Synthesis of new sugar-based surfactants and evaluation of their hemolytic activities

Journal of Organic Chemistry

Volumn 71, Issue 9, 2006, Pages 3623-3626

  Neimert Andersson, Kristina ^a   Sauer, Sven ^a   Panknin, Olaf ^a   Borg, Tessie ^a   Söderlind, Erik ^b   Somfai, Peter ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYSTEARIC ACID; MYRISTOYL CHLORIDE; WATER SOLUBILITY;

DRUG PRODUCTS; HYDROXYLATION; SOLUBILITY; STABILIZATION; SUGARS; SYNTHESIS (CHEMICAL);

SURFACE ACTIVE AGENTS;

12 HYDROXYSTEARIC ACID; 12 HYDROXYSTEARYLBIS(METHYL 6 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE) AMINE; ACETYL CHLORIDE; HEXANOYL CHLORIDE; MYRISTOYL CHLORIDE; SOLUBILIZER; STEARIC ACID DERIVATIVE; SURFACTANT; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CELL STRAIN CACO 2; CHEMICAL STRUCTURE; EVALUATION; HEMOLYSIS; HUMAN; HUMAN CELL; HYDROPHOBICITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SOLUBILITY; STRUCTURE ANALYSIS; SYNTHESIS;

CARBOHYDRATES; CHEMISTRY, PHARMACEUTICAL; HEMOLYSIS; STRUCTURE-ACTIVITY RELATIONSHIP; SURFACE-ACTIVE AGENTS;

EID: 33646249655     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051904b     Document Type: Article

References (38)

1. Attwood, D.; Florence, A. T. Surfactant Systems: Their chemistry, pharmacy and biology; Chapman and Hall: London, 1983.
2. von Rybinski, W.; Hill, K. In Novel Surfactants. Preparation, Applications, and Biodegraeability, 2nd ed.; Holmberg, K., Ed.; Marcel Dekker: New York, 2003; Vol. 114, pp 35-93.
3. Lawrence, M. J. Chem. Soc. Rev. 1994, 23, 417-424.
4. Macián, M.; Seguer, J.; Infante, M. R.; Selve, C.; Vinardell, M. P. Toxicology 1996, 106, 1-9.
5. Bevinakatti, H. S.; Mishra, B. K. Annu. Surf. Rev. 1999, 2, 1-50.
6. Söderlind, E. PCT Int. Appl. WO 03039511, 2003.
7. von Corswant, C.; Hult, K.; Söderlind, E.; Viklund, F. PCT Int. Appl. WO 2004089869, 2004.
8. Sommerdijk, N. A. J. M.; Hoeks, T. L.; Booy, K. J.; Feiters, M. C.; Nolle, R. J. M.; Zwanenburg, B. Chem. Commun. 1998, 743-744.
9. Both Solutol HS15 and Cremophor EL contain mainly ethoxylated 12-hydroxystearic acid.
10. Neimert-Andersson, K.; Blomberg, E.; Somfai, P. J. Org. Chem. 2004, 69, 3746-3752.
11. Burczyk, B. In Novel Surfactants, Preparation, Applications, and Biodegradability, 2 ed.; Holmberg, K., Ed.; Marcel Dekker: New York, 2003; Vol. 114, pp 129-192.
12. Syper, L.; Wilk, K. A.; Sokolowski, A.; Burczyk, B. Prog. Colloid Polym. Sci. 1832, 110, 199-203.
13. Zhang, T.; Marchant, R. E. J. Colloid Interface Sci. 1996, 177, 419-426.
14. Söderman, O.; Johansson, I. Curr. Opin. Coll. Interface Sci. 2000, 4, 391-401.
15. The enantiomeric purity of 12-hydroxy stearic acid was determined to be >95% in analogy with the method described in: Sonnet, P. E.; Hayes, D. J. Am. Oil Chem. Soc. 1995, 72, 1069-1071.
16. Ishikawa, T.; Shimizu, Y.; Kudoh, T.; Saito, S. Org. Lett. 2003, 5, 3879-3882.
17. Kobertz, W. R.; Bertozzi, C. R. J. Org. Chem. 1996, 61, 1894-1897.
18. Klausner, Y. S.; Bodansky, M. Synthesis 1972, 453-463.
19. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride.
20. Patist, A.; Bhagwat, S. S.; Penfield, K. W.; Aikens, P.; Shah, D. O. J. Surfact. Deterg. 2000, 3, 53-58.
21. The limiting values were determined by setting the correlation coefficient >0.99.
22. Jin, X.; Zhang, S.; Yang, J.; Lu, R. Tenside Surf. Del. 2004, 41, 126-129.
23. Griffiths, P. C.; Whatton, M. L.; Abbott, R. J.; Kwan, W.; Pitt, A. R.; Howe, A. M.; King, S. M.; Heenan, R. K. J. Colloid Interface Sci. 1999, 215, 114-123.
24. Söderlind, E.; Karlsson, L. Eur. J. Pharm. Biopharm. 2006, in press.
25. Lindman, B. In Handbook of Applied Surface and Colloid Chemistry, Holmberg, K., Ed.; Wiley: Chichester, 2002; Vol. 1, pp 421-443.
26. Patist, A. In Handbook of Applied Surface and Colloid Chemistry; Holmberg, K., Ed.; Wiley: Chichester, 2002; Vol. 2, p 239-249.
27. Viklund, F. Ph.D. Thesis, Royal Institute of Technology, 2003.
28. Jones, M. N. Int. J. Pharm. 1999, 177, 137-159.
29. Kondo, T. Adv. Colloid Interface Sci. 1976, 6, 139-172.
30. Shalel, S.; Streichman, S.; Marmur, A. J. Colloid Interface Sci. 2002, 255, 265-269.
31. Ohnishi, M.; Sagitani, H. J. Am. Oil Chem. Soc. 1993, 70, 679-684.
32. Söderlind, E.; Wollbratt, M.; von Corswant, C. Int. J. Pharm. 2003, 252, 61-71.
33. Isomaa, B.; Hägerstrand, H.; Paatero, G. Biochim. Biophys. Acta 1987, 899, 93-103.
34. Isomaa, B.; Hägerstrand, H.; Paatero, G.; Engblom, A. C. Biochim. Biophys. Acta 1986, 860, 510-524.
35. Reinhart, T.; Bauer, K. H. Pharmazie 1995, 50, 403-407.
36. Claesson, P. M.; Kjellin, U. R. M. In Encyclopedia of Surface and Colloid Science; Hubbard, A. T., Ed.; Marcel Dekker: New York, 2002; pp 4909-4925.
37. Yalkowsky, S. H. Solubilization by surfactants; Oxford University Press: New York, 1999.
38. Bauer, K. J. Clin. Chem. Clin. Biochem. 1981, 19, 971-976.