Myxin
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| Category | Others |
| Catalog number | BBF-01979 |
| CAS | 13925-12-7 |
| Molecular Weight | 258.23 |
| Molecular Formula | C13H10N2O4 |
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Description
Myxin is a phenazine derivative produced by Sorangium sp. 3C. It has activity against gram-positive bacteria, negative bacteria, mycobacteria, yeasts and fungi.
Specification
| Synonyms | 6-Methoxy-1-phenazinol 5,10-dioxide |
| IUPAC Name | 6-methoxy-5,10-dioxidophenazine-5,10-diium-1-ol |
| Canonical SMILES | COC1=CC=CC2=[N+](C3=C(C=CC=C3O)[N+](=C21)[O-])[O-] |
| InChI | InChI=1S/C13H10N2O4/c1-19-11-7-3-5-9-13(11)15(18)8-4-2-6-10(16)12(8)14(9)17/h2-7,16H,1H3 |
| InChI Key | JIDVGUQUQSOHOL-UHFFFAOYSA-N |
Properties
| Appearance | Red Needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; mycobacteria; fungi; yeast |
| Boiling Point | 538.8°C at 760 mmHg |
| Density | 1.53 g/cm3 |
| Solubility | Soluble in Acetone, Ether |
Reference Reading
1. New prodrugs and analogs of the phenazine 5,10-dioxide natural products iodinin and myxin promote selective cytotoxicity towards human acute myeloid leukemia cells
Elvar Örn Viktorsson, Reidun Aesoy, Sindre Støa, Viola Lekve, Stein Ove Døskeland, Lars Herfindal, Pål Rongved RSC Med Chem. 2021 Apr 19;12(5):767-778. doi: 10.1039/d1md00020a.
Novel chemotherapeutic strategies for acute myeloid leukemia (AML) treatment are called for. We have recently demonstrated that the phenazine 5,10-dioxide natural products iodinin (3) and myxin (4) exhibit potent and hypoxia-selective cell death on MOLM-13 human AML cells, and that the N-oxide functionalities are pivotal for the cytotoxic activity. Very few structure-activity relationship studies dedicated to phenazine 5,10-dioxides exist on mammalian cell lines and the present work describes our efforts regarding in vitro lead optimizations of the natural compounds iodinin (3) and myxin (4). Prodrug strategies reveal carbamate side chains to be the optimal phenol-attached group. Derivatives with no oxygen-based substituent (-OH or -OCH3) in the 6th position of the phenazine skeleton upheld potency if alkyl or carbamate side chains were attached to the phenol in position 1. 7,8-Dihalogenated- and 7,8-dimethylated analogs of 1-hydroxyphenazine 5,10-dioxide (21) displayed increased cytotoxic potency in MOLM-13 cells compared to all the other compounds studied. On the other hand, dihalogenated compounds displayed high toxicity towards the cardiomyoblast H9c2 cell line, while MOLM-13 selectivity of the 7,8-dimethylated analogs were less affected. Further, a parallel artificial membrane permeability assay (PAMPA) demonstrated the majority of the synthesized compounds to penetrate cell membranes efficiently, which corresponded to their cytotoxic potency. This work enhances the understanding of the structural characteristics essential for the activity of phenazine 5,10-dioxides, rendering them promising chemotherapeutic agents.
2. Resistance-Nodulation-Division Efflux Pump, LexABC, Contributes to Self-Resistance of the Phenazine Di- N-Oxide Natural Product Myxin in Lysobacter antibioticus
Yangyang Zhao, Jiayu Liu, Tianping Jiang, Rongxian Hou, Gaoge Xu, Huiyong Xu, Fengquan Liu Front Microbiol. 2021 Feb 17;12:618513. doi: 10.3389/fmicb.2021.618513. eCollection 2021.
Antibiotic-producing microorganisms have developed several self-resistance mechanisms to protect them from autotoxicity. Transporters belonging to the resistance- nodulation-division (RND) superfamily commonly confer multidrug resistance in Gram-negative bacteria. Phenazines are heterocyclic, nitrogen-containing and redox-active compounds that exhibit diverse activities. We previously identified six phenazines from Lysobacter antibioticus OH13, a soil bacterium emerging as a potential biocontrol agent. Among these phenazines, myxin, a di-N-oxide phenazine, exhibited potent activity against a variety of microorganisms. In this study, we identified a novel RND efflux pump gene cluster, designated lexABC, which is located far away in the genome from the myxin biosynthesis gene cluster. We found a putative LysR-type transcriptional regulator encoding gene lexR, which was adjacent to lexABC. Deletion of lexABC or lexR gene resulted in significant increasing susceptibility of strains to myxin and loss of myxin production. The results demonstrated that LexABC pump conferred resistance against myxin. The myxin produced at lower concentrations in these mutants was derivatized by deoxidation and O-methylation. Furthermore, we found that the abolishment of myxin with deletion of LaPhzB, which is an essential gene in myxin biosynthesis, resulted in significant downregulation of the lexABC. However, exogenous supplementation with myxin to LaPhzB mutant could efficiently induce the expression of lexABC genes. Moreover, lexR mutation also led to decreased expression of lexABC, which indicates that LexR potentially positively modulated the expression of lexABC. Our findings reveal a resistance mechanism against myxin of L. antibioticus, which coordinates regulatory pathways to protect itself from autotoxicity.
3. Monooxygenase LaPhzX is Involved in Self-Resistance Mechanisms during the Biosynthesis of N-Oxide Phenazine Myxin
Jiayu Liu, Yangyang Zhao, Zheng Qing Fu, Fengquan Liu J Agric Food Chem. 2021 Nov 17;69(45):13524-13532. doi: 10.1021/acs.jafc.1c05206. Epub 2021 Nov 4.
Self-resistance genes are deployed by many microbial producers of bioactive natural products to avoid self-toxicity. Myxin, a di-N-oxide phenazine produced by Lysobacter antibioticus OH13, is toxic to many microorganisms and tumor cells. Here, we uncovered a self-defense strategy featuring the antibiotic biosynthesis monooxygenase (ABM) family protein LaPhzX for myxin degradation. The gene LaPhzX is located in the myxin biosynthetic gene cluster (LaPhz), and its deletion resulted in bacterial mutants that are more sensitive to myxin. In addition, the LaPhzX mutants showed increased myxin accumulation and reduction of its derivative, compound 4, compared to the wild-type strain. Meanwhile, in vitro biochemical assays demonstrated that LaPhzX significantly degraded myxin in the presence of nicotinamide adenine dinucleotide phosphate (NADPH), nicotinamide adenine dinucleotide (NADH), flavin mononucleotide (FMN), and flavin adenine dinucleotide (FAD). In addition, heterologous expression of LaPhzX in Xanthomonas oryzae pv. oryzae and Escherichia coli increased their resistance to myxin. Overall, our work illustrates a monooxygenase-mediated self-resistance mechanism for phenazine antibiotic biosynthesis.
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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 ╳
