Prodrug of green tea epigallocatechin-3-gallate (Pro-EGCG) as a potent anti-angiogenesis agent for endometriosis in mice

Angiogenesis

Volumn 16, Issue 1, 2013, Pages 59-69

  Wang, Chi Chiu ^a,b   Xu, Hui ^a   Man, Gene Chi Wai ^a   Zhang, Tao ^a   Chu, Kai On ^a,b   Chu, Ching Yan ^a   Cheng, Jimmy Tin Yan ^a   Li, Gang ^a   He, Yi Xin ^a   Qin, Ling ^a   Lau, Tat San ^a   Kwong, Joseph ^a   Chan, Tak Hang ^c,d  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^b CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^c MCGILL UNIVERSITY   (Canada)

^d HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

Anti angiogenesis; Endometriosis; Epigallocatechin 3 gallate; Green tea

Indexed keywords

ALPHA TOCOPHEROL; EPIGALLOCATECHIN GALLATE; PRODRUG; SODIUM CHLORIDE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIANGIOGENIC ACTIVITY; ANTIOXIDANT ACTIVITY; APOPTOSIS; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; ENDOMETRIOSIS; ENDOMETRIUM; HISTOPATHOLOGY; IMAGING SYSTEM; MICRO-COMPUTED TOMOGRAPHY; MICROVASCULATURE; MOUSE; NONHUMAN; OVARY FOLLICLE; PRIORITY JOURNAL; TEA; TISSUE GROWTH; TISSUE TRANSPLANTATION; TREATMENT DURATION;

ANGIOGENESIS INHIBITORS; ANIMALS; APOPTOSIS; BIOLOGICAL AVAILABILITY; CATECHIN; ENDOMETRIOSIS; ENDOMETRIUM; FEMALE; MICE; NEOVASCULARIZATION, PATHOLOGIC; OVARIAN FOLLICLE; OXIDATION-REDUCTION; PRODRUGS; TEA;

MUS;

EID: 84871600501     PISSN: 09696970     EISSN: 15737209     Source Type: Journal    
DOI: 10.1007/s10456-012-9299-4     Document Type: Article

References (48)

1. Carmeliet P, Jain RK (2000) Angiogenesis in cancer and other diseases. Nature 407:249-257
2. Simons M (2005) Angiogenesis: where do we stand now? Circulation 111:1556-1566
3. Taylor RN, Lebovic DI, Mueller MD (2002) Angiogenic factors in endometriosis. Ann N Y Acad Sci 955:89-100
4. Groothuis PG, Nap AW, Winterhager E, Grümmer R (2005) Vascular development in endometriosis. Angiogenesis 8:147-156
5. Nisolle M, Casanas-Roux F, Anaf V, Mine JM, Donnez J (1993) Morphometric study of the stromal vascularization in peritoneal endometriosis. Fertil Steril 59:681-684
6. Becker CM, Rohwer N, Funakoshi T, Cramer T, Bernhardt W, Birsner A, Folkman J, D'Amato RJ (2008) 2-Methoxyestradiol inhibits hypoxia-inducible factor-1α and suppresses growth of lesions in a mouse model of endometriosis. Am J Pathol 172:534-544
7. Xu H, Lui WT, Chu CY, Ng PS, Wang CC, Rogers MS (2009) Anti-angiogenic effects of green tea catechin on an experimental endometriosis mouse model. Hum Reprod 24:608-618
8. Hull ML, Charnock-Jones DS, Chan CL, Bruner-Tran KL, Osteen KG, Tom BD, Fan TP, Smith SK (2003) Antiangiogenic agents are effective inhibitors of endometriosis. J Clin Endocrinol Metab 88:2889-2899
9. Heiss ML, Heiss RJ (ed) The story of tea, Ten Speed Press, Berkeley, 2007
10. Yamamoto T (ed) Chemistry and applications of green tea, CRC Press, Boca Raton, 1997
11. Nagle DG, Ferreira D, Zhou YD (2006) Epigallocatechin-3-gallate (EGCG): chemical and biomedical perspectives. Phytochemistry 67:1849-1855
12. Cao YH, Cao RH (1999) Angiogenesis inhibited by drinking tea. Nature 398:381
13. Xu H, Becker CM, Lui WT, Chu CY, Davis TN, Kung AL, Birsner AE, D'Amato RJ, Wai Man GC, Wang CC (2011) Green tea epigallocatechin-3-gallate inhibits angiogenesis and suppresses vascular endothelial growth factor C/vascular endothelial growth factor receptor 2 expression and signaling in experimental endometriosis in vivo. Fertil Steril 96:1021-1028
14. Chen Z, Zhu QY, Tsang D, Huang Y (2001) Degradation of green tea catechins in tea drinks. J Agric Food Chem 49:477-482
15. Lam WH, Kazi A, Kuhn DJ, Chow LM, Chan AS, Dou QP, Chan TH (2004) A potential prodrug for a green tea polyphenol proteasome inhibitor: evaluation of the peracetate ester of (-)-epigallocatechin gallate [(-)-EGCG]. Bioorg Med Chem 12:5587-5593
16. Nap AW, Griffioen AW, Dunselman GAJ, Bouma-Ter Steege JCA, Tijssen VJL, Evers JLH, Groothuis PG (2004) Antiangiogenesis therapy for endometriosis. J Clin Endocrinol Metab 89:1089-1095
17. Bruner-Tran KL, Osteen KG, Duleba AJ (2009) Simvastatin protects against the development of endometriosis in a nude mouse model. J Clin Endocrinol Metab 94:2489-2494
18. Sang S, Lambert JD, Hong J, Tian S, Lee MJ, Stark RE, Ho CT, Yang CS (2005) Synthesis and structure identification of thiol conjugates of (-)-epigallocatechin gallate and their urinary levels in mice. Chem Res Toxicol 18:1762-1769
19. Villayandre BM, Paniagua MA, Fernandez-Lopez A, Chinchetrua MA, Calvo P (2004) Effect of vitamin E treatment on N-methyl-d-aspartate receptor at different ages in the rat brain. Brain Res 1028:148-155
20. Song C, Xiang J, Tang J, Hirst DG, Zhou J, Chan KM, Li G (2011) Thymidine kinase gene modified bone marrow mesenchymal stem cells as vehicles for antitumor therapy. Hum Gene Ther 22:439-449
21. Sun MH, Leung KS, Zheng YP, Huang YP, Wang LK, Qin L, Leung AH, Chow SK, Cheung WH (2012) Three-dimensional high frequency power Doppler ultrasonography for the assessment of microvasculature during fracture healing in a rat model. J Orthop Res 30:137-143
22. Chu KO, Wang CC, Chu CY, Rogers MS, Choy KW, Pang CP (2004) Method for determination of catechins and catechin gallates in tissues by HPLC with coulometric array detection and selective solid-phase extraction. J Chromat B 810:187-195
23. Chu KO, Wang CC, Rogers MS, Choy KW, Pang CP (2004) Determination of catechins and catechin gallates in biological fluids by liquid chromatography with coulometric array detection and solid-phase extraction. Anal Chim Acta 510:69-76
24. Wang CC, Chu CY, Chu KO, Choy KW, Rogers MS, Khaw KS, Pang CP (2004) Trolox-equivalent antioxidant capacity (TEAC) assay versus oxygen radical absorbance capacity (ORAC) assay in plasma. Clin Chem 50:952-954
25. Graham HN (1992) Green tea composition, consumption and polyphenol chemistry. Preventive Med 21:334-350
26. Lea CH, Swoboda PAT (1957) The antioxidant action of some polyphenolic constituents of tea. Chem Ind 1073-1074
27. Zhu QY, Zhang A, Tsang D, Huang Y, Chen ZY (1997) Stability of green tea catechins. J Agric Food Chem 45:4624-4628
28. Lambert JD, Sang S, Hong J, Kwon SJ, Lee MJ, Ho CT, Yang CS (2006) Peracetylation as a means of enhancing in vitro bioactivity and bioavailability of epigallocatechin-3-gallate. Drug Metab Dispos 34:2111-2116
29. Fassina G, Vene R, Morini M, Minghelli S, Benelli R, Noonan DM, Albini A (2004) Mechanisms of inhibition of tumor angiogenesis and vascular tumor growth by epigallocatechin-3-gallate. Clin Cancer Res 10:4865-4873
30. Liao J, Yang GY, Park ES, Meng X, Sun Y, Jia D, Seril DN, Yang CS (2004) Inhibition of lung carcinogenesis and effects on angiogenesis and apoptosis in A/J mice by oral administration of green tea. Nutr Cancer 48:44-53
31. Lamy S, Gingras D, Beliveau R (2002) Green teas catechins inhibit vascular endothelial growth factor receptor phosphorylation. Cancer Res 62:381-385
32. Kojima-Yuasa A, Hua JJ, Kennedy DO, Matsui-Yuasa I (2003) Green tea extract inhibits angiogenesis of human umbilical vein endothelial cells through reduction of expression of VEGF receptors. Life Sci 73:1299-1313
33. Kondo T, Ohta T, Igura K, Hara Y, Kaji K (2002) Tea catechins inhibit angiogenesis in vitro, measured by human endothelial cell growth, migration and tube formation, through inhibition of VEGF receptor binding. Cancer Lett 180:139-144
34. Jung YD, Kim MS, Shin BA, Chay KO, Ahn BW, Liu W, Bucana CD, Gallick GE, Ellis LM (2001) EGCG, a major component of green tea, inhibits tumor growth by inhibiting VEGF induction in human colon carcinoma cells. Br J Cancer 84:844-850
35. Sartippour MR, Shao ZM, Heber D, Beatty P, Zhang L, Liu C, Ellis L, Liu W, Go VL, Brooks MN (2002) Green tea inhibits vascular endothelial growth factor (VEGF) induction in human breast cancer cells. J Nutr 132:2307-2311
36. Lee SC, Chan WK, Lee TW, Lam WH, Wang X, Chan TH, Wong YC (2008) Effect of a prodrug of the green tea polyphenol (-)-epigallocatechin-3-gallate on the growth of androgen-independent prostate cancer in vivo. Nutr Cancer 60:483-491
37. Kuhn D, Lam WH, Kazi A, Daniel KG, Song S, Chow LM, Chan TH, Dou QP (2005) Synthetic peracetate tea polyphenols as potent proteasome inhibitors and apoptosis inducers in human cancer cells. Front Biosci 10:1010-1023
38. Becker CM, Wright RD, Satchi-Fainaro R, Funakoshi T, Folkman J, Kung AL, D'Amato RJ (2006) A novel noninvasive model of endometriosis for monitoring the efficacy of antiangiogenesi therapy. Am J Pathol 168:2074-2084
39. Rice VM (2002) Conventional medical therapies for endometriosis. Ann N Y Acad Sci 955:343-352
40. Xu H, Wang CC (2010) Angiogenesis and anti-angiogenesis therapy of endometriosis. In: Mitchell LA (ed) Endometriosis: symptoms, diagnosis and treatments, Chapter 1. Nova Science, New York, pp 1-40
41. Dabrosin C, Gyorffy S, Margetts P, Ross C, Gauldie J (2002) Therapeutic effect of angiostatin gene transfer in a murine model of endometriosis. Am J Pathol 161:909-918
42. Yagyu T, Kobayashi H, Matsuzaki H, Wakahara K, Kondo T, Kurita N, Sekino H, Inagaki K, Suzuki M, Kanayama N, Terao T (2005) Thalidomide inhibits tumor necrosis factor-alpha-induced interleukin-8 expression in endometriotic stromal cells, possibly through suppression of nuclear factor-kappaB activation. J Clin Endocrinol Metab 90:3017-3021
43. Scarpellini F, Sbracia M, Lecchini S, Scarpellini L (2002) Anti-angiogenesis treatment with thalidomide in endometriosis: a pilot study. Fertil Steril 78:S87
44. Nyberg P, Xie L, Kalluri R (2005) Endogenous inhibitors of angiogenesis. Cancer Res 65:3967-3979
45. Klauber N, Rohan RM, Flynn E, D'Amato RJ (1997) Critical components of the female reproductive pathway are suppressed by the angiogenesis inhibitor AGM-1470. Nat Med 3:443-446
46. Becker CM, Sampson DA, Rupnick MA, Rohan RM, Efstathiou JA, Short SM, Taylor GA, Folkman J, D'Amato RJ (2005) Endostatin inhibits the growth of endometriotic lesions but does not affect fertility. Fertil Steril 84(Suppl 2):1144-1155
47. Kazi A, Wang Z, Kumar N, Falsetti SC, Chan TH, Dou QP (2004) Structure-activity relationships of synthetic analogs of (-)-epigallocatechin-3- gallate as proteasome inhibitors. Anticancer Res 24:943-954
48. Cao YH, Cao RH, Bråkenhielm E (2002) Antiangiogenic mechanisms of diet-derived polyphenols. J Nutr Biochem 13:380-390