Iodinin
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| Category | Antibiotics |
| Catalog number | BBF-01879 |
| CAS | 68-81-5 |
| Molecular Weight | 244.20 |
| Molecular Formula | C12H8N2O4 |
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Description
Iodinin is an antibiotic produced by the strain of Chromobacterium iodinum etc. It has antibacterial and fungal properties
Specification
| Synonyms | 5,6-dihydroxy-10-oxidophenazin-10-ium-1-one; 1,6-Phenazinediol 5,10-dioxide |
| IUPAC Name | 5,10-dioxidophenazine-5,10-diium-1,6-diol |
| Canonical SMILES | C1=CC2=C(C(=C1)O)[N+](=C3C=CC=C(C3=[N+]2[O-])O)[O-] |
| InChI | InChI=1S/C12H8N2O4/c15-9-5-1-3-7-11(9)14(18)8-4-2-6-10(16)12(8)13(7)17/h1-6,15-16H |
| InChI Key | NBMOVCYIGUDQJE-UHFFFAOYSA-N |
Properties
| Appearance | Purple Acicular Crystalline |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 557.8°C at 760 mmHg |
| Melting Point | 230-236°C |
| Density | 1.7 g/cm3 |
Reference Reading
1. Type Strains of Entomopathogenic Nematode-Symbiotic Bacterium Species, Xenorhabdus szentirmaii (EMC) and X. budapestensis (EMA), Are Exceptional Sources of Non-Ribosomal Templated, Large-Target-Spectral, Thermotolerant-Antimicrobial Peptides (by Both), and Iodinin (by EMC)
András Fodor, Maxime Gualtieri, Matthias Zeller, Eustachio Tarasco, Michael G Klein, Andrea M Fodor, Leroy Haynes, Katalin Lengyel, Steven A Forst, Ghazala M Furgani, Levente Karaffa, Tibor Vellai Pathogens. 2022 Mar 11;11(3):342. doi: 10.3390/pathogens11030342.
Antimicrobial multidrug resistance (MDR) is a global challenge, not only for public health, but also for sustainable agriculture. Antibiotics used in humans should be ruled out for use in veterinary or agricultural settings. Applying antimicrobial peptide (AMP) molecules, produced by soil-born organisms for protecting (soil-born) plants, seems a preferable alternative. The natural role of peptide-antimicrobials, produced by the prokaryotic partner of entomopathogenic-nematode/bacterium (EPN/EPB) symbiotic associations, is to sustain monoxenic conditions for the EPB in the gut of the semi-anabiotic infective dauer juvenile (IJ) EPN. They keep pathobiome conditions balanced for the EPN/EPB complex in polyxenic (soil, vanquished insect cadaver) niches. Xenorhabdus szentirmaii DSM16338(T) (EMC), and X. budapestensis DSM16342(T) (EMA), are the respective natural symbionts of EPN species Steinernema rarum and S. bicornutum. We identified and characterized both of these 15 years ago. The functional annotation of the draft genome of EMC revealed 71 genes encoding non-ribosomal peptide synthases, and polyketide synthases. The large spatial Xenorhabdus AMP (fabclavine), was discovered in EMA, and its biosynthetic pathway in EMC. The AMPs produced by EMA and EMC are promising candidates for controlling MDR prokaryotic and eukaryotic pathogens (bacteria, oomycetes, fungi, protozoa). EMC releases large quantity of iodinin (1,6-dihydroxyphenazine 5,10-dioxide) in a water-soluble form into the media, where it condenses to form spectacular water-insoluble, macroscopic crystals. This review evaluates the scientific impact of international research on EMA and EMC.
2. 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.
3. Enhancement of iodinin solubility by encapsulation into cyclodextrin nanoparticles
Anthony Prandina, Lars Herfindal, Sylvie Radix, Pål Rongved, Stein O Døskeland, Marc Le Borgne, Florent Perret J Enzyme Inhib Med Chem. 2018 Dec;33(1):370-375. doi: 10.1080/14756366.2017.1421638.
Phenazine is known to regroup planar nitrogen-containing heterocyclic compounds. It was used here to enhance the bioavailability of the biologically important compound iodinin, which is near insoluble in aqueous solutions. Its water solubility has led to the development of new formulations using diverse amphiphilic α-cyclodextrins (CDs). With the per-[6-desoxy-6-(3-perfluorohexylpropanethio)-2,3-di-O-methyl]-α-CD, we succeeded to get iodinin-loaded nanoformulations with good parameters such as a size of 97.9 nm, 62% encapsulation efficiency and efficient control release. The study presents an interesting alternative to optimizing the water solubility of iodinin by chemical modifications of iodinin.
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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 ╳
