Synthesis and antiangiogenic activity of new silybin galloyl esters

Journal of Medicinal Chemistry

Volumn 54, Issue 20, 2011, Pages 7397-7407

  Gažák, Radek ^a   Valentová, Kateřina ^b   Fuksová, Kateřina ^a   Marhol, Petr ^a   Kuzma, Marek ^a   Medina, Miguel Ángel ^c   Oborná, Ivana ^b   Ulrichová, Jitka ^b   Křen, Vladimír ^a  

^a INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^b PALACKÝ UNIVERSITY   (Czech Republic)

^c UNIVERSITY OF MÁLAGA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

20 O GALLOYLSILYBIN; 23 O (3',4',5' TRI O METHOXYMETHYLGALLOYL)SILYBIN; 23 O GALLOYLSILYBIN; 23 O TERT BUTYLDIMETHYLSILYL 3 O [(3',4',5' TRI O METHOXYMETHYL)GALLOYL]SILYBIN; 3 O GALLOYLSILYBIN; 5,7,20 TRI O BENZYL 23 O (TERT BUTYLDIMETHYLSILYL)SILYBIN; 7 O (3',4',5' TRI O BENZYLGALLOYL)SILYBIN; 7 O BENZYL 20 O [(3',4',5' TRI O BENZYL)GALLOYL]SILYBIN; 7 O GALLOYLSILYBIN; 7 O GALLOYLSILYBIN A; 7 O GALLOYLSILYBIN B; ANGIOGENESIS INHIBITOR; SILIBININ; SILYBIN GALLOYL ESTER; UNCLASSIFIED DRUG;

ANTIANGIOGENIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANGIOGENESIS INHIBITORS; CELL DIFFERENTIATION; CELL MOVEMENT; CELL PROLIFERATION; COLLAGEN; DRUG COMBINATIONS; ENDOTHELIAL CELLS; ESTERS; GALLIC ACID; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; LAMININ; PROTEOGLYCANS; SILYMARIN; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80054888276     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201034h     Document Type: Article

References (37)

1. Gažák, R.; Walterová, D.; Křen, V. Silybin and silymarin: new and emerging applications in medicine Curr. Med. Chem. 2007, 14, 315-338
2. Lee, D. Y.-W.; Liu, Y. Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, isolated from Silybum marianum (milk thistle) J. Nat. Prod. 2003, 66, 1171-1174 (Pubitemid 37204213)
3. Kim, N.-C.; Graf, T. N.; Sparacino, C. M.; Wani, M. C.; Wall, M. E. Complete isolation and characterization of silybins and isosilybins from milk thistle (Silybum marianum) Org. Biomol. Chem. 2003, 1, 1684-1689
4. Ding, T.-M.; Tian, S.-J.; Zhang, Z.-X.; Gu, D.-Z.; Chen, Y.-F.; Shi, Y.-H.; Sun, Z.-P. Determination of active component in silymarin by RP-LC and LC/MS J. Pharm. Biomed. Anal. 2001, 26, 155-161 (Pubitemid 32635293)
5. Marhol, P.; Gažák, R.; Bednár̂, P.; Křen, V. Narrow-bore core-shell particles and monolithic columns in the analysis of silybin diastereoisomers J. Sep. Sci. 2011, 34, 2206-2213
6. Monti, D.; Gažák, R.; Marhol, P.; Biedermann, D.; Purchartová, K.; Fedrigo, M.; Riva, S.; Křen, V. Enzymatic kinetic resolution of silybin diastereoisomers J. Nat. Prod. 2010, 73, 613-619
7. Gažák, R.; Marhol, P.; Purchartová, K.; Monti, D.; Biedermann, D.; Riva, S.; Cvak, L.; Křen, V. Large-scale separation of silybin diastereoisomers using lipases Process Biochem. 2010, 45, 1657-1663
8. Trouillas, P.; Marsal, P.; Svobodová, A.; Vostálová, J.; Gažák, R.; Hrbáĉ, J.; Sedmera, P.; Křen, V.; Lazzaroni, R.; Duroux, J.-L.; Walterová, D. Mechanism of the antioxidant action of silybin and 2,3-dehydrosilybin flavonolignans: a joint experimental and theoretical study J. Phys. Chem. A 2008, 112, 1054-1063 (Pubitemid 351288191)
9. Gažák, R.; Sedmera, P.; Vrbacký, M.; Vostálová, J.; Drahota, Z.; Marhol, P.; Walterová, D.; Křen, V. Molecular mechanisms of silybin and 2,3-dehydrosilybin antiradical activity: role of individual hydroxyl groups Free Radical Biol. Med. 2009, 46, 745-758
10. Payer, B. A.; Reiberger, T.; Rutter, K.; Beinhardt, S.; Staettermayer, A. F.; Peck-Radosavljevic, M.; Ferenci, P. Successful HCV eradication and inhibition of HIV replication by intravenous silibinin in an HIV-HCV coinfected patient J. Clin. Virol. 2010, 49, 131-133
11. Agarwal, R.; Agarwal, Ch.; Ichikawa, H.; Singh, R. P.; Aggarwal, B. B. Anticancer potential of silymarin: from bench to bed side Anticancer Res. 2006, 26, 4457-4498 (Pubitemid 46031522)
12. Singh, R. P.; Raina, K.; Sharma, G.; Agarwal, R. Silybin inhibits established prostate tumor growth, progression, invasion, and metastasis and suppresses tumor angiogenesis and epithelial-mesenchymal transition in transgenic adenocarcinoma of the mouse prostate model mice Clin. Cancer Res. 2008, 14, 7773-7780
13. Mateen, S.; Tyagi, A.; Agarwal, C.; Singh, R. P.; Agarwal, R. Silibinin inhibits human nonsmall cell lung cancer cell growth through cell-cycle arrest by modulating expression and function of key cell-cycle regulators Mol. Carcinog. 2010, 49, 247-258
14. Velmurugan, B.; Gangar, S. C.; Kaur, M.; Tyagi, A.; Deep, G.; Agarwal, R. Silibinin exerts sustained growth suppressive effect against human colon carcinoma SW480 xenograft by targeting multiple signaling molecules Pharm. Res. 2010, 27, 2085-2097
15. Deep, G.; Agarwal, R. Antimetastatic efficacy of silibinin: molecular mechanisms and therapeutic potential against cancer Cancer Metastasis Rev. 2010, 29, 447-463
16. Singh, R. P.; Dhanalakshmi, S.; Agarwal, C.; Agarwal, R. Silibinin strongly inhibits growth and survival of human endothelial cells via cell cycle arrest and downregulation of survivin, Akt and NF-kappaB: implications for angioprevention and antiangiogenic therapy Oncogene 2005, 24, 1188-1202 (Pubitemid 40313920)
17. Plíŝková, M.; Vondráĉek, J.; Křen, V.; Gažák, R.; Sedmera, P.; Walterová, D.; Psotová, J.; Ŝimánek, V.; Machala, M. Effects of silymarin flavonolignans and synthetic silybin derivatives on estrogen and aryl hydrocarbon receptor activation Toxicology 2005, 215, 80-89 (Pubitemid 41430276)
18. Davis-Searles, P. R.; Nakanishi, Y.; Kim, N.-Ch.; Graf, T. N.; Oberlies, N. H.; Wani, M. C.; Wall, M. E.; Agarwal, R.; Kroll, D. J. Milk thistle and prostate cancer: differential effects of pure flavonolignans from Silybum marianum on antiproliferative end points in human prostate carcinoma cells Cancer Res. 2005, 65, 4448-4457 (Pubitemid 40775685)
19. Deep, G.; Oberlies, N. H.; Kroll, D. J.; Agarwal, R. Identifying the differential effects of silymarin constituents on cell growth and cell cycle regulatory molecules in human prostate cancer cells Int. J. Cancer 2008, 123, 41-50 (Pubitemid 351705190)
20. Kondo, T.; Ohta, T.; Igura, K.; Hara, Y.; Kaji, K. Tea catechins inhibit angiogenesis in vitro, measured by human endothelial cell growth, migration and tube formation, through inhibition of VEGF receptor binding Cancer Lett. 2002, 180, 139-144 (Pubitemid 34327366)
21. Dẑubák, P.; Hajdúch, M.; Gažák, R.; Walterová, D.; Svobodová, A.; Psotová, J.; Sedmera, P.; Křen, V. New derivatives of silybin and 2,3-dehydrosilybin and their cytotoxic and P-glycoprotein modulatory activity Bioorg. Med. Chem. 2006, 14, 3793-3810
22. Gažák, R.; Purchartová, K.; Marhol, P.; Ẑivná, L.; Sedmera, P.; Valentová, K.; Kato, N.; Matsumura, H.; Kaihatsu, K.; Křen, V. Antioxidant and antiviral activities of silybin fatty acid conjugates Eur. J. Med. Chem. 2010, 45, 1059-1067
23. Wang, F.; Huang, K.; Yang, L.; Gong, J.; Tao, Q.; Li, H.; Zeng, S.; Wu, X.; Stöckigt, J.; Li, X.; Qu, J.; Zhao, Y. Preparation of C-23 esterified silybin derivatives and evaluation of their lipid peroxidation inhibitory and DNA protective properties Bioorg. Med. Chem. 2009, 17, 6380-6389
24. Theodosiou, E.; Katsoura, M. H.; Loutrari, H.; Purchartová, K.; Křen, V.; Kolisis, F. N.; Stamatis, H. Enzymatic preparation of acylated derivatives of silybin in organic and ionic liquid media and evaluation of their antitumor proliferative activity Biocatal. Biotransform. 2009, 27, 161-169
25. Ardhaoui, M.; Falcimaigne, A.; Engasser, J. M.; Moussou, P.; Pauly, G.; Ghoul, M. Enzymatic synthesis of new aromatic and aliphatic esters of flavonoids using Candida antarctica lipase as biocatalyst Biocatal. Biotransform. 2004, 22, 253-259 (Pubitemid 40057503)
26. Guyot, B.; Bosquette, B.; Pina, M.; Graille, J. Esterification of phenolic acids from green coffee with an immobilized lipase from Candida antarctica in solvent-free medium Biotechnol. Lett. 1997, 19, 529-532 (Pubitemid 27267843)
27. Kodera, Y.; Takahashi, K.; Nishimura, H.; Matshushima, A.; Saito, Y.; Inada, Y. Ester synthesis from substituted carboxylic acid catalyzed by polyethylene glycol-modified lipase from Candida cylindracea in benzene Biotechnol. Lett. 1986, 8, 881-884 (Pubitemid 17214522)
28. Otto, R. T.; Scheib, H.; Bornscheuer, U. T.; Pleiss, J.; Syldatk, C.; Schmid, R. D. Substrate specificity of lipase B from Candida antarctica in the synthesis of aryl-aliphatic glycolipids J. Mol. Catal. B: Enzym. 2000, 8, 201-211 (Pubitemid 30119847)
29. Shintre, M. S.; Ghadge, R. S.; Sawant, S. B. Lipolase catalysed synthesis of benzyl esters of fatty acids Biochem. Eng. J. 2002, 12, 131-141 (Pubitemid 35167949)
30. Takahashi, K.; Yoshimoto, T.; Ajima, A.; Tamaura, Y.; Inada, Y. Modified lipoprotein lipase catalyzes ester synthesis in benzene. Substrate specificity Enzyme 1984, 32, 235-240 (Pubitemid 15164168)
31. Gažák, R.; Svobodová, A.; Psotová, J.; Sedmera, P.; Pr̂ikrylová, V.; Walterová, D.; Křen, V. Oxidised derivatives of silybin and their antiradical and antioxidant activity Bioorg. Med. Chem. 2004, 12, 5677-5687 (Pubitemid 39304066)
32. Lee, D. Y. W.; Zhang, X.; Ji, X. S. Preparation of tritium-labeled silybin-A protectant for common liver diseases J. Labelled Compd. Radiopharm. 2006, 49, 1125-1130 (Pubitemid 46141421)
33. Aranda, E.; Owen, G. I. A semi-quantitative assay to screen for angiogenic compounds and compounds with angiogenic potential using the EA.hy926 endothelial cell line Biol. Res. 2009, 42, 377-389
34. Dehmlow, C.; Murawski, N.; de Groot, H. Scavenging of reactive oxygen species and inhibition of arachidonic acid metabolism by silibinin in human cells Life Sci. 1996, 58, 1591-1600 (Pubitemid 26129234)
35. Bergmeyer, H. U.; Bernt, E. Lactate Dehydrogenase: UV-Assay with Pyruvate and NADH; Academic Press: New York and London, 1974.
36. Sieuwerts, A. M.; Klijn, J. G. M.; Peters, H. A.; Foekens, J. A. The MTT tetrazolium salt assay scrutinized. How to use this assay reliably to measure metabolic-activity of cell-cultures in-vitro for the assessment of growth-characteristics, IC50-values and cell-survival Eur. J. Clin. Chem. Clin. Biochem. 1995, 33, 813-823
37. Martinez-Poveda, B.; Quesada, A. R.; Medina, M. A. Hypericin in the dark inhibits key steps of angiogenesis in vitro Eur. J. Pharmacol. 2005, 516, 97-103 (Pubitemid 40799344)