WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H585390
CAS#: 27127-62-4
Description: Viscosin is a peptidolipid biosurfactant and phytopathogenic.
Hodoodo Cat#: H585390
Name: Viscosin
CAS#: 27127-62-4
Chemical Formula: C54H95N9O16
Exact Mass: 1,125.69
Molecular Weight: 1,126.401
Elemental Analysis: C, 57.58; H, 8.50; N, 11.19; O, 22.73
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Synonym: Viscosin
IUPAC/Chemical Name: (4R)-5-[[(3S,6R,9S,12R,15S,18R,21R,22R)-3-[(2S)-butan-2-yl]-6,12-bis(hydroxymethyl)-22-methyl-9,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-18-propan-2-yl-1-oxa-4,7,10,13,16,19-hexazacyclodocos-21-yl]amino]-4-[[(2S)-2-[[(3R)-3-hydroxydecanoyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoic acid
InChi Key: QYEWAEAWMXRMHB-YFTUCIGFSA-N
InChi Code: InChI=1S/C54H95N9O16/c1-13-15-16-17-18-19-34(66)25-41(67)55-36(22-28(3)4)47(71)56-35(20-21-42(68)69)46(70)63-45-33(12)79-54(78)44(32(11)14-2)62-51(75)40(27-65)60-48(72)37(23-29(5)6)57-50(74)39(26-64)59-49(73)38(24-30(7)8)58-52(76)43(31(9)10)61-53(45)77/h28-40,43-45,64-66H,13-27H2,1-12H3,(H,55,67)(H,56,71)(H,57,74)(H,58,76)(H,59,73)(H,60,72)(H,61,77)(H,62,75)(H,63,70)(H,68,69)/t32-,33+,34+,35+,36-,37-,38-,39+,40+,43+,44-,45+/m0/s1
SMILES Code: O=C(O)CC[C@@H](NC([C@@H](NC(C[C@H](O)CCCCCCC)=O)CC(C)C)=O)C(N[C@H]1C(N[C@H](C(C)C)C(N[C@@H](CC(C)C)C(N[C@H](CO)C(N[C@@H](CC(C)C)C(N[C@H](CO)C(N[C@@H]([C@H](CC)C)C(O[C@@H]1C)=O)=O)=O)=O)=O)=O)=O)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 1,126.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Bonnichsen L, Bygvraa Svenningsen N, Rybtke M, de Bruijn I, Raaijmakers JM, Tolker-Nielsen T, Nybroe O. Lipopeptide biosurfactant viscosin enhances dispersal of Pseudomonas fluorescens SBW25 biofilms. Microbiology. 2015 Dec;161(12):2289-97. doi: 10.1099/mic.0.000191. Epub 2015 Sep 28. PubMed PMID: 26419730; PubMed Central PMCID: PMC4811653.
2: Geudens N, Nasir MN, Crowet JM, Raaijmakers JM, Fehér K, Coenye T, Martins JC, Lins L, Sinnaeve D, Deleu M. Membrane Interactions of Natural Cyclic Lipodepsipeptides of the Viscosin Group. Biochim Biophys Acta Biomembr. 2017 Mar;1859(3):331-339. doi: 10.1016/j.bbamem.2016.12.013. Epub 2016 Dec 20. PubMed PMID: 28007479.
3: Kissoyan KAB, Drechsler M, Stange EL, Zimmermann J, Kaleta C, Bode HB, Dierking K. Natural C. elegans Microbiota Protects against Infection via Production of a Cyclic Lipopeptide of the Viscosin Group. Curr Biol. 2019 Mar 18;29(6):1030-1037.e5. doi: 10.1016/j.cub.2019.01.050. Epub 2019 Feb 28. PubMed PMID: 30827913.
4: Bak F, Bonnichsen L, Jørgensen NO, Nicolaisen MH, Nybroe O. The biosurfactant viscosin transiently stimulates n-hexadecane mineralization by a bacterial consortium. Appl Microbiol Biotechnol. 2015 Feb;99(3):1475-83. doi: 10.1007/s00253-014-6054-3. Epub 2014 Sep 14. PubMed PMID: 25216581; PubMed Central PMCID: PMC4306737.
5: Saini HS, Barragán-Huerta BE, Lebrón-Paler A, Pemberton JE, Vázquez RR, Burns AM, Marron MT, Seliga CJ, Gunatilaka AA, Maier RM. Efficient purification of the biosurfactant viscosin from Pseudomonas libanensis strain M9-3 and its physicochemical and biological properties. J Nat Prod. 2008 Jun;71(6):1011-5. doi: 10.1021/np800069u. Epub 2008 May 10. PubMed PMID: 18471020.
6: Geudens N, De Vleeschouwer M, Fehér K, Rokni-Zadeh H, Ghequire MG, Madder A, De Mot R, Martins JC, Sinnaeve D. Impact of a stereocentre inversion in cyclic lipodepsipeptides from the viscosin group: a comparative study of the viscosinamide and pseudodesmin conformation and self-assembly. Chembiochem. 2014 Dec 15;15(18):2736-46. doi: 10.1002/cbic.201402389. Epub 2014 Nov 7. PubMed PMID: 25382202.
7: Martin H C, Ibáñez R, Nothias LF, Boya P CA, Reinert LK, Rollins-Smith LA, Dorrestein PC, Gutiérrez M. Viscosin-like lipopeptides from frog skin bacteria inhibit Aspergillus fumigatus and Batrachochytrium dendrobatidis detected by imaging mass spectrometry and molecular networking. Sci Rep. 2019 Feb 28;9(1):3019. doi: 10.1038/s41598-019-39583-7. PubMed PMID: 30816229; PubMed Central PMCID: PMC6395710.
8: Braun PG, Hildebrand PD, Ells TC, Kobayashi DY. Evidence and characterization of a gene cluster required for the production of viscosin, a lipopeptide biosurfactant, by a strain of Pseudomonas fluorescens. Can J Microbiol. 2001 Apr;47(4):294-301. PubMed PMID: 11358168.
9: Alsohim AS, Taylor TB, Barrett GA, Gallie J, Zhang XX, Altamirano-Junqueira AE, Johnson LJ, Rainey PB, Jackson RW. The biosurfactant viscosin produced by Pseudomonas fluorescens SBW25 aids spreading motility and plant growth promotion. Environ Microbiol. 2014 Jul;16(7):2267-81. doi: 10.1111/1462-2920.12469. Epub 2014 Apr 29. PubMed PMID: 24684210.
10: de Bruijn I, Raaijmakers JM. Diversity and functional analysis of LuxR-type transcriptional regulators of cyclic lipopeptide biosynthesis in Pseudomonas fluorescens. Appl Environ Microbiol. 2009 Jul;75(14):4753-61. doi: 10.1128/AEM.00575-09. Epub 2009 May 15. PubMed PMID: 19447950; PubMed Central PMCID: PMC2708414.
11: Weisshoff H, Hentschel S, Zaspel I, Jarling R, Krause E, Pham TL. PPZPMs--a novel group of cyclic lipodepsipeptides produced by the Phytophthora alni associated strain Pseudomonas sp. JX090307--the missing link between the viscosin and amphisin group. Nat Prod Commun. 2014 Jul;9(7):989-96. PubMed PMID: 25230511.
12: Burke TR Jr, Chandrasekhar B. Preparative reversed-phase high-performance liquid chromatography in the synthesis of viscosin, a cyclic depsipeptide. J Chromatogr. 1989 Dec 22;484:293-8. PubMed PMID: 2613788.
13: GROUPE V, PUGH LH, WEISS D, KOCHI M. Observations on antiviral activity of viscosin. Proc Soc Exp Biol Med. 1951 Oct;78(1):354-8. PubMed PMID: 14892017.
14: Deveau A, Gross H, Palin B, Mehnaz S, Schnepf M, Leblond P, Dorrestein PC, Aigle B. Role of secondary metabolites in the interaction between Pseudomonas fluorescens and soil microorganisms under iron-limited conditions. FEMS Microbiol Ecol. 2016 Aug;92(8). pii: fiw107. doi: 10.1093/femsec/fiw107. Epub 2016 May 18. PubMed PMID: 27199346; PubMed Central PMCID: PMC5975829.
15: Yang MM, Wen SS, Mavrodi DV, Mavrodi OV, von Wettstein D, Thomashow LS, Guo JH, Weller DM. Biological control of wheat root diseases by the CLP-producing strain Pseudomonas fluorescens HC1-07. Phytopathology. 2014 Mar;104(3):248-56. doi: 10.1094/PHYTO-05-13-0142-R. PubMed PMID: 24512115; PubMed Central PMCID: PMC5523110.
16: Lallana E, Rios de la Rosa JM, Tirella A, Pelliccia M, Gennari A, Stratford IJ, Puri S, Ashford M, Tirelli N. Chitosan/Hyaluronic Acid Nanoparticles: Rational Design Revisited for RNA Delivery. Mol Pharm. 2017 Jul 3;14(7):2422-2436. doi: 10.1021/acs.molpharmaceut.7b00320. Epub 2017 Jun 19. PubMed PMID: 28597662.
17: Rokni-Zadeh H, Mangas-Losada A, De Mot R. PCR detection of novel non-ribosomal peptide synthetase genes in lipopeptide-producing Pseudomonas. Microb Ecol. 2011 Nov;62(4):941-7. doi: 10.1007/s00248-011-9885-9. Epub 2011 Jun 7. PubMed PMID: 21647696.
18: Acebo-Guerrero Y, Hernández-Rodríguez A, Vandeputte O, Miguélez-Sierra Y, Heydrich-Pérez M, Ye L, Cornelis P, Bertin P, El Jaziri M. Characterization of Pseudomonas chlororaphis from Theobroma cacao L. rhizosphere with antagonistic activity against Phytophthora palmivora (Butler). J Appl Microbiol. 2015 Oct;119(4):1112-26. doi: 10.1111/jam.12910. PubMed PMID: 26218193.
19: Hiramoto M, Okada K, Nagai S, Kawamoto H. The structure of viscosin, a peptide antibiotic. I. Syntheses of D- and L-3-hydroxyacyl-L-leucine hydrazides related to viscosin. Chem Pharm Bull (Tokyo). 1971 Jul;19(7):1308-14. PubMed PMID: 4998540.
20: Hiramoto M, Okada K, Nagai S. The structure of viscosin, a peptide antibiotic. II. Syntheses of D- and L-3-hydroxyacylhexapeptides including the proposed structure of viscosin and its optical isomers. Chem Pharm Bull (Tokyo). 1971 Jul;19(7):1315-20. PubMed PMID: 4935900.
