Synthesis, spectroscopic, and biological studies of novel estolides derived from anticancer active 4-O-podophyllotoxinyl 12-hydroxyl-octadec-Z-9-enoate

Lipids

Volumn 39, Issue 7, 2004, Pages 659-666

  Mustafa, Jamal ^a   Khan, Shabana I ^a   Ma, Guoyi ^a   Walker, Larry A ^a,b   Khan, Ikhlas A ^a,b  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGENTS; CATALYST ACTIVITY; CELLS; ENZYMES; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL); TOXICITY;

ANTITUMOR AGENTS; BIOLOGICAL STUDIES; CYTOTOXICITY; THERAPEUTIC POTENTIALS;

ORGANIC COMPOUNDS;

4 O PODOPHYLLOTOXINYL 12 HYDROXYL OCTADEC Z 9 ENOATE; AMINOPYRIDINE DERIVATIVE; ANTINEOPLASTIC AGENT; DICYCLOHEXYLCARBODIIMIDE; DIMETHYLAMINOPYRIDINE; DNA TOPOISOMERASE (ATP HYDROLYSING); ESTOLIDE; PODOPHYLLOTOXIN; TUBULIN; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; LEUKEMIA CELL; LIPOPHILICITY; MICROTUBULE ASSEMBLY; SPECTROSCOPY;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; DNA TOPOISOMERASES, TYPE II; FATTY ACIDS; HUMANS; MICROTUBULES; MOLECULAR STRUCTURE; PODOPHYLLOTOXIN;

EID: 8444235411     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-004-1279-2     Document Type: Article

References (21)

1. Gordaliza, M., Castro, M.A., Miguel del Correl, J.M., and Feliciano, A.S. (2000) Antitumor Properties of Podophyllotoxin and Related Compounds, Curr. Pharm. Design 6, 1811-1839.
2. Brewer, C.F., Loike, J.D., Horwitz, S.B., Sternlicht, H., and Gensler, W.J. (1979) Conformational Analysis of Podophyllotoxin and Its Congeners. Structure-Activity Relationship in Microtuble Assembly, J. Med. Chem. 22, 215-221.
3. Jardine, I. (1980) Podophyllotoxin, in Anticancer Agents Based on Natural Product Models (Cassady, J.M., and Douras, J.D., eds.), Academic Press, New York, pp. 319-351.
4. Keller-Juslen, C., Kuhn, M., Stahelin, H., and von Wartburg, A. (1971) Synthesis and Antimitotic Activity of Glycosidic Lignan Derivatives Related to Podophyllotoxin, J. Med. Chem. 14, 936-940.
5. Weiss, S.G., Tin-wa, M., Perdue, R.E., Jr., and Farnsworth, N.R. (1975) Potential Anticancer Agents II: Antitumor and Cytotoxic Lignans from Linum album (Linaceae), J. Pharm. Sci. 64, 95-98.
6. O'Dwyer, P.J., Alonso, M.T., Leyland-Jones, B., and Marsoni, S. (1984) Teniposide: A Review of 12 Years of Experience, Cancer Treat. Rep. 68, 1455-1466.
7. Issell, B.F., Muggia, F.M., and Carter, S.K. (eds.) (1984) Etoposide (VP-16) Current Status and New Developments, Academic Press, New York.
8. VePesid Product Information Overview, Bristol Lab, New York, 1983.
9. van Maanen, J.M.S., Retel, J., De Vries, J., and Pinedo, H.M. (1988) Mechanism of Action of Antitumor Drug Etoposide: A Review, J. Natl. Cancer Inst. 80, 1526-1533.
10. Damayanthi, Y., and Lown, J.W. (1998) Podophyllotoxins: Current Status and Recent Developments, Curr. Med. Chem. 5, 205-252.
11. Lee, K.H. (1999) Novel Anticancer Agents from Higher Plants, Med. Res. Rev. 19, 569-596.
12. Nagao, Y., Mustafa, J., Sano, S., Ochiai, M., Tazuko, T., and Shigeru, T. (1991) Different Mechanism of Action of Long Chain Fatty Acid Esters of Podophyllotoxin and Esters of Epipodophyllotoxin Against P388 Lymphocytic Leukemia in Mice, Med. Chem. Res. 1, 295-299.
13. Mustafa, J., Khan, S.I., Ma, G., Walker, L.A., and Khan, I.A. (2004), Synthesis and Anticancer Activities of Fatty Acid Analogs of Podophyllotoxin, Lipids 39, 167-172.
14. Coon, J.S. (1993) Methods and Compositions Using Fatty Acid Esters for Reducing Multi-drug Resistance in Cancer Treatment, PCTInt. Appl. 38, Application WO 92-US10563.
15. Scott, C.A., and Horrobin, D.F. (1998) Fatty Acids for the Prevention of Side Effects of Chemotherapy, PCT Int. Appl. 17, Application WO 97-GB2362 19970902.
16. Lundberg, B. (1994) The Solubilization of Lipophilic Derivatives of Podophyllotoxins in Sub-micron Sized Lipid Emulsions and Their Cytotoxic Activity Against Cancer Cells in Culture, Int. J. Pharm. 109, 73-81.
17. Levy, R.K., Hall, I.H., and Lee, K.L. (1983) Antitumor Agents LXII: Synthesis and Biological Evaluation of Podophyllotoxin Esters and Related Derivatives, J. Pharm. Sci. 72, 1158-1161.
18. Paddon-Jones, G.C., McErlean, C.S.P., Hayes, P., Moore, C.J., Konig, W.A., and Kitching, W. (2001) Synthesis and Stereochemistry of Some Bicyclic γ-Lactones from Parasitic Wasps (Hymenoptera: Braconidae). Utility of Hydrolytic Kinetic Resolution of Epoxides and Palladium(II)-Catalyzed Hydroxycyclization-Carbonylation-Lactonization of Ene-diols, J. Org. Chem. 66, 7487-7495.
19. Lie Ken Ji, M.S.F., Mustafa, J., and Pasha, M.K. (1999) Synthesis and Spectral Characteristics of Some Unusual Fatty Esters of Podophyllotoxin, Chem. Phys. Lipids 100, 165-170.
20. Shi, Q., Chen, K., Morris-Natschke, S.L., and Lee, K.H. (1998) Recent Progress in the Development of Tubulin Inhibitors as Antimitotic Antitumor Agents, Curr. Pharm. Des. 4, 219-248.
21. Wang, H.K., Morris-Natschke, S.L., and Lee, K.H. (1997) Recent Advances in the Discovery and Development of Topoisomerase Inhibitors as Antitumor Agents, Med. Res. Rev. 4, 367-425.