Inclusion complex of novel curcumin analogue CDF and β-cyclodextrin (1:2) and its enhanced in vivo anticancer activity against pancreatic cancer

Pharmaceutical Research

Volumn 29, Issue 7, 2012, Pages 1775-1786

  Dandawate, Prasad R ^a   Vyas, Alok ^a,b   Ahmad, Aamir ^c   Banerjee, Sanjeev ^c   Deshpande, Jyoti ^b   Swamy, K Venkateswara ^b   Jamadar, Abeda ^d   Dumhe Klaire, Anne Catherine ^d   Padhye, Subhash ^a,c   Sarkar, Fazlul H ^c  

^a ISTRA   (India)

^b DR D Y PATIL BIOTECHNOLOGY AND BIOINFORMATICS INSTITUTE   (India)

^c WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d UNIVERSITY OF YORK   (United Kingdom)

Author keywords

CDF; CDF cyclodextrin; Curcumin analog; Pancreatic cancer

Indexed keywords

BETA CYCLODEXTRIN DERIVATIVE; CURCUMIN; DIFLUORINATEDCURCUMIN; DIFLUORINATEDCURCUMIN BETA CYCLODEXTRIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG BINDING SITE; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG POTENCY; DRUG SCREENING; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TISSUE LEVEL; FEMALE; IC 50; IN VIVO STUDY; INFRARED SPECTROSCOPY; MOUSE; NONHUMAN; PANCREAS CANCER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SCANNING ELECTRON MICROSCOPY; SINGLE DRUG DOSE; STRUCTURE ANALYSIS; TISSUE DISTRIBUTION; X RAY DIFFRACTION;

ANIMALS; ANTINEOPLASTIC AGENTS; BETA-CYCLODEXTRINS; CELL LINE, TUMOR; CELL SURVIVAL; CURCUMA; CURCUMIN; DRUG CARRIERS; FEMALE; HALOGENATION; HUMANS; MICE; MODELS, MOLECULAR; PANCREAS; PANCREATIC NEOPLASMS; SOLUBILITY;

EID: 84866782159     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-012-0700-1     Document Type: Article

References (40)

1. Shishodia S, Sethi G, Aggarwal BB. Curcumin: getting back to the roots. Ann N Y Acad Sci. 2005;1056:206-17. (Pubitemid 43030979)
2. Ravindran J, Prasad S, Aggarwal BB. Curcumin and cancer cells: how many ways can curry kill tumor cells selectively? AAPS J. 2009;11:495-510.
3. Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB. Bioavailability of curcumin: problems and promises. Mol Pharm. 2007;4:807-18.
4. Padhye S, Banerjee S, Chavan D, Pandye S, Swamy KV, Ali S, et al. Fluorocurcumins as cyclooxygenase-2 inhibitor: molecular docking, pharmacokinetics and tissue distribution in mice. Pharm Res. 2009;26:2438-45.
5. Padhye S, Yang H, Jamadar A, Cui QC, Chavan D, Dominiak K, et al. New difluoro Knoevenagel condensates of curcumin, their Schiff bases and copper complexes as proteasome inhibitors and apoptosis inducers in cancer cells. Pharm Res. 2009;26:1874-80.
6. Ali S, Ahmad A, Banerjee S, Padhye S, Dominiak K, Schaffert JM, et al. Gemcitabine sensitivity can be induced in pancreatic cancer cells through modulation of miR-200 and miR-21 expression by curcumin or its analogue CDF. Cancer Res. 2010;70:3606-17.
7. Bao B, Ali S, Kong D, Sarkar SH, Wang Z, Banerjee S, et al. Anti-tumor activity of a novel compound-CDF is mediated by regulating miR-21, miR-200, and PTEN in pancreatic cancer. PLoS One. 2011;6:e17850.
8. Bao B, Ali S, Banerjee S, Wang Z, Logna F, Azmi AS, et al. Curcumin analog CDF inhibits pancreatic tumor growth by switching on suppressor microRNAs and attenuating EZH2 expression. Cancer Res. 2012;72:335-45.
9. Li Y, Kong D, Wang Z, Ahmad A, Bao B, Padhye S, et al. Inactivation of AR/TMPRSS2-ERG/Wnt signaling networks attenuates the aggressive behavior of prostate cancer cells. Cancer Prev Res (Phila). 2011;4:1495-506.
10. Kanwar SS, Yu Y, Nautiyal J, Patel BB, Padhye S, Sarkar FH, et al. Difluorinated-curcumin (CDF): a novel curcumin analog is a potent inhibitor of colon cancer stem-like cells. Pharm Res. 2011;28:827-38.
11. Yallapu MM, Dobberpuhl MR, Maher DM, Jaggi M, Chauhan SC. Design of Curcumin loaded Cellulose Nanoparticles for Prostate Cancer. Curr Drug Metab. 2011.
12. Mazzarino L, Silva LF, Curta JC, Licinio MA, Costa A, Pacheco LK, et al. Curcumin-loaded lipid and polymeric nanocapsules stabilized by nonionic surfactants: an in vitro and In vivo antitumor activity on B16-F10 melanoma and macrophage uptake comparative study. J Biomed Nanotechnol. 2011;7:406-14.
13. Pandelidou M, Dimas K, Georgopoulos A, Hatziantoniou S, Demetzos C. Preparation and characterization of lyophilised egg PC liposomes incorporating curcumin and evaluation of its activity against colorectal cancer cell lines. J Nanosci Nanotechnol. 2011;11:1259-66.
14. Dhule SS, Penfornis P, Frazier T, Walker R, Feldman J, Tan G et al. Curcumin-loaded gamma-cyclodextrin liposomal nanoparticles as delivery vehicles for osteosarcoma. Nanomedicine. 2011.
15. Harada T, Pham DT, Leung MH, Ngo HT, Lincoln SF, Easton CJ, et al. Cooperative binding and stabilization of the medicinal pigment curcumin by diamide linked gamma-cyclodextrin dimers: a spectroscopic characterization. J Phys Chem B. 2011;115:1268-74.
16. Hegge AB, Schuller RB, Kristensen S, Tonnesen HH. In vitro release of curcumin from vehicles containing alginate and cyclodextrin. Studies of curcumin and curcuminoides. XXXIII. Pharmazie. 2008;63:585-92.
17. Yadav VR, Suresh S, Devi K, Yadav S. Effect of cyclodextrin complexation of curcumin on its solubility and antiangiogenic and anti-inflammatory activity in rat colitis model. AAPS PharmSciTech. 2009;10:752-62.
18. Yadav VR, Prasad S, Kannappan R, Ravindran J, Chaturvedi MM, Vaahtera L, et al. Cyclodextrin-complexed curcumin exhibits anti-inflammatory and antiproliferative activities superior to those of curcumin through higher cellular uptake. Biochem Pharmacol. 2010;80:1021-32.
19. Yallapu MM, Jaggi M, Chauhan SC. beta-Cyclodextrin-curcumin self-assembly enhances curcumin delivery in prostate cancer cells. Colloids Surf B Biointerfaces. 2010;79:113-25.
20. Higuchi T, Connors KA. Phase solubility techniques. Adv Anal Chem Instrum. 1965;4:117-212.
21. Renner S, Schwab CH, Gasteiger J, Schneider G. Impact of conformational flexibility on three-dimensional similarity searching using correlation vectors. J Chem Inf Model. 2006;46:2324-32. (Pubitemid 46008107)
22. Anderson AM, Mitchell MS, Mohan RS. Isolation of curcumin from turmeric. J Chem Ed. 2000;77:359-60.
23. Shen YL, Ying W, Yang SH, Wu LM. Determinations of the inclusion complex between gossypol and beta-cyclodextrin. Spectrochim Acta A Mol Biomol Spectrosc. 2006;65:169-72. (Pubitemid 44163274)
24. Wu H, Liang H, Yuan Q, Wang T, Yan X. Preparation and Stability investigation of the inclusion complex of sulforaphane with hydroxypropyl-beta- cyclodextrin. Carbohydr Polym. 2010;82:613-7.
25. Song LX, Wang HM, Guo XQ, Bai L. A comparative study on the binding behaviors of beta-cyclodextrin and its two derivatives to four fanlike organic guests. J Org Chem. 2008;73:8305-16.
26. Uner M. Preparation, characterization and physico-chemical properties of solid lipid nanoparticles (SLN) and nanostructured lipid carriers (NLC): their benefits as colloidal drug carrier systems. Pharmazie. 2006;61:375-86. (Pubitemid 43724410)
27. Santander-Ortega MJ, Bastos-Gonzalez D, Ortega-Vinuesa JL, Alonso MJ. Insulin-loaded PLGA nanoparticles for oral administration: an in vitro physico-chemical characterization. J Biomed Nanotechnol. 2009;5:45-53.
28. Craparo EF, Cavallaro G, Bondi ML, Mandracchia D, Giammona G. PEGylated Nanoparticles based on a polyaspartamide. preparation, physico-chemical characterization, and intracellular uptake. Biomacromolecules. 2006;7:3083-92. (Pubitemid 46039964)
29. Lemarchand C, Gref R, Lesieur S, Hommel H, Vacher B, Besheer A, et al. Physico-chemical characterization of polysaccharide-coated nanoparticles. J Control Release. 2005;108:97-111. (Pubitemid 41476678)
30. Horvath G, Premkumar T, Boztas A, Lee E, Jon S, Geckeler KE. Supramolecular nanoencapsulation as a tool: solubilization of the anticancer drug trans-dichloro(dipyridine)platinum(II) by complexation with beta-cyclodextrin. Mol Pharm. 2008;5:358-63. (Pubitemid 351579138)
31. Yallapu MM, Jaggi M, Chauhan SC. Poly(beta-cyclodextrin)/curcumin self-assembly: a novel approach to improve curcumin delivery and its therapeutic efficacy in prostate cancer cells. Macromol Biosci. 2010;10:1141-51.
32. Komura T, Yamaguchi T, Noda K, Hayashi S. Inclusion complexation of (11-ferrocenylundecyl)trimethylammonium bromide by beta-cyclodextrin and its effects on elctrochemical behavior of the surfactant. Electrochim Acta. 2002;47:3315-25. (Pubitemid 34862798)
33. Kolivoska V, Ga'l M, Hromadova M, Valasek M, Pospisil L. Correlation of the formation constant of ferrocene-cyclodextrin complexes with dielectric properties of the aqueous DMSO solution. J Organomet Chem. 2011;696:1404-8.
34. Srinivasan K, Kayalvizhi K, Sivakumar K, Stalin T. Study of inclusion complex of beta-cyclodextrin and diphenylamine: photophysical and electrochemical behaviors. Spectrochim Acta A Mol Biomol Spectrosc. 2011;79:169-78.
35. Garnero C, Zoppi A, Genovese D, Longhi M. Studies on trimethoprim: hydroxypropyl-beta-cyclodextrin: aggregate and complex formation. Carbohydr Res. 2010;345:2550-6.
36. Inoue Y. NMR studies of the structure and properties of cyclodextrins and their inclusion complexes. Annu Re NMR Spectrosc. 1993;27:59-101.
37. Bernini A, Spiga O, Ciutti A, Scarselli M, Bottoni G, Mascagni P, et al. NMR studies of the inclusion complex between beta-cyclodextrin and paroxetine. Eur J Pharm Sci. 2004;22:445-50. (Pubitemid 38953903)
38. Marcolino VA, Zanin GM, Durrant LR, Benassi MT, Matioli G. Interaction of curcumin and bixin with beta-cyclodextrin: complexation methods, stability, and applications in food. J Agric Food Chem. 2011;59:3348-57.
39. Faucci MT, Melani F, Mura P. Computer-aidedmolecular modeling techniques for predicting the stability of drug-cyclodextrin inclusion complexes in aqueous solutions. Cmeical Physics Letters. 2002;358:383-90.
40. Jemal A, Bray F, Center MM, Ferlay J, Ward E, Forman D. Global cancer statistics. CA Cancer J Clin. 2011;61:69-90.