PAC, a novel curcumin analogue, has anti-breast cancer properties with higher efficiency on ER-negative cells

Breast Cancer Research and Treatment

Volumn 128, Issue 1, 2011, Pages 97-107

  Al Hujaily, Ensaf M ^a   Mohamed, Ameera Gaafar ^a   Al Sharif, Ibtehaj ^a   Youssef, Khairia M ^b,c   Manogaran, Pulicat S ^a   Al Otaibi, Basem ^a   Al Haza'A, Amal ^b   Al Jammaz, Ibrahim ^a   Al Hussein, Khaled ^a   Aboussekhra, Abdelilah ^a,d  

^a KING FAISAL SPECIALIST HOSPITAL AND RESEARCH CENTER   (Saudi Arabia)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

^c FUTURE UNIVERSITY IN EGYPT   (Egypt)

^d ALFAISAL UNIVERSITY   (Saudi Arabia)

Author keywords

Biodistribution; Breast cancer; Curcumin analogue; Estrogen receptor; Tumour xenograft

Indexed keywords

1,7 BIS(4 HYDROXY 3 ETHOXYPHENYL) 1,6 HEPTADIEN 3,5 DIONE; 5 BIS(4 HYDROXY 3 METHOXYBENZYLIDINE) N METHYL 4 PIPERIDONE; ANTINEOPLASTIC AGENT; CURCUMIN; CURCUMIN DERIVATIVE; CYCLIN D1; CYCLIN DEPENDENT KINASE INHIBITOR 1; ESTROGEN RECEPTOR; ESTROGEN RECEPTOR ALPHA; FLUORINE 18; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INTERLEUKIN 10; INTERLEUKIN 4; LIPOCORTIN 5; PROPIDIUM IODIDE; PROTEIN BAX; PROTEIN BCL 2; SURVIVIN; TUMOR PROTEIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CANCER INHIBITION; CANCER RESISTANCE; CANCER SIZE; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOKINE PRODUCTION; CYTOKINE RELEASE; DRUG BIOAVAILABILITY; DRUG CYTOTOXICITY; DRUG DISTRIBUTION; DRUG EFFICACY; DRUG SAFETY; DRUG STABILITY; DRUG STRUCTURE; ENZYME LINKED IMMUNOSPOT ASSAY; FLOW CYTOMETRY; HUMAN; HUMAN CELL; IMMUNOBLOTTING; IN VITRO STUDY; IN VIVO STUDY; MITOCHONDRIAL RESPIRATION; MOUSE; NONHUMAN; NUDE MOUSE; PERIPHERAL BLOOD MONONUCLEAR CELL; PRIORITY JOURNAL; PROTEIN EXPRESSION; SIGNAL TRANSDUCTION; TH2 CELL; TISSUE DISTRIBUTION; TREATMENT DURATION; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; APOPTOSIS REGULATORY PROTEINS; BENZYLIDENE COMPOUNDS; BRAIN CHEMISTRY; BREAST NEOPLASMS; CELL LINE, TUMOR; CYCLIN-DEPENDENT KINASE INHIBITOR P21; FEMALE; G2 PHASE; GENES, NEOPLASM; HUMANS; INTERFERON-GAMMA; INTERLEUKIN-10; INTERLEUKIN-4; MICE; MICE, NUDE; MITOCHONDRIA; MYOCARDIUM; PIPERIDONES; RECEPTORS, ESTROGEN; TISSUE DISTRIBUTION; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 79959202798     PISSN: 01676806     EISSN: 15737217     Source Type: Journal    
DOI: 10.1007/s10549-010-1089-3     Document Type: Article

References (43)

1. C Smigal A Jemal E Ward V Cokkinides R Smith HL Howe M Thun 2006 Trends in breast cancer by race and ethnicity: update 2006 CA Cancer J Clin 56 168 183 16737949 10.3322/canjclin.56.3.168 (Pubitemid 43847927)
2. AK Garg TA Buchholz BB Aggarwal 2005 Chemosensitization and radiosensitization of tumors by plant polyphenols Antioxid Redox Signal 7 1630 1647 16356126 10.1089/ars.2005.7.1630 1:CAS:528:DC%2BD2MXhtlWht73M (Pubitemid 41767998)
3. A Goel AB Kunnumakkara BB Aggarwal 2007 Curcumin as "Curecumin" : from kitchen to clinic Biochem Pharmacol 19 19
4. P Anand SG Thomas AB Kunnumakkara C Sundaram KB Harikumar B Sung ST Tharakan K Misra IK Priyadarsini KN Rajasekharan, et al. 2008 Biological activities of curcumin and its analogues (Congeners) made by man and mother nature Biochem Pharmacol 76 1590 1611 18775680 10.1016/j.bcp.2008.08.008 1:CAS:528:DC%2BD1cXhtl2qtb7I
5. S Bhattacharyya D Mandal B Saha GS Sen T Das G Sa 2007 Curcumin prevents tumor-induced T cell apoptosis through Stat-5a-mediated Bcl-2 induction J Biol Chem 282 15954 15964 17392282 10.1074/jbc.M608189200 1:CAS:528: DC%2BD2sXlvVajs78%3D (Pubitemid 47100378)
6. M Labbozzetta M Notarbartolo P Poma A Maurici L Inguglia P Marchetti M Rizzi R Baruchello D Simoni N D'Alessandro 2009 Curcumin as a possible lead compound against hormone-independent, multidrug-resistant breast cancer Ann NY Acad Sci 1155 278 283 19250217 10.1111/j.1749-6632.2009.03699.x 1:CAS:528:DC%2BD1MXktFKlt7g%3D
7. HI Kim H Huang S Cheepala S Huang J Chung 2008 Curcumin inhibition of integrin (alpha6beta4)-dependent breast cancer cell motility and invasion Cancer Prev Res (Phila PA) 1 385 391 10.1158/1940-6207.CAPR-08-0087 1:CAS:528:DC%2BC3cXptFOit70%3D
8. EP Moiseeva GM Almeida GD Jones MM Manson 2007 Extended treatment with physiologic concentrations of dietary phytochemicals results in altered gene expression, reduced growth, and apoptosis of cancer cells Mol Cancer Ther 6 3071 3079 18025290 10.1158/1535-7163.MCT-07-0117 1:CAS:528:DC%2BD2sXhtlWkt7fF (Pubitemid 350206785)
9. P Anand C Sundaram S Jhurani AB Kunnumakkara BB Aggarwal 2008 Curcumin and cancer: an "old-age" disease with an "age-old" solution Cancer Lett 267 133 164 18462866 10.1016/j.canlet.2008.03.025 1:CAS:528:DC%2BD1cXotlCgtbs%3D
10. BB Aggarwal S Shishodia Y Takada S Banerjee RA Newman CE Bueso-Ramos JE Price 2005 Curcumin suppresses the paclitaxel-induced nuclear factor-kappaB pathway in breast cancer cells and inhibits lung metastasis of human breast cancer in nude mice Clin Cancer Res 11 7490 7498 16243823 10.1158/1078-0432.CCR- 05-1192 1:CAS:528:DC%2BD2MXhtFartbjM (Pubitemid 41507710)
11. P Anand AB Kunnumakkara RA Newman BB Aggarwal 2007 Bioavailability of curcumin: problems and promises Mol Pharm 4 807 818 17999464 10.1021/mp700113r 1:CAS:528:DC%2BD2sXht12gsrnF
12. MW Amolins LB Peterson BS Blagg 2009 Synthesis and evaluation of electron-rich curcumin analogues Bioorg Med Chem 17 360 367 19019687 10.1016/j.bmc.2008.10.057 1:CAS:528:DC%2BD1cXhsFamtrzO
13. D Simoni M Rizzi R Rondanin R Baruchello P Marchetti FP Invidiata M Labbozzetta P Poma V Carina M Notarbartolo, et al. 2008 Antitumor effects of curcumin and structurally beta-diketone modified analogs on multidrug resistant cancer cells Bioorg Med Chem Lett 18 845 849 18039573 10.1016/j.bmcl.2007.11.021 1:CAS:528:DC%2BD1cXosFajsg%3D%3D
14. BK Adams J Cai J Armstrong M Herold YJ Lu A Sun JP Snyder DC Liotta DP Jones M Shoji 2005 EF24, a novel synthetic curcumin analog, induces apoptosis in cancer cells via a redox-dependent mechanism Anticancer Drugs 16 263 275 15711178 10.1097/00001813-200503000-00005 1:CAS:528:DC%2BD2MXht1Omtr4%3D (Pubitemid 40283941)
15. S Padhye S Banerjee D Chavan S Pandye KV Swamy S Ali J Li QP Dou FH Sarkar 2009 Fluorocurcumins as cyclooxygenase-2 inhibitor: molecular docking, pharmacokinetics and tissue distribution in mice Pharm Res 26 2438 2445 19714451 10.1007/s11095-009-9955-6 1:CAS:528:DC%2BD1MXhtVGiurjO
16. S Padhye H Yang A Jamadar QC Cui D Chavan K Dominiak J McKinney S Banerjee QP Dou FH Sarkar 2009 New difluoro Knoevenagel condensates of curcumin, their Schiff bases and copper complexes as proteasome inhibitors and apoptosis inducers in cancer cells Pharm Res 26 1874 1880 19421843 10.1007/s11095-009- 9900-8 1:CAS:528:DC%2BD1MXlsFOmtrc%3D
17. K Selvendiran L Tong S Vishwanath A Bratasz NJ Trigg VK Kutala K Hideg P Kuppusamy 2007 EF24 induces G2/M arrest and apoptosis in cisplatin-resistant human ovarian cancer cells by increasing PTEN expression J Biol Chem 282 28609 28618 17684018 10.1074/jbc.M703796200 1:CAS:528:DC%2BD2sXhtVOmtb3M (Pubitemid 47606012)
18. KM Youssef MA El-Sherbeny FS El-Shafie HA Farag OA Al-Deeb SA Awadalla 2004 Synthesis of curcumin analogues as potential antioxidant, cancer chemopreventive agents Arch Pharm (Weinheim) 337 42 54 10.1002/ardp.200300763 1:CAS:528:DC%2BD2cXhtFKksr8%3D (Pubitemid 38222249)
19. AM Abukhdeir BG Blair K Brenner B Karakas H Konishi J Lim V Sahasranaman Y Huang J Keen N Davidson, et al. 2006 Physiologic estrogen receptor alpha signaling in non-tumorigenic human mammary epithelial cells Breast Cancer Res Treat 99 23 33 16541319 10.1007/s10549-006-9177-0 1:CAS:528:DC%2BD28XnslShsLs%3D (Pubitemid 44168600)
20. MA Al-Mohanna PS Manogaran Z Al-Mukhalafi AK Al-Hussein A Aboussekhra 2004 The tumor suppressor p16(INK4a) gene is a regulator of apoptosis induced by ultraviolet light and cisplatin Oncogene 23 201 212 14712225 10.1038/sj.onc.1206927 1:CAS:528:DC%2BD2cXovVKhsA%3D%3D (Pubitemid 38142254)
21. BB Aggarwal A Kumar AC Bharti 2003 Anticancer potential of curcumin: preclinical and clinical studies Anticancer Res 23 363 398 12680238 1:CAS:528:DC%2BD3sXislaqtLo%3D (Pubitemid 36361976)
22. TM Rowlands IV Pechenkina S Hatsell P Cowin 2004 Beta-catenin and cyclin D1: connecting development to breast cancer Cell Cycle 3 145 148 14712077 10.4161/cc.3.2.665 1:CAS:528:DC%2BD2cXisFGnu7c%3D (Pubitemid 40268685)
23. DC Guttridge C Albanese JY Reuther RG Pestell AS Baldwin Jr 1999 NF-kappaB controls cell growth and differentiation through transcriptional regulation of cyclin D1 Mol Cell Biol 19 5785 5799 10409765 1:CAS:528: DyaK1MXkvVKjtrc%3D (Pubitemid 29339933)
24. M Hinz D Krappmann A Eichten A Heder C Scheidereit M Strauss 1999 NF-kappaB function in growth control: regulation of cyclin D1 expression and G0/G1-to-S-phase transition Mol Cell Biol 19 2690 2698 10082535 1:CAS:528:DyaK1MXit1amt7s%3D (Pubitemid 29144513)
25. DC Altieri 2008 Survivin, cancer networks and pathway-directed drug discovery Nat Rev Cancer 8 61 70 18075512 10.1038/nrc2293 1:CAS:528: DC%2BD2sXhsVKku73M
26. M Lacroix RA Toillon G Leclercq 2006 p53 and breast cancer, an update Endocr Relat Cancer 13 293 325 16728565 10.1677/erc.1.01172 1:CAS:528: DC%2BD28XntF2mtL4%3D (Pubitemid 43886660)
27. GP Dotto 2000 p21(WAF1/Cip1): more than a break to the cell cycle? Biochim Biophys Acta 1471 M43 M56 10967424 1:CAS:528:DC%2BD3cXmtVGiu7k%3D
28. AL Gartel AL Tyner 2002 The role of the cyclin-dependent kinase inhibitor p21 in apoptosis Mol Cancer Ther 1 639 649 12479224 1:CAS:528: DC%2BD38XlsFSlsr0%3D
29. ES Hickman MC Moroni K Helin 2002 The role of p53 and pRB in apoptosis and cancer Curr Opin Genet Dev 12 60 66 11790556 10.1016/S0959-437X(01)00265-9 1:CAS:528:DC%2BD38XktFGlsw%3D%3D (Pubitemid 34094991)
30. J Stanelle BM Putzer 2006 E2F1-induced apoptosis: turning killers into therapeutics Trends Mol Med 12 177 185 16530485 10.1016/j.molmed.2006.02.002 1:CAS:528:DC%2BD28XjvFWltr0%3D
31. Y Cao M Karin 2003 NF-kappaB in mammary gland development and breast cancer J Mammary Gland Biol Neoplasia 8 215 223 14635796 10.1023/A:1025905008934 (Pubitemid 38129943)
32. MC Haffner C Berlato W Doppler 2006 Exploiting our knowledge of NF-kappaB signaling for the treatment of mammary cancer J Mammary Gland Biol Neoplasia 11 63 73 16900390 10.1007/s10911-006-9013-5 (Pubitemid 44309190)
33. C Van Waes 2007 Nuclear factor-kappaB in development, prevention, and therapy of cancer Clin Cancer Res 13 1076 1082 17317814 10.1158/1078-0432.CCR- 06-2221 (Pubitemid 46424045)
34. S Paul A Dey 2008 Wnt signaling and cancer development: therapeutic implication Neoplasma 55 165 176 18348648 1:CAS:528:DC%2BD1MXhtFyitL8%3D
35. CP Prasad SD Gupta G Rath R Ralhan 2007 Wnt signaling pathway in invasive ductal carcinoma of the breast: relationship between beta-catenin, dishevelled and cyclin D1 expression Oncology 73 112 117 18337623 10.1159/000120999 1:CAS:528:DC%2BD1cXktVSgtL0%3D (Pubitemid 351465609)
36. J Bartkova J Lukas M Strauss J Bartek 1995 Cyclin D1 oncoprotein aberrantly accumulates in malignancies of diverse histogenesis Oncogene 10 775 778 7862456 1:CAS:528:DyaK2MXktF2ltro%3D
37. C Yang S Trent V Ionescu-Tiba L Lan T Shioda D Sgroi EV Schmidt 2006 Identification of cyclin D1- and estrogen-regulated genes contributing to breast carcinogenesis and progression Cancer Res 66 11649 11658 17178859 10.1158/0008-5472.CAN-06-1645 1:CAS:528:DC%2BD28XhtlagurbF (Pubitemid 46094176)
38. K Tanaka S Iwamoto G Gon T Nohara M Iwamoto N Tanigawa 2000 Expression of survivin and its relationship to loss of apoptosis in breast carcinomas Clin Cancer Res 6 127 134 10656440 1:CAS:528:DC%2BD3cXhtVCjsr4%3D (Pubitemid 30064984)
39. GM Callagy PD Pharoah SE Pinder FD Hsu TO Nielsen J Ragaz IO Ellis D Huntsman C Caldas 2006 Bcl-2 is a prognostic marker in breast cancer independently of the Nottingham Prognostic Index Clin Cancer Res 12 2468 2475 16638854 10.1158/1078-0432.CCR-05-2719 1:CAS:528:DC%2BD28XjvValurs%3D
40. S Nagai M Toi 2000 Interleukin-4 and breast cancer Breast Cancer 7 181 186 11029795 10.1007/BF02967457 1:STN:280:DC%2BD3M3mvFKrsA%3D%3D
41. S Mocellin FM Marincola HA Young 2005 Interleukin-10 and the immune response against cancer: a counterpoint J Leukoc Biol 78 1043 1051 16204623 10.1189/jlb.0705358 1:CAS:528:DC%2BD2MXht1ShsL%2FN (Pubitemid 41572467)
42. EK Ryu YS Choe KH Lee Y Choi BT Kim 2006 Curcumin and dehydrozingerone derivatives: synthesis, radiolabeling, and evaluation for beta-amyloid plaque imaging J Med Chem 49 6111 6119 17004725 10.1021/jm0607193 1:CAS:528: DC%2BD28XpsF2itbo%3D (Pubitemid 44484955)
43. BK Adams EM Ferstl MC Davis M Herold S Kurtkaya RF Camalier MG Hollingshead G Kaur EA Sausville FR Rickles, et al. 2004 Synthesis and biological evaluation of novel curcumin analogs as anti-cancer and anti-angiogenesis agents Bioorg Med Chem 12 3871 3883 15210154 10.1016/j.bmc.2004.05.006 1:CAS:528:DC%2BD2cXltVKisr8%3D (Pubitemid 38798249)