polyenes

Summary

Summary: Hydrocarbons with more than one double bond. They are a reduced form of POLYYNES.

Top Publications

  1. Vandeputte P, Tronchin G, Larcher G, Ernoult E, Berg s T, Chabasse D, et al. A nonsense mutation in the ERG6 gene leads to reduced susceptibility to polyenes in a clinical isolate of Candida glabrata. Antimicrob Agents Chemother. 2008;52:3701-9 pubmed publisher
    ..We investigated the molecular mechanisms responsible for the reduced susceptibility to polyenes of a clinical isolate of Candida glabrata...
  2. Kleigrewe K, Söhnel A, Humpf H. A new high-performance liquid chromatography-tandem mass spectrometry method based on dispersive solid phase extraction for the determination of the mycotoxin fusarin C in corn ears and processed corn samples. J Agric Food Chem. 2011;59:10470-6 pubmed publisher
    ..In addition, the stability of fusarin C under storage conditions was evaluated. ..
  3. Xiong Z, Zhang Z, Li J, Wei S, Tu G. Characterization of Streptomyces padanus JAU4234, a producer of actinomycin X?, fungichromin, and a new polyene macrolide antibiotic. Appl Environ Microbiol. 2012;78:589-92 pubmed publisher
    ..Antifungalmycin 702 had good general antifungal activity and may have potential future agricultural and/or clinical applications. ..
  4. Belecki K, Crawford J, Townsend C. Production of octaketide polyenes by the calicheamicin polyketide synthase CalE8: implications for the biosynthesis of enediyne core structures. J Am Chem Soc. 2009;131:12564-6 pubmed publisher
    ..We now disclose the simultaneous in vitro production of three octaketide polyenes by biosynthetic enzymes for the 10-membered enediyne calicheamicin gamma(1)(I), including the elusive beta-keto ..
  5. Kim D, Moon K, Kim S, Park S, Park S, Lee S, et al. Bahamaolides A and B, antifungal polyene polyol macrolides from the marine actinomycete Streptomyces sp. J Nat Prod. 2012;75:959-67 pubmed publisher
    ..Bahamaolide A displayed significant inhibitory activity against Candida albicans isocitrate lyase and antifungal activity against various pathogenic fungi. ..
  6. Chandrasekar P. Management of invasive fungal infections: a role for polyenes. J Antimicrob Chemother. 2011;66:457-65 pubmed publisher
    ..of antifungal drugs continues to grow; the three main classes of commonly administered drugs are the polyenes, azoles and echinocandins...
  7. Sharma M, Manoharlal R, Negi A, Prasad R. Synergistic anticandidal activity of pure polyphenol curcumin I in combination with azoles and polyenes generates reactive oxygen species leading to apoptosis. FEMS Yeast Res. 2010;10:570-8 pubmed publisher
    ..present study we demonstrate that CUR-I at non-antifungal concentration interacts synergistically with azoles and polyenes. For this, pure polyphenol CUR-I was tested for synergy with five azole and two polyene drugs - fluconazole (FLC),..
  8. Surendra K, Corey E. Highly enantioselective proton-initiated polycyclization of polyenes. J Am Chem Soc. 2012;134:11992-4 pubmed publisher
    ..The process is practical as well as efficient, because the chiral ligand is both readily prepared from R,R- or S,S-BINOL and easily recovered from the reaction mixture by extraction. ..
  9. Santos Aberturas J, Vicente C, Guerra S, Payero T, Martin J, Aparicio J. Molecular control of polyene macrolide biosynthesis: direct binding of the regulator PimM to eight promoters of pimaricin genes and identification of binding boxes. J Biol Chem. 2011;286:9150-61 pubmed publisher

More Information

Publications62

  1. Oh D, Scott J, Currie C, Clardy J. Mycangimycin, a polyene peroxide from a mutualist Streptomyces sp. Org Lett. 2009;11:633-6 pubmed publisher
    ..Its structure, absolute configuration, and biological activity were determined by spectral analysis, chemical modification followed by the modified Mosher method, and growth inhibitory assays, respectively. ..
  2. Cochrane N, Nguyen H, GAGNE M. Catalytic enantioselective cyclization and C3-fluorination of polyenes. J Am Chem Soc. 2013;135:628-31 pubmed publisher
    ..Isolated yields were typically in the 60-69% range while enantioselectivities reached as high as 87%. The data are consistent with a stereoretentive fluorination of a P(2)Pt-alkyl cation intermediate. ..
  3. Godeau J, Fontaine Vive F, Antoniotti S, Duñach E. Experimental and theoretical studies on the bismuth-triflate-catalysed cycloisomerisation of 1,6,10-trienes and aryl polyenes. Chemistry. 2012;18:16815-22 pubmed publisher
    Cycloisomerisation of polyenes such as diethyl geranylprenylmalonate [(E)-1 a], diethyl geranylphenylmalonate [(E)-2 a] and diethyl cinnamylgeranylmalonate [(E,E)-3 a] catalysed by bismuth triflate was studied from experimental and ..
  4. Godeau J, Olivero S, Antoniotti S, Duñach E. Biomimetic cationic polyannulation reaction catalyzed by Bi(OTf)3: cyclization of 1,6-dienes, 1,6,10-trienes, and aryl polyenes. Org Lett. 2011;13:3320-3 pubmed publisher
    ..For some specific substrates, the cyclization was followed by a methyl shift as encountered in terpenoid biosynthesis. ..
  5. Sondergaard T, Hansen F, Purup S, Nielsen A, Bonefeld Jørgensen E, Giese H, et al. Fusarin C acts like an estrogenic agonist and stimulates breast cancer cells in vitro. Toxicol Lett. 2011;205:116-21 pubmed publisher
    ..To the best of our knowledge this is the first report on the mycoestrogenic properties of fusarin C. ..
  6. Stodulkova E, Kuzma M, Hench I, Cerny J, Kralova J, Novak P, et al. New polyene macrolide family produced by submerged culture of Streptomyces durmitorensis. J Antibiot (Tokyo). 2011;64:717-22 pubmed publisher
    ..Striking feature of DDHR is its internal fluorescence allowing visualization of labeled plasma membranes and internal membrane structures. ..
  7. Santos Aberturas J, Payero T, Vicente C, Guerra S, Cañibano C, Martin J, et al. Functional conservation of PAS-LuxR transcriptional regulators in polyene macrolide biosynthesis. Metab Eng. 2011;13:756-67 pubmed publisher
    ..avermitilis, boosted the production of both polyenes, thus indicating that the expression of the PAS-LuxR regulator constitutes a bottleneck in the biosynthesis of ..
  8. Yeung S, Xu G, Pan J, Christgen M, Bamiagis A. Manumycin enhances the cytotoxic effect of paclitaxel on anaplastic thyroid carcinoma cells. Cancer Res. 2000;60:650-6 pubmed
    ..The lack of synergy observed in this in vivo experiment may be due to a ceiling effect, and further experimentation is warranted to ascertain the optimal way to combine these two agents for maximal therapeutic effects. ..
  9. Di Paolo A, Danesi R, Nardini D, Bocci G, Innocenti F, Fogli S, et al. Manumycin inhibits ras signal transduction pathway and induces apoptosis in COLO320-DM human colon tumour cells. Br J Cancer. 2000;82:905-12 pubmed
  10. Millar J, Grant G, McElfresh J, Strong W, Rudolph C, Stein J, et al. (3Z,6Z,9Z, 12Z, 15Z)-Pentacosapentaene, a key pheromone component of the fir coneworm moth, Dioryctria abietivorella. J Chem Ecol. 2005;31:1229-34 pubmed
    ..These combinations of components from two distinct structural classes may represent an important and widespread new pheromone blend motif within the Lepidoptera. ..
  11. Xu G, Pan J, Martin C, Yeung S. Angiogenesis inhibition in the in vivo antineoplastic effect of manumycin and paclitaxel against anaplastic thyroid carcinoma. J Clin Endocrinol Metab. 2001;86:1769-77 pubmed
    ..In conclusion, manumycin plus paclitaxel is an effective combination against ATC, and inhibition of angiogenesis plays a role in the antineoplastic effect of this combination. ..
  12. Vandeputte P, Tronchin G, Berges T, Hennequin C, Chabasse D, Bouchara J. Reduced susceptibility to polyenes associated with a missense mutation in the ERG6 gene in a clinical isolate of Candida glabrata with pseudohyphal growth. Antimicrob Agents Chemother. 2007;51:982-90 pubmed
    ..A clinical isolate of Candida glabrata with a poor susceptibility to polyenes, as determined by disk diffusion method and confirmed by determination of MIC, was recovered from a patient ..
  13. Shih H, Liu Y, Hsu F, Mulabagal V, Dodda R, Huang J. Fungichromin: a substance from Streptomyces padanus with inhibitory effects on Rhizoctonia solani. J Agric Food Chem. 2003;51:95-9 pubmed
    ..This is the first report of fungichromin from S. padanus as an active ingredient for the control of Rhizoctonia damping-off of cabbage. ..
  14. Recio E, Aparicio J, Rumbero A, Martin J. Glycerol, ethylene glycol and propanediol elicit pimaricin biosynthesis in the PI-factor-defective strain Streptomyces natalensis npi287 and increase polyene production in several wild-type actinomycetes. Microbiology. 2006;152:3147-56 pubmed
    ..In summary, glycerol, ethylene glycol and propanediol exert a bypass of the PI-factor inducing effect on pimaricin biosynthesis. ..
  15. Liu R, Yang L, Liu J. Mechanisms of photoisomerization of polyenes in confined media: from organic glasses to protein binding cavities. Photochem Photobiol. 2007;83:2-10 pubmed
    ..e. torsional relaxation) or bicycle-pedal or an extended HT process in photoisomerization. ..
  16. McCluskey A, Sim A, Sakoff J. Serine-threonine protein phosphatase inhibitors: development of potential therapeutic strategies. J Med Chem. 2002;45:1151-75 pubmed
  17. Aparicio J, Mendes M, Anton N, Recio E, Martin J. Polyene macrolide antibiotic biosynthesis. Curr Med Chem. 2004;11:1645-56 pubmed
    b>Polyenes constitute a large class of natural metabolites produced by giant multifunctional enzymes in a process resembling fatty acid biosynthesis...
  18. Jin M, Fischbach M, Clardy J. A biosynthetic gene cluster for the acetyl-CoA carboxylase inhibitor andrimid. J Am Chem Soc. 2006;128:10660-1 pubmed
    ..Therefore, future efforts can exploit the genetic manipulability of E. coli to engineer the andrimid synthase with the goal of producing a diverse set of andrimid analogues for clinical evaluation. ..
  19. Caffrey P, Aparicio J, Malpartida F, Zotchev S. Biosynthetic engineering of polyene macrolides towards generation of improved antifungal and antiparasitic agents. Curr Top Med Chem. 2008;8:639-53 pubmed
    ..of the streptomycetes that produce nystatin, amphotericin B, candicidin, pimaricin and rimocidin/CE-108-related polyenes. This has led to engineered biosynthesis of several new polyenes that are not easily obtained as semi-synthetic ..
  20. Udwary D, Zeigler L, Asolkar R, Singan V, Lapidus A, Fenical W, et al. Genome sequencing reveals complex secondary metabolome in the marine actinomycete Salinispora tropica. Proc Natl Acad Sci U S A. 2007;104:10376-81 pubmed
    ..This study firmly establishes the genus Salinispora as a rich source of drug-like molecules and importantly reveals the powerful interplay between genomic analysis and traditional natural product isolation studies. ..
  21. Millar J. Polyene hydrocarbons and epoxides: a second major class of lepidopteran sex attractant pheromones. Annu Rev Entomol. 2000;45:575-604 pubmed
    ..This review summarizes the taxonomic distribution, mechanisms used to generate unique pheromone blends, and the identification, synthesis, and biosynthesis of these compounds. ..
  22. Guaratini T, Gates P, Pinto E, Colepicolo P, Lopes N. Differential ionisation of natural antioxidant polyenes in electrospray and nanospray mass spectrometry. Rapid Commun Mass Spectrom. 2007;21:3842-8 pubmed
    ..The increased understanding afforded by this study will help in the development of unequivocal microanalytical methods for carotenoids and related antioxidant polyenes.
  23. Hac Wydro K, Dynarowicz Latka P. Interaction between nystatin and natural membrane lipids in Langmuir monolayers--the role of a phospholipid in the mechanism of polyenes mode of action. Biophys Chem. 2006;123:154-61 pubmed
    ..A thorough analysis of the Langmuir experiment results performed for both polyenes enabled us to conclude that the presence of DPPC can be considered as a key factor affecting their antifungal ..
  24. Thawai C, Kittakoop P, Tanasupawat S, Suwanborirux K, Sriklung K, Thebtaranonth Y. Micromonosporin A, a novel 24-membered polyene lactam macrolide from Micromonospora sp. isolated from peat swamp forest. Chem Biodivers. 2004;1:640-5 pubmed
    ..strain TT1-11, which was isolated from a very acidic peat swamp forest...
  25. Masiá Canuto M, Gutiérrez Rodero F. Antifungal drug resistance to azoles and polyenes. Lancet Infect Dis. 2002;2:550-63 pubmed
    ..In addition, antifungal control programmes to prevent extensive and inappropriate use of antifungals may be needed. ..
  26. Liu T, Lee R, Barker K, Lee R, Wei L, Homayouni R, et al. Genome-wide expression profiling of the response to azole, polyene, echinocandin, and pyrimidine antifungal agents in Candida albicans. Antimicrob Agents Chemother. 2005;49:2226-36 pubmed
    ..Genes responding similarly to two or more drugs were also identified. These data shed new light on the effects of these classes of antifungal agents on C. albicans. ..
  27. Mendes M, Recio E, Fouces R, Luiten R, Martin J, Aparicio J. Engineered biosynthesis of novel polyenes: a pimaricin derivative produced by targeted gene disruption in Streptomyces natalensis. Chem Biol. 2001;8:635-44 pubmed
    ..This novel epoxidase could prove to be valuable for the introduction of epoxy substituents into designer macrolides. ..
  28. Ganesan L, Manavathu E, Cutright J, Alangaden G, Chandrasekar P. In-vitro activity of nikkomycin Z alone and in combination with polyenes, triazoles or echinocandins against Aspergillus fumigatus. Clin Microbiol Infect. 2004;10:961-6 pubmed
    The in-vitro activity of nikkomycin Z was investigated in combination with polyenes, triazoles or echinocandins against 20 clinical isolates of Aspergillus fumigatus with the fractional inhibitory concentration index (FICI) method...
  29. Wang S, Miller A. A rapid liquid chromatography-tandem mass spectrometry analysis of whole blood sirolimus using turbulent flow technology for online extraction. Clin Chem Lab Med. 2008;46:1631-4 pubmed publisher
    ..Good correlation with an in-house commercial LC-MS was observed. The LC-MS/MS method coupled with turbulent flow technology is rapid and efficient in TDM of whole blood sirolimus. ..
  30. Récamier K, Hernandez Gomez A, González Damián J, Ortega Blake I. Effect of membrane structure on the action of polyenes: I. Nystatin action in cholesterol- and ergosterol-containing membranes. J Membr Biol. 2010;237:31-40 pubmed publisher
    ..The present results and those of a companion paper lead us to propose that membrane structure is the determining factor for drug selectivity in membranes with different sterols. ..
  31. Narayan R, Frohlich R, Würthwein E. Synthesis of pyrroles through a 4?-electrocyclic ring-closure reaction of 1-azapentadienyl cations. J Org Chem. 2012;77:1868-79 pubmed publisher
    ..They support the proposed mechanism of a 4?-conrotatory Möbius-type electrocyclic ring-closure reaction. ..
  32. Zhang C, Moretti R, Jiang J, Thorson J. The in vitro characterization of polyene glycosyltransferases AmphDI and NysDI. Chembiochem. 2008;9:2506-14 pubmed publisher
  33. Duval S, Santini J, Nitschke W, Hille R, Schoepp Cothenet B. The small subunit AroB of arsenite oxidase: lessons on the [2Fe-2S] Rieske protein superfamily. J Biol Chem. 2010;285:20442-51 pubmed publisher
    ..However, two cysteine residues, strictly conserved in the Rieske-cyt b-Rieske and considered to be crucial for its function, are not conserved in the arsenite oxidase counterpart. We discuss the role of these residues...
  34. Kondo C, Aoki M, Yamamoto E, Tonomura Y, Ikeda M, Kaneto M, et al. Predictive genomic biomarkers for drug-induced nephrotoxicity in mice. J Toxicol Sci. 2012;37:723-37 pubmed
    ..This study provides novel evidence that these nephrotoxicity biomarker genes identified are translatable to mice, and that they are useful for early and sensitive detection of nephrotoxicity. ..
  35. Mizukami W, Kurashige Y, Ehara M, Yanai T, Itoh T. Ab initio study of the excited singlet states of all-trans alpha,omega-diphenylpolyenes with one to seven polyene double bonds: Simulation of the spectral data within Franck-Condon approximation. J Chem Phys. 2009;131:174313 pubmed publisher
    ..This indicates that the geometric differences of the energy minima between the ground (1 (1)A(g)) and 2 (1)A(g) states grow larger towards the direction of the C-C stretching mode with increasing N. ..
  36. Voelkel A, Strzemiecka B, Marek A, Zawadiak J. Inverse gas chromatography investigation of oxidized polyolefins: surface properties. J Chromatogr A. 2014;1337:194-201 pubmed publisher
    ..The use of principal component analysis allowed to select four parameters offering complete information on the physiochemical character of examined materials (?S(D)), acid volume or saponification number, KA or KD and KA/KD. ..
  37. Ginzburg A, Macko T, Malz F, Schroers M, Troetsch Schaller I, Strittmatter J, et al. Characterization of functionalized polyolefins by high-temperature two-dimensional liquid chromatography. J Chromatogr A. 2013;1285:40-7 pubmed publisher
    ..of methyl methacrylate respectively. Using porous graphite as a stationary phase and a solvent gradient 1-decanol?1,2,4-trichlorobenzene as mobile phase 2D-LC separations of both grafted polyolefins were realized. ..
  38. Dixit D, Sharma V, Ghosh S, Koul N, Mishra P, Sen E. Manumycin inhibits STAT3, telomerase activity, and growth of glioma cells by elevating intracellular reactive oxygen species generation. Free Radic Biol Med. 2009;47:364-74 pubmed publisher
    ..In addition manumycin (i) induced the DNA-damage repair response, (ii) affected cell-cycle-regulatory molecules, and (iii) impaired the colony-forming ability of glioma cells in a ROS-dependent manner. ..
  39. Zhao J, Chen M, Wang X, Zhao X, Wang Z, Dang Z, et al. Triple shape memory effects of cross-linked polyethylene/polypropylene blends with cocontinuous architecture. ACS Appl Mater Interfaces. 2013;5:5550-6 pubmed publisher
    ..This new strategy of chemically cross-linked immiscible blends with cocontinuous architecture can be used to design and prepare new SMPs with triple SMEs. ..
  40. Ellepola A, Samaranayake L, Khan Z. Extracellular phospholipase production of oral Candida albicans isolates from smokers, diabetics, asthmatics, denture wearers and healthy individuals following brief exposure to polyene, echinocandin and azole antimycotics. Braz J Microbiol. 2016;47:911-916 pubmed publisher
    ..Oral candidosis can be treated with polyenes, and azoles, and the more recently introduced echinocandins...
  41. Phornphisutthimas S, Sudtachat N, Bunyoo C, Chotewutmontri P, Panijpan B, Thamchaipenet A. Development of an intergeneric conjugal transfer system for rimocidin-producing Streptomyces rimosus. Lett Appl Microbiol. 2010;50:530-6 pubmed publisher
    ..The conjugation system developed provides a convenient gene expression system for S. rimosus R7 and will enable the genetic manipulation of the rimocidin gene cluster. ..
  42. Lebitasy M, Hecq J, Vanbeckbergen D, Jamart J, Galanti L. Long-term stability of tramadol hydrochloride and droperidol mixture in 5% dextrose infusion polyolefin bags at 5+/-3 degrees C. Ann Pharm Fr. 2009;67:272-7 pubmed publisher
    ..5mg in 100 ml of 5% dextrose infusions stored up to 32 days at 5+/-3 degrees C remain stable and may be prepared in advance by CIVAS to improve safety and management. ..
  43. Peman J, Cantón E, Espinel Ingroff A. Antifungal drug resistance mechanisms. Expert Rev Anti Infect Ther. 2009;7:453-60 pubmed publisher
    ..Acquired resistance to flucytosine results from defects in its metabolism through enzymatic mutations, whereas resistance to amphotericin B may be mediated by increased catalase activity or defects in ergosterol biosynthesis. ..
  44. Mathew B, Nath M. Recent approaches to antifungal therapy for invasive mycoses. ChemMedChem. 2009;4:310-23 pubmed publisher
    ..Apart from the previously known polyenes and imidazole-based azoles, newly discovered triazoles and echinocandins are more effective in terms of ..
  45. Serranti S, Gargiulo A, Bonifazi G. Characterization of post-consumer polyolefin wastes by hyperspectral imaging for quality control in recycling processes. Waste Manag. 2011;31:2217-27 pubmed publisher
  46. Elkinton J, Lance D, Boettner G, Khrimian A, Leva N. Evaluation of pheromone-baited traps for winter moth and Bruce spanworm (Lepidoptera: Geometridae). J Econ Entomol. 2011;104:494-500 pubmed
    ..We are thus doubtful that we can use the isomer to trap winter moths without also catching Bruce spanworm. Pheromone-baited survey traps will catch both species. ..
  47. Lichtenstern C, Swoboda S, Hirschburger M, Domann E, Hoppe Tichy T, Winkler M, et al. [Update: invasive fungal infections: Diagnosis and treatment in surgical intensive care medicine]. Anaesthesist. 2010;59:30-52 pubmed publisher
    ..Depending on the species detected de-escalating to an azole is feasible if organ dysfunctions have resolved. An invasive aspergillosis is primarily treated with voriconazole. ..
  48. Walker P, Allen G, Davies N, Smith J, Molesworth P, Nilsson A, et al. Identification, synthesis and field testing of (3Z,6Z,9Z)-3,6,9-henicosatriene, a second bioactive component of the sex pheromone of the autumn gum moth, Mnesampela privata. J Chem Ecol. 2009;35:1411-22 pubmed publisher
    ..privata in plantations. Traps baited with a 16:1 ratio caught significantly more moths than those baited with a ratio approximating that of females. ..
  49. Ihara C, Takahashi H, Matsui R, Yamanaka T, Ueno T. Bonding durability of custom-made mouthpiece for scuba diving after water storage under pressure. Dent Mater J. 2009;28:487-92 pubmed
    ..The displacements at SD and FR were significantly influenced by the material. These results suggest that both materials can be employed for making a diving custom mouthpiece. ..
  50. Sharma V, Shaheen S, Dixit D, Sen E. Farnesyltransferase inhibitor manumycin targets IL1?-Ras-HIF-1? axis in tumor cells of diverse origin. Inflammation. 2012;35:516-9 pubmed publisher
    ..Manumycin abrogated IL-1?-induced HIF-1? activation in both glioma and non-glioma tumor cells. In addition, manumycin also decreased IL-1? induced pro-inflammatory responses in tumor cells. ..
  51. Yamakawa R, Takubo Y, Shibasaki H, Murakami Y, Yamamoto M, Ando T. Characterization of epoxytrienes derived from (3Z,6Z,9Z)-1,3,6,9-tetraenes, sex pheromone components of arctiid moths and related compounds. J Chem Ecol. 2012;38:1042-9 pubmed publisher
    ..GC-EAD analysis of the optically pure epoxides showed that the antennae of male H. cunea were stimulated more strongly (>100 times) by the (9S,10R)-isomers than the antipodes. ..
  52. Kong R, Liu X, Su C, Ma C, Qiu R, Tang L. Elucidation of the biosynthetic gene cluster and the post-PKS modification mechanism for fostriecin in Streptomyces pulveraceus. Chem Biol. 2013;20:45-54 pubmed publisher
    ..Based on this study, a comprehensive post-PKS modification mechanism for fostriecin biosynthesis was proposed. ..
  53. Bhaskar N, Kinami T, Miyashita K, Park S, Endo Y, Fujimoto K. Occurrence of conjugated polyenoic fatty acids in seaweeds from the Indian Ocean. Z Naturforsch C. 2004;59:310-4 pubmed
    ..of red marine macro algae (Rhodophyta) from the Indian Ocean were analysed for the occurrence of conjugated polyenes. The composition of different lipid classes in these seaweeds along with their fatty acid composition has also ..