Inhibition of multidrug resistance of cancer cells by natural diterpenes, triterpenes and carotenoids

Current Pharmaceutical Design

Volumn 12, Issue 3, 2006, Pages 287-311

  Molnár, Joseph ^a   Gyémánt, Nóra ^a   Tanaka, Masaru ^a   Hohmann, Judith ^b   Bergmann Leitner, Elke ^c   Molnár, Péter ^d   Deli, Joseph ^d   Didiziapetris, Remigijus ^e   Umbelino Ferreira, Maria José ^f  

^a UNIVERSITY OF SZEGED   (Hungary)

^b UNIVERSITY OF SZEGED   (Hungary)

^c WALTER REED ARMY INSTITUTE OF RESEARCH   (United States)

^d UNIVERSITY OF PÉCS   (Hungary)

^e Pharma Algorithms Inc   (Lithuania)

^f UNIVERSITY OF LISBON   (Portugal)

Author keywords

Cancer cells; Carotenoids; Diterpenoids; Multidrug resistance; Triterpenoids

Indexed keywords

ABC TRANSPORTER; ABIETANE DERIVATIVE; ALPHA CAROTENE; AUROCHROME; BETA CAROTENE; BETA CRYPTOXANTHIN; CAPSANTHIN; CAROTENOID; DITERPENE; DRIMANE DERIVATIVE; EPIRUBICIN; EUPHORACTINE DERIVATIVE; JATROPHANE DERIVATIVE; LATHYRANE DERIVATIVE; LYCOPENE; MULTIDRUG RESISTANCE PROTEIN; MULTIDRUG RESISTANCE PROTEIN 1; NEOXANTHIN; PARALIANE DERIVATIVE; PEPLUANE; PORTLANQUINOL; RHODAMINE; TERPENOID; TRITERPENE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VERAPAMIL; VIOLAXANTHIN; VITAMIN; XANTHOPHYLL; ZEAXANTHIN; ANTINEOPLASTIC AGENT;

BIOACCUMULATION; BREAST CANCER; CANCER; CANCER CELL CULTURE; CANCER RESISTANCE; CELL MEMBRANE; CELL STRAIN MCF 7; CELL TRANSPORT; CONFORMATIONAL TRANSITION; DRUG BINDING; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG ISOLATION; DRUG STRUCTURE; GENETIC TRANSFECTION; HUMAN; IN VITRO STUDY; LYMPHOMA CELL LINE; MEDICINAL PLANT; MULTIDRUG RESISTANCE; NONHUMAN; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN FAMILY; PROTEIN FUNCTION; PROTEIN TRANSPORT; REVERSAL REACTION; REVIEW; TREATMENT FAILURE; TUMOR CELL; TUMOR CELL CULTURE; VEGETABLE; ANIMAL; DRUG RESISTANCE; NEOPLASM; PATHOLOGY; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; CAROTENOIDS; CELL LINE, TUMOR; DITERPENES; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; HUMANS; NEOPLASMS; TRITERPENES;

EID: 33644854911     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/138161206775201893     Document Type: Review

References (66)

1. La Vechia C, Tavani A.: Fruit and vegetables and human cancer. Eur J Cancer Prev 1998; 7: 3-8.
2. Doll R, Peto R. The causes of cancer Quantitative estimates of avoidable risks of cancer in United States today. J Natl Cancer Inst 1981; 66: 1191-1308.
3. Molnár J, Szabó D, Pusztai R, Mucsi I, Berek L, Ocsovszki I, et al. Membrane associated antitumor effects of crocine, ginsenoside-, and cannabinoid derivatives. Anticancer Res 2000; 20: 861-8.
4. Molnár J, Gyémánt N, Mucsi I, Molnár M, Szabó M, Körtvélyesi T, et al. Modulation of multidrug resistance and apoptosis of cancer cells by selected carotenoids. In Vivo 2004; 18: 237-44.
5. Molnár J, Mucsi I, Nacsa J, Hevér A, Gyémánt N, Ugocsai K, et al. New silicon compounds as resistance modifiers against multidrugresistant cancer cells. Anticancer Res 2004; 24: 865-72.
6. Nishino H, Tokuda H, Satomi Y, Masuda M, Bu P, Onozuka M, et al. Cancer prevention by carotenoids. Pure Appl Chem 1999; 71: 2273-8.
7. Murakoshi M, Nishino H. Comparison of cancer preventive effect of five kinds of carotenoids on mouse lung carcinogenesis. Cancer Res 1992; 52: 6583-7.
8. Smaller B, Isenberg I, Baird SL. Spin resonance and electrical conductivity of indole-iodine. Nature 1961; 191: 168-9.
9. Hohmann J, Molnár J, Rédei D, Evanics F, Forgó P, Kálmán A, et al. Discovery and biological evaluation of a new family of potent modulators of multidrug resistance: reversal of MDR of mouse lymphoma cells by new natural jatrophane diterpenoids isolated from Euphorbia species. J Med Chem 2002; 45: 2425-31.
10. Hohmann J, Rédei D, Evanics F, Kálmán A, Argay Gy, Bartók T. Serrulatin A and B, new diterpene polyesters from Euphorbia serrulata. Tetrahedron 2000; 56: 3619-23.
11. Hohmann J, Forgo P, Csupor D, Schlosser G. Isolation and structure determination of new jatrophane diterpenoids from Euphorbia platyphyllos L. Helv Chim Acta 2003; 86: 3386-93.
12. Hohmann J, Vasas A, Günther G, Máthé I, Evanics F, Dombi Gy, et al. Macrocyclic diterpene polyesters of the jatrophane type from Euphorbia esula. J Nat Prod 1997; 60: 331-5.
13. Günther G, Hohmann J, Vasas A, Máthé I, Dombi Gy, Jerkovich Gy. Jatrophane diterpenoids from Euphorbia esula. Phytochemistry 1998; 47: 1309-13.
14. Günther G, Martinek T, Dombi Gy, Hohmann J, Vasas A. Structural characterisation and dynamic NMR studies of a new peracylated macrocyclic diterpene. Magn Res Chem 1999; 37: 365-70.
15. Hohmann J, Evanics F, Dombi Gy, Molnár J, Szabó P. Euphosalicin, a new diterpene polyester with multidrug resistance reversing activity from Euphorbia salicifolia. Tetrahedron 2001; 57: 211-15.
16. Hohmann J, Vasas A, Günther G, Dombi Gy, Blazsó G, Falkay GY, et al. Jatrophane diterpenoids from Euphorbia peplus. Phytochemistry 1999; 51: 673-7.
17. Hohmann J, Günther G, Vasas A, Kálmán A, Argay Gy. Isolation and structure revision of pepluane diterpenoids from Euphorbia peplus. J Nat Prod 1999; 62: 107-9.
18. Hohmann J, Rédei D, Forgó P, Molnár J, Dombi Gy, Zorig T. Jatrophane diterpenoids from Euphorbia mongolica as modulators of the multidrug resistance of tumor cells. J Nat Prod 2003; 66: 976-9.
19. Vasas A, Hohmann J, Forgo P, Szabó P. New tri- and tetracyclic diterpenes from Euphorbia villosa. Tetrahedron 2004; 60: 5025-30.
20. Valente C, Ferreira MJU, Abreu PM, Pedro M, Cerqueira F, Nascimento MSJ. Three new jatrophane-type diterpenes from Euphorbia pubescens. Plants Med 2003; 69: 361-6.
21. Valente C, Ferreira MJU, Abreu PM, Gyémánt N, Ugocsai K, Hohmann J, et al. Pubescenes, jatrophane diterpenes, from Euphorbia pubescens with multidrug resistance reversing activity on mouse lymphoma cells. Plants Med 2004; 70: 81-4.
22. Madureira AM, Gyémánt N, Ugocsai K, Ascenso JR, Abreu PM, Hohmann J, et al. Rearranged jatrophane-type diterpenes from Euphorbia species. Evaluation of their effect on the reversal of multidrug resistance. Plants Med 2004; 70: 45-9.
23. Ferreira MJU, Madureira AM, Ascenso JR. A tetracyclic diterpene and triterpenes from Euphorbia segetalis. Phytochemistry 1998; 49: 179-83.
24. Corea G, Fattorusso E, Lanzotti V, Taglialatela-Scafati O, Appendino G, Ballero M, et al. Jatrophane diterpenes as P-glycoprotein inhibitors. First insights of structure-activity relationships and discovery of a new, powerful lead. J Med Chem 2003; 46: 3395-402.
25. Madureira AM, Molnár A, Abreu PM, Molnár J, Ferreira MJU. A new sesquiterpene-coumarin ether and a new abietane diterpene and their effects as inhibitors of P-glycoprotein. Plants Med 2004; 24: 859-64.
26. Ferreira MJU, Pinto FC, Ascenso JR. Cycloartane triterpenes from Euphorbia tuckeyana. Nat Prod Lett 2001; 15: 363-9.
27. Madureira AM, Ascenso JR, Valdeira L, Duarte A, Frade JP, Freitas G, et al. Evaluation of the antiviral and antimicrobial activities of triterpenes isolated from Euphorbia segetalis. Nat Prod Res 2003; 17: 375-80.
28. Madureira AM, Duarte MT, Piedade MFM, Ascenso JR, Ferreira MJU. Isoprenoid compounds from Euphorbia portlandica. X-ray structure of lupeportlandol, a new lupane triterpene. J Braz Chem Soc 2004; 15: 742-7.
29. Madureira AM, Spengler G, Molnár A, Varga A, Molnár J, Abreu PM, et al. Effect of cycloartanes on reversal of multidrug resistance and apoptosis induction on mouse lymphoma cells. Anticancer Res 2004; 70: 828-33.
30. Corea G, Fattorusso E, Lanzotti V, Taglialatela-Scafati O, Appendino G, Ballero M, et al. Modified jatrophane diterpenes as modulators of multidrug resistance from Euphorbia dendroides. Bioorg Med Chem J Med Chem 2003; 11: 5221-7.
31. Corea G, Fattorusso E, Lanzotti V, Motti R, Simon PN, Dumontet C, et al. Jatrophane diterpenes as modulators of multidrug resistance. Advances of structure-activity relationships and discovery of the potent lead pepluanin A. J Med Chem 2004; 47: 988-92.
32. Corea G, Fattorusso E, Lanzotti V, Motti R, Simon PN, Dumontet C, et al. Structure-activity relationships for Euphocharactins A-L, a new series of jatrophane diterpenes, as inhibitors of cancer cell P-glycoprotein. Planta Med 2004; 70: 657-65.
33. Okuno M, Kojima S, Matsushima-Nishiwaki R, Tsurumi H, Muto Y, Friedman SL, et al. Retinoids in cancer chemopreventiom. Current Cancer Drug Targets 2004; 3: 285-98.
34. Chen Q, Catharine Ross A. Retinoic acid regulastes cell cycle progression and cell differentiation in humans monocytic THP-1 cells. Biomed Pharmother 2004; 58: 100-10.
35. Khachik F, Nir Z, Ausich RL.In: Ohigashi H Ed, Distribution of carotenoids in fruits and vegetables as a criterion for the selection of appropriate chemopreventive agents. Proceedings of the Second International Conference on Food Factors: Chemistry and Cancer Prevention: Springer-Verlag: Tokyo 1997; 204.
36. Deli J, Molnár P, Matus Z, Traber B, Pfander H. "Prenigroxanthin" (β, γ-carotene-3, 3, 6′-triol) a novel carotenoid from red paprika (Capsicum annum). Tetrahedron Lett 2001; 42: 1395-7.
37. Deli J, Molnár P, Tóth G, Baumeler A, Eugster CH. Cycloviolaxanthin, ein neues Carotinoid aus Paprika (Capsicum annum). Helv Chim Acta 1991; 74: 819-24.
38. Deli J, Molnár P, Õsz E, Tóth G. Capsoneoxanthin, a New carotenoid isolated from the fruits of Asparagus falcatus. Tetrahedron Lett 2000; 41: 8153-5.
39. Kleinman D, Karas M, Roberts CT, LeRoith D, Phillip M, Segev Y, et al. Modulation of insulin-like growth factor I (IGF-I) receptors and membrane-associated IGF-binding proteins in endometrial cancer cells by estradiol. Endocrinol 1995; 136: 2531-7.
40. Nishino H, Tokuda H, Murakoshi M, Satomi Y, Masuda M, Onozuka M, et al. Cancer prevention by natural carotenoids. Biofactors 2000; 13: 90-4.
41. Motohashi N, Kurihara T, Wakabayashi H, Yaji M, Mucsi I, Molnar J, et al. Biological activity of a fruit vegetable "Anastasia green" species of sweet pepper. In Vivo 2001; 15: 437-42.
42. Gutmann F, Jonhson C, Keyzer H, Molnár J: Charge transfer complexes in biological systems, Marcel Dekker, Inc, New York, Basel, Honkong, 1997; 323.
43. Utsun C, Beksac M, Dalva K, Koc H, Konuk N, Ilhan O, et al. In vivo use of all-trans-retinoic acid prior to induction chemotherapy improves complete remission rate and increases rhodamine 123 uptake in patients with de novo acute myeloid leukemia. Med Oncol, 2002; 19: 59-67.
44. Debal V, Breillout F, Manfait M. Concomitant decrease of resistance and modifications of the cytoskeleton after all-trans-retinoic acid and phorbol ester treatments in a navelbine-resistant bladder carcinoma cell line. Anticancer Res 1997; 17: 1147-54.
45. Simoni D, Tolomeo M. Retinoids, apoptosis and cancer. Curr Pharm Des 2001; 17: 1823-37.
46. Szakacs G, Ozvegy C, Bakos E, Sarkadi B, Varadi A. Transition-state formation in ATPase- negative mutants of Human MDR1 protein. Biochem.Biophys Res Commun 2000; 276: 1314-9.
47. Budworth J, Grant TW, Gescher A. Coordinate loss of protein kinase C and multidrug resistance gene expression in revertant MCF-7/Adr breast carcinoma cells. Br J Cancer 1997, 75: 1330-5.
48. Nguyen KT, Liu B, Ueda K, Gottesman MM, Pastan I. Chin KV: Transactivation of human multidrug resistance (MDR1) gene opromoter by p53 mutants. Oncol Res 1994; 6: 71-7.
49. Vo QD, Gruol DJ. Identification of P-glycoprotein mutations causing a loss of steroid recognition and transport. J Biol Chem 1999; 274: 20318-27.
50. Grandjean F, Bremaud L, Verdier M, Robert J. Ratinaud M.H.: Sequential gene expression of P*glycoprotein (P-gp), multidrug resistance associated protein (MRP) and lung resistance proteoin: functional activity of P-gp and MRP present in the doxorubicin-resistant human K562 cell lines. Anticancer Drugs 2001; 12: 247-58.
51. Tombline G, Bartholomew L, Gimi K, Tyndall GA, Senior AE. Synergy between conserved ABC signature Ser residues in P-glycoprotei n catalysis. J Biol Chem 2004; 279: 5363-73.
52. Zhang DW, Cole SP, Deeley RG. Identification of an amino acid residue in multidrug resistance protein 1 critical for conferring resistance to anthracyclines. J Biol Chem 2001; 276: 13231-9.
53. Hrycyna CA, Airan LE, Germann UA, Ambudkar SV, Pastan I. Gottesman MM: Structural flexibility of the linker region of human P-glycoprotein permits ATP hydrolysis and drug transport. Biochemistry 1998; 37: 13660-73.
54. Kwan T, Gros P. Mutational analysis of the P-glycoprotein first intracellulkar loop and flanking transmembrane domains. Biochemistry 1998; 37: 3337-50.
55. Drori S, Eytan GD, Assaraf YG. Potentiation of anticancer-drug cytotoxicity by multidrug-resistance chemosensitizers involves alterations in membrane fluidity leading to increased membrane permeability. Eur J Biochem 1995; 228: 1020-29.
56. Szabo D, Molnar J. The role of stereoselectivity of chemosensitizers in the reversal of multidrug resistance of mouse lymphoma cells. Anticancer Research 1998; 18: 3039-44.
57. Székely Z, Konya Z, Becskei A, Goldring WPD, Percel A, Penke B, et al. Suggested binding mechanism of HIV gp120 to its CD4 receptor. J Mol Struct (Theochem) 1996; 367: 159-86.
58. Székely Z, Percel A, Penke B, Molnar J. Conformational behavior of wild type ond several mutants of CD4: A new method for interpretation of dynamics trajectories in the conformational analysis of HIV receptor mutants. J Mol Struct 1993; 286: 165-82.
59. Molnar J, Földeák S, Nakamura MJ, Gaizer F, Gutmann F. The influence of charge transfer formation on the antibacterial activity of some tricyclic drugs. Xenobiotica 1991; 21: 309-11.
60. Hewlett I, Lee S, Molnar J, Földeák S, Scott Pine F, Weaver JL, et al. Inhibition of HIV infection of H9 cells by chlorpromazine derivatives. Journal of Acquired Immune Defficiency Syndromes and Human Retrovirology 1997;15: 16-20.
61. Kidd SE, Nelson MJ. Epstein M. Aszalos A. Pine S, Molnar J. Inhibition of gp120 antibodies binding to CD4 by metal complexes of promazines. Antiinfective Drugs and Chemotherapy1997; 15: 71-7.
62. Pfander H Ed. Key to Carotenoids Birkhauser Verlag, Basel-Boston, 1987.
63. Britton G, Liaaen-Jensen S, Pfander H Ed, Carotenoids, Handbook, Birkhauser Verlag, Basel-Boston-Berlin, 2004.
64. Secchiero P, Vaccarezza M, Gonelli A, Zauli G. TNF-related apoptosis-inducing ligand (TRAIL): a potential candidate for combined treatment of hematological malignancies. Curr Pharm Design 2004; 10(29): 3673-81.
65. Sorokin A. Cyclooxygenase-2: potential role in regulation of drug efflux and multidrug resistance phenotype. Curr Pharm Design 2004; 10(6): 647-57.
66. Vaidyanathan G, Zalutsky MR. Imaging drug resistance with radiolabeled molecules. Curr Pharm Design 2004; 10(24): 2965-79.