Characterization of the cytotoxic activity of the indoloquinoline alkaloid cryptolepine in human tumour cell lines and primary cultures of tumour cells from patients

Investigational New Drugs

Volumn 27, Issue 5, 2009, Pages 402-411

  Laryea, Daniel ^a   Isaksson, Anders ^a   Wright, Colin W ^b   Larsson, Rolf ^a   Nygren, Peter ^a  

^a UPPSALA UNIVERSITY HOSPITAL   (Sweden)

^b UNIVERSITY OF BRADFORD   (United Kingdom)

Author keywords

Chemotherapy; Cross resistance; Cryptolepine; Gene expression; In vitro; Tumour cells

Indexed keywords

ACRIFLAVINE; ARSENIC TRIOXIDE; BENOMYL; BORTEZOMIB; CISPLATIN; CRYPTOLEPINE; CURCUMIN; DAUNORUBICIN; DISULFIRAM; DNA TOPOISOMERASE (ATP HYDROLYSING); DOXORUBICIN; FENBENDAZOLE; FLUOROURACIL; LACTACYSTIN; LYCORINE; MEBENDAZOLE; MELPHALAN; MEPACRINE; PENTOSTATIN; PYRITHIONE ZINC; RAPAMYCIN; ROTENONE; SPERMIDINE; SPERMINE; TENIPOSIDE; VINCRISTINE;

ARTICLE; CANCER RESISTANCE; CONTROLLED STUDY; CYTOTOXICITY; GENE EXPRESSION; HEMATOLOGIC MALIGNANCY; HUMAN; HUMAN CELL; IC 50; MAJOR CLINICAL STUDY; MICROTUBULE; PRIORITY JOURNAL; SOLID TUMOR; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; DNA TOPOISOMERASES, TYPE II; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; GENE EXPRESSION PROFILING; HUMANS; INDOLE ALKALOIDS; MOLECULAR STRUCTURE; NEOPLASMS; OLIGONUCLEOTIDE ARRAY SEQUENCE ANALYSIS; QUINOLINES; TUMOR CELLS, CULTURED; TUMOR MARKERS, BIOLOGICAL;

EID: 70349229773     PISSN: 01676997     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10637-008-9185-5     Document Type: Article

References (27)

1. CW Wright 2007 Recent developments in naturally derived antimalarials: cryptolepine analogues J Pharm Pharmacol 59 6 899 904 17637183 10.1211/jpp.59.6.0017 1:CAS:528:DC%2BD2sXmtlKntbc%3D doi:10.1211/jpp.59.6.0017 (Pubitemid 47051103)
2. AO Oyekan 1995 Cryptolepine-induced vasodilation in the isolated perfused kidney of the rat: role of G-proteins, K+ and Ca2+ channels Eur J Pharmacol 285 1 1 9 8846804 10.1016/0014-2999(95)00289-W 1:CAS:528:DyaK2MXosVOisrs%3D doi:10.1016/0014-2999(95)00289-W
3. DE Bierer LG Dubenko P Zhang Q Lu PA Imbach AW Garofalo PW Phuan DM Fort J Litvak RE Gerber B Sloan J Luo R Cooper GM Reaven 1998 Antihyperglycemic activities of cryptolepine analogues: an ethnobotanical lead structure isolated from Cryptolepis sanguinolenta J Med Chem 41 15 2754 2764 9667966 10.1021/jm970735n 1:CAS:528:DyaK1cXksVKrsbs%3D doi:10.1021/jm970735n (Pubitemid 28350342)
4. SO Bamgbose BK Noamesi 1981 Studies on cryptolepine. II: Inhibition of carrageenan induced oedema by cryptolepine Planta Med 41 4 392 396 7255566 10.1055/s-2007-971733 1:CAS:528:DyaL3MXktFyhtr4%3D doi:10.1055/s-2007-971733
5. C Bailly W Laine B Baldeyrou MC De Pauw-Gillet P Colson C Houssier K Cimanga S Van Miert AJ Vlietinck L Pieters 2000 DNA intercalation, topoisomerase II inhibition and cytotoxic activity of the plant alkaloid neocryptolepine Anticancer Drug Des 15 3 191 201 11049087 1:CAS:528:DC%2BD3cXnsFOksro%3D
6. K Bonjean MC De Pauw-Gillet MP Defresne P Colson C Houssier L Dassonneville C Bailly R Greimers C Wright J Quetin-Leclercq M Tits L Angenot 1998 The DNA intercalating alkaloid cryptolepine interferes with topoisomerase II and inhibits primarily DNA synthesis in B16 melanoma cells Biochemistry 37 15 5136 5146 9548744 10.1021/bi972927q 1:CAS:528:DyaK1cXisVyltLY%3D doi:10.1021/bi972927q (Pubitemid 28176514)
7. J Lavrado A Paulo J Gut PJ Rosenthal R Moreira 2008 Cryptolepine analogues containing basic aminoalkyl side-chains at C-11: synthesis, antiplasmodial activity, and cytotoxicity Bioorg Med Chem Lett 18 4 1378 1381 18207399 10.1016/j.bmcl.2008.01.015 1:CAS:528:DC%2BD1cXitlais78%3D doi:10.1016/j.bmcl.2008.01.015 (Pubitemid 351226539)
8. DG Kingston BT Li F Ionescu 1977 Plant anticancer agents III: isolation of indole and bisindole alkaloids from Tabernaemontana holstii roots J Pharm Sci 66 8 1135 1138 561182 10.1002/jps.2600660821 1:CAS:528:DyaE2sXlsFOjtLY%3D doi:10.1002/jps.2600660821 (Pubitemid 8167339)
9. M Kidwai R Venkataramanan R Mohan P Sapra 2002 Cancer chemotherapy and heterocyclic compounds Curr Med Chem 9 12 1209 1228 12052173 1:CAS:528:DC%2BD38XktlGhsbY%3D
10. L Dassonneville A Lansiaux A Wattelet N Wattez C Mahieu S Van Miert L Pieters C Bailly 2000 Cytotoxicity and cell cycle effects of the plant alkaloids cryptolepine and neocryptolepine: relation to drug-induced apoptosis Eur J Pharmacol 409 1 9 18 11099695 10.1016/S0014-2999(00)00805-0 1:CAS:528: DC%2BD3cXotlGjurw%3D doi:10.1016/S0014-2999(00)00805-0 (Pubitemid 30950631)
11. TA Matsui Y Sowa H Murata K Takagi R Nakanishi S Aoki M Yoshikawa M Kobayashi T Sakabe T Kubo T Sakai 2007 The plant alkaloid cryptolepine induces p21WAF1/CIP1 and cell cycle arrest in a human osteosarcoma cell line Int J Oncol 31 4 915 922 17786325 1:CAS:528:DC%2BD2sXht1SjurfJ
12. H Zhu NJ Gooderham 2006 Mechanisms of induction of cell cycle arrest and cell death by cryptolepine in human lung adenocarcinoma a549 cells Toxicol Sci 91 1 132 139 16510557 10.1093/toxsci/kfj146 1:CAS:528:DC%2BD28Xjtlamu7Y%3D doi:10.1093/toxsci/kfj146
13. S Seville RM Phillips SD Shnyder CW Wright 2007 Synthesis of cryptolepine analogues as potential bioreducible anticancer agents Bioorg Med Chem 15 19 6353 6360 17643990 10.1016/j.bmc.2007.06.062 1:CAS:528:DC%2BD2sXovFOit7w%3D doi:10.1016/j.bmc.2007.06.062 (Pubitemid 47212739)
14. K Csoka R Larsson B Tholander E Gerdin M de la Torre P Nygren 1994 Cytotoxic drug sensitivity testing of tumor cells from patients with ovarian carcinoma using the fluorometric microculture cytotoxicity assay (FMCA) Gynecol Oncol 54 2 163 170 7520407 10.1006/gyno.1994.1187 1:STN:280:DyaK2czktFOisg%3D%3D doi:10.1006/gyno.1994.1187 (Pubitemid 24256464)
15. S Dhar P Nygren K Csoka J Botling K Nilsson R Larsson 1996 Anti-cancer drug characterisation using a human cell line panel representing defined types of drug resistance Br J Cancer 74 6 888 896 8826854 1:CAS:528:DyaK28XmsFCjsb4%3D
16. L Rickardson M Fryknas S Dhar H Lovborg J Gullbo M Rydaker P Nygren MG Gustafsson R Larsson A Isaksson 2005 Identification of molecular mechanisms for cellular drug resistance by combining drug activity and gene expression profiles Br J Cancer 93 4 483 492 16012520 10.1038/sj.bjc.6602699 1:CAS:528: DC%2BD2MXnvFymtLg%3D doi:10.1038/sj.bjc.6602699 (Pubitemid 43080025)
17. R Larsson P Nygren 1990 Pharmacological modification of multi-drug resistance (MDR) in vitro detected by a novel fluorometric microculture cytotoxicity assay. Reversal of resistance and selective cytotoxic actions of cyclosporin A and verapamil on MDR leukemia T-cells Int J Cancer 46 1 67 72 2194983 10.1002/ijc.2910460114 1:CAS:528:DyaK3cXls1Gjt7Y%3D doi:10.1002/ijc. 2910460114 (Pubitemid 20225789)
18. EA Ostrakhovitch PE Olsson J von Hofsten MG Cherian 2007 P53 mediated regulation of metallothionein transcription in breast cancer cells J Cell Biochem 102 6 1571 1583 17477370 10.1002/jcb.21381 1:CAS:528: DC%2BD2sXhsVeitL%2FK doi:10.1002/jcb.21381 (Pubitemid 350223957)
19. L Guittat P Alberti F Rosu S Van Miert E Thetiot L Pieters V Gabelica E De Pauw A Ottaviani JF Riou JL Mergny 2003 Interactions of cryptolepine and neocryptolepine with unusual DNA structures Biochimie 85 5 535 547 12763313 10.1016/S0300-9084(03)00035-X 1:CAS:528:DC%2BD3sXjvV2ntb8%3D doi:10.1016/S0300-9084(03)00035-X (Pubitemid 36626024)
20. P Nygren R Larsson 2003 Overview of the clinical efficacy of investigational anticancer drugs J Intern Med 253 1 46 75 12588538 10.1046/j.1365-2796.2003.01098.x 1:CAS:528:DC%2BD3sXht1WrtLo%3D doi:10.1046/j.1365-2796.2003.01098.x (Pubitemid 36120997)
21. H Fridborg E Jonsson P Nygren R Larsson 1999 Relationship between diagnosis-specific activity of cytotoxic drugs in fresh human tumour cells ex vivo and in the clinic Eur J Cancer 35 3 424 432 10448294 10.1016/S0959-8049(98) 00286-X 1:CAS:528:DyaK1MXisVGqs7s%3D doi:10.1016/S0959-8049(98)00286-X (Pubitemid 29151940)
22. JM Zamora HL Pearce WT Beck 1988 Physical-chemical properties shared by compounds that modulate multidrug resistance in human leukemic cells Mol Pharmacol 33 4 454 462 3162758 1:CAS:528:DyaL1cXitFGqt7o%3D
23. N Chakraborty SR Bose JR Chowdhury 1984 Acriflavine-induced surface changes in three tumor cell types and differential sensitivity to lectins Tumori 70 2 127 130 6730013 1:CAS:528:DyaL2cXktlKktrw%3D
24. D Magda P Lecane Z Wang W Hu P Thiemann X Ma PK Dranchak X Wang V Lynch W Wei V Csokai JG Hacia JL Sessler 2008 Synthesis and anticancer properties of water-soluble zinc ionophores Cancer Res 68 13 5318 5325 18593933 10.1158/0008-5472.CAN-08-0601 1:CAS:528:DC%2BD1cXnvFyjtro%3D doi:10.1158/0008-5472.CAN-08-0601
25. K Kurata R Yanagisawa M Ohira M Kitagawa A Nakagawara T Kamijo 2008 Stress via p53 pathway causes apoptosis by mitochondrial Noxa upregulation in doxorubicin-treated neuroblastoma cells Oncogene 27 741 754 17653088 10.1038/sj.onc.1210672 1:CAS:528:DC%2BD1cXhtl2msb0%3D (Pubitemid 351186310)
26. M Fryknas S Dhar F Oberg L Rickardson M Rydaker H Goransson M Gustafsson U Pettersson P Nygren R Larsson A Isaksson 2007 STAT1 signaling is associated with acquired crossresistance to doxorubicin and radiation in myeloma cell lines Int J Cancer 120 1 189 195 17072862 10.1002/ijc.22291 doi:10.1002/ijc.22291 (Pubitemid 44901935)
27. J Lamb ED Crawford D Peck JW Modell IC Blat MJ Wrobel J Lerner JP Brunet A Subramanian KN Ross M Reich H Hieronymus G Wei SA Armstrong SJ Haggarty PA Clemons R Wei SA Carr ES Lander TR Golub 2006 The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease Science 313 5795 1929 1935 17008526 10.1126/science.1132939 1:CAS:528: DC%2BD28XhtVSnsrbN doi:10.1126/science.1132939 (Pubitemid 44497995)