Hydraphiles: A rigorously studied class of synthetic channel compounds with in vivo activity

International Journal of Biomedical Imaging

Volumn 2013, Issue , 2013, Pages

  Negin, Saeedeh ^a   Smith, Bryan A ^b   Unger, Alexandra ^b   Leevy, W Matthew ^b   Gokel, George W ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

^b UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL TOXICITY; CHANNEL BEHAVIOR; FLUORESCENCE IMAGING; IN-VITRO; IN-VITRO ASSAYS; IN-VIVO; ION FLOW; ION HOMEOSTASIS; MAMMALIAN CELLS; MUSCLE TISSUES; PATCH CLAMPING; PLANAR BILAYERS; STRUCTURE ACTIVITY RELATIONSHIPS; SYNTHETIC ION CHANNELS;

BIOACTIVITY; EXPERIMENTS; ION SELECTIVE ELECTRODES; MAMMALS; TISSUE; TOXICITY;

IONS;

EID: 84873396129     PISSN: 16874188     EISSN: 16874196     Source Type: Journal    
DOI: 10.1155/2013/803579     Document Type: Article

References (53)

1. Luckey M., Membrane Structural Biology 2008 Cambridge, UK Cambridge University Press
2. Oparin A. I., Modern concepts of the origin of life on the earth. Scientia 1978 113 7 25
3. Cairns-Smith A. G., Seven Clues to the Origin of Life: A Scientific Detective Story 1985 Cambridge, UK Canto/Cambridge University Press
4. Campelo F., Malhotra V., Membrane fission: the biogenesis of transport carriers. Annual Review of Biochemistry 2012 81 405 427
5. Yeagle P. L., The Structure of Biological Membranes 2012 Boca Raton, Fla, USA CRC Press
6. Sten-Knudsen O., Biological Membranes: Theory of Transport, Potentials, and Electric Impulses 2002 Cambridge, UK Cambridge University Press
7. Boon J. M., Smith B. D., Synthetic membrane transporters. Current Opinion in Chemical Biology 2002 6 6 749 756 2-s2.0-0036897959 10.1016/S1367-5931(02) 00399-X (Pubitemid 35449333)
8. Davis A. P., Sheppard D. N., Smith B. D., Development of synthetic membrane transporters for anions. Chemical Society Reviews 2007 36 2 348 357 2-s2.0-33846667747 10.1039/b512651g
9. Gokel G. W., Schlesinger P. H., Djedovič N. K., Ferdani R., Harder E. C., Hu J., Leevy W. M., Pajewska J., Pajewski R., Weber M. E., Functional, synthetic organic chemical models of cellular ion channels. Bioorganic and Medicinal Chemistry 2004 12 6 1291 1304 2-s2.0-12144286976 10.1016/j.bmc.2003. 08.036 (Pubitemid 38304877)
10. Fyles T. M., Synthetic ion channels in bilayer membranes. Chemical Society Reviews 2007 36 2 335 347 2-s2.0-33846666853 10.1039/b603256g
11. Gokel G. W., Barkey N., Transport of chloride ion through phospholipid bilayers mediated by synthetic ionophores. New Journal of Chemistry 2009 33 5 947 963 2-s2.0-77949594579 10.1039/b817245p
12. Matile S., Vargas Jentzsch A., Montenegro J., Fin A., Recent synthetic transport systems. Chemical Society Reviews 2011 40 2453 2474 10.1039/c0cs00209g
13. Chui J. K., Fyles T. M., Ionic conductance of synthetic channels: analysis, lessons, and recommendations. Chemical Society Reviews 2012 41 148 175 10.1039/c1cs15099e
14. Gokel G. W., Hydraphiles: design, synthesis and analysis of a family of synthetic, cation-conducting channels. Chemical Communications 2000 1 1 9 2-s2.0-0034614425 (Pubitemid 30066861)
15. Abel E., Maguire G. E. M., Meadows E. S., Murillo O., Jin T., Gokel G. W., Planar bilayer conductance and fluorescence studies confirm the function and location of a synthetic, sodium-ion-conducting channel in a phospholipid bilayer membrane. Journal of the American Chemical Society 1997 119 38 9061 9062 2-s2.0-0030843106 10.1021/ja971098t (Pubitemid 27421400)
16. Leevy W. M., Donato G. M., Ferdani R., Goldman W. E., Schlesinger P. H., Gokel G. W., Synthetic hydraphile channels of appropriate length kill Escherichia coli. Journal of the American Chemical Society 2002 124 31 9022 9023 2-s2.0-0037036764 10.1021/ja017052o (Pubitemid 34847642)
17. Leevy W. M., Gammon S. T., Levchenko T., Daranciang D. D., Murillo O., Torchilin V., Piwnica-Worms D., Huettner J. E., Gokel G. W., Structure-activity relationships, kinetics, selectivity, and mechanistic studies of synthetic hydraphile channels in bacterial and mammalian cells. Organic and Biomolecular Chemistry 2005 3 19 3544 3550 2-s2.0-27144523746 10.1039/b508157b (Pubitemid 41497562)
18. Leevy W. M., Gokel M. R., Hughes-Strange G. B., Schlesinger P. H., Gokel G. W., Structure and medium effects on hydraphile synthetic ion channel toxicity to the bacterium E. coli. New Journal of Chemistry 2005 29 1 205 209 2-s2.0-13244267165 10.1039/b413048k (Pubitemid 40187978)
19. Atkins J. L., Patel M. B., Cusumano Z., Gokel G. W., Enhancement of antimicrobial activity by synthetic ion channel synergy. Chemical Communications 2010 46 43 8166 8167 2-s2.0-77958511068 10.1039/c0cc03138k
20. 23Na NMR. Journal of the American Chemical Society 1990 112 3 1287 1289 2-s2.0-0025257385 (Pubitemid 20127109)
21. Jullien L., Lehn J. M., The "chundle" approach to molecular channels synthesis of a macrocycle-based molecular bundle. Tetrahedron Letters 1988 29 31 3803 3806 2-s2.0-0000701073
22. Carmichael V. E., Dutton P. J., Fyles T. M., James T. D., Swan J. A., Zojaji M., Biomimetic ion transport: a functional model of a unimolecular ion channel. Journal of the American Chemical Society 1989 111 2 767 769 2-s2.0-0024587360 (Pubitemid 19050575)
23. Deisenhofer J., Epp O., Miki K., Structure of the protein subunits in the photosynthetic reaction centre of Rhodopseudomonas viridis at 3 Angstrom resolution. Nature 1985 318 6047 618 624 2-s2.0-0022348605 (Pubitemid 16172409)
24. Gokel G. W., Hydraphiles: design, synthesis and analysis of a family of synthetic, cation-conducting channels. Chemical Communications 2000 1 1 9 2-s2.0-0034614425 (Pubitemid 30066861)
25. Gokel G. W., Echegoyen L., Dugas H., Lariat ethers in membranes and as membranes. Advances in Bio-Organic Frontiers 1990 1 Berlin, Germany Springer 116 141
26. Nakano A., Hernandez J. C., De Wall S. L., Wang K., Berger D. R., Gokel G. W., Steroidal azalariat ethers: syntheses and aggregation behavior. Supramolecular Chemistry 1997 8 209 220
27. Muñoz S., Mallén J., Nakano A., Chen Z., Gay I., Echegoyen L., Gokel G. W., Ultrathin monolayer lipid membranes from a new family of crown ether-based bola-amphiphiles. Journal of the American Chemical Society 1993 115 1705 1711 10.1021/ja00058a014
28. De Wall S. L., Wang K., Berger D. R., Watanabe S., Hernandez J. C., Gokel G. W., Azacrown ethers as amphiphile headgroups: formation of stable aggregates from two- and three-armed lariat ethers. Journal of Organic Chemistry 1997 62 20 6784 6791 2-s2.0-0001076606 (Pubitemid 127494612)
29. 23Na-NMR spectroscopy. Biochimica et Biophysica Acta 1985 817 2 313 317 2-s2.0-0021878599 10.1016/0005-2736(85)90033-1 (Pubitemid 15010858)
30. Sanders J. K. M., Hunter B. K., Modern NMR Spectroscopy 1993 2nd chapter 7 Oxford, UK Oxford University Press
31. Wallace B. A., Gramicidin and Related Ion Channel-Forming Peptides 1999 225 Chichester, UK Novartis Foundation, John Wiley & Sons
32. Murillo O., Suzuki I., Abel E., Murray C. L., Meadows E. S., Jin T., Gokel G. W., Synthetic transmembrane channels: functional characterization using solubility calculations, transport studies, and substituent effects. Journal of the American Chemical Society 1997 119 24 5540 5549 2-s2.0-0030861688 10.1021/ja962694a (Pubitemid 27321412)
33. Murillo O., Watanabe S., Nakano A., Gokel G. W., Synthetic models for transmembrane channels: structural variations that alter cation flux. Journal of the American Chemical Society 1995 117 29 7665 7679 2-s2.0-0001144532
34. Hille B., Ionic Channels of Excitable Membranes 2001 3rd Sunderland, Mass, USA Sinauer Associates
35. Kraayenhof R., Visser G A. J. W., Gerritsen H. C., Fluorescence Spectroscopy, Imaging and Probes 2002 New York, NY, USA Springer
36. Abel E., Maguire G. E. M., Murillo O., Suzuki I., De Wall S. L., Gokel G. W., Hydraphile channels: structural and fluorescent probes of position and function in a phospholipid bilayer. Journal of the American Chemical Society 1999 121 39 9043 9052 2-s2.0-0032880508 10.1021/ja9909172 (Pubitemid 29477371)
37. Selvin P. R., Fluorescence resonance energy transfer. Methods in Enzymology 1995 246 300 334 2-s2.0-0028913136 10.1016/0076-6879(95)46015-2
38. Chattopadhyay A., London E., Parallax method for direct measurement of membrane penetration depth utilizing fluorescence quenching by spin-labeled phospholipids. Biochemistry 1987 26 1 39 45 2-s2.0-0023652259
39. Ohki S., Arnold K., Surface dielectric constant, surface hydrophobicity and membrane fusion. Journal of Membrane Biology 1990 114 3 195 203 2-s2.0-0025230394 (Pubitemid 20115401)
40. + conduction and selectivity. Science 1998 280 5360 69 77 2-s2.0-0032478818 10.1126/science.280.5360.69 (Pubitemid 28169082)
41. MacKinnon R., Potassium channels and the atomic basis of selective ion conduction (nobel lecture). Angewandte Chemie 2004 43 33 4265 4277 2-s2.0-4544342928 10.1002/anie.200400662 (Pubitemid 39257401)
42. http://www.microbelibrary.org/component/resource/laboratory-test/ 3189-kirby-bauer-disk-diffusion-susceptibility-test-protocol
43. 23Na NMR methods in phospholipid bilayers. Chemical Communications 1998 22 2477 2478 2-s2.0-0032556388
44. Weber M. E., Schlesinger P. H., Gokel G. W., Dynamic assessment of bilayer thickness by varying phospholipid and hydraphile synthetic channel chain lengths. Journal of the American Chemical Society 2005 127 2 636 642 2-s2.0-12944297746 10.1021/ja044936+ (Pubitemid 40174389)
45. Leevy W. M., Huettner J. E., Pajewski R., Schlesinger P. H., Gokel G. W., Synthetic ion channel activity documented by electrophysiological methods in living cells. Journal of the American Chemical Society 2004 126 48 15747 15753 2-s2.0-10044242874 (Pubitemid 39602433)
46. Greenwood D., O'Grady F., Variety in the response of Escherichia coli to erythromycin. Journal of Medical Microbiology 1972 5 3 321 326 2-s2.0-0015387581
47. Gourevitch A., Tynda J. M., Puglisi T. A., Lein J., Studies on the mechanism of action of kanamycin. Antibiotics Annual 1958 6 784 789
48. Trnka L., Mechanism of rifampicin action on mycobacterial cells. Consideration to the potentiation problem of antimycobacterial treatment. Acta tuberculosea et pneumologica Belgica 1969 60 3 356 365 2-s2.0-0014644723
49. Brodersen D. E., Clemons W. M. Jr., Carter A. P., Morgan-Warren R. J., Wimberly B. T., Ramakrishnan V., The structural basis for the action of the antibiotics tetracycline, pactamycin, and hygromycin B, on the 30S ribosomal subunit. Cell 2000 103 7 1143 1154 2-s2.0-0034704217 10.1016/S0092-8674(00) 00216-6 (Pubitemid 32037400)
50. Zhang Z., Achilefu S., Spectral properties of pro-multimodal imaging agents derived from a NIR dye and a metal chelator. Photochemistry and Photobiology 2005 81 6 1499 1504 2-s2.0-29644440786 10.1562/2005-06-08-RA-568 (Pubitemid 43035863)
51. Smith B. A., Gammon S. T., Xiao S., Wang W., Chapman S., McDermott R., Suckow M. A., Johnson J. R., Piwnica-Worms D., Gokel G. W., Smith B. D., Leevy W. M., In vivo optical imaging of acute cell death using a near-infrared fluorescent zinc-dipicolylamine probe. Molecular Pharmaceutics 2011 8 2 583 590 2-s2.0-79953807412 10.1021/mp100395u
52. Leevy W. M., Weber M. E., Gokel M. R., Hughes-Strange G. B., Daranciang D. D., Ferdani R., Gokel G. W., Correlation of bilayer membrane cation transport and biological activity in alkyl-substituted lariat ethers. Organic and Biomolecular Chemistry 2005 3 9 1647 1652 2-s2.0-18844430055 10.1039/b418194h (Pubitemid 40683088)
53. Smith B.A.,Daschbach M.M., Gammon S.T., Xiao S., Chapman S.E., Hudson C., Suckow M., Piwnica-Worms D.,Gokel G.W., Leevy W.M. In vivo cell death mediated by synthetic ion channels Chemical Communications 2011 47 7977-7979 10.1039/c1cc12933c