Lenoremycin
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| Category | Antibiotics |
| Catalog number | BBF-03028 |
| CAS | 51257-84-2 |
| Molecular Weight | 851.11 |
| Molecular Formula | C47H78O13 |
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Description
It is a polyether antibiotic produced by the strain of Streptomyces hygroscopicus A-130. It has the effect of anti-gram-positive bacteria, mycobacterium and protozoa, and can be used as a feed additive to control Eimeriatenella infection.
Specification
| Related CAS | 58399-44-3 (sodium salt) |
| Synonyms | Antibiotic A-130A; A-130A; Antibiotic Ro 21 6150; Dianemycin, 10-demethyl-19-de[(tetrahydro-5-methoxy-6-methyl-2H-pyran-2-yl)oxy]-12-methyl-11-O-(tetrahydro-5-methoxy-6-methyl-2H-pyran-2-yl)-, [11(2R,5S,6R),12R]-; 6-Nonenoic acid, 8-[2,4',10,10'-tetramethyl-2'-[tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl]-9-[(tetrahydro-5-methoxy-6-methyl-2H-pyran-2-yl)oxy][2,7'-bi-1,6-dioxaspiro[4.5]dec]-7-yl]-2,4,6-trimethyl-5-oxo-, [2S-[2a[2'S*,4'R*,5'S*,7'S*[2R*,5S*,7R*(2R*,4S*,6E,8R*),9S*(2S*,5R*,6S*),10S*],10'S*],3b,5b,6b]]- |
| IUPAC Name | (E,2S,4R,8S)-8-[(2S,5R,6R,7R,9S)-2-[(2R,4S,5R,6R,9R)-2-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-4,6-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-7-[(2R,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-2,6-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2,4,6-trimethyl-5-oxonon-6-enoic acid |
| Canonical SMILES | CC1CCC(OC12C(CC(O2)C3C(CC(C(O3)(CO)O)C)C)C)C4(CCC5(O4)C(C(CC(O5)C(C)C=C(C)C(=O)C(C)CC(C)C(=O)O)OC6CCC(C(O6)C)OC)C)C |
| InChI | InChI=1S/C47H78O13/c1-25(19-26(2)41(49)27(3)20-29(5)43(50)51)36-23-37(55-40-16-14-35(53-12)34(10)54-40)33(9)46(56-36)18-17-44(11,60-46)39-15-13-30(6)47(58-39)32(8)22-38(57-47)42-28(4)21-31(7)45(52,24-48)59-42/h19,25,27-40,42,48,52H,13-18,20-24H2,1-12H3,(H,50,51)/b26-19+/t25-,27+,28-,29-,30+,31+,32-,33+,34+,35-,36-,37+,38+,39+,40-,42-,44-,45-,46+,47+/m0/s1 |
| InChI Key | LQFPDTISEHAMNQ-JRSQRZRGSA-N |
Properties
| Appearance | Colorless Amorphous Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Mycobacteria; Parasites |
| Boiling Point | 875.5°C at 760 mmHg |
| Density | 1.18 g/cm3 |
| Solubility | Soluble in Ethanol, Chloroform |
Reference Reading
1. Crystal structure of the NEMO ubiquitin-binding domain in complex with Lys 63-linked di-ubiquitin
Azusa Yoshikawa, Yusuke Sato, Masami Yamashita, Hisatoshi Mimura, Atsushi Yamagata, Shuya Fukai FEBS Lett. 2009 Oct 20;583(20):3317-22. doi: 10.1016/j.febslet.2009.09.028. Epub 2009 Sep 18.
NEMO is essential for activation of the NF-kappaB signaling pathway, which is regulated by ubiquitination of proteins. The C-terminal leucine zipper of NEMO and its adjacent coiled-coil region (CC2-LZ) reportedly bind to linear ubiquitin chains with 1 microM affinity and to Lys 63-linked chains with 100 microM affinity. Here we report the crystal structure of the CC2-LZ region of mouse NEMO in complex with Lys 63-linked di-ubiquitin (K63-Ub(2)) at 2.7A resolution. The ubiquitin-binding region consists of a 130A-long helix and forms a parallel coiled-coil dimer. The Ile 44-centered hydrophobic patch of ubiquitin is recognized in the middle of the NEMO ubiquitin-binding region. NEMO interacts with each K63-Ub(2)via a single ubiquitin-binding site, consistent with low affinity binding with K63-Ub(2).
2. Identification of the polyether ionophore lenoremycin through a new screening strategy for targeting cancer stem cells
Hiroaki Ikeda, Misato Kawami, Masaya Imoto, Hideaki Kakeya J Antibiot (Tokyo). 2022 Dec;75(12):671-678. doi: 10.1038/s41429-022-00571-1. Epub 2022 Oct 8.
Targeting and eradicating cancer stem cells (CSCs), also termed tumor-initiating cells, are promising strategies for preventing cancer progression and recurrence. To identify candidate compounds targeting CSCs, we established a new screening strategy with colorectal CSC spheres and non-CSC spheres in three-dimensional (3D) culture system. Through chemical screening using our system with in-house microbial metabolite library, we identified polyether cation ionophores that selectively inhibited CSC sphere formation, whereas CSC spheres were resistant to conventional anticancer agents. One of the hit compounds, the most selective and effective microbial metabolite lenoremycin, decreased CSC populations via inducing reactive oxygen species production. This study demonstrated that our newly established screening system is useful for discovering agents that selectively eliminate CSCs.
3. Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6
Khaled A Shaaban, Meredith A Saunders, Yinan Zhang, Tuan Tran, Sherif I Elshahawi, Larissa V Ponomareva, Xiachang Wang, Jianjun Zhang, Gregory C Copley, Manjula Sunkara, Madan K Kharel, Andrew J Morris, James C Hower, Matthew S Tremblay, Mark A Prendergast, Jon S Thorson J Nat Prod. 2017 Jan 27;80(1):2-11. doi: 10.1021/acs.jnatprod.6b00948. Epub 2016 Dec 28.
The isolation and structure elucidation of six new bacterial metabolites [spoxazomicin D (2), oxachelins B and C (4, 5), and carboxamides 6-8] and 11 previously reported bacterial metabolites (1, 3, 9-12a, and 14-18) from Streptomyces sp. RM-14-6 is reported. Structures were elucidated on the basis of comprehensive 1D and 2D NMR and mass spectrometry data analysis, along with direct comparison to synthetic standards for 2, 11, and 12a,b. Complete 2D NMR assignments for the known metabolites lenoremycin (9) and lenoremycin sodium salt (10) were also provided for the first time. Comparative analysis also provided the basis for structural revision of several previously reported putative aziridine-containing compounds [exemplified by madurastatins A1, B1, C1 (also known as MBJ-0034), and MBJ-0035] as phenol-dihydrooxazoles. Bioactivity analysis [including antibacterial, antifungal, cancer cell line cytotoxicity, unfolded protein response (UPR) modulation, and EtOH damage neuroprotection] revealed 2 and 5 as potent neuroprotectives and lenoremycin (9) and its sodium salt (10) as potent UPR modulators, highlighting new functions for phenol-oxazolines/salicylates and polyether pharmacophores.
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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 ╳
