Selective growth inhibition of human malignant melanoma cells by syringic acid-derived proteasome inhibitors

Cancer Cell International

Volumn 13, Issue 1, 2013, Pages

  Orabi, Khaled Y ^a   Abaza, Mohamed S ^a   El Sayed, Khalid A ^b   Elnagar, Ahmed Y ^c   Al Attiyah, Rajaa ^a   Guleri, Radhika P ^a  

^a KUWAIT UNIVERSITY   (Kuwait)

^b UNIVERSITY OF LOUISIANA AT MONROE   (United States)

^c UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

Anti mitogenic; Apoptosis; Molecular docking; Proteasome inhibitor; Rational design; Syringic acid; Tamarixaucheriana

Indexed keywords

3 ' METHOXYBENZYL 3,5 DIMETHOXY 4 (3 METHOXYBENZYLOXY)BENZOATE; 3 ,5 DIMETHOXYBENZYL 4 HYDROXY 3,5 DIMETHOXYBENZOATE; 3 METHOXYBENZYL BROMIDE; 3' METHOXYBENZYL 4 HYDROXY 3,5 DIMETHOXYBENZOATE; 3,5 DIMETHOXYBENZYL CHLORIDE; BENZOIC ACID DERIVATIVE; BENZYL 4 (BENZYLOXY) 3,5 DIMETHOXYBENZOATE; BENZYL 4 HYDROXY 3,5 DIMETHOXYBENZOATE; BENZYL BROMIDE; BORTEZOMIB; CHYMOTRYPSIN; LENALIDOMIDE; PLANT EXTRACT; SYRINGIC ACID; TAMARIX AUCHERIANA EXTRACT; TRYPTASE; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER; CANCER INHIBITION; CARBON NUCLEAR MAGNETIC RESONANCE; CELL CYCLE; CELL CYCLE G1 PHASE; CELL CYCLE G2 PHASE; CELL GROWTH; COLORECTAL CANCER; CRYSTAL STRUCTURE; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG SYNTHESIS; FIBROBLAST; FLOW CYTOMETRY; GROWTH INHIBITION; HUMAN; IN VITRO STUDY; MELANOMA; MELANOMA CELL; MITOGENICITY; MOLECULAR DOCKING; MOLECULAR MODEL; MULTIPLE MYELOMA; NONHODGKIN LYMPHOMA; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SCORING SYSTEM; TAMARIX AUCHERIANA; TUMOR CELL LINE;

EID: 84883015834     PISSN: None     EISSN: 14752867     Source Type: Journal    
DOI: 10.1186/1475-2867-13-82     Document Type: Article

References (54)

1. Parkin DM, Pisani P, Ferlay J. Global cancer statistics. CA Cancer J Clin 1999, 1:33-64.
2. Parkin DM, Bray F, Ferlay J, Pisani P. Estimating the world cancer burden: Globocan 2000. Int J Cancer 2001, 2:153-156.
3. Hanahan D, Weinberg RA. The hallmarks of cancer. Cell 2000, 1:57-70.
4. Zimmermann KC, Green DR. How cells die: apoptosis pathways. J Allergy Clin Immunol 2001, 4:99-103.
5. Goldberg AL. Protein degradation and protection against misfolded or damaged proteins. Nature 2003, 426:695-699.
6. Cecarini V, Gee J, Fioretti E, Amici M, Angeletti M, Eleuteri AM, Keller JN. Protein oxidation and cellular homeostasis on metabolism. Biochim Biophys Acta 2007, 1773:93-104. 10.1016/j.bbamcr.2006.08.039, 17023064.
7. Amici M, Cecarini V, Pettinari A, Bonfili L, Angeletti M, Barocci S, Biagetti M, Fioretti E, Eleuteri AM. Binding of aflatoxins to the 20S proteasome: effects on enzyme functionality and implications for oxidative stress and apoptosis. Biol Chem 2007, 388:107-117.
8. Li B, Dou PQ. Bax degradation by the ubiquitin/proteasome-dependent pathway: involvement in tumor survival and progression. Proc Natl Acad Sci U S A 2000, 8:3850-3855.
9. An B, Goldfarb RH, Siman R, Dou QP. Novel dipeptidyl proteasome inhibitors overcome Bcl-2 protective function and selectively accumulate the cyclin-dependent kinase inhibitor p27 and induce apoptosis in transformed, but not normal, human fibroblasts. Cell Death Differ 1998, 12:1062-1075.
10. Dou QP, Li B. Update Proteasome inhibitors as potential novel anticancer agents. Drug Resist 1999, 4:215-223. Update.
11. Kazi A, Urbizu DA, Kuhn DJ, Acebo AL, Jackson ER, Greenfelder GP. A natural musaceas plant extract inhibits proteasome activity and induces apoptosis selectively in human tumor and transformed, but not normal and non-transformed, cells. Int J Mol Med 2003, 6:879-887.
12. Admas J. The proteasome: A suitable anti-neoplastic target. Nat Rev Cancer 2004, 4:349-360. 10.1038/nrc1361, 15122206.
13. Richardson PG, Sonneveld P, Schuster MW. Bortezomib or high dose dexamethasone for relapsed multiple myeloma. N Engl J Med 2005, 352:2487-2498. 10.1056/NEJMoa043445, 15958804.
14. Goy A, Younes A, McLaughin P. Phase II study of proteasome inhibitor bortezomib in relapsed or refractory B-cell non-Hodgkin's lymphoma. J Clin Oncol 2005, 23:667-675. 10.1200/JCO.2005.03.108, 15613697.
15. Yang H, Landis-Piwowar KR, Chen D, Milacic V, Dou QP. Natural compounds with proteasome inhibitory activity for cancer prevention and treatment. Curr Protein Pept Sci 2008, 9:227-239. 10.2174/138920308784533998, 3303152, 18537678.
16. Orlowski RZ, Kuhn DJ. Proteasome inhibitors in cancer therapy: lessons from the first decade. Clin Cancer Res 2008, 14:1649-1657. 10.1158/1078-0432.CCR-07-2218, 18347166.
17. Gulder TA, Moore BS. Salinosporamide natural products: Potent 20 S proteasome inhibitors as promising cancer chemotherapeutics. Angew Chem Int Ed 2010, 49:9346-9367.
18. Mayer AM, Glaser KB, Cuevas C, Jacobs RS, Kem W, Little DR, McIntosch JM, Newman DJ, Potts BC, Shuster DE. The odyssey of marine pharmaceuticals: A current pipeline perspective. Trends Pharmacol Sci 2010, 31:255-265. 10.1016/j.tips.2010.02.005, 20363514.
19. Singh R, Sharma M, Joshi P, Rawat DS. Clinical status of anti-cancer agents derived from marine sources. Anti-Cancer Ag Med Chem 2008, 8:603-617.
20. Ojima I. Modern natural products chemistry and drug discovery. J Med Chem 2008, 51:2587-2588. 10.1021/jm701291u, 18393400.
21. Groll M, Koguchi Y, Huber R. Crystal structure of the 20S proteasome: TMC-95A complex: a non-covalent proteasome inhibitor. J Mol Biol 2001, 311:543-548. 10.1006/jmbi.2001.4869, 11493007.
22. Kohno J, Koguchi Y, Nishio M, Nakao K, Kuroda M, Shimizu R, Ohnuki T, Komatsubara S. Structures of TMC-95A - D: novel proteasome inhibitors from Apiosporamontagnei Sacc. TC 1093. J Org Chem 2000, 65:990-995. 10.1021/jo991375+, 10814045.
23. Kontoyianni M, McClellan LM, Sokol GS. Evaluation of docking performance: comparative data on docking algorithms. J Med Chem 2004, 47:558-565. 10.1021/jm0302997, 14736237.
24. Wang R, Lu Y, Wang S. Comparative evaluation of 11 scoring functions for molecular docking. J Med Chem 2003, 46:2287-2303. 10.1021/jm0203783, 12773034.
25. Pettinari A, Amici M, Cuccioloni M, Angeletti M, Fioretti E, Eleuteri AM. Effect of polyphenolic compounds on the proteolytic activities of constitutive and immuno-proteasomes. Antioxid Redox Signal 2006, 8:121-129. 10.1089/ars.2006.8.121, 16487045.
26. Dosenko VE, Nagibin VS, Tumanovskaia LV, Zagorii V, Moibenko AA. The influence of quercetin on the activity of purified 20S, 26S proteasome and proteasomal activity in isolated cardiomyocytes. Biomed Khim 2006, 52:138-145.
27. Kumar AP, Garcia GE, Ghosh R, Rajnarayanan RV, Alworth WL, Slaga TJ. 4-Hydroxy-3-methoxybenzoic acid methyl ester: a curcumin derivative targets Akt/NF kappa B cell survival signaling pathway: potential for prostate cancer management. Neoplasia 2003, 5:255-266. 1502412, 12869308.
28. Yin MC, Lin CC, Wu HC, Tsao SM, Hsu CK. Apoptotic effects of protocatechuic acid in human breast, lung, liver, cervix, and prostate cancer cells: potential mechanisms of action. J Agric Food Chem 2009, 57:6468-6473. 10.1021/jf9004466, 19601677.
29. Ho HH, Chang CS, Ho WC, Liao SY, Wu CH, Wang CJ. Anti-metastasis effects of gallic acid on gastric cancer cells involve inhibition of NF-kappaB activity and down-regulation of PI3K/AKT/small GTPase signals. Food Chem Toxicol 2010, 48:2508-2516. 10.1016/j.fct.2010.06.024, 20600540.
30. Kampa M, Alexaki VI, Notas G, Nifli AP, Nistikaki A, Hatzoglou A. Antiproliferative and apoptotic effects of selective phenolic acids on T47D human breast cancer cells: potential mechanisms of action. Breast Cancer Res 2004, 6:R63-R74. 10.1186/bcr752, 400651, 14979919.
31. Nam S, Smith DM, Dou QP. Ester bond-containing tea polyphenols potently inhibit proteasome activity in vitro and in vivo. J Biol Chem 2001, 276:13322-13330. 10.1074/jbc.M004209200, 11278274.
32. Smith DM, Wang Z, Kazi A, Li LH, Chan TH, Dou QP. Synthetic analogs of green tea polyphenols as proteasome inhibitors. Mol Med 2002, 8:382-392. 2040000, 12393936.
33. Wan SB, Chen D, Dou QP, Chan TH. Study of the green tea polyphenols catechin-3-gallate (CG) and epicatechin-3-gallate (ECG) as proteasome inhibitors. Bioorg Med Chem 2004, 12:3521-3527. 10.1016/j.bmc.2004.04.033, 15186836.
34. Chen D, Daniel KG, Chen MS, Kuhn DL, Landis-Piwowar KR, Dou QP. Dietary flavonoids as proteasome inhibitors and apoptosis inducers in human leukemia cells. Biochem Pharmacol 2005, 69:1421-1432. 10.1016/j.bcp.2005.02.022, 15857606.
35. Dikshit P, Goswami A, Mishra A, Chatterjee M, Jana NR. Curcumin induces stress response, neurite outgrowth and prevent NF-kappaB activation by inhibiting the proteasome function. Neurotox Res 2006, 9:29-37. 10.1007/BF03033305, 16464750.
36. Ali RE, Rattan SI. Curcumin's biphasic hormetic response on proteasome activity and heat-shock protein synthesis in human keratinocytes. Ann NY Acad Sci 2006, 1067:394-399. 10.1196/annals.1354.056, 16804017.
37. Si X, Wang Y, Wong J, Zhang J, McManus BM, Luo H. Dysregulation of the ubiquitin-proteasome system by curcumin suppresses coxsackievirus B3 replication. J Virol 2007, 81:3142-3150. 10.1128/JVI.02028-06, 1866032, 17229707.
38. Kazi A, Daniel KG, Smith DM, Kumar NB, Dou QP. Inhibition of the proteasome activity, a novel mechanism associated with the tumor cell apoptosis-inducing ability of genistein. Biochem Pharmacol 2003, 66:965-976. 10.1016/S0006-2952(03)00414-3, 12963483.
39. Kuhn D, Lam WH, Kazi A, Daniel KG, Song S, Chow LM, Chan TH, Dou QP. Synthetic peracetate tea polyphenols as potent proteasome inhibitors and apoptosis inducers in human cancer cells. Front Biosci 2005, 10:1010-1023. 10.2741/1595, 15769601.
40. Osanai K, Landis-Piwowar KR, Dou QP, Chan TH. A para-amino substituent on the O-ring of green tea polyphenol epigallocatechin-3-gallate as a novel proteasome inhibitor and cancer cell apoptosis inducer. Bioorg Med Chem 2007, 15:5076-5082. 10.1016/j.bmc.2007.05.041, 2963865, 17544279.
41. Ding Q, Keller JN. Proteasome inhibition in oxidative stress neurotoxicity: implications for heat shock proteins. J Neurochem 2001, 77:1010-1017. 10.1046/j.1471-4159.2001.00302.x, 11359866.
42. Okada K, Wangpoengtrakul C, Osawa T, Toyokuni S, Tanaka S, Uchida K. 4-hydroxy-2-nonenal-mediated impairment of intracellular proteolysis during oxidative stress. Identification of proteasomes as target molecules. J Biol Chem 1999, 274:23787-23793. 10.1074/jbc.274.34.23787, 10446139.
43. Chauhan D, Hideshima T, Anderson KC. Targeting proteasomes as therapy in multiple myeloma. Adv Exp Med Biol 2008, 615:251-260. 10.1007/978-1-4020-6554-5_12, 18437898.
44. Mukherjee S, Raje N, Schoonmaker JA, Liu JC, Hideshima T, Wein MN, Jones DC, Vallet S, Bouxsein ML, Pozzi S, Chhetri S, Seo YD, Aronson JP, Patel C, Fulciniti M, Purton LE, Glimcher LH, Lian JB, Stein G, Anderson KC, Scadden DT. Pharmacologic targeting of a stem/progenitor population in vivo is associated with enhanced bone regeneration in mice. J Clin Invest 2008, 118:491-504. 2213372, 18219387.
45. Bloom J, Amador V, Bartolini F, DeMartino G, Pagano M. Proteasome-mediated degradation of p21 via N-terminal ubiquitinylation. Cell 2003, 115:71-82. 10.1016/S0092-8674(03)00755-4, 14532004.
46. Roberto P, Bruce R, Michael W, Giulia C, Ilaria T, Dario F, Valentina G, Marta C, Silvia P, Massimo M, Gabriella P, Cecilia A, Nicoletta P, Mara C, di Stefano G, Paola N, de Paola F, Ivan S, Ilaria R, Riccardo F, Benedetta B, Giovanni C, Susan JB, Kathryn H, Hugh Z, Antonino N, Antonio P, Celia B, Huib O, Alberto B, et al. CEP-18770: A novel, orally active proteasome inhibitor with a tumor-selective pharmacologic profile competitive with bortezomib. Blood 2008, 111:2765-2775. 10.1182/blood-2007-07-100651, 18057228.
47. Chen D, Frezza M, Schmitt S, Kanwar J, Dou QP. Bortezomib as the first proteasome inhibitor anticancer drug: current status and future perspectives. Curr Cancer Drug Targets 2011, 11:239-253. 10.2174/156800911794519752, 3306611, 21247388.
48. Scagliotti G. Proteasome inhibitors in lung cancer. Crit Rev Oncol Hematol 2006, 58:177-189. 10.1016/j.critrevonc.2005.12.001, 16427303.
49. Nalepa G, Rolfe M, Harper JW. Drug discovery in the ubiquitin-proteasome system. Nat Rev Drug Discov 2006, 5:596-613. 10.1038/nrd2056, 16816840.
50. Kuhn DJ, Chen Q, Voorhees PM, Strader JS, Shennk KD, Sun CM, Demo SD, Bennett MK, van Leeuwen FW, Chanan-Khan AA, Orlowski RZ. Potent activity of carfilzomib, a novel, irreversible inhibitor of the ubiquitin-proteasome pathway, against preclinical models of multiple myeloma. Blood 2007, 110:3281-3290. 10.1182/blood-2007-01-065888, 2200918, 17591945.
51. Abaza MS. Augmentation of the anticancer effects of proteasome inhibitors by combination with sodium butyrate in human colorectal cancer cells. Exp Ther Med 2010, 1:675-693.
52. Tripos Associates SYBYL Molecular Modelling Software, version X 2009, St. Louis, MO: Tripos Associates, Technical tips online. Available at http://www.tripos.com. Accessed on August 1, 2012, Tripos Associates.
53. Welch W, Ruppert J, Jain A. Hammerhead: fast, fully automated docking of flexible ligands to protein binding sites. Chem Biol 1996, 3:449-462. 10.1016/S1074-5521(96)90093-9, 8807875.
54. Jain AN. Surflex: fully automatic flexible molecular docking using a molecular similarity-based search engine. J Med Chem 2003, 46:499-511. 10.1021/jm020406h, 12570372.