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Journal articles on the topic 'Squalestatin'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Lebe, Karen E., and Russell J. Cox. "Oxidative steps during the biosynthesis of squalestatin S1." Chemical Science 10, no. 4 (2019): 1227–31. http://dx.doi.org/10.1039/c8sc02615g.

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Two enzymes of previously unknown function encoded by the squalestatin biosynthetic gene cluster from the fungus Phoma MF5453 catalyse a remarkable series of six consecutive oxidations to form the 4,8-dioxa-bicyclo[3.2.1]octane core of the squalestatins.

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2

Bonsch, B., V. Belt, C. Bartel, N. Duensing, M. Koziol, C. M. Lazarus, A. M. Bailey, T. J. Simpson, and R. J. Cox. "Identification of genes encoding squalestatin S1 biosynthesis and in vitro production of new squalestatin analogues." Chemical Communications 52, no. 41 (2016): 6777–80. http://dx.doi.org/10.1039/c6cc02130a.

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3

Roberts, Douglas M., Christoph Bartel, Alan Scott, David Ivison, Thomas J. Simpson, and Russell J. Cox. "Substrate selectivity of an isolated enoyl reductase catalytic domain from an iterative highly reducing fungal polyketide synthase reveals key components of programming." Chemical Science 8, no. 2 (2017): 1116–26. http://dx.doi.org/10.1039/c6sc03496a.

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4

Gabriel, Heloisa B., Marcia F. Silva, Emília A. Kimura, Gerhard Wunderlich, Alejandro M. Katzin, and Mauro F. Azevedo. "Squalestatin Is an Inhibitor of Carotenoid Biosynthesis in Plasmodium falciparum." Antimicrobial Agents and Chemotherapy 59, no. 6 (March 16, 2015): 3180–88. http://dx.doi.org/10.1128/aac.04500-14.

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ABSTRACTThe increasing resistance of malaria parasites to almost all available drugs calls for the characterization of novel targets and the identification of new compounds. Carotenoids are polyisoprenoids from plants, algae, and some bacteria, and they are biosynthesized byPlasmodium falciparumbut not by mammalian cells. Biochemical and reverse genetics approaches were applied to demonstrate that phytoene synthase (PSY) is a key enzyme for carotenoid biosynthesis inP. falciparumand is essential for intraerythrocytic growth. The known PSY inhibitor squalestatin reduces biosynthesis of phytoene and kills parasites during the intraerythrocytic cycle. PSY-overexpressing parasites showed increased biosynthesis of phytoene and its derived product phytofluene and presented a squalestatin-resistant phenotype, suggesting that this enzyme is the primary target of action of this drug in the parasite.

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5

Nicolaou, Kyriacos Costa, Alan Nadin, James E. Leresche, Eddy W. Yue, and Susan La Greca. "Totalsynthese von Saragossasäure A/Squalestatin S1." Angewandte Chemie 106, no. 21 (November 3, 1994): 2312–13. http://dx.doi.org/10.1002/ange.19941062129.

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6

Abdel-Rahman, Hesham, Joseph P. Adams, Alastair L. Boyes, Mike J. Kelly, Darren J. Mansfield, Panayiotis A. Procopiou, Stanley M. Roberts, Deborah H. Slee, and Nigel S. Watson. "A synthetic approach to squalestatin 1." Journal of the Chemical Society, Chemical Communications, no. 24 (1993): 1839. http://dx.doi.org/10.1039/c39930001839.

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7

Nicolaou, K. C., Eddy W. Yue, Susan la Greca, Alan Nadin, Zhen Yang, James E. Leresche, Tatsuo Tsuri, Yoshimitsu Naniwa, and Francesco de Riccardis. "Synthesis of Zaragozic Acid A/Squalestatin S1." Chemistry - A European Journal 1, no. 7 (October 1995): 467–94. http://dx.doi.org/10.1002/chem.19950010712.

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8

da Silva, Marcia F., Alexandre Y. Saito, Valnice J. Peres, Antonio C. Oliveira, and Alejandro M. Katzin. "In VitroAntimalarial Activity of Different Inhibitors of the Plasmodial Isoprenoid Synthesis Pathway." Antimicrobial Agents and Chemotherapy 59, no. 8 (June 8, 2015): 5084–87. http://dx.doi.org/10.1128/aac.04161-14.

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ABSTRACTPrevious studies have shown that fosmidomycin, risedronate, and nerolidol exert antimalarial activityin vitro. We included squalestatin, an inhibitor of the isoprenoid metabolism inErwinia uredovora, and found that combinations of compounds which act on different targets of the plasmodial isoprenoid pathway possess important supra-additivity effects.

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9

Hodgson, David M., and Hasanain A. A. Almohseni. "Evolution of a Cycloaddition–Rearrangement Approach to the Squalestatins: A Quarter-Century Odyssey." Synlett 31, no. 16 (June 4, 2020): 1555–72. http://dx.doi.org/10.1055/s-0040-1707127.

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The highs, lows, and diversions of a journey leading to two syntheses of 6,7-dideoxysqualestatin H5 is described. Both syntheses relied on highly diastereoselective n-alkylations of a tartrate acetonide enolate and subsequent oxidation–hydrolysis to provide an asymmetric entry to β-hydroxy-α-ketoester motifs. The latter were differentially elaborated to diazoketones which underwent stereo- and regioselective Rh(II)-catalysed cyclic carbonyl ylide formation–cycloaddition and then acid-catalysed transketalisation to generate the 2,8-dioxabicyclo[3.2.1]octane core of the squalestatins/zaragozic acids at the correct tricarboxylate oxidation level. The unsaturated side chain was either protected with a bromide substituent during the transketalisation or introduced afterwards by a stereoretentive Ni-catalyzed Csp3–Csp2 cross-electrophile coupling.1 Introduction 2 Racemic Model Studies to the Squalestatin/Zaragozic Acid Core3 Asymmetric Model Studies to a Keto α-Diazoester3.1 Dialkyl Squarate Desymmetrisation3.2 Tartrate Alkylation3.2.1 Further Studies on Seebach’s Alkylation Chemistry 4 Failure at the Penultimate Step to DDSQ 5 Second-Generation Approach to DDSQ: A Bromide Substituent Strategy 5.1 Stereoselective Routes to E-Alkenyl Halides via β-Oxido Phosphonium Ylides 5.2 Back to DDSQ Synthesis6 An Alternative Strategy to DDSQ: By Cross-Electrophile Coupling7 Alkene Ozonolysis in the Presence of Diazo Functionality: Accessing α-Ketoester Intermediates8 Summary

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10

Nicolaou, Kyriacos C., Alan Nadin, James E. Leresche, Eddy W. Yue, and Susan La Greca. "Total Synthesis of Zaragozic Acid A/Squalestatin S1." Angewandte Chemie International Edition in English 33, no. 21 (November 17, 1994): 2190–91. http://dx.doi.org/10.1002/anie.199421901.

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11

ABDEL-RAHMAN, H., J. P. ADAMS, A. L. BOYES, M. J. KELLY, D. J. MANSFIELD, P. A. PROCOPIOU, S. M. ROBERTS, D. H. SLEE, and N. S. WATSON. "ChemInform Abstract: A Synthetic Approach to Squalestatin 1." ChemInform 25, no. 20 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199420254.

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12

Nicolaou, Kyriacos Costa, Eddy W. Yue, Yoshimitsu Naniwa, Francesco De Riccardis, Alan Nadin, James E. Leresche, Susan La Greca, and Zhen Yang. "Saragossasäure A/Squalestatin S1: synthetische und retrosynthetische Untersuchungen." Angewandte Chemie 106, no. 21 (November 3, 1994): 2306–9. http://dx.doi.org/10.1002/ange.19941062127.

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13

HASUMI, KEIJI, KIYOSHI TACHIKAWA, KAORU SAKAI, SHIGEO MURAKAWA, NOBUJI YOSHIKAWA, SHIGENORI KUMAZAWA, and AKIRA ENDO. "Competitive inhibition of squalene synthetase by squalestatin 1." Journal of Antibiotics 46, no. 4 (1993): 689–91. http://dx.doi.org/10.7164/antibiotics.46.689.

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14

CANNELL, RICHARD J. P., MICHAEL J. DAWSON, RICHARD S. HALE, Richard M. HALL, DAVID NOBLE, SEAN LYNN, and NICHOLAS L. TAYLOR. "Production of additional squalestatin analogues by directed biosynthesis." Journal of Antibiotics 47, no. 2 (1994): 247–49. http://dx.doi.org/10.7164/antibiotics.47.247.

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15

Nicolaou, Kyriacos C., Eddy W. Yue, Yoshimitsu Naniwa, Francesco De Riccardis, Alan Nadin, James E. Leresche, Susan La Greca, and Zhen Yang. "Zaragozic Acid A/Squalestatin S1: Synthetic and Retrosynthetic Studies." Angewandte Chemie International Edition in English 33, no. 21 (November 17, 1994): 2184–87. http://dx.doi.org/10.1002/anie.199421841.

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16

NICOLAOU, K. C., E. W. YUE, S. LA GRECA, A. NADIN, Z. YANG, J. E. LERESCHE, T. TSURI, Y. NANIWA, and F. DE RICCARDIS. "ChemInform Abstract: Synthesis of Zaragozic Acid A/Squalestatin S1." ChemInform 27, no. 4 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199604214.

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17

Abdel-Rahman, Hesham, Joseph P. Adams, Alastair L. Boyes, Mike J. Kelly, Darren J. Mansfield, Panayiotis A. Procopiou, Stanley M. Roberts, et al. "Synthesis of the bicyclic core structure of squalestatin 1." Journal of the Chemical Society, Chemical Communications, no. 24 (1993): 1841. http://dx.doi.org/10.1039/c39930001841.

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18

Reid, Alison M., and Patrick G. Steel. "Squalestatin synthetic studies: tethered control in a bicycloketalisation step." Journal of the Chemical Society, Perkin Transactions 1, no. 17 (1998): 2795–802. http://dx.doi.org/10.1039/a804233k.

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19

Wilson, Rona, Clive Bate, Ronald Boshuizen, Alun Williams, and James Brewer. "Squalestatin alters the intracellular trafficking of a neurotoxic prion peptide." BMC Neuroscience 8, no. 1 (2007): 99. http://dx.doi.org/10.1186/1471-2202-8-99.

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20

NICOLAOU, K. C., A. NADIN, J. E. LERESCHE, E. W. YUE, and S. LA GRECA. "ChemInform Abstract: Total Synthesis of Zaragozic Acid A/Squalestatin S1." ChemInform 26, no. 17 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199517240.

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21

Bate, Clive, Mario Salmona, Luisa Diomede, and Alun Williams. "Squalestatin Cures Prion-infected Neurons and Protects Against Prion Neurotoxicity." Journal of Biological Chemistry 279, no. 15 (January 29, 2004): 14983–90. http://dx.doi.org/10.1074/jbc.m313061200.

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22

Crick, Dean C., Julie Suders, Catherine M. Kluthe, Douglas A. Andres, and Charles J. Waechter. "Selective Inhibition of Cholesterol Biosynthesis in Brain Cells by Squalestatin 1." Journal of Neurochemistry 65, no. 3 (November 23, 2002): 1365–73. http://dx.doi.org/10.1046/j.1471-4159.1995.65031365.x.

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23

ABDEL-RAHMAN, H., J. P. ADAMS, A. L. BOYES, M. J. KELLY, D. J. MANSFIELD, P. A. PROCOPIOU, S. M. ROBERTS, et al. "ChemInform Abstract: Synthesis of the Bicyclic Core Structure of Squalestatin 1." ChemInform 25, no. 20 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199420255.

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24

REID, A. M., and P. G. STEEL. "ChemInform Abstract: Squalestatin Synthetic Studies: Tethered Control in a Bicycloketalization Step." ChemInform 30, no. 3 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199903230.

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25

Shaw, Rupert E., Colin Burgess, Richard P. C. Cousins, Gerard M. P. Giblin, David G. H. Livermore, Anthony H. Shingler, Colin Smith, and Peter M. Youds. "Synthesis of novel monocyclic squalestatin analogues as potential inhibitors of squalene synthase." Bioorganic & Medicinal Chemistry Letters 4, no. 18 (September 1994): 2155–60. http://dx.doi.org/10.1016/s0960-894x(00)80062-1.

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26

Ito, Hisanaka, Miyoko Matsumoto, Takeshi Yoshizawa, Ken-ichi Takao, and Susumu Kobayashi. "Structurally simplified zaragozic acid (squalestatin): Stereoselective preparation of a 3,4-unsubstituted derivative." Tetrahedron Letters 38, no. 52 (December 1997): 9009–12. http://dx.doi.org/10.1016/s0040-4039(97)10407-5.

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27

Hartmann, M. A., L. Wentzinger, A. Hemmerlin, and T. J. Bach. "Metabolism of farnesyl diphosphate in tobacco BY-2 cells treated with squalestatin." Biochemical Society Transactions 28, no. 6 (December 1, 2000): 794–96. http://dx.doi.org/10.1042/bst0280794.

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Plant isoprenoids represent a large group of compounds with a wide range of physiological functions. In the cytosol, isoprenoids are synthesized via the classical acetate/mevalonate pathway. In this pathway, farnesyl diphosphate (FPP) occupies a central position, from which isoprene units are dispatched to the different classes of isoprenoids, with sterols as the major end products. The present work deals with effects of squalestatin (SQ) on the metabolism of FPP in proliferating and synchronized cultured tobacco cv. Bright Yellow-2 cells. SQ is a potent inhibitor of squalene synthase (SQS), the first committed enzyme in the sterol pathway. At nanomolar concentrations, SQ severely impaired cell growth and sterol biosynthesis, as attested by the rapid decrease in SQS activity. At the same time, it triggered a several-fold increase in both the enzymic activity and mRNA levels of 3-hydroxy-3-methylglutaryl CoA reductase. When SQ was added to cells synchronized by aphidicolin treatment, it was found to block the cell cycle at the end of G1 phase, but no cell death was induced. Tobacco cells were also fed exogenous tritiated trans-trans farnesol, the allylic alcohol derived from FPP, in the presence and absence of SQ. Evidence is presented that this compound was incorporated into sterols and ubiquinone Q10. In the presence of SQ, the sterol pathway was inhibited, but no increase in the radioactivity of ubiquinone was observed, suggesting that this metabolic channel was already saturated under normal conditions.

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28

NICOLAOU, K. C., E. W. YUE, Y. NANIWA, F. DE RICCARDIS, A. NADIN, J. E. LERESCHE, S. LA GRECA, and Z. YANG. "ChemInform Abstract: Zaragozic Acid A/Squalestatin S1(I): Synthetic and Retrosynthetic Studies." ChemInform 26, no. 17 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199517238.

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29

Bal, Wojciech, Alex F. Drake, Malgorzata Jezowska-Bojczuk, Henryk Kozlowski, Leslie D. Pettit, and Peter J. Sadler. "Unusually strong binding of Ca2+ ions by the novel antibiotic squalestatin-1." Journal of the Chemical Society, Chemical Communications, no. 5 (1994): 555. http://dx.doi.org/10.1039/c39940000555.

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30

Thelin, Anders, Elisabeth Peterson, Julie L. Hutson, Alun D. McCarthy, Johan Ericsson, and Gustav Dallner. "Effect of squalestatin 1 on the biosynthesis of the mevalonate pathway lipids." Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism 1215, no. 3 (December 1994): 245–49. http://dx.doi.org/10.1016/0005-2760(94)90049-3.

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31

Abdel-Rahman, Hesham, Joseph P. Adams, Alastair L. Boyes, Mike J. Kelly, R. Brian Lamont, Darren J. Mansfield, Panayiotis A. Procopiou, Stanley M. Roberts, Deborah H. Slee, and Nigel S. Watson. "Synthesis of a novel spirocyclic lactone in a potential route to squalestatin 1." Journal of the Chemical Society, Perkin Transactions 1, no. 10 (1994): 1259. http://dx.doi.org/10.1039/p19940001259.

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32

Caron, Stéphane, Doris Stoermer, Anna Kathryn Mapp, and Clayton H. Heathcock. "Total Synthesis of Zaragozic Acid A (Squalestatin S1). Synthesis of the Relay Compound." Journal of Organic Chemistry 61, no. 26 (January 1996): 9126–34. http://dx.doi.org/10.1021/jo961534e.

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33

Sintim, Herman O., Anne Valade, David C. Harling, and David M. Hodgson. "Squarate desymmetrisation–ozonolysis as an approach to β-substituted-α-ketosuccinates and squalestatin synthesis." Tetrahedron 75, no. 50 (December 2019): 130747. http://dx.doi.org/10.1016/j.tet.2019.130747.

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34

Bate, Clive, and Alun Williams. "Squalestatin protects neurons and reduces the activation of cytoplasmic phospholipase A2 by Aβ1–42." Neuropharmacology 53, no. 2 (August 2007): 222–31. http://dx.doi.org/10.1016/j.neuropharm.2007.05.003.

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35

Baxter, A., B. J. Fitzgerald, J. L. Hutson, A. D. McCarthy, J. M. Motteram, B. C. Ross, M. Sapra, M. A. Snowden, N. S. Watson, and R. J. Williams. "Squalestatin 1, a potent inhibitor of squalene synthase, which lowers serum cholesterol in vivo." Journal of Biological Chemistry 267, no. 17 (June 1992): 11705–8. http://dx.doi.org/10.1016/s0021-9258(19)49754-8.

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36

ITO, H., M. MATSUMOTO, T. YOSHIZAWA, K. TAKAO, and S. KOBAYASHI. "ChemInform Abstract: Structurally Simplified Zaragozic Acid (Squalestatin): Stereoselective Preparation of a 3,4-Unsubstituted Derivative." ChemInform 29, no. 15 (June 23, 2010): no. http://dx.doi.org/10.1002/chin.199815259.

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37

SHAW, R. E., C. BURGESS, R. P. C. COUSINS, G. M. P. GIBLIN, D. G. H. LIVERMORE, A. H. SHINGLER, C. SMITH, and P. M. YOUDS. "ChemInform Abstract: Synthesis of Novel Monocyclic Squalestatin Analogues as Potential Inhibitors of Squalene Synthase." ChemInform 26, no. 13 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199513286.

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38

Almohseni, Hasanain A. A., Younes Fegheh-Hassanpour, Tanzeel Arif, and David M. Hodgson. "Alkene Ozonolysis in the Presence of Diazo Functionality: Accessing an Intermediate for Squalestatin Synthesis." Synthesis 51, no. 22 (September 13, 2019): 4231–38. http://dx.doi.org/10.1055/s-0039-1690180.

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Studies on both the propensity for intramolecular cycloaddition between diazo and alkene functionality, and the tolerance of α-substituted α-diazoesters towards ozone in the presence of an alkene, led to chemoselective alkene ozonolysis of an ε-unsaturated-α-diazoester to give a key racemic diazoketone for the synthesis of 6,7-dideoxysqualestatin H5.

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39

Cox, Russell J., Frank Glod, Deirdre Hurley, Colin M. Lazarus, Thomas P. Nicholson, Brian A. M. Rudd, Thomas J. Simpson, Barrie Wilkinson, and Ying Zhang. "Rapid cloning and expression of a fungal polyketide synthase gene involved in squalestatin biosynthesis." Chemical Communications, no. 20 (2004): 2260. http://dx.doi.org/10.1039/b411973h.

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40

ABDEL-RAHMAN, H., J. P. ADAMS, A. L. BOYES, M. J. KELLY, R. B. LAMONT, D. J. MANSFIELD, P. A. PROCOPIOU, S. M. ROBERTS, D. H. SLEE, and N. S. WATSON. "ChemInform Abstract: Synthesis of a Novel Spirocyclic Lactone in a Potential Route to Squalestatin 1." ChemInform 25, no. 38 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199438259.

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41

Maezaki, Naoyoshi, Harrie J. M. Gijsen, Li-Qiang Sun, and Leo A. Paquette. "Evaluation of Furan Photooxygenation as a Device for Construction of the Zaragozic Acid (Squalestatin) Core." Journal of Organic Chemistry 61, no. 19 (January 1996): 6685–92. http://dx.doi.org/10.1021/jo960963+.

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42

Procopiou, Panayiotis A., Brian W. Dymock, Graham G. A. Inglis, Michael G. Lester, Andrew D. Roberts, Philip J. Sidebottom, Stephen J. Spooner, Anton R. P. Srikantha, and Nigel S. Watson. "Novel squalestatin derivatives arising from reactions at the allylic centre of the C1-side chain." Journal of the Chemical Society, Perkin Transactions 1, no. 2 (1998): 327–34. http://dx.doi.org/10.1039/a704363e.

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43

AMINI, Sayed-Asadollah, Leila SHABANI, Ladan AFGHANI, Zohreh JALALPOUR, and Majid SHARIFI-TEHRANI. "Squalestatin-induced production of taxol and baccatin in cell suspension culture of yew (Taxus baccata L.)." TURKISH JOURNAL OF BIOLOGY 38 (2014): 528–36. http://dx.doi.org/10.3906/biy-1401-47.

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44

CARON, S., D. STOERMER, A. K. MAPP, and C. H. HEATHCOCK. "ChemInform Abstract: Total Synthesis of Zaragozic Acid A (Squalestatin S1) (XIII). Synthesis of the Relay Compound (XII)." ChemInform 28, no. 18 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199718275.

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45

MAEZAKI, N., H. J. M. GIJSEN, L. Q. SUN, and L. A. PAQUETTE. "ChemInform Abstract: Evaluation of Furan Photooxygenation as a Device for Construction of the Zaragozic Acid (Squalestatin) Core." ChemInform 28, no. 5 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199705147.

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46

PROCOPIOU, P. A., B. W. DYMOCK, G. G. A. INGLIS, M. G. LESTER, A. D. ROBERTS, P. J. SIDEBOTTOM, S. J. SPOONER, A. R. P. SRIKANTHA, and N. S. WATSON. "ChemInform Abstract: Novel Squalestatin Derivatives Arising from Reactions at the Allylic Centre of the C1-Side Chain." ChemInform 29, no. 19 (June 22, 2010): no. http://dx.doi.org/10.1002/chin.199819193.

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47

Aldred, D., N. Magan, and B. S. Lane. "Influence of water activity and nutrients on growth and production of squalestatin S1 by a Phoma sp." Journal of Applied Microbiology 87, no. 6 (December 1999): 842–48. http://dx.doi.org/10.1046/j.1365-2672.1999.00931.x.

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48

Hartmann, Michael, Andrea Hemmerlin, Elisabet Gas-Pascual, Esther Gerber, Denis Tritsch, Michel Rohmer, and Thomas J. Bach. "The effect of MEP pathway and other inhibitors on the intracellular localization of a plasma membrane-targeted, isoprenylable GFP reporter protein in tobacco BY-2 cells." F1000Research 2 (August 12, 2013): 170. http://dx.doi.org/10.12688/f1000research.2-170.v1.

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We have established an in vivo visualization system for the geranylgeranylation of proteins in a stably transformed tobacco BY-2 cell line, based on the expression of a dexamethasone-inducible GFP fused to the carboxy-terminal basic domain of the rice calmodulin CaM61, which naturally bears a CaaL geranylgeranylation motif (GFP-BD-CVIL). By using pathway-specific inhibitors it was demonstrated that inhibition of the methylerythritol phosphate (MEP) pathway with known inhibitors like oxoclomazone and fosmidomycin, as well as inhibition of the protein geranylgeranyltransferase type 1 (PGGT-1), shifted the localization of the GFP-BD-CVIL protein from the membrane to the nucleus. In contrast, the inhibition of the mevalonate (MVA) pathway with mevinolin did not affect the localization. During the present work, this test system has been used to examine the effect of newly designed inhibitors of the MEP pathway and inhibitors of sterol biosynthesis such as squalestatin, terbinafine and Ro48-8071. In addition, we also studied the impact of different post-prenylation inhibitors or those suspected to affect the transport of proteins to the plasma membrane on the localization of the geranylgeranylable fusion protein GFP-BD-CVIL.

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49

Hartmann, Michael, Andrea Hemmerlin, Elisabet Gas-Pascual, Esther Gerber, Denis Tritsch, Michel Rohmer, and Thomas J. Bach. "The effect of MEP pathway and other inhibitors on the intracellular localization of a plasma membrane-targeted, isoprenylable GFP reporter protein in tobacco BY-2 cells." F1000Research 2 (November 15, 2013): 170. http://dx.doi.org/10.12688/f1000research.2-170.v2.

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We have established an in vivo visualization system for the geranylgeranylation of proteins in a stably transformed tobacco BY-2 cell line, based on the expression of a dexamethasone-inducible GFP fused to the carboxy-terminal basic domain of the rice calmodulin CaM61, which naturally bears a CaaL geranylgeranylation motif (GFP-BD-CVIL). By using pathway-specific inhibitors it was demonstrated that inhibition of the methylerythritol phosphate (MEP) pathway with known inhibitors like oxoclomazone and fosmidomycin, as well as inhibition of the protein geranylgeranyltransferase type 1 (PGGT-1), shifted the localization of the GFP-BD-CVIL protein from the membrane to the nucleus. In contrast, the inhibition of the mevalonate (MVA) pathway with mevinolin did not affect the localization. During the present work, this test system has been used to examine the effect of newly designed inhibitors of the MEP pathway and inhibitors of sterol biosynthesis such as squalestatin, terbinafine and Ro48-8071. In addition, we also studied the impact of different post-prenylation inhibitors or those suspected to affect the transport of proteins to the plasma membrane on the localization of the geranylgeranylable fusion protein GFP-BD-CVIL.

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Stoermer, Doris, Stéphane Caron, and Clayton H. Heathcock. "Total Synthesis of Zaragozic Acid A (Squalestatin S1). Degradation to a Relay Compound and Reassembly of the Natural Product." Journal of Organic Chemistry 61, no. 26 (January 1996): 9115–25. http://dx.doi.org/10.1021/jo961533m.

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