Skip to main content

P-gp Inhibitory Activity from Marine Sponges, Tunicates and Algae

  • Chapter
  • First Online:
Handbook of Anticancer Drugs from Marine Origin

Abstract

The only effective therapy for metastasis in cancer patients is chemotherapy, which all too frequently fails due to innate or acquired multi-drug resistance (MDR). Historically, ATP binding cassette (ABC) transporters, such as P-glycoprotein (P-gp), are recognized as the major culprits responsible for MDR. Over-expressing of P-gp in cancer cells, can lead to premature efflux of clinical chemotherapeutic agents and correlate with poor chemotherapeutic outcome and relapse of some cancers. The most likely strategy to overcome MDR is to search for inhibitors from natural products. With unique and novel chemical structures, marine-derived metabolites are an attractive new resource, to prime the search for new P-gp inhibitors. This chapter summarizes P-gp inhibitory activity in marine natural products (MNPs) and validates that MNPs can deliver new ABC transporter inhibitor scaffolds.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Morgan G, Ward R, Barton M (2004) Clin Oncol (R Coll Radiol) 16:549

    Google Scholar 

  2. Longley DB, Johnston PG (2005) J Pathol 205:275

    CAS  Google Scholar 

  3. Szakacs G, Paterson JK, Ludwig JA, Booth-Genthe C, Gottesman MM (2006) Nat Rev Drug Discov 5:219

    CAS  Google Scholar 

  4. Takano M, Otani Y, Tanda M, Kawami M, Nagai J, Yumoto R (2009) Drug Metab Pharmacokinet 24:418

    CAS  Google Scholar 

  5. Guo W, Healey JH, Meyers PA, Ladanyi M, Huvos AG, Bertino JR, Gorlick R (1999) Clin Cancer Res 5:621

    CAS  Google Scholar 

  6. Rodrigues AS, Dinis J, Gromicho M, Martins C, Laires A, Rueff J (2012) Curr Pharm Biotechnol 13:651

    CAS  Google Scholar 

  7. Dano K (1973) Biochim Biophys Acta 323:466

    CAS  Google Scholar 

  8. Juliano RL, Ling V (1976) Biochim Biophys Acta 455:152

    CAS  Google Scholar 

  9. Dean M, Rzhetsky A, Allikmets R (2001) Genome Res 11:1156

    CAS  Google Scholar 

  10. Leslie EM, Deeley RG, Cole SP (2005) Toxicol Appl Pharmacol 204:216

    CAS  Google Scholar 

  11. Chan HSL, Haddad G, Thorner PS, Deboer G, Lin YP, Ondrusek N, Yeger H, Ling VN (1991) Engl J Med 325:1608

    CAS  Google Scholar 

  12. Penson RT, Oliva E, Skates SJ, Glyptis T, Fuller AF, Goodman A, Seiden MV (2004) Gynecol Oncol 93:98

    CAS  Google Scholar 

  13. Steinbach D, Sell W, Voigt A, Hermann J, Zintl F, Sauerbrey A (2002) Leukemia 16:1443

    CAS  Google Scholar 

  14. George JDG (1979) JJ marine life. Wiley, New York

    Google Scholar 

  15. Barnes RD (1980) Invertebrate zoology. WB Sauders Company, Philadelphia

    Google Scholar 

  16. Faulkner DJ, Ghiselin MT (1983) Mar Ecol Prog Ser 13:295

    Google Scholar 

  17. Coll JC, Bowden BF, Tapiolas DM, Willis RH, Djura P, Streamer M, Trott L (1985) Tetrahedron 41:1085

    CAS  Google Scholar 

  18. Spitaler M, Utz I, Hilbe W, Hofmann J, Grunicke HH (1998) Biochem Pharmacol 56:861

    CAS  Google Scholar 

  19. Aoki S, Okano M, Matsui K, Itoh T, Satari R, Akiyama S, Kobayashi M (2001) Tetrahedron 57:8951

    CAS  Google Scholar 

  20. Tanaka J, Trianto A, Musman M, Issa HH, Ohtani II, Ichiba T, Higa T, Yoshida WY, Scheuer PJ (2002) Tetrahedron 58:6259

    CAS  Google Scholar 

  21. Sarkadi B, Homolya L, Szakacs G, Varadi A (2006) Physiol Rev 86:1179

    CAS  Google Scholar 

  22. Deeley RG, Westlake C, Cole SPC (2006) Physiol Rev 86:849

    CAS  Google Scholar 

  23. Seeger MA, van Veen HW (2009) Biochim Biophys Acta Proteins Proteom 1794:725

    CAS  Google Scholar 

  24. Aller SG, Yu J, Ward A, Weng Y, Chittaboina S, Zhuo R, Harrell PM, Trinh YT, Zhang Q, Urbatsch IL, Chang G (2009) Science 323:1718

    CAS  Google Scholar 

  25. Gutmann DA, Ward A, Urbatsch IL, Chang G, van Veen HW (2010) Trends Biochem Sci 35:36

    CAS  Google Scholar 

  26. Bell DR, Gerlach JH, Kartner N, Buick RN, Ling V (1985) J Clin Oncol 3:311

    CAS  Google Scholar 

  27. Evers R, Zaman GJ, van Deemter L, Jansen H, Calafat J, Oomen LC, Oude Elferink RP, Borst P, Schinkel AH (1996) J Clin Invest 97:1211

    CAS  Google Scholar 

  28. Germann UA, Willingham MC, Pastan I, Gottesman MM (1990) Biochemistry 29:2295

    CAS  Google Scholar 

  29. Wu CP, Calcagno AM, Ambudkar SV (2008) Curr Mol Pharmacol 1:93

    CAS  Google Scholar 

  30. Shukla S, Wu CP, Ambudkar SV (2008) Expert Opin Drug Metab Toxicol 4:205

    CAS  Google Scholar 

  31. Chan HS, DeBoer G, Thiessen JJ, Budning A, Kingston JE, O’Brien JM, Koren G, Giesbrecht E, Haddad G, Verjee Z, Hungerford JL, Ling V, Gallie BL (1996) Clin Cancer Res 2:1499

    CAS  Google Scholar 

  32. Gottesman MM (2002) Annu Rev Med 53:615

    CAS  Google Scholar 

  33. Tsuruo T, Iida H, Tsukagoshi S, Sakurai Y (1981) Cancer Res 41:1967

    CAS  Google Scholar 

  34. Benson AB, Koeller JM, Trump DC, Egorin M, Olman E, Witte RS, Davis TE, Tormey DC (1984) Proc Am Assoc Canc Res 25:162

    Google Scholar 

  35. Dreyfuss M, Harri E, Hofmann H, Kobel H, Pache W, Tscherter H (1976) Eur J Appl Microbiol Biotechnol 3:125

    CAS  Google Scholar 

  36. Twentyman PR, Fox NE, White DJG (1987) Br J Cancer 56:55

    CAS  Google Scholar 

  37. Verweij J, Herweijer H, Oosterom R, Vanderburg MEL, Planting AST, Seynaeve C, Stoter G, Nooter K (1991) Br J Cancer 64:361

    CAS  Google Scholar 

  38. Bartlett NL, Lum BL, Fisher GA, Brophy NA, Ehsan MN, Halsey J, Sikic BI (1994) J Clin Oncol 12:835

    CAS  Google Scholar 

  39. Twentyman PR (1992) Biochem Pharmacol 43:109

    CAS  Google Scholar 

  40. Shepard RL, Cao J, Starling JJ, Dantzig AH (2003) Int J Cancer 103:121

    CAS  Google Scholar 

  41. Martin C, Berridge G, Mistry P, Higgins C, Charlton P, Callaghan R (1999) Br J Pharmacol 128:403

    CAS  Google Scholar 

  42. Kruijtzer CMF, Beijnen JH, Rosing H, Huinink WWT, Schot M, Jewell RC, Paul EM, Schellens JHM (2002) J Clin Oncol 20:2943

    CAS  Google Scholar 

  43. Kuppens IE L, M, Witteveen EO, Jewell RC, Radema SA, Paul EM, Mangum SG, Beijnen JH, Voest EE, Schellens JHM (2007) Clin Cancer Res 13:3276

    Google Scholar 

  44. Morschhauser F, Zinzani PL, Burgess M, Sloots L, Bouafia F, Dumontet C (2007) Leuk Lymphoma 48:708

    CAS  Google Scholar 

  45. Szakacs G, Annereau JP, Lababidi S, Shankavaram U, Arciello A, Bussey KJ, Reinhold W, Guo YP, Kruh GD, Reimers M, Weinstein JN, Gottesman MM (2004) Cancer Cell 6:129

    CAS  Google Scholar 

  46. Ludwig JA, Szakacs G, Martin SE, Chu BF, Cardarelli C, Sauna ZE, Caplen NJ, Fales HM, Ambudkar SV, Weinstein JN, Gottesman MM (2006) Cancer Res 66:4808

    CAS  Google Scholar 

  47. Wu CP, Shulkla S, Calcagno AM, Hall MD, Gottesman MM, Ambudkar SV (2007) Mol Cancer Ther 6:3287

    CAS  Google Scholar 

  48. Turk D, Hall MD, Chu BF, Ludwig JA, Fales HM, Gottesman MM, Szakacs G (2009) Cancer Res 96:8293

    Google Scholar 

  49. Tsuruo T, Hamada H, Sato S, Heike Y (1989) Jpn J Cancer Res 80:627

    CAS  Google Scholar 

  50. Watanabe T, Naito M, Kokubu N, Tsuruo TJ (1997) Natl Cancer Inst 89:512

    CAS  Google Scholar 

  51. Efferth T, Volm M (1993) Oncology 50:303

    CAS  Google Scholar 

  52. Mamot C, Drummond DC, Hong K, Kirpotin DB, Park JW (2003) Drug Resist Updates 6:271

    CAS  Google Scholar 

  53. Kanzaki A, Takebayashi Y, Ren XQ, Miyashita H, Mori S, Akiyama S, Pommier Y (2002) Mol Cancer Ther 1:1327

    CAS  Google Scholar 

  54. Kobayashi H, Takemura Y, Wang FS, Oka T, Ohnuma T (1999) Int J Cancer 81:944

    CAS  Google Scholar 

  55. Li L, Xu J, Min T, Huang W (2006) Eur J Pharmacol 536:93

    CAS  Google Scholar 

  56. Crooke ST, Bennett CF (1996) Annu Rev Pharmacol Toxicol 36:107

    CAS  Google Scholar 

  57. van Vlerken LE, Duan Z, Seiden MV, Amiji MM (2007) Cancer Res 67:4843

    CAS  Google Scholar 

  58. Komarov PG, Shtil AA, Buckingham LE, Balasubramanian M, Piraner O, Emanuele RM, Roninson IB, Coon JS (1996) Int J Cancer 68:245

    CAS  Google Scholar 

  59. Wu CP, Ohnuma S, Ambudkar SV (2011) Curr Pharm Biotechnol 12:609

    CAS  Google Scholar 

  60. Boumendjel A, Di Pietro A, Dumontet C, Barron D (2002) Med Res Rev 22:512

    CAS  Google Scholar 

  61. Aoki S, Yoshioka Y, Miyamoto Y, Higuchi K, Setiawan A, Murakami N, Chen ZS, Sumizawa T, Akiyama S, Kobayashi M (1998) Tetrahedron Lett 39:6303

    CAS  Google Scholar 

  62. Aoki S, Chen ZS, Higasiyama K, Setiawan A, Akiyama S, Kobayashi M (2001) Jpn J Cancer Res 92:886

    CAS  Google Scholar 

  63. Chen ZS, Aoki S, Komatsu M, Ueda K, Sumizawa T, Furukawa T, Okumura H, Ren XQ, Belinsky MG, Lee K, Kruh GD, Kobayashi M, Akiyama S (2001) Int J Cancer 93:107

    CAS  Google Scholar 

  64. Jain S, Abraham I, Carvalho P, Kuang YH, Shaala LA, Youssef DT, Avery MA, Chen ZS, El Sayed KA J (2009) Nat Prod 72:1291

    CAS  Google Scholar 

  65. Abraham I, Jain S, Wu CP, Khanfar MA, Kuang Y, Dai CL, Shi Z, Chen X, Fu L, Ambudkar SV, Sayed KE, Chen ZS (2010) Biochem Pharmacol 80:1497

    Google Scholar 

  66. Shi Z, Jain S, Kim IW, Peng XX, Abraham I, Youssef DT, Fu LW, El Sayed K, Ambudkar SV, Chen ZS (2007) Cancer Sci 98:1373

    CAS  Google Scholar 

  67. Kawakami A, Miyamoto T, Higuchi R, Uchiumi T, Kuwano M, Van Soest RWM (2001) Tetrahedron Lett 42:3335

    CAS  Google Scholar 

  68. Emura C, Higuchi R, Miyamoto T (2006) Tetrahedron 62:5682

    CAS  Google Scholar 

  69. Aoki S, Cao LW, Matsui K, Rachmat R, Akiyama S, Kobayashi M (2004) Tetrahedron 60:7053

    CAS  Google Scholar 

  70. White TC, Marr KA, Bowden RA (1998) Clin Microbiol Rev 11:382

    CAS  Google Scholar 

  71. Sanglard D (2002) Enferm Infecc Microbiol Clin 20:462

    Google Scholar 

  72. Jacob MR, Hossain CF, Mohammed KA, Smillie TJ, Clark AM, Walker LA, Nagle DG (2003) J Nat Prod 66:1618

    CAS  Google Scholar 

  73. Andersen RJF, DJ, He C-H, Duyne GDV, Clardy J (1985) J Am Chem Soc 107:5492

    Google Scholar 

  74. Lindquist N, Fenical W, Vanduyne GD, Clardy JJ (1988) Org Chem 53:4570

    CAS  Google Scholar 

  75. Carroll AR, Bowden BF, Coll JC (1993) Aust J Chem 46:489

    CAS  Google Scholar 

  76. Urban S, Capon RJ (1996) Aust J Chem 49:711

    CAS  Google Scholar 

  77. Reddy MVR, Faulkner DJ, Venkateswarlu Y, Rao MR (1997) Tetrahedron 53:3457

    CAS  Google Scholar 

  78. Davis RA, Carroll AR, Pierens GK, Quinn RJ (1999) J Nat Prod 62:419

    CAS  Google Scholar 

  79. Reddy MVR, Rao MR, Rhodes D, Hansen MST, Rubins K, Bushman FD, Venkateswarlu Y, Faulkner DJ (1999) J Med Chem 42:1901

    CAS  Google Scholar 

  80. Urban S, Butler MS, Capon RJ (1994) Aust J Chem 47:1919

    CAS  Google Scholar 

  81. Urban S, Hobbs L, Hooper JNA, Capon RJ (1995) Aust J Chem 48:1491

    CAS  Google Scholar 

  82. Fan H, Peng J, Hamann MT, Hu JF (2008) Chem Rev 108:264

    CAS  Google Scholar 

  83. Cantrell CL, Groweiss A, Gustafson KR, Boyd MR (1999) Nat Prod Lett 14:39

    CAS  Google Scholar 

  84. Reddy SM, Srinivasulu M, Satyanarayana N, Kondapi AK, Venkateswarlu Y (2005) Tetrahedron 61:9242

    CAS  Google Scholar 

  85. Chittchang M, Batsomboon P, Ruchirawat S, Ploypradith P (2009) Chem Med Chem 4:457

    CAS  Google Scholar 

  86. Thipnate P, Chittchang M, Thasana N, Saparpakorn P, Ploypradith P, Hannongbua S (2011) Monatsh Chem 142:97

    CAS  Google Scholar 

  87. Baunbaek D, Trinkler N, Ferandin Y, Lozach O, Ploypradith P, Rucirawat S, Ishibashi F, Iwao M, Meijer L (2008) Mar Drugs 6:514

    CAS  Google Scholar 

  88. Carroll AR, Bowden BF, Coll JC (1993) Aust J Chem 46:489

    CAS  Google Scholar 

  89. Quesada AR, Garcia Gravalos MD, Fernandez Puentes JL (1996) Br J Cancer 74:677

    CAS  Google Scholar 

  90. Puentes JLF, Garcia Gravalos D, Rodriguez Quesada A (1997) WO patent 1,997,001,336

    Google Scholar 

  91. Plisson F, Huang XC, Zhang H, Khalil Z, Capon RJ (2012) Chem Asian J 7:1616

    CAS  Google Scholar 

  92. Fan H, Peng JN, Hamann MT, Hu JF (2010) Chem Rev 110:3850

    CAS  Google Scholar 

  93. Ploypradith P, Petchmanee T, Sahakitpichan P, Litvinas ND, Ruchirawat SJ (2006) Org Chem 71:9440

    CAS  Google Scholar 

  94. Koehnke J, Bent A, Houssen WE, Zollman D, Morawitz F, Shirran S, Vendome J, Nneoyiegbe AF, Trembleau L, Botting CH, Smith MCM, Jaspars M, Naismith JH (2012) Nat Struct Mol Biol 19:767

    CAS  Google Scholar 

  95. Ireland CM, Durso AR, Newman RA, Hacker MP (1982) J Org Chem 47:1807

    CAS  Google Scholar 

  96. Schmitz FJ, Ksebati MB, Chang JS, Wang JL, Hossain MB, Vanderhelm D, Engel MH, Serban A, Silfer JA (1989) J Org Chem 54:3463

    CAS  Google Scholar 

  97. Degnan BM, Hawkins CJ, Lavin MF, McCaffrey EJ, Parry DL, van den Brenk AL, Watters DJ (1989) J Med Chem 32:1349

    CAS  Google Scholar 

  98. Mcdonald LA, Ireland CM (1992) J Nat Prod 55:376

    CAS  Google Scholar 

  99. Rashid MA, Gustafson KR, Cardellina JH, Boyd MR (1995) J Nat Prod 58:594

    CAS  Google Scholar 

  100. Fu X, Do T, Schmitz FJ, Andrusevich V, Engel MH (1998) J Nat Prod 61:1547

    CAS  Google Scholar 

  101. Williams AB, Jacobs RS (1993) Cancer Lett 71:97

    CAS  Google Scholar 

  102. Rinehart KL, Holt TG, Fregeau NL, Stroh JG, Keifer PA, Sun F, Li LH, Martin DG (1990) J Org Chem 55:4512

    CAS  Google Scholar 

  103. Wright AE, Forleo DA, Gunawardana GP, Gunasekera SP, Koehn FE, Mcconnell OJ (1990) J Org Chem 55:4508

    CAS  Google Scholar 

  104. Carter NJ, Keam SJ (2007) Drugs 67:2257

    CAS  Google Scholar 

  105. D’Incalci M, Galmarini CM (2010) Mol Cancer Ther 9:2157

    Google Scholar 

  106. Carter NJ, Keam SJ (2010) Drugs 70:355

    CAS  Google Scholar 

  107. Hurley LH, Zewail-Foote M (2001) Adv Exp Med Biol VI 500:289

    CAS  Google Scholar 

  108. Bonfanti M, La Valle E, Faro JM F, S, Faircloth G, Caretti G, Mantovani R, D’Incalci M (1999) Anti-Cancer Drug Des 14:179

    CAS  Google Scholar 

  109. Kanzaki A, Takebayashi Y, Ren XQ, Miyashita H, Mori S, Akiyama S, Pommier Y (2002) Mol Cancer Ther 1:1327

    CAS  Google Scholar 

  110. Schmitz FJ, Michaud DP, Schmidt PG (1982) J Am Chem Soc 104:6415

    CAS  Google Scholar 

  111. Suzuki T, Takeda S, Hayama N, Tanaka I, Komiyama K (1989) Chem Lett 10:969

    Google Scholar 

  112. Tsukamoto S, Yamashita Y, Yoshida T, Ohta T (2004) Mar Drugs 2:170

    CAS  Google Scholar 

  113. Ioannou E, Nappo M, Avila C, Vagias C, Roussis VJ (2009) Nat Prod 72:1716

    CAS  Google Scholar 

  114. Higgs MD, Faulkner DJ (1982) Phytochemistry 21:789

    CAS  Google Scholar 

  115. Takeda S, Kurosawa E, Komiyama K, Suzuki T (1990) Bull Chem Soc Jpn 63:3066

    CAS  Google Scholar 

  116. Rochfort SJ, Capon RJ (1996) Aust J Chem 49:19

    CAS  Google Scholar 

  117. Kurata K, Taniguchi K, Agatsuma Y, Suzuki M (1998) Phytochemistry 47:363

    CAS  Google Scholar 

  118. Lyakhova EG, Kalinovsky AI, Kolesnikova SA, Vaskovsky VE, Stonik VA (2004) Phytochemistry 65:2527

    CAS  Google Scholar 

  119. Awad NE (2004) Phytother Res 18:275

    CAS  Google Scholar 

  120. Huang XC, Sun YL, Salim AA, Chen ZS, Capon RJ (2013) Biochem Pharmacol 85:1257

    CAS  Google Scholar 

  121. Stratmann K, Moore RE, Bonjouklian R, Deeter JB, Patterson GML, Shaffer S, Smith CD, Smitka TA (1994) J Am Chem Soc 116:9935

    CAS  Google Scholar 

  122. Smith CD, Zilfou JT, Stratmann K, Patterson GML, Moore RE (1995) Mol Pharmacol 47:241

    CAS  Google Scholar 

  123. Fairchild CR, Ivy SP, Kaoshan CS, Whangpeng J, Rosen N, Israel MA, Melera PW, Cowan KH, Goldsmith ME (1987) Cancer Res 47:5141

    CAS  Google Scholar 

  124. Zhang XQ, Smith CD (1996) Mol Pharmacol 49:288

    CAS  Google Scholar 

  125. Stratmann K, Burgoyne DL, Moore RE, Patterson GML, Smith CD (1994) J Org Chem 59:7219

    CAS  Google Scholar 

  126. Okuno T, Ohmori K, Nishiyama S, Yamamura S, Nakamura K, Houk KN, Okamoto K (1996) Tetrahedron 52:14723

    CAS  Google Scholar 

  127. Ohmori K, Okuno T, Nishiyama S, Yamamura S (1996) Tetrahedron Lett 37:3467

    CAS  Google Scholar 

  128. Kashihara N, To-e S, Nakamura K, Umezawa K, Yamamura S, Nishiyama S (2000) Bioorg Med Chem Lett 10:101

    CAS  Google Scholar 

  129. Wagner B, Gonzalez GI, Dau METH, Zhu JP (1999) Bioorg Med Chem 7:737

    CAS  Google Scholar 

  130. O’connell CE, Salvato KA, Meng ZY, Littlefield BA, Schwartz CE (1999) Bioorg Med Chem Lett 9:1541

    Google Scholar 

  131. Dinh TQ, Du XH, Smith CD, Armstrong RW (1997) J Org Chem 62:6773

    CAS  Google Scholar 

  132. Dinh TQ, Smith CD, Du XH, Armstrong RW (1998) J Med Chem 41:981

    CAS  Google Scholar 

  133. Prinsep MR, Caplan FR, Moore RE, Patterson GML, Smith CD (1992) J Am Chem Soc 114:385

    CAS  Google Scholar 

  134. Smith CD, Prinsep MR, Caplan FR, Moore RE, Patterson GML (1994) Oncol Res 6:211

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Zhe-Sheng Chen .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Huang, Xc., Kumar, P., Anreddy, N., Xiao, X., Yang, DH., Chen, ZS. (2015). P-gp Inhibitory Activity from Marine Sponges, Tunicates and Algae. In: Kim, SK. (eds) Handbook of Anticancer Drugs from Marine Origin. Springer, Cham. https://doi.org/10.1007/978-3-319-07145-9_28

Download citation

Publish with us

Policies and ethics