Synthesis of macrocyclic diacyl/dialkyl glycerols containing disulfide tether and studies of their effects upon incorporation in DPPC membranes. Implications in the design of phospholipase A2 modulators

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9232-9242

  Bhattacharya, Santanu ^a,b   Ghosh, Sangita ^a   Easwaran, Kalpathy R K ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BIS(12 THIOHEXACOSYL)GLYCEROL; 1,2 BIS(12 THIOOCTADECANOYL)GLYCEROL; 1,2 BIS(16 THIOTETRATRIACONTA 1,34 DIOYL)GLYCEROL; 1,2 BIS(2 THIOHEXADECANOYL)GLYCEROL; 1,2 BIS(6 THIOTETRADECA 1,14 DIOYL)GLYCEROL; BEE VENOM; BENZYLTRIETHYLAMMONIUM TETRATHIOMOLYBDATE; DIACYLGLYCEROL DERIVATIVE; DITHIOTHREITOL; PHOSPHOLIPASE A2; REAGENT; SNAKE VENOM; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CONFORMATION; CYCLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DISULFIDE BOND; ENZYME ACTIVITY; LIPID BILAYER; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS;

EID: 0032509258     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980866b     Document Type: Article

References (48)

1. (a) Pelech, S.; Vance, D. E. Trends Biochem. Soc. 1989, 14, 28-30.
2. (b) Cunningham, B. A.; Tsujita, T.; Brockman, H. L. Biochemistry 1989, 28, 32-40.
3. (c) Dawson, R. M. C.; Hemington, N. L.; Irvine, R. F. Biochem. Biophys. Res. Commun. 1983, 117, 196-201.
4. (d) Nishizuka, Y. Nature (London) 1984, 308, 693-698.
5. (e) Nishizuka, Y. Science (Washington, DC) 1986, 233, 305-311.
6. (f) Berridge, M. J. Annu. Rev. Biochem. 1987, 56, 159-193.
7. (a) Dawson, R. M. C.; Irvine, R. F.; Bray, J.; Quinn, P. J. Biochem. Biophys. Res. Commun. 1984, 125, 836-842.
8. (b) Das, S.; Rand, R. P. Biochemistry 1986, 25, 2882-2889.
9. (c) Epand, R. M. Biochemistry 1985, 24, 7092-7095.
10. (d) Epand, R. M.; Bottega, R. Biochim. Biophys. Acta. 1988, 944, 144-154.
11. (e) Siegel, D. P.; Banschbach, J.; Yeagle, P. L. Biochemistry 1989, 28, 5010-5019.
12. Siegel, D. P.; Banschbach, J.; Alford, D.; Ellens, H.; Lis, L. J.; Quinn, P. J.; Yeagle, P. L. Biochemistry 1989, 28, 3703-3709.
13. Ohki, K.; Sekiya, T.; Yamauchi, T.; Nozawa, Y. Biochim. Biophys. Acta 1982, 693, 341-350.
14. (a) Upreti, G. C.; Rainier, S.; Jain, M. K. J. Membr. Biol. 1980, 55, 97-112.
15. (b) Bell, J. D.; Baker, M. L.; Bent, E. D.; Ashton, R. W.; Hemming, D. J. B.; Hansen, L. D. Biochemistry 1995, 34, 11551-11560.
16. (c) Bell, J. D.; Burnside, M.; Owen, J. A.; Royall, M. L.; Baker, M. L. Biochemistry 1996, 35, 4945-4955.
17. (a) Kishimoto, A.; Takai, Y.; Mori, T.; Kikkawa, U.; Nishizuka, Y. J. Biol. Chem. 1980, 255, 2273-2276.
18. (b) Bonser, R. W.; Thompson, N. T.; Hodson, H. F.; Beams, R. M.; Garland, L. G. FEBS Lett. 1988, 234, 341-344.
19. (c) De Boeck, H.; Zidovetzki, R. Biochemistry 1989, 28, 7439-7466.
20. (d) Zidovetzki, R.; Laptalo, L.; Crawford, J. Biochemistry 1992, 31, 7683-7691.
21. Samuel, N. K. P.; Singh, M.; Yamaguchi, K.; Regen, S. L. J. Am. Chem. Soc. 1985, 107, 42-47.
22. Ghosh, S.; Easwaran, K. R. K.; Bhattacharya, S. Tetrahedron Lett. 1996, 37, 5769-5772.
23. (a) Eguchi, T.; Arakawa, K.; Terachi, T.; Kakinuma, K. J. Org. Chem. 1997, 62, 1924-1933.
24. (b) Eguchi, T.; Kano, H.; Kakinuma, K. Chem. Commun. 1996, 365.
25. (c) Herbert, N.; Beck, A.; Lennox, R. B.; Just, G. J. Org. Chem. 1992, 57, 1777.
26. (d) Menger, F. M.; Chen, X. Y.; Brocchini, S.; Hopkins, H. P.; Hamilton, D. J. Am. Chem. Soc. 1993, 115, 6600-6608.
27. (e) Moss, R. A.; Li, J.-M. J. Am. Chem. Soc. 1992, 114, 9227.
28. (f) Kim, J.-M.; Thompson, D. H. Langmuir 1992, 8, 637-644.
29. (g) Fuhrhop, J.-H.; Hungerbuhler, H.; Siggel, U. Langmuir 1990, 6, 1295-1300.
30. Breitenback, J.; Boosfeld, J.; Vögtle, F. In Comprehensive Supramolecular Chemistry; Vögtle, F., Eds.; Elsevier Science Ltd: Oxford, U.K. 1996, Vol. 2, pp 29-67.
31. Ramesha, A. R.; Chandrasekaran, S. J. Org. Chem. 1994, 59, 1354-1357.
32. Prabhu, K. R.; Ramesha, A. R.; Chandrasekaran, S. J. Org. Chem. 1995, 60, 7142-7143.
33. Ellman, G. L. Arch. Biochem. Biophys. 1959, 82, 70.
34. (a) Pearson, R. H.; Pascher, I. Nature 1979, 281, 499.
35. (b) Pascher, I.; Sundell, S.; Hauser, H. J. Mol. Biol. 1981, 153, 791.
36. (a) Ortiz, A.; Aranda, F. J.; Villálain, J.; San Martin, C.; Micol, V.; Gómez-Fernandez, J. C. Chem. Phys. Lipids 1992, 62, 215-224.
37. (b) Basáñez, G.; Nieva, J. L.; Rivas, E.; Alonso, A.; Goñi, F. M. Biophys. J. 1996, 70, 2299-2306.
38. Ghosh, S.; Easwaran, K. R. K.; Bhattacharya, S. Unpublished results.
39. (a) Heimburg, T.; Weurz, U.; Marsh, D. Biophys. J. 1992, 63, 1369-1378.
40. (b) Lopez-Garcia, F.; Villálain, J.; Gomez-Fernandez, J. C.; Quinn, P. J. Biophys. J. 1994, 66, 1991-2004.
41. c is the calorimetric enthalpy.
42. Ramesha, A. R.; Chandrasekaran, S. Synth. Commun. 1992, 22, 3277.
43. (a) Bhattacharya, S.; Snehalatha, K.; George, S. K. J. Org. Chem. 1998, 63, 27.
44. (b) Bhattacharya, S.; Snehalatha, K. J. Org. Chem. 1997, 62, 2198.
45. (c) Bhattacharya, S.; Haldar, S. Biochim. Biophys. Acta 1996, 1283, 21-30.
46. Yamauchi, K.; Hihara, M.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1987, 60, 2169-2172.
47. Kates, M.; Chan, T. H.; Stanacev, N. Z. Biochemistry 1963, 2, 394-397.
48. Blume, A. Biochemistry 1983, 22, 5436.