Semisynthesis of SY-1 for investigation of breast cancer stem cell selectivity of C-ring-modified salinomycin analogues

ACS Chemical Biology

Volumn 9, Issue 7, 2014, Pages 1587-1594

  Huang, Xiaoli ^a   Borgström, Björn ^a   Månsson, Linda ^a   Persson, Lo ^b   Oredsson, Stina ^a   Hegardt, Cecilia ^c   Strand, Daniel ^a  

^a LUND UNIVERSITY   (Sweden)

^b LUND UNIVERSITY   (Sweden)

^c LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

20 DEOXY SALINOMYCIN; CD24 ANTIGEN; CD44V ANTIGEN; HYDROXYL GROUP; NATURAL PRODUCT; PACLITAXEL; SALINOMYCIN; UNCLASSIFIED DRUG; 20-DEOXYSALINOMYCIN; ANTINEOPLASTIC AGENT; HERMES ANTIGEN; IONOPHORE; PYRAN DERIVATIVE;

ARTICLE; ASSAY; BREAST CANCER; CANCER CELL LINE; CONFORMATION; CONTROLLED STUDY; DOSE RESPONSE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; PHENOTYPE; PRIORITY JOURNAL; STEM CELL; BREAST; BREAST NEOPLASMS; CANCER STEM CELL; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; FEMALE; PATHOLOGY; TUMOR CELL LINE;

ANTIGENS, CD24; ANTIGENS, CD44; ANTINEOPLASTIC AGENTS; BREAST; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL PROLIFERATION; FEMALE; HUMANS; IONOPHORES; MODELS, MOLECULAR; NEOPLASTIC STEM CELLS; PYRANS;

EID: 84904544019     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb5002153     Document Type: Article

References (47)

1. Wender, P. A., Verma, V. A., Paxton, T. J., and Pillow, T. H. (2008) Function-oriented synthesis, step economy, and drug design Acc. Chem. Res. 41, 40-49
2. Lu, W., Roongsawang, N., and Mahmud, T. (2011) Biosynthetic studies and genetic engineering of pactamycin analogs with improved selectivity toward malarial parasites Chem. Biol. 18, 425-431
3. Parra, A., Lopez, P. E., and Garcia-Granados, A. (2010) Different pathways for the deoxygenation of the A-ring of natural triterpene compounds Nat. Prod. Res. 24, 177-196
4. Anderson, J. A., Lin, B. K., Williams, H. J., and Scott, A. I. (1988) Deoxygenation of phenolic natural products. Enzymatic conversion of emodin to chrysophanol J. Am. Chem. Soc. 110, 1623-1624 (Pubitemid 18066751)
5. Rasmussen, J. R., Slinger, C. J., Kordish, R. J., and Newman-Evans, D. D. (1981) Synthesis of deoxy sugars. Deoxygenation by treatment with N, N ′-thiocarbonyldiimidazole/tri- n -butylstannane J. Org. Chem. 46, 4843-4846
6. Wender, P. A., Kee, J.-M., and Warrington, J. M. (2008) Practical synthesis of prostratin, DPP, and their analogs, adjuvant leads against latent HIV Science 320, 649-652 (Pubitemid 351928343)
7. Beans, E. J., Fournogerakis, D., Gauntlett, C., Heumann, L. V., Kramer, R., Marsden, M. D., Murray, D., Chun, T.-W., Zack, J. A., and Wender, P. A. (2013) Highly potent, synthetically accessible prostratin analogs induce latent HIV expression in vitro and ex vivo Proc. Natl. Acad. Sci. U.S.A. 110, 11698-11703
8. Jordan, P. A. and Miller, S. J. (2012) An approach to the site-selective deoxygenation of hydroxy groups based on catalytic phosphoramidite transfer Angew. Chem., Int. Ed. 51, 2907-2911
9. Miyazaki, Y., Shibuya, M., Sugawara, H., Kawaguchi, O., Hirose, C., Nagatsu, J., and Esumi, S. (1974) Salinomycin, a new polyether antibiotic J. Antibiot. 27, 814-821
10. Gupta, P. B., Onder, T. T., Jiang, G., Tao, K., Kuperwasser, C., Weinberg, R. A., and Lander, E. S. (2009) Identification of selective inhibitors of cancer stem cells by high-throughput screening Cell 138, 645-659
11. Huczyński, A. (2012) Polyether ionophores-promising bioactive molecules for cancer therapy Bioorg. Med. Chem. Lett. 22, 7002-7010
12. Naujokat, C. and Steinhart, R. (2012) Salinomycin as a drug for targeting human cancer stem cells J. Biomed. Biotechnol. 10.1155/2012/950658
13. Gupta, P. B., Chaffer, C. L., and Weinberg, R. A. (2009) Cancer stem cells: Mirage or reality? Nat. Med. 15, 1010-1012
14. Frank, N. Y., Schatton, T., and Frank, M. H. (2010) The therapeutic promise of the cancer stem cell concept J. Clin. Invest. 120, 41-50
15. Nguyen, L. V., Vanner, R., Dirks, P., and Eaves, C. J. (2012) Cancer stem cells: An evolving concept Nature Rev. Cancer 12, 133-143
16. Sugihara, E. and Saya, H. (2013) Complexity of cancer stem cells Int. J. Cancer. 132, 1249-1259
17. Al-Hajj, M., Wicha, M. S., Benito-Hernandez, A., Morrison, S. J., and Clarke, M. F. (2003) Prospective identification of tumorigenic breast cancer cells Proc. Natl. Acad. Sci. U.S.A. 100, 3983-3988 (Pubitemid 36418143)
18. Antoszczak, M., Popiel, K., Stefańska, J., Wietrzyk, J., Maj, E., Janczak, J., Michalska, G., Brzezinski, B., and Huczyński, A. (2014) Synthesis, cytotoxicity, and antibacterial activity of new esters of polyether antibiotic-salinomycin Eur. J. Med. Chem. 10.1016/j.ejmech.2014.02.031
19. Antoszczak, M., Maj, E., Stefańska, J., Wietrzyk, J., Janczak, J., Brzezinski, B., and Huczyński, A. (2014) Synthesis, antiproliferative and antibacterial activity of new amides of salinomycin Bioorg. Med. Chem. Lett. 24, 1724-1729
20. Huczyński, A., Janczak, J., Antoszczak, M., Wietrzyk, J., Maj, E., and Brzezinski, B. (2012) Antiproliferative activity of salinomycin and its derivatives Bioorg. Med. Chem. Lett. 22, 7146-7150
21. Huczyński, A., Janczak, J., Stefańska, J., Antoszczak, M., and Brzezinski, B. (2012) Synthesis and antimicrobial activity of amide derivatives of polyether antibiotic-salinomycin Bioorg. Med. Chem. Lett. 22, 4697-4702
22. Borgström, B., Huang, X., Pošta, M., Hegardt, C., Oredsson, S., and Strand, D. (2013) Synthetic modification of salinomycin: Selective O -acylation and biological evaluation Chem. Commun. 49, 9944-9946
23. Miyazaki, Y., Kinashi, H., Otake, N., Mitani, M., and Yamanishi, T. (1976) Chemical modification and structure-activity correlation of salinomycin Agric. Biol. Chem. 40, 1633-1640
24. Yurkovich, M. E., Tyrakis, P. A., Hong, H., Sun, Y., Samborskyy, M., Kamiya, K., and Leadlay, P. F. (2012) A late-stage intermediate in salinomycin biosynthesis is revealed by specific mutation in the biosynthetic genecluster ChemBioChem. 13, 66-71
25. Westley, J. W., Blount, J. F., Evans, R. H., Jr., and Liu, C.-M. (1977) C-17 epimers of deoxy-(O -8)-salinomycin from Streptomyces albus (ATCC 21838) J. Antibiot. 30, 610-612 (Pubitemid 8167043)
26. Miyazaki, Y., Shibata, A., Tsuda, K., Kinashi, H., and Otake, N. (1978) Isolation, characterization, and structure of SY-1 (20-deoxysalinomycin) Agric. Biol. Chem. 42, 2129-2132
27. Miyazaki, Y., Mitani, M., and Otake, N. (1978) Ionophorous properties of SY-1 (20-deoxysalinomycin) in rat liver mitochondria Agric. Biol. Chem. 42, 2133-2138
28. Kawada, M., Sumi, S., Umezawa, K., Inouye, S., Sawa, T., and Seto, H. (1992) Circumvention of multidrug resistance in human carcinoma KB cells by polyether antibiotics J. Antibiot. 45, 556-562
29. Crich, D. and Quintero, L. (1989) Radical chemistry associated with the thiocarbonyl group Chem. Rev. 89, 1413-1432
30. Wustrow, D. J., Smith, W. J., III, and Wise, L. D. (1994) Selective deoxygenation of allylic alcohols and acetates by lithium perchlorate promoted triethylsilane reduction Tetrahedron Lett. 35, 61-64 (Pubitemid 24046118)
31. Watsuda, A., Okajima, H., Masuda, A., Kakefuda, A., Yoshimura, Y., and Ueda, T. (1992) Nucleosides and nucleotides. 104. Radical and palladium-catalyzed deoxygenation of the allylic alcohol systems in the sugar moiety of pyrimidine nucleosides Nucleosides Nucleotides 11, 197-226
32. Nicolaou, K. C., Nantermet, P. G., Ueno, H., Guy, R. K., Couladouros, E. A., and Sorensen, E. J. (1995) Total synthesis of taxol. 1. Retrosynthesis, degradation, and reconstitution J. Am. Chem. Soc. 117, 624-633
33. Kinashi, H., Otake, N., Yonehara, H., Sato, S., and Saito, Y. (1975) Studies on the ionophorous antibiotics. I. The crystal and molecular structure of salinomycin p -iodophenacyl ester Acta Crystallogr. B31, 2411-2415
34. 3B. Easy access to hydrocarbons from secondary alcohols Tetrahedron Lett. 29, 6125-6126
35. Evans, D. A., Kim, A. S., Metternich, R., and Novack, V. J. (1998) General strategies toward the syntheses of macrolide antibiotics. The total syntheses of 6-deoxyerythronolide B and oleandolide J. Am. Chem. Soc. 120, 5921-5942 (Pubitemid 28306976)
36. 3OH Z. Kristallogr. 218, 575-577
37. Schrödinger Release 2013-3, MacroModel, version 10.2, (2013), Schrödinger, LLC, New York.
38. Jönsson, G., Staaf, J., Olsson, E., Heidenblad, M., Vallon-Christersson, J., Osoegawa, K., de Jong, P., Oredsson, S., Ringnér, M., Höglund, M., and Borg, Å. (2007) High-resolution genomic profiles of breast cancer cell lines assessed by tiling BAC array comparative genomic hybridization Genes Chromosomes Cancer 46, 543-558 (Pubitemid 46649569)
39. Tanner, M., Kapanen, A. I., Junttila, T., Raheem, O., Grenman, S., Elo, J., Elenius, K., and Isola, J. (2004) Characterization of a novel cell line established from a patient with Herceptin-resistant breast cancer Mol. Cancer Ther. 3, 1585-1592 (Pubitemid 40136714)
40. Tomlinson, G. E., Chen, T. T.-L., Stastny, V. A., Virmani, A. K., Spillman, M. A., Tonk, V., Blum, J. L., Schneider, N. R., Wistuba, I. I., Shay, J. W., Minna, J. D., and Gazdar, A. F. (1998) Characterization of a breast cancer cell line derived from a germ-line BRCA1 mutation carrier Cancer Res. 58, 3237-3242 (Pubitemid 28371058)
41. Mao, J., Song, B., Shi, Y., Wang, B., Fan, S., Yu, X., Tang, J., and Li, L. (2013) ShRNA targeting Notch1 sensitizes breast cancer stem cell to paclitaxel Int. J. Biochem. Cell Biol. 45, 1064-1073
42. Dontu, G., Abdallah, W. M., Foley, J. M., Jackson, K. W., Clarke, M. F., Kawamura, M. J., and Wicha, M. S. (2003) In vitro propagation and transcriptional profiling of human mammary stem/progenitor cells Genes Dev. 17, 1253-1270 (Pubitemid 36583168)
43. Fillmore, C. M. and Kuperwasser, C. (2008) Human breast cancer cell lines contain stem-like cells that self-renew, give rise to phenotypically diverse progeny, and survive chemotherapy Breast Cancer Res. 10, R25
44. Ginestier, C., Hur, M. H., Charafe-Jauffret, E., Monville, F., Dutcher, J., Brown, M., Jacquemier, J., Viens, P., Kleer, C. G., Liu, S., Schott, A., Hayes, D., Birnbaum, D., Wicha, M. S., and Dontu, G. (2007) ALDH1 is a marker of normal and malignant human mammary stem cells and a predictor of poor clinical outcome Cell Stem Cell 1, 555-567 (Pubitemid 350056407)
45. Mosmann, T. (1983) Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays J. Immunol. Methods 65, 55-63 (Pubitemid 14203433)
46. Gerlier, D. and Thomasset, N. (1986) Use of MTT colorimetric assay to measure cell activation J. Immunol. Methods 94, 57-63 (Pubitemid 17186343)
47. Vega-Avila, E. and Pugsley, M. K. (2011) An overview of colorimetric assay methods used to assess survival or proliferation of mammalian cells Proc. West. Pharmacol. Soc. 54, 10-14