depsipeptides

Summary

Summary: Compounds consisting of chains of AMINO ACIDS alternating with CARBOXYLIC ACIDS via ester and amide linkages. They are commonly cyclized.

Top Publications

  1. Teixidó C, Arguelaguet E, Pons B, Aracil M, Jimeno J, Somoza R, et al. ErbB3 expression predicts sensitivity to elisidepsin treatment: in vitro synergism with cisplatin, paclitaxel and gemcitabine in lung, breast and colon cancer cell lines. Int J Oncol. 2012;41:317-24 pubmed publisher
    ..These results provide a rationale for further development of these combinations in an ongoing clinical trial. ..
  2. Váradi T, Roszik J, Lisboa D, Vereb G, Molina Guijarro J, Galmarini C, et al. ErbB protein modifications are secondary to severe cell membrane alterations induced by elisidepsin treatment. Eur J Pharmacol. 2011;667:91-9 pubmed publisher
    ..We assume that induction of liquid ordered domains is the primary action of elisidepsin leading to all the other observed changes. ..
  3. Kajiwara K, Muneoka T, Watanabe Y, Karashima T, Kitagaki H, Funato K. Perturbation of sphingolipid metabolism induces endoplasmic reticulum stress-mediated mitochondrial apoptosis in budding yeast. Mol Microbiol. 2012;86:1246-61 pubmed publisher
  4. Zhang T, Jia X, Zhuo Y, Liu M, Gao H, Liu J, et al. Cloning and characterization of a novel 2-ketoisovalerate reductase from the beauvericin producer Fusarium proliferatum LF061. BMC Biotechnol. 2012;12:55 pubmed publisher
  5. Tsukimoto M, Nagaoka M, Shishido Y, Fujimoto J, Nishisaka F, Matsumoto S, et al. Bacterial production of the tunicate-derived antitumor cyclic depsipeptide didemnin B. J Nat Prod. 2011;74:2329-31 pubmed publisher
    ..A favorable strategy for the production of such compounds is to use culturable microorganisms. Here we report that didemnin B, a tunicate-derived depsipeptide, has been isolated from a culturable bacterium, Tistrella mobilis YIT 12409...
  6. Sy Cordero A, Pearce C, Oberlies N. Revisiting the enniatins: a review of their isolation, biosynthesis, structure determination and biological activities. J Antibiot (Tokyo). 2012;65:541-9 pubmed publisher
    ..Structurally, these depsipeptides are biosynthesized by a multifunctional enzyme, termed enniatin synthetase, and are composed of six residues ..
  7. Salazar R, Jones R, Oaknin A, Crawford D, Cuadra C, Hopkins C, et al. A phase I and pharmacokinetic study of elisidepsin (PM02734) in patients with advanced solid tumors. Cancer Chemother Pharmacol. 2012;70:673-81 pubmed publisher
    ..Elisidepsin is well tolerated with predictable reversible transaminase increases. Encouraging preliminary evidence of antitumor activity was observed. ..
  8. Zhdanko A, Schmauder A, Ma C, Sibley L, Sept D, Sasse F, et al. Synthesis of chondramide A analogues with modified ?-tyrosine and their biological evaluation. Chemistry. 2011;17:13349-57 pubmed publisher
    ..Some of them even reach the activity of jasplakinolide. It can be concluded that the 4-position of the aryl ring in the ?-tyrosine of chondramide A tolerates structural modifications quite well. ..
  9. Rasimus S, Mikkola R, Andersson M, Teplova V, Venediktova N, Ek Kommonen C, et al. Psychrotolerant Paenibacillus tundrae isolates from barley grains produce new cereulide-like depsipeptides (paenilide and homopaenilide) that are highly toxic to mammalian cells. Appl Environ Microbiol. 2012;78:3732-43 pubmed publisher
    ..cereus. Paenilide represents the first potassium ionophoric compound described for Paenibacillus. The findings in this paper indicate that paenilide from P. tundrae is a potential food-poisoning agent. ..

More Information

Publications61

  1. Teixidó C, Mares R, Aracil M, Ramon Y Cajal S, Hernandez Losa J. Epithelial-mesenchymal transition markers and HER3 expression are predictors of elisidepsin treatment response in breast and pancreatic cancer cell lines. PLoS ONE. 2013;8:e53645 pubmed publisher
    ..These results show that HER3 expression is an important marker of sensitivity to elisidepsin treatment. ..
  2. Munoz Alonso M, Alvarez E, Guillén Navarro M, Pollan M, Aviles P, Galmarini C, et al. c-Jun N-terminal kinase phosphorylation is a biomarker of plitidepsin activity. Mar Drugs. 2013;11:1677-92 pubmed publisher
    ..These findings suggest that changes in JNK activity provide a reliable biomarker for plitidepsin activity and this could be useful for designing clinical trials and maximizing the efficacy of plitidepsin. ..
  3. Thornburg C, Thimmaiah M, Shaala L, Hau A, Malmo J, Ishmael J, et al. Cyclic depsipeptides, grassypeptolides D and E and Ibu-epidemethoxylyngbyastatin 3, from a Red Sea Leptolyngbya cyanobacterium. J Nat Prod. 2011;74:1677-85 pubmed publisher
  4. Mansson M, Nielsen A, Kjærulff L, Gotfredsen C, Wietz M, Ingmer H, et al. Inhibition of virulence gene expression in Staphylococcus aureus by novel depsipeptides from a marine photobacterium. Mar Drugs. 2011;9:2537-52 pubmed publisher
    ..aureus strain 8325-4 and the highly virulent, community-acquired strain USA300 (CA-MRSA). To our knowledge, this is the first report of inhibitors of the agr system by a marine bacterium...
  5. Robertson B, Wengryniuk S, Coltart D. Asymmetric total synthesis of apratoxin D. Org Lett. 2012;14:5192-5 pubmed publisher
    ..Other key asymmetric transformations employed were an Evans syn-aldol and a Paterson anti-aldol, both of which also proceeded with excellent stereoselectivity. ..
  6. Okada I, Fujiki S, Iwase S, Abe H. Stabilization of actin filaments prevents germinal vesicle breakdown and affects microtubule organization in Xenopus oocytes. Cytoskeleton (Hoboken). 2012;69:312-23 pubmed publisher
    ..Based on these results, intranuclear and cytoplasmic actin filament dynamics appear to be required for the completion of GVBD and critically involved in the regulation of microtubule assembly during oocyte maturation in Xenopus laevis. ..
  7. Xu Y, Kersten R, Nam S, Lu L, Al Suwailem A, Zheng H, et al. Bacterial biosynthesis and maturation of the didemnin anti-cancer agents. J Am Chem Soc. 2012;134:8625-32 pubmed publisher
  8. Shanks R, Stella N, Lahr R, Wang S, Veverka T, Kowalski R, et al. Serratamolide is a hemolytic factor produced by Serratia marcescens. PLoS ONE. 2012;7:e36398 pubmed publisher
    ..Genetic and biochemical analysis implicate the biosurfactant serratamolide as a hemolysin. This novel hemolysin may contribute to irritation and infections associated with contact lens use...
  9. Shilabin A, Hamann M. In vitro and in vivo evaluation of select kahalalide F analogs with antitumor and antifungal activities. Bioorg Med Chem. 2011;19:6628-32 pubmed publisher
    ..The TGI of these analogs using the NCI-60 cell line screening revealed promising results when compared to paclitaxel. The result of in vivo hollow fiber and animal toxicity assays are presented. ..
  10. Tran T, Pham N, Fechner G, Zencak D, Vu H, Hooper J, et al. Cytotoxic cyclic depsipeptides from the Australian marine sponge Neamphius huxleyi. J Nat Prod. 2012;75:2200-8 pubmed publisher
    Three new cyclic depsipeptides, neamphamides B (2), C (3), and D (4), were isolated from the Australian sponge Neamphius huxleyi...
  11. Thornburg C, Cowley E, Sikorska J, Shaala L, Ishmael J, Youssef D, et al. Apratoxin H and apratoxin A sulfoxide from the Red Sea cyanobacterium Moorea producens. J Nat Prod. 2013;76:1781-8 pubmed publisher
  12. Prince H, Dickinson M. Romidepsin for cutaneous T-cell lymphoma. Clin Cancer Res. 2012;18:3509-15 pubmed publisher
    ..Romidepsin provides a subset of patients with an opportunity for prolonged clinical responses with a tolerable side effect profile. ..
  13. Meng X, Xu X, Hu J, Jin F, Hu Q, Sun Q, et al. Toxicity and differential protein analysis following destruxin A treatment of Spodoptera litura (Lepidoptera: Noctuidae) SL-1 cells. Toxicon. 2011;58:327-35 pubmed publisher
  14. Suárez Jiménez G, Burgos Hernandez A, Ezquerra Brauer J. Bioactive peptides and depsipeptides with anticancer potential: sources from marine animals. Mar Drugs. 2012;10:963-86 pubmed publisher
    ..This review focuses on the latest studies and critical research in this field, and evidences the immense potential of marine animals as bioactive peptide sources. ..
  15. Stepień Ł, Gromadzka K, Chełkowski J. Polymorphism of mycotoxin biosynthetic genes among Fusarium equiseti isolates from Italy and Poland. J Appl Genet. 2012;53:227-36 pubmed publisher
    ..The analysis of the mycotoxin biosynthetic gene sequences can be used to differentiate the studied genotypes even more precisely than the analysis of the non-coding regions (like tef-1?). ..
  16. Kanno S, Maeda N, Tomizawa A, Yomogida S, Katoh T, Ishikawa M. Involvement of p21waf1/cip1 expression in the cytotoxicity of the potent histone deacetylase inhibitor spiruchostatin B towards susceptible NALM-6 human B cell leukemia cells. Int J Oncol. 2012;40:1391-6 pubmed publisher
    ..Our findings may be useful when establishing a therapeutic strategy based on SP-B. ..
  17. Gammelsrud A, Solhaug A, Dendelé B, Sandberg W, Ivanova L, Kocbach Bølling A, et al. Enniatin B-induced cell death and inflammatory responses in RAW 267.4 murine macrophages. Toxicol Appl Pharmacol. 2012;261:74-87 pubmed publisher
    ..Caspase-1 appeared to be involved in the apoptosis and release of IL-1? and possibly activation of the inflammasome through lysosomal damage and leakage of cathepsin B. ..
  18. Stępień L, Waśkiewicz A. Sequence divergence of the enniatin synthase gene in relation to production of beauvericin and enniatins in Fusarium species. Toxins (Basel). 2013;5:537-55 pubmed publisher
    ..The phylogenetic analysis based on the partial sequence of the esyn1 gene clearly discriminates species producing exclusively BEA from those synthesizing mainly enniatin analogues. ..
  19. Morande P, Zanetti S, Borge M, Nannini P, Jancic C, Bezares R, et al. The cytotoxic activity of Aplidin in chronic lymphocytic leukemia (CLL) is mediated by a direct effect on leukemic cells and an indirect effect on monocyte-derived cells. Invest New Drugs. 2012;30:1830-40 pubmed publisher
  20. Han B, Gross H, McPhail K, Goeger D, Maier C, Gerwick W. Wewakamide A and guineamide G, cyclic depsipeptides from the marine cyanobacteria Lyngbya semiplena and Lyngbya majuscula. J Microbiol Biotechnol. 2011;21:930-6 pubmed
    Two new cyclic depsipeptides wewakamide A (1) and guineamide G (2) have been isolated from the marine cyanobacterium Lyngbya semiplena and Lyngbya majuscula, respectively, collected from Papua New Guinea...
  21. Lee J, Currano J, Carroll P, Joullie M. Didemnins, tamandarins and related natural products. Nat Prod Rep. 2012;29:404-24 pubmed publisher
    Since the discovery and isolation of the didemnin family of marine depsipeptides in 1981, the synthesis and biological activity of its congeners have been of great interest to the scientific community...
  22. Skillman K, Diraviyam K, Khan A, Tang K, Sept D, Sibley L. Evolutionarily divergent, unstable filamentous actin is essential for gliding motility in apicomplexan parasites. PLoS Pathog. 2011;7:e1002280 pubmed publisher
    ..These results identify the molecular basis for short, dynamic filaments in apicomplexan parasites and demonstrate that inherent instability of parasite actin filaments is a critical adaptation for gliding motility. ..
  23. Ruiz Sanchez E, Lange A, Orchard I. Effects of the mycotoxin destruxin A on Locusta migratoria visceral muscles. Toxicon. 2010;56:1043-51 pubmed publisher
  24. Nalda Molina R, Valenzuela B, Ramon Lopez A, Miguel Lillo B, Soto Matos A, Perez Ruixo J. Population pharmacokinetics meta-analysis of plitidepsin (Aplidin) in cancer subjects. Cancer Chemother Pharmacol. 2009;64:97-108 pubmed publisher
    ..The distribution to red blood cells can be considered linear at doses lower than 5 mg/m(2) administered as 3-h or longer infusion. No clinically relevant covariates were identified as predictors of plitidepsin pharmacokinetics. ..
  25. Fotie J, Morgan R. Depsipeptides from microorganisms: a new class of antimalarials. Mini Rev Med Chem. 2008;8:1088-94 pubmed
    b>Depsipeptides are a large group of natural products produced by fungi, actinomycetes, cyanobacteria, higher plants and marine organisms...
  26. Izquierdo M, Bowman A, Garcia M, Jodrell D, Martinez M, Pardo B, et al. Phase I clinical and pharmacokinetic study of plitidepsin as a 1-hour weekly intravenous infusion in patients with advanced solid tumors. Clin Cancer Res. 2008;14:3105-12 pubmed publisher
    ..2 +/- 219.3 L). The recommended dose for plitidepsin given as a weekly 1-hour schedule was 3.2 mg/m2/week. Muscular and liver toxicity were dose limiting at 3.6 mg/m2/week. Additional evaluation of this dose dense schedule is warranted. ..
  27. Schoffski P, Guillem V, Garcia M, Rivera F, Tabernero J, Cullell M, et al. Phase II randomized study of Plitidepsin (Aplidin), alone or in association with L-carnitine, in patients with unresectable advanced renal cell carcinoma. Mar Drugs. 2009;7:57-70 pubmed publisher
    ..Coadministration of L-carnitine did not prevent muscular toxicity or CPK-elevation associated with Plitidepsin. ..
  28. Zampella A, Sepe V, Luciano P, Bellotta F, Monti M, D Auria M, et al. Homophymine A, an anti-HIV cyclodepsipeptide from the sponge Homophymia sp. J Org Chem. 2008;73:5319-27 pubmed publisher
    ..In a cell-based XTT assay, homophymine A exhibited cytoprotective activity against HIV-1 infection with a IC50 of 75 nM. ..
  29. Tang H, Yuen K, Tang H, Fung M. Reversibility of apoptosis in cancer cells. Br J Cancer. 2009;100:118-22 pubmed publisher
    ..Our findings show that cancer cells can survive after initiation of apoptosis, thereby revealing an unexpected potential escape mechanism of cancer cells from chemotherapy. ..
  30. Schmauder A, Sibley L, Maier M. Total synthesis and configurational assignment of chondramide A. Chemistry. 2010;16:4328-36 pubmed publisher
    ..This synthesis should allow for the preparation of various analogues. ..
  31. Matthew S, Schupp P, Luesch H. Apratoxin E, a cytotoxic peptolide from a guamanian collection of the marine cyanobacterium Lyngbya bouillonii. J Nat Prod. 2008;71:1113-6 pubmed publisher
    ..The 5- to 15-fold reduced activity compared with apratoxin A (2) is attributed to the dehydration in the long-chain polyketide unit, which could affect the conformation of the molecule. ..
  32. Jiménez J, López Macià A, Gracia C, Varón S, Carrascal M, Caba J, et al. Structure-activity relationship of kahalalide F synthetic analogues. J Med Chem. 2008;51:4920-31 pubmed publisher
    ..The N-terminal aliphatic acid appears to be a hydrophobic buoy in a membrane-like environment. Moreover, significant improvement of the in vitro activity was achieved. ..
  33. Crabb S, Howell M, Rogers H, Ishfaq M, Yurek George A, Carey K, et al. Characterisation of the in vitro activity of the depsipeptide histone deacetylase inhibitor spiruchostatin A. Biochem Pharmacol. 2008;76:463-75 pubmed publisher
    ..Our results demonstrate that spiruchostatin A is a potent inhibitor of class I HDACs and anti-cancer agent. Differences in the kinetics of action of HDI may be important for the clinical application of these compounds. ..
  34. Suenaga K, Kajiwara S, Kuribayashi S, Handa T, Kigoshi H. Synthesis and cytotoxicity of aurilide analogs. Bioorg Med Chem Lett. 2008;18:3902-5 pubmed publisher
    ..The artificial analogs of aurilide (1), a potent cytotoxic cyclodepsipeptide of marine origin, were synthesized, and the structure-activity relationships were investigated. ..
  35. Sørensen J, Phipps R, Nielsen K, Schroers H, Frank J, Thrane U. Analysis of Fusarium avenaceum metabolites produced during wet apple core rot. J Agric Food Chem. 2009;57:1632-9 pubmed publisher
    ..During wet apple core rot, F. avenaceum produced high amounts of mycotoxins, which may pose a risk for consumers of apple or processed apple products. ..
  36. Mevers E, Liu W, Engene N, Mohimani H, Byrum T, Pevzner P, et al. Cytotoxic veraguamides, alkynyl bromide-containing cyclic depsipeptides from the marine cyanobacterium cf. Oscillatoria margaritifera. J Nat Prod. 2011;74:928-36 pubmed publisher
    ..Veraguamide A showed potent cytotoxicity to the H-460 human lung cancer cell line (LD50=141 nM). ..
  37. Lazarus M, Schneider T, Taraschi T. A new model for hemoglobin ingestion and transport by the human malaria parasite Plasmodium falciparum. J Cell Sci. 2008;121:1937-49 pubmed publisher
    ..Evidence is provided for a new model, in which hemoglobin transport to the FV occurs by a vesicle-independent process. ..
  38. Baudin E, Droz J, Paz Ares L, Van Oosterom A, Cullell Young M, Schlumberger M. Phase II study of plitidepsin 3-hour infusion every 2 weeks in patients with unresectable advanced medullary thyroid carcinoma. Am J Clin Oncol. 2010;33:83-8 pubmed publisher
    ..Single-agent plitidepsin given as 3-hour i.v. infusions every 2 weeks was generally well tolerated but showed limited clinical activity in patients with unresectable advanced MTC. ..
  39. Lang G, Kalvelage T, Peters A, Wiese J, Imhoff J. Linear and cyclic peptides from the entomopathogenic bacterium Xenorhabdus nematophilus. J Nat Prod. 2008;71:1074-7 pubmed publisher
    ..Xenematide and xenocoumacin II showed moderate antibacterial activities. Xenocoumacin II, nematophin, and the two xenortides were active in the Artemia salina assay, and xenematide acted weakly insecticidal...
  40. Lázaro Diéguez F, Aguado C, Mato E, Sanchez Ruiz Y, Esteban I, Alberch J, et al. Dynamics of an F-actin aggresome generated by the actin-stabilizing toxin jasplakinolide. J Cell Sci. 2008;121:1415-25 pubmed publisher
  41. Hu Q, An X, Jin F, Freed S, Ren S. Toxicities of destruxins against Bemisia tabaci and its natural enemy, Serangium japonicum. Toxicon. 2009;53:115-21 pubmed publisher
    ..Generally, the toxicity decreased about 50% from 1st to 3rd-5th day of post-treatment. Specially, the residual toxicity at 50mg/L and the 7th day post-treatment was down to a value not differing significantly from the control. ..
  42. Gunasekera S, Ritson Williams R, Paul V. Carriebowmide, a new cyclodepsipeptide from the marine cyanobacterium Lyngbya polychroa. J Nat Prod. 2008;71:2060-3 pubmed publisher
    ..The stereochemistry of the beta-aminoacid moiety, 3-amino-2-methylhexanoic acid, was established by Marfey analysis of the acid hydrolysate. ..
  43. Ying Y, Taori K, Kim H, Hong J, Luesch H. Total synthesis and molecular target of largazole, a histone deacetylase inhibitor. J Am Chem Soc. 2008;130:8455-9 pubmed publisher
    ..In addition, structure-activity relationship (SAR) studies revealed that the thiol group is the pharmacophore of the natural product. Largazole's HDAC inhibitory activity correlates with its antiproliferative activity. ..
  44. Ling Y, Aracil M, Jimeno J, Perez Soler R, Zou Y. Molecular pharmacodynamics of PM02734 (elisidepsin) as single agent and in combination with erlotinib; synergistic activity in human non-small cell lung cancer cell lines and xenograft models. Eur J Cancer. 2009;45:1855-64 pubmed publisher
    ..These results have provided a rational basis for an ongoing clinical trial to explore this combination in patients with advanced malignant solid tumours. ..
  45. Li W, Gan J, Ma D. A concise route to the proposed structure of lydiamycin B, an antimycobacterial depsipeptide. Org Lett. 2009;11:5694-7 pubmed publisher
    ..None of them shows identical NMR data with those reported for natural lydiamycin B, indicating that further structural revisions are required. ..
  46. Heemstra J, Walsh C. Tandem action of the O2- and FADH2-dependent halogenases KtzQ and KtzR produce 6,7-dichlorotryptophan for kutzneride assembly. J Am Chem Soc. 2008;130:14024-5 pubmed publisher
    ..These findings provide further insights into the enzymatic logic of carbon-chloride bond formation during the biosynthesis of halogenated secondary metabolites. ..
  47. Tripathi A, Puddick J, Prinsep M, Lee P, Tan L. Hantupeptin A, a cytotoxic cyclic depsipeptide from a Singapore collection of Lyngbya majuscula. J Nat Prod. 2009;72:29-32 pubmed publisher
    ..Hantupeptin A showed cytotoxicity to MOLT-4 leukemia cells and MCF-7 breast cancer cells with IC(50) values of 32 and 4.0 microM, respectively. ..
  48. Bowers A, West N, Newkirk T, Troutman Youngman A, Schreiber S, Wiest O, et al. Synthesis and histone deacetylase inhibitory activity of largazole analogs: alteration of the zinc-binding domain and macrocyclic scaffold. Org Lett. 2009;11:1301-4 pubmed publisher
    ..Olefin cross-metathesis was used to efficiently access six variants of the side-chain zinc-binding domain, while adaptation of our previously reported modular synthesis allowed probing of the macrocyclic cap group. ..
  49. Prince H, Bishton M, Harrison S. Clinical studies of histone deacetylase inhibitors. Clin Cancer Res. 2009;15:3958-69 pubmed publisher
    ..The use of the biomarker of histone hyperacetylation has been useful as a guide to target specificity, but generally does not predict for response and the search for more clinically relevant biomarkers must continue. ..
  50. Kiuchi T, Nagai T, Ohashi K, Mizuno K. Measurements of spatiotemporal changes in G-actin concentration reveal its effect on stimulus-induced actin assembly and lamellipodium extension. J Cell Biol. 2011;193:365-80 pubmed publisher
  51. Wilson C, Tsuchida M, Allen G, Barnhart E, Applegate K, Yam P, et al. Myosin II contributes to cell-scale actin network treadmilling through network disassembly. Nature. 2010;465:373-7 pubmed publisher
  52. Tripathi A, Puddick J, Prinsep M, Lee P, Tan L. Hantupeptins B and C, cytotoxic cyclodepsipeptides from the marine cyanobacterium Lyngbya majuscula. Phytochemistry. 2010;71:307-11 pubmed publisher
    ..Compounds 2 and 3 are cyclic depsipeptides consisting of five alpha-amino/hydroxy acid residues, including phenyllactic acid, proline, N-methyl-valine, ..