Kasugamycin
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| Category | Antibiotics |
| Catalog number | BBF-01886 |
| CAS | 6980-18-3 |
| Molecular Weight | 379.36 |
| Molecular Formula | C14H25N3O9 |
| Purity | ≥95% |
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Description
It is produced by the strain of Str. sugaensis M-388 (ATCC-15714, -15715). Kasugamycin has antibacterial properties against certain bacteria and fungi.
Specification
| Related CAS | 19408-46-9 (mono-hydrochloride) 78822-08-9 (sulfate salt) |
| Synonyms | D-chiro-Inositol, 3-O-[2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranosyl]-; 3-O-[2-Amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranosyl]-D-chiro-inositol; Kasu B; Kasumin 2L; Kasumin 4WP; Kasumin L; KSM; NSC 100858 |
| Storage | Store at -20°C |
| IUPAC Name | 2-amino-2-[(2R,3S,5S,6R)-5-amino-2-methyl-6-[(2R,3S,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxyoxan-3-yl]iminoacetic acid |
| Canonical SMILES | CC1C(CC(C(O1)OC2C(C(C(C(C2O)O)O)O)O)N)N=C(C(=O)O)N |
| InChI | InChI=1S/C14H25N3O9/c1-3-5(17-12(16)13(23)24)2-4(15)14(25-3)26-11-9(21)7(19)6(18)8(20)10(11)22/h3-11,14,18-22H,2,15H2,1H3,(H2,16,17)(H,23,24)/t3-,4+,5+,6-,7+,8+,9-,10+,11+,14-/m1/s1 |
| InChI Key | PVTHJAPFENJVNC-MHRBZPPQSA-N |
Properties
| Appearance | Pale Beige Solid |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 585.9±60.0°C at 760 mmHg |
| Density | 1.97±0.1 g/cm3 |
| Solubility | Soluble in Aqueous Base (Slightly), Water (Slightly) |
Reference Reading
1. Phage Cocktail in Combination with Kasugamycin as a Potential Treatment for Fire Blight Caused by Erwinia amylovora
Sang-Guen Kim, Sung-Bin Lee, Su-Jin Jo, Kevin Cho, Jung-Kum Park, Jun Kwon, Sib Sankar Giri, Sang-Wha Kim, Jeong-Woo Kang, Won-Joon Jung, Young-Min Lee, Eunjung Roh, Se-Chang Park Antibiotics (Basel). 2022 Nov 6;11(11):1566. doi: 10.3390/antibiotics11111566.
Recently, there has been an increasing number of blight disease reports associated with Erwinia amylovora and Erwinia pyrifoliae in South Korea. Current management protocols that have been conducted with antibiotics have faced resistance problems and the outbreak has not decreased. Because of this concern, the present study aimed to provide an alternative method to control the invasive fire blight outbreak in the nation using bacteriophages (phages) in combination with an antibiotic agent (kasugamycin). Among 54 phage isolates, we selected five phages, pEa_SNUABM_27, 31, 32, 47, and 48, based on their bacteriolytic efficacy. Although only phage pEa_SNUABM_27 showed host specificity for E. amylovora, all five phages presented complementary lytic potential that improved the host infectivity coverage of each phage All the phages in the cocktail solution could lyse phage-resistant strains. These strains had a decreased tolerance to the antibiotic kasugamycin, and a synergistic effect of phages and antibiotics was demonstrated both in vitro and on immature wound-infected apples. It is noteworthy that the antibacterial effect of the phage cocktail or phage cocktail-sub-minimal inhibitory concentration (MIC) of kasugamycin was significantly higher than the kasugamycin at the MIC. The selected phages were experimentally stable under environmental factors such as thermal or pH stress. Genomic analysis revealed these are novel Erwinia-infecting phages, and did not encode antibiotic-, virulence-, or lysogenic phage-related genes. In conclusion, we suggest the potential of the phage cocktail and kasugamycin combination as an effective strategy that would minimize the use of antibiotics, which are being excessively used in order to control fire blight pathogens.
2. Evaluation of kasugamycin as a chiral selector in capillary electrophoresis
Chunyan Zhang, Yifeng Fan, Liangliang Cai, Xiaofei Ma Analyst. 2023 Feb 28. doi: 10.1039/d2an01949c. Online ahead of print.
The discovery of novel chiral selectors always fascinates us. This work describes the chiral separation performances of a new chiral selector (kasugamycin, KAS) in capillary electrophoresis (CE) for six pairs of stereoisomers, including ephedrine and pseudoephedrine, quinine and quinidine, cinchonine and cinchonidine, and amlodipine, promethazine and ofloxacin enantiomers. Kasugamycin, an aminoglycoside antibiotic in agriculture, shows significant biological activity against rice blast with low toxicity. As it turns out, this new chiral selector possesses good CE compatibility and stereoselectivity towards model analytes. In this work, we systematically investigated several separation parameters including kasugamycin concentration, buffer pH, separation voltage and the composition of the buffer solution. A detailed discussion about the chiral recognition mechanism was made based on Statistical Product and Service Solution (SPSS) analysis, NMR experiments (1D and 2D) and molecular modeling. This is the first time that kasugamycin is utilized as a chiral selector in CE, and the development of new chiral selectors from agricultural or veterinary antibiotics deserves more attention.
3. Kasugamycin Is a Novel Chitinase 1 Inhibitor with Strong Antifibrotic Effects on Pulmonary Fibrosis
Jae-Hyun Lee, Chang-Min Lee, Joyce H Lee, Mun-Ock Kim, Jin Wook Park, Suchitra Kamle, Bedia Akosman, Erica L Herzog, Xue Yan Peng, Jack A Elias, Chun Geun Lee Am J Respir Cell Mol Biol. 2022 Sep;67(3):309-319. doi: 10.1165/rcmb.2021-0156OC.
Pulmonary fibrosis is a devastating lung disease with few therapeutic options. CHIT1 (chitinase 1), an 18 glycosyl hydrolase family member, contributes to the pathogenesis of pulmonary fibrosis through the regulation of TGF-β (transforming growth factor-β) signaling and effector function. Therefore, CHIT1 is a potential therapeutic target for pulmonary fibrosis. This study aimed to identify and characterize a druggable CHIT1 inhibitor with strong antifibrotic activity and minimal toxicity for therapeutic application to pulmonary fibrosis. Extensive screening of small molecule libraries identified the aminoglycoside antibiotic kasugamycin (KSM) as a potent CHIT1 inhibitor. Elevated concentrations of CHIT1 were detected in the lungs of patients with pulmonary fibrosis. In in vivo bleomycin- and TGF-β-stimulated murine models of pulmonary fibrosis, KSM showed impressive antifibrotic effects in both preventive and therapeutic conditions. In vitro studies also demonstrated that KSM inhibits fibrotic macrophage activation, fibroblast proliferation, and myofibroblast transformation. Null mutation of TGFBRAP1 (TGF-β-associated protein 1), a recently identified CHIT1 interacting signaling molecule, phenocopied antifibrotic effects of KSM in in vivo lungs and in vitro fibroblasts responses. KSM inhibits the physical association between CHIT1 and TGFBRAP1, suggesting that the antifibrotic effect of KSM is mediated through regulation of TGFBRAP1, at least in part. These studies demonstrate that KSM is a novel CHIT1 inhibitor with a strong antifibrotic effect that can be further developed as an effective and safe therapeutic drug for pulmonary fibrosis.
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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 ╳
