A comprehensive study of Sansalvamide A derivatives: The structure-activity relationships of 78 derivatives in two pancreatic cancer cell lines

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 16, 2009, Pages 5806-5825

  Pan, Po Shen ^a   Vasko, Robert C ^a   Lapera, Stephanie A ^a   Johnson, Victoria A ^a   Sellers, Robert P ^a   Lin, Chun Chieh ^a   Pan, Chung Mao ^a   Davis, Melinda R ^a   Ardi, Veronica C ^a   McAlpine, Shelli R ^a  

^a SAN DIEGO STATE UNIVERSITY   (United States)

Author keywords

Cyclic peptides; Cytotoxicity; Macrocycle; Natural products; Pancreatic cancer; Sansalvamide A; Structure activity relationship

Indexed keywords

AMIDE; ANTINEOPLASTIC AGENT; CYCLOPEPTIDE; LEUCINE; LYSINE; METHIONINE; PEPTIDE DERIVATIVE; PHENYLALANINE; SANSALVAMIDE A DERIVATIVE; SERINE; THYMIDINE; UNCLASSIFIED DRUG; VALINE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CELL PROLIFERATION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; FUSARIUM; HUMAN; HUMAN CELL; IC 50; PANCREAS CANCER; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DEPSIPEPTIDES; DRUG DESIGN; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; PANCREATIC NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 68149175130     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.07.017     Document Type: Article

References (37)

1. Cueto M., Jensen P.R., and Fenical W. Phytochemistry 55 (2000) 223
2. Hwang Y., Rowley D., Rhodes D., Gertsch J., Fenical W., and Bushman F. Mol. Pharmacol. 55 (1999) 1049
3. Belofsky G.N., Jensen P.R., and Fenical W. Tetrahedron Lett. 40 (1999) 2913
4. Liu S., Gu W.D.L., Ding X.-Z., Ujiki M., Adrian T.E., Soff G.A., and Silverman R.B. J. Med. Chem. 48 (2005) 3630
5. Ujiki M., Milam B., Ding X.-Z., Roginsky A.B., Salabat M.R., Talamonti M.S., Bell R.H., Gu W., Silverman R.B., and Adrian T.E. Biochem. Biophys. Res. Commun. 340 (2006) 1224
6. Styers T.J., Kekec A., Rodriguez R.A., Brown J.D., Cajica J., Pan P.-S., Parry E., Carroll C.L., Medina I., Corral R., Lapera S., Otrubova K., Pan C.-M., Mcguire K.L., and Mcalpine S.R. Bioorg. Med. Chem. 14 (2006) 5625
7. Rodriguez R.A., Pan P.-S., Pan C.-M., Ravula S., Lapera S.A., Singh E.K., Styers T.J., Brown J.D., Cajica J., Parry E., Otrubova K., and Mcalpine S.R. J. Org. Chem. 72 (2007) 1980
8. Pan P.S., Curtis F.A., Carroll C.L., Medina I., Liotta L.A., Sharples G., and Mcalpine S.R. Bioorg. Med. Chem. 14 (2006) 4731
9. Otrubova K., Styers T.J., Pan P.-S., Rodriguez R., Mcguire K.L., and Mcalpine S.R. Chem. Commun. (2006) 1033
10. Carroll C.L., Johnston J.V.C., Kekec A., Brown J.D., Parry E., Cajica J., Medina I., Cook K.M., Corral R., Pan P.-S., and Mcalpine S.R. Org. Lett. 7 (2005) 3481
11. Lee Y., and Silverman R.B. Org. Lett. 2 (2000) 3743
12. Gu W., Liu S., and Silverman R.B. Org. Lett. 4 (2002) 4171
13. Otrubova K., Lushington G.H., Vander Velde D., Mcguire K.L., and Mcalpine S.R. J. Med. Chem. 51 (2008) 530
14. Pan P.S., Mcguire K., and Mcalpine S.R. Bioorg. Med. Chem. Lett. 17 (2007) 5072
15. Amidon G.L., and Lee H.J. Annu. Rev. Pharmacol. Toxicol. 34 (1994) 321
16. Wenger R.M. Prog. Allergy 38 (1986) 46
17. Jarvis, L. M. Chem. Eng. News 2006.
18. Marx V. Chem. Eng. News 83 (2005) 17. http://pubs.acs.org/cen/business/83/i11/8311bus1.html http://pubs.acs.org/cen/business/83/i11/8311bus1.html
19. The most recent peptide drugs include Byetta from Amylin: http://www.drugs.com/pro/byetta.html, and from Aileron comes stapled peptides: http://pubs.acs.org/cen/coverstory/86/8622cover.html.
20. Singh E.K., Sellers R.P., Alexander L.D., and Mcalpine S.R. Curr. Opin. Drug Disc. Dev. 11 (2008) 544
21. Loffet A. Eur. Peptide Soc. 8 (2002) 1
22. Murr M.M., Sarr M.G., Oishi A.J., and Heerden J.A. CA Cancer J. Clin. 44 (1994) 304
23. Burris H.A., Moore M.J., Andersen J., Greem M.R., Rothenberg M.I., Modiano M.R., Cripps M.C., Portenoy R.K., Sotorniolo A.M., Tarassaoff P., Nelson R., Dorr F.A., Stephens C.D., and Vonhoff D. J. Clin. Oncol. 15 (1997) 2403
24. Sener S.F., Fremgen A., Menck H.R., and Winchester D.P. J. Am. Coll. Surg. 189 (1999) 1
25. Styers T.J., Rodriguez R.A., Pan P.-S., and Mcalpine S.R. Tetrahedron Lett. 47 (2006) 515
26. water), is a well established measure of the compound's hydrophilicity. Low hydrophilicities and therefore high log P values cause poor absorption or permeation. It has been shown for compounds to have a reasonable probability of being well absorbt their log P value must not be greater than 5.0. The distribution of calculated log P values of more than 3000 drugs on the market underlines this fact.
27. Lipinskis rules state that the ideal drug contains no more than five H-doners, no more than 10 H-acceptors, molecular weights of less than 500, and log P values ≤5.0.
28. 1H NMR were taken for cyclized peptides, but due to their complexity, they were not seen as the primary confirmation for cyclized compounds.) See Supplementary data for spectra.
29. Geistlinger T.R., Mcreynolds A.C., and Guy R.K. Chem. Biol. 11 (2004) 273 Multiple coupling agents reference
30. Bolla M.L., Azevedo E.V., Smith J.M., Taylor R.E., Ranjit D.K., Segall A.M., and Mcalpine S.R. Org. Lett. 5 (2003) 109
31. Two cell lines were chosen to provide evidence that our compounds were targeting a type of cancer, that is, pancreatic. PL-45 is a primary pancreatic ductial adenocarcinoma and BxPC3 is the cell line of choice for xenograft mouse model studies.
32. Chatterjee J., Mierke D.F., and Kessler H. J. Am. Chem. Soc. 128 (2006) 15164
33. Heller M., Sukopp M., Tsomaia N., John M., Mierke D.F., Reif B., and Kessler H. J. Am. Chem. Soc. 128 (2006) 13806
34. Zhang X., Nikiforovich G.V., and Marshall G.R. J. Med. Chem. 50 (2007) 2921
35. Tyndall J.D., Pfieiffer B., Abbenante G., and Fairlie D.P. Chem. Rev. 105 (2005) 793
36. Viles J.H., Mitchell J.B., Gough S.L., Doyle P.M., Harris C.J., Sadler P.J., and Thornton J.M. Eur. J. Biochem. 242 (1996) 352
37. See Supplementary data for C log P values.