Kigamicin A
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| Category | Antibiotics |
| Catalog number | BBF-01543 |
| CAS | |
| Molecular Weight | 665.64 |
| Molecular Formula | C34H35NO13 |
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Description
Kigamicin A is produced by the strain of Amycolatopsis sp. ML-630-mFl. It showed activity against gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA) with MIC of 0.025-0.78 μg/mL.
Specification
| IUPAC Name | 2,6,9,30-tetrahydroxy-8-(5-hydroxy-6-methyloxan-2-yl)oxy-23-methyl-11,14,16,24-tetraoxa-27-azaoctacyclo[15.14.1.03,12.05,10.013,32.019,31.021,29.023,27]dotriaconta-1(32),2,5(10),12,19,21(29),30-heptaene-4,28-dione |
| Canonical SMILES | CC1C(CCC(O1)OC2CC(C3=C(C2O)OC4=C5C6=C(C7=C(C8=C(CC9(N(C8=O)CCO9)C)C=C7CC6OCO5)O)C(=C4C3=O)O)O)O |
| InChI | InChI=1S/C34H35NO13/c1-12-15(36)3-4-19(46-12)47-18-9-16(37)22-28(40)25-29(41)24-20-13(7-14-10-34(2)35(5-6-45-34)33(42)21(14)27(20)39)8-17-23(24)31(44-11-43-17)32(25)48-30(22)26(18)38/h7,12,15-19,26,36-39,41H,3-6,8-11H2,1-2H3 |
| InChI Key | SERZVTAEVZZGKX-UHFFFAOYSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 225-227°C |
Reference Reading
1. Carbamothioic S-acid derivative and kigamicins, the activated production of silent metabolites in Amycolatopsis alba DSM 44262Δ abm9 elicited by N-acetyl-D-glucosamine
Xiaomei Li, Xiaoman Li, Jing Zhu, Haoxin Wang, Chunhua Lu Nat Prod Res. 2020 Dec;34(24):3514-3521. doi: 10.1080/14786419.2019.1574783. Epub 2019 Feb 20.
One new carbamothioic S-acid derivative (1) and five known kigamicin derivatives (2-6) were isolated from the fermentation extract of Amycolatopsis alba DSM 44262Δabm9 elicited by N-acetyl-D-glucosamine. HPLC-DAD-UV analyses indicated that the DSM 44262Δabm9 strain did not produce these metabolites originally and the production of 1-6 was induced by adding 25 mM N-acetyl-D-glucosamine in the culture medium. The structures of 1-6 were identified on the basis of NMR spectroscopic data and high-resolution ESIMS. These results highlight that addition of N-acetyl-D-glucosamine in the microbial culture medium could activate cryptic gene expression, induce and increase the production of new or known secondary metabolites.
2. Absolute configuration of kigamicins A, C and D
Tetsuya Someno, Setsuko Kunimoto, Hikaru Nakamura, Hiroshi Naganawa, Daishiro Ikeda J Antibiot (Tokyo). 2005 Jan;58(1):56-60. doi: 10.1038/ja.2005.6.
The stereochemistry of kigamicins A (1), C (2) and D (3) were elucidated by a combination of X-ray crystallographic analysis and degradation studies. The absolute structures of kigamicins thus determined were depicted as shown in Fig. 2.
3. Induction of necrosis in human myeloma cells by kigamicin
Miki Nakamura, Hiroyasu Esumi, Lu Jin, Hiroaki Mitsuya, Hiroyuki Hata Anticancer Res. 2008 Jan-Feb;28(1A):37-43.
Background: Kigamicin (KGM) is a novel compound derived from Actinomycetes that was originally reported to induce necrosis in pancreatic cancer cells only under nutrient-starved conditions via inhibition of PI3-kinase. The effects of KGM on myeloma cells were investigated. Materials and methods: Cytotoxic activity was quantified using WST8 assay. Necrosis was determined by Annexin V/PI staining. Regulatory protein levels were assessed by Western blot. LY294002 was utilized as a PI3-kinase inhibitor. Results: KGM induced necrosis in myeloma cells in nutrient rich conditions with a CC50 of approximately 100 nM. KGM did not induce necrosis in normal lymphocytes. Cyclin D1, p21, p-AKT and p-ERK were inhibited by KGM while LY294002 did not inhibit cell death by KGM. A melphalan-resistant myeloma cell line was more susceptible to KGM than the melphalan-sensitive parental cell line. Conclusion: KGM-induced necrosis in myeloma cells even at very low concentration. The present data warrant further investigation into the use of KGM as a potential therapeutic agent for multiple myeloma.
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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 ╳
