WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 561189
CAS#: 65101-87-3
Description: Nanchangmycin is a polyether antibiotic that acts against a broad spectrum of harmful nematodes and insects.
MedKoo Cat#: 561189
Name: Nanchangmycin
CAS#: 65101-87-3
Chemical Formula: C47H77NaO14
Exact Mass:
Molecular Weight: 889.1088
Elemental Analysis: C, 63.49; H, 8.73; Na, 2.59; O, 25.19
Synonym: Nanchangmycin; CCRIS 8440; CCRIS-8440; CCRIS8440; Nanchangmycin A
IUPAC/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
InChi Key: XMAIRYYXDCNFKP-DYTQFKGPSA-M
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
SMILES Code: C[C@H]([C@@H](O1)[C@H](C)[C@@H](O)C[C@@]21CC[C@@](C)([C@@H](C[C@H](OC3O[C@H](C)[C@@H](OC)CC3)[C@H]4C)O[C@]54[C@@H](C)C[C@H]([C@H]6O[C@](CO)(O)[C@H](C)C[C@@H]6C)O5)O2)/C=C(C)/C([C@H](C)C[C@H](C)C([O-])=O)=O.[Na+]
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
| Biological target: | Nanchangmycin, a polyether antibiotic produced by Streptomyces nanchangensis NS3226, inhibits gram-positive bacteria. |
| In vitro activity: | Importantly, this study identified nanchangmycin as a potent inhibitor of Zika virus entry across all cell types tested, including physiologically relevant primary cells. Nanchangmycin also was active against other medically relevant viruses, including West Nile, dengue, and chikungunya viruses that use a similar route of entry. Reference: Cell Rep. 2017 Jan 17;18(3):804-815. https://pubmed.ncbi.nlm.nih.gov/28099856/ |
| In vivo activity: | As showed in Fig. 7a, tumors grew rapidly in the vehicle group, but the growth was strikingly suppressed by Nam and it was almost completely inhibited by Nam at the dosage of 4 mg/kg (Fig. 7a), in contrast, Nam had no effects on mice growth in terms of body weight (Fig. 7b) or biochemical assays including aspartate aminotransferase (AST), or alanine aminotransferase (ALT), alkaline phosphatase (ALP), urea, total bilirubin and total proteins (Fig. 7c), further demonstrating Nam was safe at least at the dosages examined. Reference: Cell Death Dis. 2020 Sep 30;11(9):818. https://pubmed.ncbi.nlm.nih.gov/32999280/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMF | 30.0 | 33.74 | |
| DMSO | 75.0 | 84.35 | |
| Ethanol | 62.5 | 70.3 |
The following data is based on the product molecular weight 889.1088 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Li W, Chen JY, Sun C, Sparks RP, Pantano L, Rahman RU, Moran SP, Pondick JV, Kirchner R, Wrobel D, Bieler M, Sauer A, Ho Sui SJ, Doerner JF, Rippmann JF, Mullen AC. Nanchangmycin regulates FYN, PTK2, and MAPK1/3 to control the fibrotic activity of human hepatic stellate cells. Elife. 2022 May 26;11:e74513. doi: 10.7554/eLife.74513. PMID: 35617485; PMCID: PMC9135407. 2. Rausch K, Hackett BA, Weinbren NL, Reeder SM, Sadovsky Y, Hunter CA, Schultz DC, Coyne CB, Cherry S. Screening Bioactives Reveals Nanchangmycin as a Broad Spectrum Antiviral Active against Zika Virus. Cell Rep. 2017 Jan 17;18(3):804-815. doi: 10.1016/j.celrep.2016.12.068. PMID: 28099856; PMCID: PMC5270376. 3. Xu Y, Sun T, Zeng K, Xu M, Chen J, Xu X, Zhang Z, Cao B, Tang X, Wu D, Kong Y, Zeng Y, Mao X. Anti-bacterial and anti-viral nanchangmycin displays anti-myeloma activity by targeting Otub1 and c-Maf. Cell Death Dis. 2020 Sep 30;11(9):818. doi: 10.1038/s41419-020-03017-4. PMID: 32999280; PMCID: PMC7527563. 4. Huang M, Liu B, Liu R, Li J, Chen J, Jiang F, Ding H, Deng Z, Liu T. Aglycone Polyether Nanchangmycin and Its Homologues Exhibit Apoptotic and Antiproliferative Activities against Cancer Stem Cells. ACS Pharmacol Transl Sci. 2018 Oct 12;1(2):84-95. doi: 10.1021/acsptsci.8b00007. PMID: 32219205; PMCID: PMC7088892. |
| In vitro protocol: | 1. Li W, Chen JY, Sun C, Sparks RP, Pantano L, Rahman RU, Moran SP, Pondick JV, Kirchner R, Wrobel D, Bieler M, Sauer A, Ho Sui SJ, Doerner JF, Rippmann JF, Mullen AC. Nanchangmycin regulates FYN, PTK2, and MAPK1/3 to control the fibrotic activity of human hepatic stellate cells. Elife. 2022 May 26;11:e74513. doi: 10.7554/eLife.74513. PMID: 35617485; PMCID: PMC9135407. 2. Rausch K, Hackett BA, Weinbren NL, Reeder SM, Sadovsky Y, Hunter CA, Schultz DC, Coyne CB, Cherry S. Screening Bioactives Reveals Nanchangmycin as a Broad Spectrum Antiviral Active against Zika Virus. Cell Rep. 2017 Jan 17;18(3):804-815. doi: 10.1016/j.celrep.2016.12.068. PMID: 28099856; PMCID: PMC5270376. |
| In vivo protocol: | 1. Xu Y, Sun T, Zeng K, Xu M, Chen J, Xu X, Zhang Z, Cao B, Tang X, Wu D, Kong Y, Zeng Y, Mao X. Anti-bacterial and anti-viral nanchangmycin displays anti-myeloma activity by targeting Otub1 and c-Maf. Cell Death Dis. 2020 Sep 30;11(9):818. doi: 10.1038/s41419-020-03017-4. PMID: 32999280; PMCID: PMC7527563. 2. Huang M, Liu B, Liu R, Li J, Chen J, Jiang F, Ding H, Deng Z, Liu T. Aglycone Polyether Nanchangmycin and Its Homologues Exhibit Apoptotic and Antiproliferative Activities against Cancer Stem Cells. ACS Pharmacol Transl Sci. 2018 Oct 12;1(2):84-95. doi: 10.1021/acsptsci.8b00007. PMID: 32219205; PMCID: PMC7088892. |
1: Guo X, Liu T, Deng Z, Cane DE. Essential role of the donor acyl carrier protein in stereoselective chain translocation to a fully reducing module of the nanchangmycin polyketide synthase. Biochemistry. 2012 Jan 31;51(4):879-87. doi: 10.1021/bi201768v. Epub 2012 Jan 17. PubMed PMID: 22229794; PubMed Central PMCID: PMC3273620.
2: Yu Q, Du A, Liu T, Deng Z, He X. The biosynthesis of the polyether antibiotic nanchangmycin is controlled by two pathway-specific transcriptional activators. Arch Microbiol. 2012 Jun;194(6):415-26. doi: 10.1007/s00203-011-0768-8. Epub 2011 Nov 23. PubMed PMID: 22109812.
3: Zhang J, An J, Wang JJ, Yan YJ, He HR, Wang XJ, Xiang WS. Genetic engineering of Streptomyces bingchenggensis to produce milbemycins A3/A4 as main components and eliminate the biosynthesis of nanchangmycin. Appl Microbiol Biotechnol. 2013 Dec;97(23):10091-101. Epub 2013 Sep 29. PubMed PMID: 24077727.
4: Liu T, Lin X, Zhou X, Deng Z, Cane DE. Mechanism of thioesterase-catalyzed chain release in the biosynthesis of the polyether antibiotic nanchangmycin. Chem Biol. 2008 May;15(5):449-58. doi: 10.1016/j.chembiol.2008.04.006. PubMed PMID: 18482697; PubMed Central PMCID: PMC2426748.
5: Liu T, You D, Valenzano C, Sun Y, Li J, Yu Q, Zhou X, Cane DE, Deng Z. Identification of NanE as the thioesterase for polyether chain release in nanchangmycin biosynthesis. Chem Biol. 2006 Sep;13(9):945-55. PubMed PMID: 16984884.
6: Guo X, Liu T, Valenzano CR, Deng Z, Cane DE. Mechanism and stereospecificity of a fully saturating polyketide synthase module: nanchangmycin synthase module 2 and its dehydratase domain. J Am Chem Soc. 2010 Oct 27;132(42):14694-6. doi: 10.1021/ja1073432. PubMed PMID: 20925339; PubMed Central PMCID: PMC2959152.
7: Sun Y, Zhou X, Dong H, Tu G, Wang M, Wang B, Deng Z. A complete gene cluster from Streptomyces nanchangensis NS3226 encoding biosynthesis of the polyether ionophore nanchangmycin. Chem Biol. 2003 May;10(5):431-41. PubMed PMID: 12770825.
8: Sun YH, Zhou XF, Tu GQ, Deng ZX. [Determination of nanchangmycin and meilingmycin by high performance liquid chromatography]. Se Pu. 2002 Jan;20(1):43-5. Chinese. PubMed PMID: 12541617.
9: Sun Y, Zhou X, Liu J, Bao K, Zhang G, Tu G, Kieser T, Deng Z. 'Streptomyces nanchangensis', a producer of the insecticidal polyether antibiotic nanchangmycin and the antiparasitic macrolide meilingmycin, contains multiple polyketide gene clusters. Microbiology. 2002 Feb;148(Pt 2):361-71. PubMed PMID: 11832500.
10: Wang XJ, Zhang B, Yan YJ, An J, Zhang J, Liu CX, Xiang WS. Characterization and analysis of an industrial strain of Streptomyces bingchenggensis by genome sequencing and gene microarray. Genome. 2013 Nov;56(11):677-89. doi: 10.1139/gen-2013-0098. PubMed PMID: 24299107.
11: Rausch K, Hackett BA, Weinbren NL, Reeder SM, Sadovsky Y, Hunter CA, Schultz DC, Coyne CB, Cherry S. Screening Bioactives Reveals Nanchangmycin as a Broad Spectrum Antiviral Active against Zika Virus. Cell Rep. 2017 Jan 17;18(3):804-815. doi: 10.1016/j.celrep.2016.12.068. PubMed PMID: 28099856; PubMed Central PMCID: PMC5270376.
12: Wang XJ, Yan YJ, Zhang B, An J, Wang JJ, Tian J, Jiang L, Chen YH, Huang SX, Yin M, Zhang J, Gao AL, Liu CX, Zhu ZX, Xiang WS. Genome sequence of the milbemycin-producing bacterium Streptomyces bingchenggensis. J Bacteriol. 2010 Sep;192(17):4526-7. doi: 10.1128/JB.00596-10. Epub 2010 Jun 25. PubMed PMID: 20581206; PubMed Central PMCID: PMC2937363.
13: Harvey BM, Mironenko T, Sun Y, Hong H, Deng Z, Leadlay PF, Weissman KJ, Haydock SF. Insights into polyether biosynthesis from analysis of the nigericin biosynthetic gene cluster in Streptomyces sp. DSM4137. Chem Biol. 2007 Jun;14(6):703-14. PubMed PMID: 17584617.
14: Wang XJ, Guo SL, Guo WQ, Xi D, Xiang WS. Role of nsdA in negative regulation of antibiotic production and morphological differentiation in Streptomyces bingchengensis. J Antibiot (Tokyo). 2009 Jun;62(6):309-13. doi: 10.1038/ja.2009.33. Epub 2009 May 15. PubMed PMID: 19444300.
15: Xie X, Garg A, Khosla C, Cane DE. Mechanism and Stereochemistry of Polyketide Chain Elongation and Methyl Group Epimerization in Polyether Biosynthesis. J Am Chem Soc. 2017 Mar 1;139(8):3283-3292. doi: 10.1021/jacs.7b00278. Epub 2017 Feb 14. PubMed PMID: 28157306; PubMed Central PMCID: PMC5332327.
16: Xie X, Garg A, Khosla C, Cane DE. Elucidation of the Cryptic Methyl Group Epimerase Activity of Dehydratase Domains from Modular Polyketide Synthases Using a Tandem Modules Epimerase Assay. J Am Chem Soc. 2017 Jul 19;139(28):9507-9510. doi: 10.1021/jacs.7b05502. Epub 2017 Jul 7. PubMed PMID: 28682630.
17: Liu X, Xie S, Ni T, Chen D, Wang X, Pan Y, Wang Y, Huang L, Cheng G, Qu W, Liu Z, Tao Y, Yuan Z. Magnetic solid-phase extraction based on carbon nanotubes for the determination of polyether antibiotic and s-triazine drug residues in animal food with LC-MS/MS. J Sep Sci. 2017 Jun;40(11):2416-2430. doi: 10.1002/jssc.201700017. Epub 2017 May 4. PubMed PMID: 28402029.
