody (loading control). Bands were visualized by chemiluminescence and quantified by densitometry [2] - Viral attachment/entry assay: Vero cells were pre-treated with Nanchangmycin (Nanchangmycin A) (1 μM) for 1 hour, then infected with ZIKV (MOI = 1) at 4°C for 1 hour (attachment phase) or 37°C for 2 hours (entry phase). Unbound virus was removed, and cells were washed and cultured for 6 hours. Viral RNA levels were measured by qRT-PCR to assess attachment/entry efficiency [2] |
| Animal Protocol |
ZIKV-infected AG129 mouse model: 6-8 week-old male AG129 mice were intraperitoneally injected with 1×105 plaque-forming units (PFU) of ZIKV. Nanchangmycin (Nanchangmycin A) was dissolved in 10% DMSO + 90% saline. The drug was administered by intraperitoneal injection at 5 mg/kg, once daily for 5 days, starting at 1 dpi. Mice were monitored daily for survival and clinical symptoms (scored as 0 = normal, 1 = ruffled fur, 2 = hunched posture, 3 = ataxia, 4 = hindlimb paralysis/death). At 7 dpi, mice were euthanized, and brain and spleen tissues were collected for qRT-PCR quantification of ZIKV RNA [2]
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| Toxicity/Toxicokinetics |
In vitro cytotoxicity: The CC50 of Vero cells was 8.3 μM, and the CC50 of HeLa cells was 9.1 μM; no obvious cytotoxicity was observed at concentrations ≤5 μM [2]
- In vivo toxicity: Intraperitoneal injection of 5 mg/kg Nanchangmycin (Nanchangmycin A) for 5 days did not cause significant changes in mouse body weight, food intake, or mortality; histological analysis of major organs (brain, liver, kidney, spleen) showed no obvious inflammatory infiltration or tissue damage [2] |
| References | |
| Additional Infomation |
Nanchangmycin (Nanchangmycin A) is a polyether antibiotic produced by Streptomyces nanchangensis, initially discovered for its antibacterial activity [1, 2]. Its biosynthetic pathway involves type I polyketide synthase (PKS), with NcmTE (thioesterase) catalyzing the final chain release step to form a mature polyether structure [1]. Its antiviral mechanism involves inhibiting flavivirus replication during the early replication phase after viral entry into the cell (before viral RNA synthesis), possibly by targeting viral non-structural proteins or host factors required for viral replication [2]. Due to its high selectivity index and in vivo efficacy against Zika virus (ZIKV), it shows potential as a lead compound for developing broad-spectrum antiflavin drugs [2].
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| Molecular Formula |
C48H80O13
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| Molecular Weight |
889.1
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| Exact Mass |
888.521
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| Elemental Analysis |
C, 63.49; H, 8.73; Na, 2.59; O, 25.19
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| CAS # |
65101-87-3
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| Related CAS # |
Dianemycin;35865-33-9
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| PubChem CID |
86278937
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| Appearance |
White to off-white solid powder
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| LogP |
6.149
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
14
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| Rotatable Bond Count |
13
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| Heavy Atom Count |
62
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| Complexity |
1580
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| Defined Atom Stereocenter Count |
21
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| SMILES |
C[C@H]1[C@@]2(O[C@]([C@@]3([H])O[C@](O)([C@H](C)C[C@@H]3C)CO)([H])C[C@@H]2C)O[C@]([C@]4(O[C@]5(O[C@]([C@H](C)[C@@H](O)C5)([H])[C@@H](C)/C=C(C)/C([C@H](C)C[C@H](C)C([O-])=O)=O)CC4)C)([H])C[C@@H]1O[C@@]6([H])O[C@@H]([C@@H](OC)CC6)C.[Na+]
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| InChi Key |
XMAIRYYXDCNFKP-DYTQFKGPSA-M
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| InChi Code |
InChI=1S/C47H78O14.Na/c1-24(40(50)25(2)18-28(5)43(51)52)17-26(3)41-31(8)34(49)22-45(59-41)16-15-44(11,61-45)38-21-36(56-39-14-13-35(54-12)33(10)55-39)32(9)47(58-38)30(7)20-37(57-47)42-27(4)19-29(6)46(53,23-48)60-42;/h17,25-39,41-42,48-49,53H,13-16,18-23H2,1-12H3,(H,51,52);/q;+1/p-1/b24-17+;/t25-,26+,27+,28+,29-,30+,31-,32-,33-,34+,35+,36+,37-,38-,39?,41-,42+,44+,45-,46+,47+;/m1./s1
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| Chemical Name |
Sodium (E,2S,4R,8S)-8-[(2S,5R,7S,8R,9R)-7-hydroxy-2-[(2R,4S,5S,7R,9S,10R)-2-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-9-[(5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-4,10-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2,4,6-trimethyl-5-oxonon-6-enoate
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| Synonyms |
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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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
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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 : ~100 mg/mL ( ~112.47 mM )
Ethanol : ~100 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.08 mg/mL (2.34 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 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: 2.08 mg/mL (2.34 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 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: ≥ 2.08 mg/mL (2.34 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: 2.08 mg/mL (2.34 mM) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.1247 mL | 5.6237 mL | 11.2473 mL | |
| 5 mM | 0.2249 mL | 1.1247 mL | 2.2495 mL | |
| 10 mM | 0.1125 mL | 0.5624 mL | 1.1247 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.
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