Reviews

Advances in Application of Marine Bioactive Peptides in Drug Development

  • Lu Wenyu ,
  • Yu Wenjing ,
  • Sun Dequn
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  • Marine College, Shandong University at Weihai, Weihai 264209

Received date: 2016-12-26

  Revised date: 2017-02-14

  Online published: 2017-03-31

Abstract

The ocean is the most resource-rich area on earth. The living environment of marine life is complicated, so that they form a special structure of the active substances. Coupled with the progress of science and technology, people are increasingly concerned about how to find new active substances from marine life, which makes the marine bioactive peptide is widely concerned. Bioactive peptides have a variety of activities, the study shows that these substances have antioxidant, antihypertensive, anti-virus and anti-tumor activity. It has the advantages of low toxicity, high targeting specificity and strong biological activity. At present, some of bioactive peptides extracted from sea cucumbers, conus, ascidians, sponges, marine fungi, molluscs, or analogues derived from these compounds have entered the market or clinical stage. The current research status of marine bioactive peptides is reviewed including their source, synthetic method, chemical structure, activity, mechanism, clinical efficacy and safety. Research prospects in this field are discussed.

Cite this article

Lu Wenyu , Yu Wenjing , Sun Dequn . Advances in Application of Marine Bioactive Peptides in Drug Development[J]. Chinese Journal of Organic Chemistry, 2017 , 37(7) : 1681 -1700 . DOI: 10.6023/cjoc201612062

References

[1] Cheung, R. C.; Ng, T. B.; Wong, J. H. Mar. Drugs 2015, 13, 4006.
[2] Jin, L.; Quan, C.; Hou, X.; Fan, S. Mar. Drugs 2016, 14, 76.
[3] (a) Suarez-Jimenez, G. M.; Burgos-Hernandez, A.; Ezquerra-Brauer, J. M. Mar. Drugs 2012, 10, 963.
(b) Ponnappan, N.; Budagavi, D. P.; Yadav, B. K.; Chugh, A. Probiotics Antimicro. Proteins 2015, 7, 75.
[4] (a) Lordan, S.; Ross, R. P.; Stanton, C. Mar. Drugs 2011, 9, 1056.
(b) Kim, S. K.; Wijesekara, I. J. Funct. Foods 2010, 2, 1.
[5] Romano, G.; Costantini, M.; Sansone, C.; Lauritano, C.; Ruocco, N.; Ianora, A. Mar. Environ. Res. 2017, 128, 58.
[6] Aneiros, A.; Garateix, A. J. Chromatogr. B:Anal. Technol. Biomed. Life Sci. 2004, 803, 41.
[7] Pan, X.; Zhao, Y. Q.; Hu, F. Y.; Wang, B. J. Funct. Foods 2016, 25, 220.
[8] Ngo, D. H.; Vo, T. S.; Ngo, D. N.; Wijesekara, I.; Kim, S. K. Int. J. Biol. Macromol. 2012, 51, 378.
[9] Castro, R. J. S. D.; Sato, H. H. Food Res. Int. 2015, 74, 185.
[10] Kang, H. K.; Seo, C. H.; Park, Y. Mar. Drugs 2015, 13, 618.
[11] Lee, J. K.; Jeon, J. K.; Byun, H. G. J. Funct. Foods 2014, 7, 381.
[12] Zhan, K. X.; Jiao, W. H.; Yang, F.; Li, J.; Wang, S. P.; Li, Y. S.; Han, B. N.; Lin, H. W. J. Nat. Prod. 2014, 77, 2678.
[13] Liu, C.-C.; Xu, X.-L.; Kong, Y.-L.; Zhang, X.-L.; Wang, C.; Zhuang, B.; Fan, Y.-F.; Zhang, G.-T.; Wang, C. Chin. J. Mar. Drugs 2015, 34, 73(in Chinese). (刘宸畅, 徐雪莲, 孙延龙, 张秀丽, 王聪, 庄波, 范迎方, 张广桃, 王成, 中国海洋药物, 2015, 34, 73.)
[14] (a) Pettit, G. R.; Kamano, Y.; Herald, C. L.; Tuinman, A. A.; Boettner, F. E.; Kizu, H.; Schmidt, J. M.; Baczynskyj, L.; Tomer, K. B.; Bontems, R. J. J. Am. Chem. Soc. 1987, 109, 6883.
(b) Pettit, G. R. Fortschritte der Chemie Organischer Naturstoffe:Progress in the Chemistry of Organic Natural Products, Vol. 70, Springer-Verlag, Wien, 1997, pp. 1~99.
(c) Pettit, G. R.; Kamano, Y.; Herald, C. L.; Fujii, Y.; Kizu, H.; Boyd, M. R.; Boettner, F. E.; Doubek, D. L.; Schmidt, J. M.; Chapuis, J. C. Tetrahedron 1993, 49, 9151.
[15] Miyazaki, K.; Kobayashi, M.; Natsume, T.; Gondo, M.; Mikami, T.; Sakakibara, K.; Tsukagoshi, S. Chem. Pharm. Bull. 1995, 43, 1706.
[16] Mordant, C.; Reymond, S.; Tone, H.; Lavergne, D.; Touati, R.; Hassine, B. B.; Ratovelomanana-Vidal, V.; Genet, J. P. Tetrahedron 2007, 63, 6115.
[17] (a) Kalemkerian, G. P.; Ou, X.; Adil, M. R.; Rosati, R.; Khoulani, M. M.; Madan, S. K.; Pettit, G. R. Cancer Chemother. Pharmacol. 1999, 43, 507.
(b) Pettit, R. K.; Pettit, G. R.; Hazen, K. C. Antimicrob. Agents Chemother. 1998, 42, 2961.
(c) Poncet, J.; Busquet, M.; Roux, F.; Pierr, A., Atassi, G.; Jouin, P. J. Med. Chem. 1998, 41, 1524.
[18] Perez, E. A.; Hillman, D. W.; Fishkin, P. A.; Krook, J. E.; Tan, W. W.; Kuriakose, P. A.; Alberts, S. R.; Dakhil, S. R. Invest. New Drugs 2005, 23, 257.
[19] Kindler, H. L.; Tothy, P. K.; Wolff, R.; Mccormack, R. A.; Abbruzzese, J. L.; Mani, S.; Wade-Oliver, K. T.; Vokes, E. E. Invest. New Drugs 2005, 23, 489.
[20] Maderna, A.; Doroski, M.; Subramanyam, C.; Porte, A.; Leverett, C. A.; Vetelino, B. C.; Chen, Z.; Risley, H.; Parris, K.; Pandit, J. J. Med. Chem. 2014, 57, 10527.
[21] (a) Diamantis, N.; Banerji, U. Br. J. Cancer 2016, 114, 362.
(b) Bakhtiar, R. Biotechnol. Lett. 2016, 38, 1.
(c) Gébleux, R.; Casi, G. Pharmacol. Ther. 2016, 167, 48
[22] Thomas, A.; Teicher, B. A.; Hassan, R. Lancet Oncol. 2016, 17, e254.
[23] Wang, Y.-M.; Hao, B.-J.; Zhong, W.; Li, S. J. Int. Pharm. Res. 2015, 42, 427(in Chinese). (王彦明, 郝伯钧, 钟武, 周辛波, 李松, 国际药学研究杂志, 2015, 42, 427.)
[24] Newman, D. J.; Cragg, G. M. Mar. Drugs 2014, 12, 255.
[25] Senter, P. D.; Sievers, E. L. Nat. Biotechnol. 2012, 30, 631.
[26] (a) Ansell, S. M. Blood 2014, 124, 3197.
(b) Deng, C.; Pan, B.; O'Connor, O. A. Clin. Cancer Res. 2013, 19, 22.
(c) Okeley, N. M.; Miyamoto, J. B.; Zhang, X.; Sanderson, R. J.; Benjamin, D. R.; Sievers, E. L.; Senter, P. D.; Alley, S. C. Clin. Cancer Res. 2010, 16, 888.
[27] (a) Francisco, J. A.; Cerveny, C. G.; Meyer, D. L.; Mixan, B. J.; Klussman, K.; Chace, D. F.; Rejniak, S. X.; Gordon, K. A.; Deblanc, R.; Toki, B. E.; Law, C. L. Blood 2003, 102, 1458.
(b) Pettit, G. R.; Barkoczy, J. US 5635483, 1997[Chem. Abstr. 1997, 122, 133848].
[28] Moskowitz, C. H.; Nademanee, A.; Masszi, T.; Agura, E.; Holowiecki, J.; Abidi, M. H.; Chen, A. I.; Stiff, P.; Gianni, A. M.; Carella, A. Lancet 2015, 385, 1853.
[29] Reilly, E. B.; Phillips, A. C.; Boghaert, E. R.; Vaidya, K. S.; Mitten, M. J.; Norvell, S.; Falls, H. D.; Devries, P. J.; Cheng, D.; Meulbroek, J. A. Mol. Cancer Ther. 2016, 15, 661.
[30] https://www.fda.gov/
[31] Reilly, E. B.; Phillips, A. C.; Buchanan, F. G.; Kingsbury, G.; Zhang, Y.; Meulbroek, J. A.; Cole, T. B.; Devries, P. J.; Falls, H. D.; Beam, C. Mol. Cancer Ther. 2015, 14, 1141.
[32] Doronina, S. O.; Mendelsohn, B. A.; Bovee, T. D.; Cerveny, C. G.; Alley, S. C.; Meyer, D. L.; Oflazoglu, E.; Toki, B. E.; Sanderson, R. J.; Zabinski, R. F. Bioconjugate Chem. 2006, 17, 114.
[33] Gan, H. K.; Fichtel, L.; Lassman, A. B.; Merrell, R.; Van, D. B., Martin J.; Kumthekar, P.; Scott, A. M.; Pedersen, M.; Gomez, E.; Fischer, J. D. J. Clinical Oncol. 2014, 32, 2021
[34] (a) Vaklavas, C.; Forero, A. BioDrugs 2014, 28, 253.
(b) Roth, M.; Barris, D. M.; Piperdi, S.; Kuo, V.; Everts, S.; Geller, D.; Houghton, P.; Kolb, E. A.; Hawthorne, T.; Gill, J. Pediatr. Blood Cancer 2016, 63, 32.
(c) Keir, C. H.; Vahdat, L. T. Expert Opin. Biol. Ther. 2012, 12, 259.
[35] Yardley, D. A.; Weaver, R.; Melisko, M. E.; Saleh, M. N.; Arena, F. P.; Forero, A.; Cigler, T.; Stopeck, A.; Citrin, D.; Oliff, I. J. Clin. Oncol. 2015, 33, 1609.
[36] Mehta, A.; Forero-Torres, A. Curr. Oncol. Rep. 2015, 17, 1.
[37] Palanca-Wessels, M. C. A.; Czuczman, M.; Salles, G.; Assouline, S.; Sehn, L. H.; Flinn, I.; Patel, M. R.; Sangha, R.; Hagenbeek, A.; Advani, R. Lancet Oncol. 2015, 16, 704.
[38] (a) Pereira, D. S.; Guevara, C. I.; Jin, L.; Mbong, N.; Verlinsky, A.; Hsu, S. J.; Aviña, H.; Karki, S.; Abad, J. D.; Yang, P. Mol. Cancer Ther. 2015, 14, 1650.
(b) Lapalombella, R.; Yeh, Y. Y.; Wang, L.; Ramanunni, A.; Rafiq, S.; Jha, S.; Staubli, J.; Lucas, D. M.; Mani, R.; Herman, S. E. M. Cancer Cell 2012, 21, 694.
[39] Sawas, A.; Savage, K. J.; Perez, R.; Advani, R. H.; Butturini, A.; Lackey, J.; Trave, F.; Anand, B.; Huang, Y.; Reyno, L. Nature 2015, 128, 413.
[40] Akashi, Y.; Okamoto, I.; Suzuki, M.; Tamura, K.; Iwasa, T.; Hisada, S.; Satoh, T.; Nakagawa, K.; Ono, K.; Fukuoka, M. Br. J. Cancer 2007, 96, 1532.
[41] Otani, M.; Natsume, T.; Watanabe, J. I.; Kobayashi, M.; Murakoshi, M.; Mikami, T.; Nakayama, T. Cancer Sci. 2000, 91, 837.
[42] Watanabe, J.; Natsume, T.; Fujio, N.; Miyasaka, K.; Kobayashi, M. Apoptosis 2000, 5, 345.
[43] Patel, S.; Keohan, M. L.; Saif, M. W.; Rushing, D.; Baez, L.; Feit, K.; Dejager, R.; Anderson, S. Cancer 2006, 107, 2881.
[44] Riely, G. J.; Gadgeel, S.; Rothman, I.; Saidman, B.; Sabbath, K.; Feit, K.; Kris, M. G.; Rizvi, N. A. Lung Cancer 2007, 55, 181.
[45] Jordan, M. A.; Walker, D.; Arruda, M. D.; Barlozzari, T.; Panda, D. Biochemistry 1999, 37, 17571.
[46] (a) Ray, A.; Okouneva, T.; Manna, T.; Miller, H. P.; Schmid, S.; Arthaud, L.; Luduena, R.; Jordan, M. A.; Wilson, L. Cancer Res. 2007, 67, 3767.
(b) Bai, R.; Edler, M. C.; Bonate, P. L.; Copeland, T. D.; Pettit, G. R.; Ludueña, R. F.; Hamel, E. Mol. Pharmacol. 2009, 75, 218.
[47] Mita, A. C.; Hammond, L. A.; Bonate, P. L.; Weiss, G.; Mccreery, H.; Syed, S.; Garrison, M.; Chu, Q. S.; Debono, J. S.; Jones, C. B. Clin. Cancer Res. 2006, 12, 5207.
[48] De, A. M.; Cocchiaro, C. A.; Nelson, C. M.; Grinnell, C. M.; Janssen, B.; Haupt, A.; Barlozzari, T. Cancer Res. 1995, 55, 3085.
[49] Kerbrat, P.; Dieras, V.; Pavlidis, N.; Ravaud, A.; Wanders, J.; Fumoleau, P. Eur. J. Cancer 2003, 39, 317.
[50] (a) Schroeder, C. I.; Craik, D. J. Future Med. Chem. 2012, 4, 1243.
(b) Vetter, I.; Lewis, R. J. Curr. Top. Med. Chem. 2012, 12, 1546.
[51] (a) Durek, T.; Craik, D. J. Expert Opin. Ther. Pat. 2015, 25, 1.
(b) Livett, B. G.; Gayler, K. R.; Khalil, Z. Curr. Med. Chem. 2004, 11, 1715.
[52] Schmidtko, A.; Lajevardi, J.; Freynhagen, R.; Geisslinger, G. Lancet 2010, 375, 1569.
[53] Dong, S.-L.; Cao, S.; Chen, Q.; Chang, M.; Peng, Y.-L. CN 103242441, 2013[Chem. Abstr. 2013, 159, 371454].
[54] Miljanich, G. P. Curr. Med. Chem. 2004, 11, 3029.
[55] Williams, J. A.; Day, M.; Heavner, J. E. Expert Opin. Pharmacother. 2008, 9, 1575.
[56] Staats, P. S.; Yearwood, T.; Charapata, S. G.; Presley, R. W.; Wallace, M. S.; Byas-Smith, M.; Fisher, R.; Bryce, D. A.; Mangieri, E. A.; Luther, R. R. J. Am. Med. Assoc. 2004, 291, 63.
[57] Vera, M. D.; Joullié, M. M. Med. Res. Rev. 2002, 22, 102.
[58] Geldof, A. A.; Mastbergen, S. C.; Henrar, R. E.; Faircloth, G. T. Cancer Chemother. Pharmacol. 1999, 44, 312.
[59] Stewart, J. A.; Low, J. B.; Roberts, J. D.; Blow, A. Cancer 1991, 68, 2550.
[60] Hamada, Y.; Kondo, Y.; Shibata, M.; Shioiri, T. J. Am. Chem. Soc. 1989, 111, 669.
[61] Kucuk, O.; Young, M. L.; Habermann, T. M.; Wolf, B. C.; Jimeno, J.; Cassileth, P. A. Am. J. Clin. Oncol. 2000, 23, 273.
[62] Danu, A.; Willekens, C.; Ribrag, V. Expert Opin. Orphan Drugs 2013, 1, 569.
[63] (a) Galmarini, C. M.; D'Incalci, M.; Allavena, P. Mar. Drugs 2014, 12, 719.
(b) Mitsiades, C. S.; Ocio, E. M.; Pandiella, A.; Maiso, P.; Gajate, C.; Garayoa, M.; Vilanova, D.; Montero, J. C.; Mitsiades, N.; Mcmullan, C. J. Cancer Res. 2008, 68, 5216.
[64] Jou, G.; Gonzalez, I.; Albericio, F.; Lloyd-Williams, P.; Giralt, E. J. Org. Chem. 1997, 62, 354.
[65] Mateos, M. V.; Cibeira, M. T.; Richardson, P. G.; Prosper, F.; Oriol, A.; De, l. R. J.; Lahuerta, J. J.; García-Sanz, R.; Extremera, S.; Szyldergemajn, S. Clin. Cancer Res. 2010, 16, 3260.
[66] Rawat, D. S.; Joshi, M. C.; Joshi, P.; Atheaya, H. Anti-Cancer Agents Med. Chem. 2006, 6, 33.
[67] (a) Anderson, H. J.; Coleman, J. E.; Andersen, R. J.; Roberge, M. Cancer Chemother. Pharmacol. 1996, 39, 223.
(b) Coleman, J. E.; Silva, E. D. D.; Kong, F.; Andersen, R. J.; Allen, T. M. J. Nat. Prod. 1996, 27, 10653.
[68] Nieman, J. A.; Coleman, J. E.; Wallace, D. J.; Piers, E.; Lim, L. Y.; Roberge, M.; Andersen, R. J. J. Nat. Prod. 2003, 66, 183.
[69] Niu, C.; Ho, D. M.; Williamson, R. T.; Zask, A.; Ayral-Kaloustian, S. Bioorg. Med. Chem. Lett. 2010, 20, 1535.
[70] Zask, A.; Birnberg, G.; Cheung, K.; Kaplan, J.; Niu, C.; Norton, E.; Suayan, R.; Yamashita, A.; Cole, D.; Tang, Z.; Krishnamurthy, G.; Williamson, R.; Khafizova, G.; Musto, S.; Hernandez, R.; Annable, T.; Yang, X.; Discafani, C.; Beyer, C.; Greenberger, L. M.; Loganzo, F.; Ayral-Kaloustian, S. J. Med. Chem. 2004, 47, 4774.
[71] Loganzo, F.; Discafani, C. M.; Annable, T.; Beyer, C.; Musto, S.; Hari, M.; Tan, X.; Hardy, C.; Hernandez, R.; Baxter, M. Cancer Res. 2003, 63, 1838.
[72] (a) Vashist, Y. K.; Tiffon, C.; Stoupis, C.; Redaelli, C. A. World J. Gastroenterol. 2006, 12, 6771.
(b) Hadaschik, B. A.; Ettinger, S.; Sowery, R. D.; Zoubeidi, A.; Andersen, R. J.; Roberge, M.; Gleave, M. E. Int. J. Cancer 2008, 122, 2368.
(c) Hadaschik, B. A.; Adomat, H.; Fazli, L.; Fradet, Y.; Andersen, R. J.; Gleave, M. E.; So, A. I. Clin. Cancer Res. 2008, 14, 1510.
[73] Kuznetsov, G.; Tendyke, K.; Towle, M. J.; Cheng, H.; Liu, J.; Marsh, J. P.; Schiller, S. E.; Spyvee, M. R.; Yang, H.; Seletsky, B. M. Mol. Cancer Ther. 2009, 8, 2852.
[74] Kowalczyk, J. J.; Kuznetsov, G.; Schiller, S.; Seletsky, B. M.; Spyvee, M.; Yang, H. WO 2003082268, 2003[Chem. Abstr. 2003, 139, 308008].
[75] Rochalima, C. M.; Bayraktar, S.; Macintyre, J.; Raez, L.; Flores, A. M.; Ferrell, A.; Rubin, E. H.; Poplin, E. A.; Tan, A. R.; Lucarelli, A. Cancer 2012, 118, 4262.
[76] (a) Yamazaki, Y.; Tanaka, K.; Nicholson, B.; Deyanatyazdi, G.; Potts, B.; Yoshida, T.; Oda, A.; Kitagawa, T.; Orikasa, S.; Kiso, Y. J. Med. Chem. 2012, 55, 1056.
(b) Hayashi, Y.; Orikasa, S.; Tanaka, K.; Kanoh, K.; Kiso, Y. J. Org. Chem. 2000, 65, 8402.
[77] Kingston, D. G. I. J. Nat. Prod. 2009, 72, 507.
[78] Yamazaki, Y.; Sumikura, M.; Hidaka, K.; Yasui, H.; Kiso, Y.; Yakushiji, F.; Hayashi, Y. Bioorg. Med. Chem. 2010, 18, 3169.
[79] Nicholson, B.; Lloyd, G. K.; Miller, B. R.; Palladino, M. A.; Kiso, Y.; Hayashi, Y.; Neuteboom, S. T. Anti-Cancer Drugs 2006, 17, 25.
[80] Ferrer, E.; Bolos, J.; Castañer, R. Drugs Future 2010, 35, 11.
[81] Heist, R. S.; Aren, O. R.; Mita, A. C.; Polikoff, J.; Bazhenova, L.; Lloyd, G. K.; Mikrut, W.; Reich, S. D.; Spear, M. A.; Huang, L. J. Clin. Oncol. 2014, 8054.
[82] (a) Stokvis, E.; Rosing, H.; López-Lázaro, L.; Rodriguez, I.; Jimeno, J. M.; Supko, J. G.; Schellens, J. H.; Beijnen, J. H. J. Mass Spectrom. 2002, 37, 992.
(b) Lopezmacia, A.; Jimenez, J. C.; Royo, M.; Giralt, E.; Albericio, F. J. Am. Chem. Soc. 2001, 123, 11398.
[83] Janmaat, M. L.; Rodriguez, J. A.; Jimeno, J.; Kruyt, F. A.; Giaccone, G. Mol. Pharmacol. 2005, 68, 502.
[84] Suarez, Y.; Gonzalez, L.; Cuadrado, A.; Berciano, M.; Lafarga, M.; Munoz, A. Mol. Cancer Ther. 2003, 2, 863.
[85] Martin-Algarra, S.; Espinosa, E.; Rubio, J.; Lopez Lopez, J. J.; Manzano, J. L.; Carrion, L. A.; Plazaola, A.; Tanovic, A.; Pazares, L. Eur. J. Cancer 2009, 45, 732.
[86] Coronado, C.; Galmarini, C. M.; Alfaro, V.; Yovine, A. Drugs Future 2010, 35, 287.
[87] (a) Teixido, C.; Mares, R.; Aracil, M.; Ramon, Y. C. S.; Hernandezlosa, J. PloS One 2013, 8, e53645.
(b) Serova, M.; Gramont, A. D.; Bieche, I.; Riveiro, M. E.; Galmarini, C. M.; Aracil, M.; Jimeno, J.; Faivre, S.; Raymond, E. Mar. Drugs 2013, 11, 944.
(c) Molinaguijarro, J. M.; Garcia, C.; Macias, A.; Moreno, C.; Reyes, F.; Martínezleal, J. F.; Fernandez, R.; Martinez, V.; Valenzuela, C.; Lillo, M. P. PloS One 2015, 10, e0140782.
(d) Hajdu, T. Ageing Soc. 2013, 20, 633.
[88] Petty, R.; Anthoney, A.; Metges, J. P.; Alsina, M.; Gonçalves, A.; Brown, J.; Montagut, C.; Gunzer, K.; Laus, G.; Iglesias Dios, J. L. Cancer Chemother. Pharmacol. 2016, 77, 819.

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