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Chemical Compound Review

LAT-B     (4S)-4- [(1R,4S,5Z,9Z,13R,15R)-15- hydroxy-4...

Synonyms: latrunculin B, Lat B, CHEMBL411879, BSPBio_001189, CHEBI:49703, ...
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Disease relevance of NSC 339663

  • Treatment with either latrunculin B (an inhibitor for actin polymerization) or Clostridium difficile toxin B (a general Rho family inhibitor) resulted in a relatively slower disappearance of coated F-actin from these vacuoles, but the vacuoles themselves remained unaffected [1].
  • Latrunculin B-induced plant dwarfism: Plant cell elongation is F-actin-dependent [2].
  • On the other hand, virion production was enhanced when EIAV-infected cells were incubated briefly (2 h) with the actin-depolymerizing drugs cytochalasin D and latrunculin B [3].
  • Leptin-induced hypertrophy was also attenuated by disruption of actin filaments with 50 nmol/L latrunculin B [4].
  • This comparison showed that the transient effects of latrunculin B were fully reversible for the NIL8 cells and not for the mouse neuroblastoma N1E-115 cells [5].

High impact information on NSC 339663

  • Induction of TCR internalization is also augmented by intersectin 2 and severely impaired by latrunculin B treatment [6].
  • The actin-depolymerizing agent latrunculin B abrogated the hyperosmolar barrier enhancement as well as the actin filament formation, suggesting a role for actin in the barrier response [7].
  • Clathrin-coated pits invaginating from the plasma membrane show definite, but highly limited, mobility within the membrane that is relaxed upon treatment with latrunculin B, an inhibitor of actin assembly, indicating that an actin-based framework may be involved in the mobility of these pits [8].
  • Importantly, latrunculin B and jasplakinolide were both found to activate SIMK in a root-derived cell culture [9].
  • Actin depolymerization by latrunculin B resulted in SIMK relocation to the nucleus [9].

Biological context of NSC 339663

  • Constitutive overexpression of ROP2 results in enhanced polar accumulation of PIN2 protein in the root elongation region and increased gravitropism, which is significantly affected by latrunculin B, an inhibitor of F-actin assembly [10].
  • These phenotypes were suppressed by depolymerizing actin with low concentrations of latrunculin B, suggesting that a critical site of action of Pet PLC1 is in regulating actin structure at the growing tip [11].
  • This study demonstrated that pretreating human platelets with inhibitors of actin polymerization, cytochalasin D or latrunculin B, dramatically enhances platelet aggregation induced by vWf [12].
  • In the present study, we demonstrate that agents that depolymerize (latrunculin B and cytochalasin D) or stabilize (jasplakinolide) the actin cytoskeleton blocked agonist-induced endocytosis of the beta isoform of the thromboxane A(2) receptor (TPbeta) in HEK293 cells [13].
  • Latrunculin B did not affect insulin-induced Tyr phosphorylation of IR or its ability to phosphorylate its substrates; still, a 30-50% reduction in the rate of IR internalization was observed in cells treated with latrunculin B [14].

Anatomical context of NSC 339663


Associations of NSC 339663 with other chemical compounds

  • Glucose stimulation transiently decreased the amount of actin coimmunoprecipitated with Syntaxin 1 and SNAP-25, and latrunculin B treatment fully ablated the coimmunoprecipitation [20].
  • Notably, expression of GFP h1 CaP, but not GFP h2 CaP, conferred increased resistance of the actin cytoskeleton to the actin polymerization antagonists cytochalasin B and latrunculin B, as well as to the protein kinase inhibitors H7-dihydrochloride and rho-kinase inhibitor Y-27632 [21].
  • The title compound, 16-epi-latrunculin B (3), has been isolated from the sponge Negombata magnifica collected from the Red Sea near Hurghada, Egypt. This new natural product was determined to be an epimer of latrunculin B (1), which was found in the same sponge collection [22].
  • METHODS: Freshly enucleated porcine eyes were perfused using the constant-pressure method at 15 mm Hg and 25 degrees C. Human trabecular meshwork (HTM) cells and Schlemm's canal (SC) cells were grown in culture, treated with BDM, H-7, and latrunculin B, and then fixed, stained for beta-tubulin and filamentous actin, and observed by epifluorescence [23].
  • Motility by C. parvum sporozoites was prevented by latrunculin B and cytochalasin D, drugs that depolymerize the parasite actin cytoskeleton, and by the myosin inhibitor 2,3-butanedione monoxime [24].

Gene context of NSC 339663

  • A novel GCS1 disruption strain (gcs1Delta) exhibited morphological defects, as well as mislocalization of cortical actin patches. gcs1Delta was hypersensitive to the actin monomer-sequestering drug, latrunculin-B [25].
  • The activation of the distal downstream effector ERK1/2 was demonstrated to be sensitive to the disrupters of cytoskeletal rearrangement, cytochalasin D and latrunculin B [26].
  • Cells treated with latrunculin B or swinholide A, which caused a progressive depolymerization of actin filaments, showed a reduction or elimination of IL-1-induced ERK activation, respectively [27].
  • Likewise, direct disintegration of the actin cytoskeleton by latrunculin B interfered with nocodazole-mediated up-regulation of CTGF expression [28].
  • Reciprocally, we found that clb5 mutant is hypersensitive to SDS, CFW, latrunculin B, or zymolyase, which suggests that, like the PKC pathway and Swi4, Clb5 is related to cell integrity [29].

Analytical, diagnostic and therapeutic context of NSC 339663


  1. Phosphatidylinositol 4,5-bisphosphate regulates adipocyte actin dynamics and GLUT4 vesicle recycling. Kanzaki, M., Furukawa, M., Raab, W., Pessin, J.E. J. Biol. Chem. (2004) [Pubmed]
  2. Latrunculin B-induced plant dwarfism: Plant cell elongation is F-actin-dependent. Baluska, F., Jasik, J., Edelmann, H.G., Salajová, T., Volkmann, D. Dev. Biol. (2001) [Pubmed]
  3. Differential effects of actin cytoskeleton dynamics on equine infectious anemia virus particle production. Chen, C., Weisz, O.A., Stolz, D.B., Watkins, S.C., Montelaro, R.C. J. Virol. (2004) [Pubmed]
  4. Essential role of Rho/ROCK-dependent processes and actin dynamics in mediating leptin-induced hypertrophy in rat neonatal ventricular myocytes. Zeidan, A., Javadov, S., Karmazyn, M. Cardiovasc. Res. (2006) [Pubmed]
  5. Latrunculins--novel marine macrolides that disrupt microfilament organization and affect cell growth: I. Comparison with cytochalasin D. Spector, I., Shochet, N.R., Blasberger, D., Kashman, Y. Cell Motil. Cytoskeleton (1989) [Pubmed]
  6. The intersectin 2 adaptor links Wiskott Aldrich Syndrome protein (WASp)-mediated actin polymerization to T cell antigen receptor endocytosis. McGavin, M.K., Badour, K., Hardy, L.A., Kubiseski, T.J., Zhang, J., Siminovitch, K.A. J. Exp. Med. (2001) [Pubmed]
  7. Hyperosmolarity enhances the lung capillary barrier. Safdar, Z., Wang, P., Ichimura, H., Issekutz, A.C., Quadri, S., Bhattacharya, J. J. Clin. Invest. (2003) [Pubmed]
  8. Spatial control of coated-pit dynamics in living cells. Gaidarov, I., Santini, F., Warren, R.A., Keen, J.H. Nat. Cell Biol. (1999) [Pubmed]
  9. Involvement of the mitogen-activated protein kinase SIMK in regulation of root hair tip growth. Samaj, J., Ovecka, M., Hlavacka, A., Lecourieux, F., Meskiene, I., Lichtscheidl, I., Lenart, P., Salaj, J., Volkmann, D., Bögre, L., Baluska, F., Hirt, H. EMBO J. (2002) [Pubmed]
  10. Brassinosteroids stimulate plant tropisms through modulation of polar auxin transport in Brassica and Arabidopsis. Li, L., Xu, J., Xu, Z.H., Xue, H.W. Plant Cell (2005) [Pubmed]
  11. Petunia phospholipase c1 is involved in pollen tube growth. Dowd, P.E., Coursol, S., Skirpan, A.L., Kao, T.H., Gilroy, S. Plant Cell (2006) [Pubmed]
  12. Cytoskeletal regulation of the platelet glycoprotein Ib/V/IX-von willebrand factor interaction. Mistry, N., Cranmer, S.L., Yuan, Y., Mangin, P., Dopheide, S.M., Harper, I., Giuliano, S., Dunstan, D.E., Lanza, F., Salem, H.H., Jackson, S.P. Blood (2000) [Pubmed]
  13. Involvement of actin in agonist-induced endocytosis of the G protein-coupled receptor for thromboxane A2: overcoming of actin disruption by arrestin-3 but not arrestin-2. Laroche, G., Rochdi, M.D., Laporte, S.A., Parent, J.L. J. Biol. Chem. (2005) [Pubmed]
  14. Extracellular matrix proteins modulate endocytosis of the insulin receptor. Boura-Halfon, S., Voliovitch, H., Feinstein, R., Paz, K., Zick, Y. J. Biol. Chem. (2003) [Pubmed]
  15. Subcellular distribution of envoplakin and periplakin: insights into their role as precursors of the epidermal cornified envelope. DiColandrea, T., Karashima, T., Määttä, A., Watt, F.M. J. Cell Biol. (2000) [Pubmed]
  16. Tobacco WLIM1 Is a Novel F-Actin Binding Protein Involved in Actin Cytoskeleton Remodeling. Thomas, C., Hoffmann, C., Dieterle, M., Van Troys, M., Ampe, C., Steinmetz, A. Plant Cell (2006) [Pubmed]
  17. Actin-related protein2/3 complex component ARPC1 is required for proper cell morphogenesis and polarized cell growth in Physcomitrella patens. Harries, P.A., Pan, A., Quatrano, R.S. Plant Cell (2005) [Pubmed]
  18. The Arabidopsis Rab GTPase RabA4b localizes to the tips of growing root hair cells. Preuss, M.L., Serna, J., Falbel, T.G., Bednarek, S.Y., Nielsen, E. Plant Cell (2004) [Pubmed]
  19. Interleukin-3-mediated cell survival signals include phosphatidylinositol 3-kinase-dependent translocation of the glucose transporter GLUT1 to the cell surface. Bentley, J., Itchayanan, D., Barnes, K., McIntosh, E., Tang, X., Downes, C.P., Holman, G.D., Whetton, A.D., Owen-Lynch, P.J., Baldwin, S.A. J. Biol. Chem. (2003) [Pubmed]
  20. Glucose-stimulated insulin secretion is coupled to the interaction of actin with the t-SNARE (target membrane soluble N-ethylmaleimide-sensitive factor attachment protein receptor protein) complex. Thurmond, D.C., Gonelle-Gispert, C., Furukawa, M., Halban, P.A., Pessin, J.E. Mol. Endocrinol. (2003) [Pubmed]
  21. Live dynamics of GFP-calponin: isoform-specific modulation of the actin cytoskeleton and autoregulation by C-terminal sequences. Danninger, C., Gimona, M. J. Cell. Sci. (2000) [Pubmed]
  22. Toward computing relative configurations: 16-epi-latrunculin B, a new stereoisomer of the actin polymerization inhibitor latrunculin B. Hoye, T.R., Ayyad, S.E., Eklov, B.M., Hashish, N.E., Shier, W.T., El-Sayed, K.A., Hamann, M.T. J. Am. Chem. Soc. (2002) [Pubmed]
  23. Acto-myosin drug effects and aqueous outflow function. Epstein, D.L., Rowlette, L.L., Roberts, B.C. Invest. Ophthalmol. Vis. Sci. (1999) [Pubmed]
  24. Gliding motility leads to active cellular invasion by Cryptosporidium parvum sporozoites. Wetzel, D.M., Schmidt, J., Kuhlenschmidt, M.S., Dubey, J.P., Sibley, L.D. Infect. Immun. (2005) [Pubmed]
  25. GCS1, an Arf guanosine triphosphatase-activating protein in Saccharomyces cerevisiae, is required for normal actin cytoskeletal organization in vivo and stimulates actin polymerization in vitro. Blader, I.J., Cope, M.J., Jackson, T.R., Profit, A.A., Greenwood, A.F., Drubin, D.G., Prestwich, G.D., Theibert, A.B. Mol. Biol. Cell (1999) [Pubmed]
  26. Cytoskeletal reorganization dependence of signaling by the gonadotropin-releasing hormone receptor. Davidson, L., Pawson, A.J., Millar, R.P., Maudsley, S. J. Biol. Chem. (2004) [Pubmed]
  27. The recruitment of the interleukin-1 (IL-1) receptor-associated kinase (IRAK) into focal adhesion complexes is required for IL-1beta -induced ERK activation. MacGillivray, M.K., Cruz, T.F., McCulloch, C.A. J. Biol. Chem. (2000) [Pubmed]
  28. Modulation of the expression of connective tissue growth factor by alterations of the cytoskeleton. Ott, C., Iwanciw, D., Graness, A., Giehl, K., Goppelt-Struebe, M. J. Biol. Chem. (2003) [Pubmed]
  29. Functional connection between the Clb5 cyclin, the protein kinase C pathway and the Swi4 transcription factor in Saccharomyces cerevisiae. Queralt, E., Igual, J.C. Genetics (2005) [Pubmed]
  30. Inositol (1,4,5)-trisphosphate receptor links to filamentous actin are important for generating local Ca2+ signals in pancreatic acinar cells. Turvey, M.R., Fogarty, K.E., Thorn, P. J. Cell. Sci. (2005) [Pubmed]
  31. Effects of latrunculin-B on outflow facility and trabecular meshwork structure in human eyes. Ethier, C.R., Read, A.T., Chan, D.W. Invest. Ophthalmol. Vis. Sci. (2006) [Pubmed]
  32. Stimulation of regulatory volume decrease (RVD) by isolated bovine articular chondrocytes following F-actin disruption using latrunculin B. Kerrigan, M.J., Hall, A.C. Biorheology. (2005) [Pubmed]
  33. Quantitative determination of latrunculins A and B in the Red Sea sponge Negombata magnifica by high performance liquid chromatography. Khalifa, S., Ahmed, S., Mesbah, M., Youssef, D., Hamann, M. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. (2006) [Pubmed]
  34. Hypersensitivity to cytoskeletal antagonists demonstrates microtubule-microfilament cross-talk in the control of root elongation in Arabidopsis thaliana. Collings, D.A., Lill, A.W., Himmelspach, R., Wasteneys, G.O. New Phytol. (2006) [Pubmed]
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