Fluopsin C
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| Category | Antibiotics |
| Catalog number | BBF-00943 |
| CAS | 32982-12-0 |
| Molecular Weight | 243.79 |
| Molecular Formula | C4H8CuN2O2S2 |
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Description
Fluopsin C is a copper-containing antibiotic produced by Pseudomonas fluorescent KY 4032 using n-alkane as a carbon source. It has strong anti-Gram-positive and negative bacteria activity and anti-tumor activity.
Specification
| Synonyms | Fluopin C; Antibiotic 4601; Cuprithioformin |
| IUPAC Name | copper;N-methyl-N-oxidomethanethioamide |
| Canonical SMILES | CN(C=S)[O-].CN(C=S)[O-].[Cu+2] |
| InChI | InChI=1S/2C2H4NOS.Cu/c2*1-3(4)2-5;/h2*2H,1H3;/q2*-1;+2 |
| InChI Key | PGYZQLIUYISMJD-UHFFFAOYSA-N |
Properties
| Appearance | Brown Black Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; neoplastics (Tumor) |
| Melting Point | 182 °C |
Reference Reading
1. DNA damage and reticular stress in cytotoxicity and oncotic cell death of MCF-7 cells treated with fluopsin C
Luan Vitor Alves de Lima, Matheus Felipe da Silva, Virginia Marcia Concato, Débora Berbel Lirio Rondina, Thalita Alves Zanetti, Ingrid Felicidade, Lilian Areal Marques, Sandra Regina Lepri, Ane Stéfano Simionato, Galdino Andrade Filho, Giuliana Castello Coatti, Mário Sérgio Mantovani J Toxicol Environ Health A. 2022 Nov 2;85(21):896-911. doi: 10.1080/15287394.2022.2108950. Epub 2022 Aug 11.
Fluopsin C is an antibiotic compound derived from secondary metabolism of different microorganisms, which possesses antitumor, antibacterial, and antifungal activity. Related to fluopsin C antiproliferative activity, the aim of this study was to examine the following parameters: cytotoxicity, genotoxicity, cell cycle arrest, cell death induction (apoptosis), mitochondrial membrane potential (MMP), colony formation, and mRNA expression of genes involved in adaptive stress responses and cellular death utilizing a monolayer. In addition, a three-dimensional cell culture was used to evaluate the effects on growth of tumor spheroids. Fluopsin C was cytotoxic (1) producing cell division arrest in the G1 phase, (2) elevating expression of mRNA of the CDKN1A gene and (3) decrease in expression of mRNA H2AFX gene. Further, fluopsin C enhanced DNA damage as evidenced by increased expression of mRNA of GADD45A and GPX1 genes, indicating that reactive oxygen species (ROS) may be involved in the observed genotoxic response. Reticulum stress was also detected as noted from activation of the ribonuclease inositol-requiring protein 1 (IRE1) pathway, since a rise in mRNA expression of the ERN1 and TRAF2 genes was observed. During the cell death process, an increase in mRNA expression of the BBC3 gene was noted, indicating participation of this antibiotic in oncotic (ischemic) cell death. Data thus demonstrated for the first time that fluopsin C interferes with the volume of tumor spheroids, in order to attenuate their growth. Our findings show that fluopsin C modulates essential molecular processes in response to stress and cell death.
2. Corrigendum: Determining the Targets of Fluopsin C Action on Gram-Negative and Gram-Positive Bacteria
Miguel Octavio Pérez Navarro, Guilherme Dilarri, Ane Stefano Simionato, Kathlen Grzegorczyk, Mickely Liuti Dealis, Barbara Gionco Cano, André Riedi Barazetti, Leandro Afonso, Andreas Lazaros Chryssafidis, Henrique Ferreira, Galdino Andrade Front Microbiol. 2020 Oct 6;11:574002. doi: 10.3389/fmicb.2020.574002. eCollection 2020.
[This corrects the article DOI: 10.3389/fmicb.2020.01076.].
3. Biosynthesis of fluopsin C, a copper-containing antibiotic from Pseudomonas aeruginosa
Jon B Patteson, Andrew T Putz, Lizhi Tao, William C Simke, L Henry Bryant rd, R David Britt, Bo Li Science. 2021 Nov 19;374(6570):1005-1009. doi: 10.1126/science.abj6749. Epub 2021 Nov 18.
Metal-binding natural products contribute to metal acquisition and bacterial virulence, but their roles in metal stress response are underexplored. We show that a five-enzyme pathway in Pseudomonas aeruginosa synthesizes a small-molecule copper complex, fluopsin C, in response to elevated copper concentrations. Fluopsin C is a broad-spectrum antibiotic that contains a copper ion chelated by two minimal thiohydroxamates. Biosynthesis of the thiohydroxamate begins with cysteine and requires two lyases, two iron-dependent enzymes, and a methyltransferase. The iron-dependent enzymes remove the carboxyl group and the α carbon from cysteine through decarboxylation, N-hydroxylation, and methylene excision. Conservation of the pathway in P. aeruginosa and other bacteria suggests a common role for fluopsin C in the copper stress response, which involves fusing copper into an antibiotic against other microbes.
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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 ╳
