Synthetic studies on the relationship between anti-HIV activities and micelle forming abilities of various alkylated glycyrrhetinate diglycoside sodium sulfates and related compounds

European Journal of Medicinal Chemistry

Volumn 31, Issue 5, 1996, Pages 365-381

  Saito, S ^a   Furumoto, T ^a   Ochiai, M ^a   Hosono, A ^a   Hoshino, H ^b   Haraguchi, U ^b   Ikeda, R ^b,c   Shimada, N ^c  

^a JOSAI UNIVERSITY   (Japan)

^b GUNMA UNIVERSITY   (Japan)

^c NIPPON KAYAKU CO LTD   (Japan)

Author keywords

Alkyl glycyrrhetinate diglycoside; Anti HIV activity; Glycyrrhizin; Micelle formation; Sodium sulfate

Indexed keywords

CD4 ANTIGEN; GLYCYRRHIZIC ACID; GLYCYRRHIZIN SODIUM SULFATE; GLYCYRRHIZIN SODIUM SULFATE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IN VITRO STUDY; MASS SPECTROMETRY; MICELLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; SYNCYTIUM; VIRUS REPLICATION;

EID: 0029979114     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/0223-5234(96)89163-X     Document Type: Article

References (37)

1. Suzuki H, Ohta Y, Takino Y, Fujisawa K, Hiroshima C, Shimizu N, Aso Y (1977) Igaku no Ayumi 102, 562-577
2. Kiso Y, Tohkin M, Hikino H, Hattori M, Sakamoto T, Namba T (1984) Planta Medico 298-302
3. Okabe S, Takata Y, Takeuchi K, Naganuma T, Takagi K (1976) Dig Dis Sci 21, 618-625
4. Yano S, Harada M, Watanabe K et al (1989) Chem Pharm Bull 37, 2500-2504
5. Sotomatsu S, Takaishi Y, Hiroi J, Namikata A, Okano N (1959) Skin Urol 21, 138-144
6. Kuroyanagi T, Kurusu A, Sugiyama H, Saito M (1962) Jpn J Med Prog 49, 458-465
7. Finney RSH, Tarnoky AL (1960) J Pharm Pharmacol 12, 49-58
8. Yamamoto S, Miyamoto A, Awachi Y, Hiroshima Y (1963) J Ther 45, 157-168
9. Pompei R, Flore O, Marccialis MA, Pani A, Loddo B (1979) Nature 218, 689-690
10. Ito M, Nakashima H, Baba M et al (1987) Anviral Res 7, 127-137
11. Nakashima H, Matsui T, Yoshida O et al (1987) Jpn J Cancer Res 78, 767-771
12. Mitsuya H, Weinhold KJ, Furman PA et al (1985) Proc Natl Acad Sci USA 82, 7096-7100
13. Mitsuya H, Broder S (1986) Proc Natl Acad Sci USA 83, 1911-1915
14. Ostertag W, Roesler G, Krieg CJ et al (1974) Proc Natl Acad Sci USA 71, 4980-4985
15. Aldhous P (1991) Nature 352, 269
16. Harada S, Koyanagi Y, Yamamoto N (1985) Virology 146, 272-281
17. Salahudin SZ, Markham PD, Wong-Staal F, Francini G, Kalyanaraman VS, Gallo RC (1983) Virology 129, 51-64
18. Ichikawa Y, Monden R, Kuzuhara H (1983) Carbohydr Res 172, 37-64
19. Broker T, Lindhorst TK, Thiem J, Vill V (1992) Carbohydr Res 230, 245-256
20. Takeda K (1938) Yakugaku Zasshi 58, 731-738
21. Haynes LJ, Newth FH (1995) Advances in Carbohydrate Chemistry (Wolfrom ML, ed) Academic, New York, 10, 207-256
22. Saito S, Sumita S, Tamura N et al (1990) Chem Pharm Bull 38, 411-414
23. Saito S, Nagase S, Ichinose K (1994) Chem Pharm Bull 42, 2342-2345
24. Saito S, Tsuchiya T (1985) Chem Pharm Bull 33, 503-508
25. Popovic M, Sarngadharan MG, Read E, Gallo RC (1984) Science 224, 497-500
26. Miyoshi I, Kubonishi I, Yoshimoto S et al (1981) Nature 297, 770-771
27. Shimizu NS, Shimizu NG, Takeuchi Y, Hoshino H (1994) J Virology 68, 6130-6135
28. Corrin ML, Klevens HB, Harkins WD (1946) J Chem Phys 14, 480-486
29. Honda A, Hoshino H, Nakajima K et al (1991) Biochem Biophys Res Commun 175, 1-9
30. Nagumo T, Hoshino H (1988) Jpn J Cancer Res (Gann) 79, 9-11
31. Seki J, Shimada N, Takahashi K, Takita T, Takeuchi T, Hoshino H (1989) Antimicrob Agents Chemother 33, 773-775
32. Shimizu N, Takeuchi Y, Naruse T et al (1992) J Mol Evol 35, 329-336
33. Khalilov LM, Baltina LA, Spirikhin LB et al (1989) Khim Prir Soedin, 500-505
34. Saito S, Kuroda K, Hayashi Y et al (1991) Chem Pharm Bull 39, 2333-2339
35. Saito S, Sasaki Y, Kuroda K et al (1993) Chem Pharm Bull 41, 539-543
36. Saito S, Sumita S, Furumoto T, Ebashi J, Nagamura Y, Ishiguro I (1994) Eur J Med Chem 29, 455-470
37. Saito S, Nagase S, Ichinose K (1994) Chem Pharm Bull 42, 2342-2345