Exciton coupled circular dichroic studies of self-assembled brevetoxin-porphyrin conjugates in lipid bilayers and polar solvents

Chemistry and Biology

Volumn 3, Issue 5, 1996, Pages 379-392

  Matile, Stefan ^a   Berova, Nina ^a   Nakanishi, Koji ^a  

^a Columbia University ^*  (United States)

Author keywords

Brevetoxins; Ionophores; Pore formation mechanisms; Porphyrin reported exciton coupled circular dichroic (CD) method; Self assembly

Indexed keywords

BREVETOXIN; IONOPHORE; MARINE TOXIN; OXOCIN DERIVATIVE; PORPHYRIN; SOLVENT;

ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; LIPID BILAYER; SPECTROFLUOROMETRY; STRUCTURE ACTIVITY RELATION;

CIRCULAR DICHROISM; IONOPHORES; LIPID BILAYERS; MARINE TOXINS; OXOCINS; PORPHYRINS; SOLVENTS; SPECTROMETRY, FLUORESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030133004     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(96)90121-0     Document Type: Article

References (30)

1. Yasumoto, T. & Murata, M. (1993). Marine toxins. Chem. Rev. 93, 1897-1909.
2. Ishida, H., et al., & Kosuge, T. (1995). BTX-B1, a new polyether marine toxin from the New Zealand shellfish, Austrovenus stutchburyi. Tetrahedron Lett. 36, 725-728.
3. Morohashi, A., et al., & Yasumoto, T. (1995). BTX-B3, a new brevetoxin analog isolated from greenshell mussel Perna canaliculus involved in neurotoxic shellfish poisoning in New Zealand. Tetrahedron Lett. 36, 8995-8998.
4. Lin, Y.Y., et al., & Nakanishi, K. (1981). Isolation and structure of BTX-B from the 'red tide' dinoflagellate Ptychodiscus brevis (Gymnodinium breve). J. Am. Chem. Soc. 103, 6773-6775.
5. Shimizu, Y., Bando, H., Chou, H-N., Van Dyne, G. & Clardy, J.C. (1986). Absolute configuration of brevetoxins. J. Chem. Soc., Chem. Commun. 1656-1658.
6. Nicolaou, K.C., et al., & Untersteller, E. (1995). Total synthesis of brevetoxin B. 2. Completion. J. Am. Chem. Soc. 117, 1173-1174.
7. Matile, S. & Nakanishi, K. (1996). Selective cation movement across lipid bilayers containing brevetoxin B. Angew. Chem. Int. Ed. Engl. 35 757-759.
8. Gawley, R.E., et al., & Baden, D.G. (1995). The relationship of brevetoxin 'length' and A-ring functionality to binding and activity in neuronal sodium channels. Chemistry & Biology 2, 533-541.
9. Czarnik, A.W. (1995). Desperately seeking sensors. Chemistry & Biology 2, 423-428.
10. Hayes, J.J. (1995). Chemical probes of DNA structure in chromatin. Chemistry & Biology 2, 127-135.
11. Matile, S., et al., & Blagoev, B. (1995). Porphyrins: powerful chromophores for structural studies by exciton coupled circular dichroism. J. Am. Chem. Soc, 117, 7021-7022.
12. Matile, S., Berova, N., Nakanishi, K., Fleischhauer, J. & Woody, R. (1996). Structural studies by exciton coupled circular dichroism over a large distance: porphyrin derivatives of steroids, dimeric steroids, and brevetoxin B. J. Am. Chem. Soc., in press.
13. Matile, S., Berova, N. & Nakanishi, K. (1996). Intramolecular porphyrin π,π-stacking: assignment of absolute configuration of single chiral centers by exciton coupled circular dichroism. Enantiomer, in press.
14. Huang, D., Matile, S., Berova, N. & Nakanishi, K. (1996). Synthesis of philanthotoxin analogs with bulky heads. Self-assembly monitored by circular dichroism. Heterocycles 42, 723-735.
15. Harada, N. & Nakanishi, K. (1983). Circular dichroic spectroscopy - Exciton coupling in organic stereochemistry. University Science Books, Mill Valley, CA.
16. Nakanishi, K. & Berova, N. (1994). The exciton chirality method. In Circular dichroism - principles and applications. (Nakanishi, K., Berova, N. & Woody, R.W., eds), VCH Publishers Inc., New York, NY.
17. Rein, K.S., Baden, D.G. & Gawley, R.E. (1994). Conformational analysis of the sodium channel modulator brevetoxin A, comparison with BTX-B conformations, and a hypothesis about the common pharmacophore of the 'site 5' toxins. J. Org. Chem. 59, 2101-2106.
18. Fuhrhop, H.-J., Demoulin, C., Boettcher, C., Köning, J. & Siggel, U. (1992). Chiral micellar porphyrin fibers with 2-aminoglycosamide head groups. J. Am. Chem. Soc. 114, 4159-4165.
19. 13C nuclear magnetic resonance. J. Am. Chem. Soc. 96, 6725-6734.
20. Izatt, R.M., Bradshaw, J.S., Nielsen, S.A., Lamb, J.D. & Christensen, J.J. (1985). Thermodynamic and kinetic data for cation-macrocycle interaction. Chem. Rev. 85, 271-339.
21. 39K NMR spectroscopy. J. Am. Chem. Soc. 110, 734-738.
22. Hilgenfeld, R. & Saenger, W. (1982). Structural chemistry of natural and synthetic ionophores and their complexes with cations. Top. Curr. Chem. 101, 3-82.
23. Mohamadi, F., et al., & Still, W.C. (1990). MacroModel - an integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J. Comput. Chem. 11, 440-467.
24. Mimms, L.T., Zampighi, G., Nozaki, Y., Tanford, C. & Reynolds, J.A. (1981). Phospholipid vesicle formation and transmembrane protein incorporation using octyl glucoside. Biochemistry 20, 833-840.
25. Ghadiri, M.R., Granja, J.R. & Buehler, L.K. (1994). Artificial transmembrane ion channels from self-assembling peptide nanotubes. Nature 369, 301-304.
26. Berg, K. & Moan, J. (1994). Lysosomes as photochemical targets. Int. J. Cancer 59, 814-822.
27. Woolley, G.A. & Wallace, B.A. (1992). Model ion channels: gramicidin and alamethicin. J. Membrane Biol. 129, 109-136.
28. Feng, W.Y. & Lifshitz, C. (1995). Influence of multiple hydrogen bonding on reactivity: ion/molecule reactions of proton-bound 12-crown-4 ether and its mixed clusters with ammonia and methanol. J. Am. Chem. Soc. 117, 11548-11554.
29. Murillo, O., Watanabe, S., Nakano, A. & Gokel, G. W. (1995). Synthetic models for transmembrane channels: structural variations that alter cation flux. J. Am. Chem. Soc. 117, 7665-7679.
30. Yamashita, K., Janout, V., Bernard, E.M., Armstrong, D. & Regen, S.L. (1995). Micelle/monomer control over the membrane-disrupting properties of an amphiphilic antibiotic. J. Am. Chem. Soc. 117, 6249-6253.