ReutericyclinCAS# 303957-69-9 |
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| Cas No. | 303957-69-9 | SDF | Download SDF |
| PubChem ID | 54696024 | Appearance | Powder |
| Formula | C20H31NO4 | M.Wt | 349.47 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in DMSO | ||
| Chemical Name | 4-acetyl-1-[(E)-dec-2-enoyl]-3-hydroxy-2-(2-methylpropyl)-2H-pyrrol-5-one | ||
| SMILES | CCCCCCCC=CC(=O)N1C(C(=C(C1=O)C(=O)C)O)CC(C)C | ||
| Standard InChIKey | GNGSBVNLHSNSDF-VAWYXSNFSA-N | ||
| Standard InChI | InChI=1S/C20H31NO4/c1-5-6-7-8-9-10-11-12-17(23)21-16(13-14(2)3)19(24)18(15(4)22)20(21)25/h11-12,14,16,24H,5-10,13H2,1-4H3/b12-11+ | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1. Reutericyclin is a unique antimicrobial tetramic acid produced by some strains of Lactobacillus reuteri. 2. Reutericyclin and nisin exhibit divergent effects on heat- and pressure-induced spore inactivation and membrane fluidity. 3. Dissipation of the membrane potential by active Reutericyclins correlated with inhibition of macromolecular synthesis in cells. 4. All reutericyclins can inhibit the growth of clinical isolates of drug-resistant Staphylococcus aureus, which exemplify the prospect of developing reutericyclins as new topical antibiotics. |
| Targets | Antifection |
Reutericyclin Dilution Calculator
Reutericyclin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.8615 mL | 14.3074 mL | 28.6148 mL | 57.2295 mL | 71.5369 mL |
| 5 mM | 0.5723 mL | 2.8615 mL | 5.723 mL | 11.4459 mL | 14.3074 mL |
| 10 mM | 0.2861 mL | 1.4307 mL | 2.8615 mL | 5.723 mL | 7.1537 mL |
| 50 mM | 0.0572 mL | 0.2861 mL | 0.5723 mL | 1.1446 mL | 1.4307 mL |
| 100 mM | 0.0286 mL | 0.1431 mL | 0.2861 mL | 0.5723 mL | 0.7154 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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In situ determination of Clostridium endospore membrane fluidity during pressure-assisted thermal processing in combination with nisin or reutericyclin.[Pubmed:23335780]
Appl Environ Microbiol. 2013 Mar;79(6):2103-6.
This study determined the membrane fluidity of clostridial endospores during treatment with heat and pressure with nisin or Reutericyclin. Heating (90 degrees C) reduced laurdan (6-dodecanoyl-2-dimethylaminonaphthalene) general polarization, corresponding to membrane fluidization. Pressure (200 MPa) stabilized membrane order. Reutericyclin and nisin exhibit divergent effects on heat- and pressure-induced spore inactivation and membrane fluidity.
Effects of nisin and reutericyclin on resistance of endospores of Clostridium spp. to heat and high pressure.[Pubmed:23498177]
Food Microbiol. 2013 May;34(1):46-51.
The effects of high pressure, temperature, and antimicrobial compounds on endospores of Clostridium spp. were examined. Minimal inhibitory concentrations (MIC) of nisin and Reutericyclin were determined for vegetative cells and endospores of Clostridium sporogenes ATCC 7955, Clostridium beijerinckii ATCC 8260, and Clostridium difficile 3195. Endospores of C. sporogenes ATCC 7955 and C. beijerinckii ATCC 8260 were exposed to 90 degrees C and 90 degrees C/600 MPa in the presence of 16 mg L(-1) nisin or 6.4 mg L(-1) Reutericyclin for 0-60 min in a 0.9% saline solution. Dipicolinic acid (DPA) release was measured using a terbium-DPA fluorescence assay, and endospore permeability was assessed using 4',6-diamidino-2-phenylindole (DAPI) fluorescence. Vegetative cells of C. sporogenes ATCC 7955 exhibited higher sensitivity to nisin relative to endospores, with MIC values 0.23 +/- 0.084 mg L(-1) and 1.11 +/- 0.48 mg L(-1), respectively. Nisin increased DPA release when endospores were treated at 90 degrees C; however, only C. sporogenes ATCC 7955 exhibited higher inactivation, suggesting strain or species specific effects. Reutericyclin did not enhance spore inactivation or DPA release. Use of nisin in combination with high pressure, thermal treatments enhanced inactivation of endospores of Clostridium spp. and may have application in foods.
Evaluation of analogs of reutericyclin as prospective candidates for treatment of staphylococcal skin infections.[Pubmed:19581456]
Antimicrob Agents Chemother. 2009 Sep;53(9):4028-31.
The potential for Reutericyclin derivatives to be used as topical antibiotics to treat staphylococcal skin infections was investigated. All Reutericyclins inhibited the growth of clinical isolates of drug-resistant Staphylococcus aureus. Unlike the standard topical agent mupirocin, most Reutericyclin derivatives eradicated staphylococcal biofilms. Moreover, two compounds formulated in hydrophilic petrolatum (10%, wt/wt) were efficacious in treating S. aureus superficial skin infections in mice. These data exemplify the prospect of developing Reutericyclins as new topical antibiotics.
Genetic determinants of reutericyclin biosynthesis in Lactobacillus reuteri.[Pubmed:25576609]
Appl Environ Microbiol. 2015 Mar;81(6):2032-41.
Reutericyclin is a unique antimicrobial tetramic acid produced by some strains of Lactobacillus reuteri. This study aimed to identify the genetic determinants of Reutericyclin biosynthesis. Comparisons of the genomes of Reutericyclin-producing L. reuteri strains with those of non-Reutericyclin-producing strains identified a genomic island of 14 open reading frames (ORFs) including genes coding for a nonribosomal peptide synthetase (NRPS), a polyketide synthase (PKS), homologues of PhlA, PhlB, and PhlC, and putative transport and regulatory proteins. The protein encoded by rtcN is composed of a condensation domain, an adenylation domain likely specific for d-leucine, and a thiolation domain. rtcK codes for a PKS that is composed of a ketosynthase domain, an acyl-carrier protein domain, and a thioesterase domain. The products of rtcA, rtcB, and rtcC are homologous to the diacetylphloroglucinol-biosynthetic proteins PhlABC and may acetylate the tetramic acid moiety produced by RtcN and RtcK, forming Reutericyclin. Deletion of rtcN or rtcABC in L. reuteri TMW1.656 abrogated Reutericyclin production but did not affect resistance to Reutericyclin. Genes coding for transport and regulatory proteins could be deleted only in the Reutericyclin-negative L. reuteri strain TMW1.656DeltartcN, and these deletions eliminated Reutericyclin resistance. The genomic analyses suggest that the Reutericyclin genomic island was horizontally acquired from an unknown source during a unique event. The combination of PhlABC homologues with both an NRPS and a PKS has also been identified in the lactic acid bacteria Streptococcus mutans and Lactobacillus plantarum, suggesting that the genes in these organisms and those in L. reuteri share an evolutionary origin.
Chemical modulation of the biological activity of reutericyclin: a membrane-active antibiotic from Lactobacillus reuteri.[Pubmed:24739957]
Sci Rep. 2014 Apr 17;4:4721.
Whilst the development of membrane-active antibiotics is now an attractive therapeutic concept, progress in this area is disadvantaged by poor knowledge of the structure-activity relationship (SAR) required for optimizing molecules to selectively target bacteria. This prompted us to explore the SAR of the Lactobacillus reuteri membrane-active antibiotic Reutericyclin, modifying three key positions about its tetramic acid core. The SAR revealed that lipophilic analogs were generally more active against Gram-positive pathogens, but introduction of polar and charged substituents diminished their activity. This was confirmed by cytometric assays showing that inactive compounds failed to dissipate the membrane potential. Radiolabeled substrate assays indicated that dissipation of the membrane potential by active Reutericyclins correlated with inhibition of macromolecular synthesis in cells. However, compounds with good antibacterial activities also showed cytotoxicity against Vero cells and hemolytic activity. Although this study highlights the challenge of optimizing membrane-active antibiotics, it shows that by increasing antibacterial potency the selectivity index could be widened, allowing use of lower non-cytotoxic doses.
