Parenterally administrable nano-micelles of 3,4-difluorobenzylidene curcumin for treating pancreatic cancer

Colloids and Surfaces B: Biointerfaces

Volumn 132, Issue , 2015, Pages 138-145

  Kesharwani, Prashant ^a   Banerjee, Sanjeev ^b   Padhye, Subhash ^c   Sarkar, Fazlul H ^b   Iyer, Arun K ^a  

^a WAYNE STATE UNIVERSITY   (United States)

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

^c UNIVERSITY OF PUNE   (India)

Author keywords

3,4 Difluorobenzylidene curcumin; Aqueous solubility; Nano micelles; Nanoparticles; Pancreatic cancer; Styrene maleic acid copolymer

Indexed keywords

CELL CULTURE; COPOLYMERS; DISEASES; HYDROPHOBICITY; MICELLES; NANOPARTICLES; PATIENT TREATMENT; SOLUBILITY; STYRENE;

AQUEOUS SOLUBILITY; CURCUMIN; NANOMICELLES; PANCREATIC CANCERS; STYRENE MALEIC ACID COPOLYMER;

DRUG PRODUCTS;

3,4 DIFLUOROBENZYLIDENE CURCUMIN; ANTINEOPLASTIC AGENT; COPOLYMER; CURCUMIN; MALEIC ACID; STYRENE; UNCLASSIFIED DRUG; MICELLE;

AMPHIPHILICITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; ASPC 1 CELL LINE; CHEMICAL PHENOMENA; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG INCOMPATIBILITY; DRUG SOLUBILITY; DRUG STABILITY; DRUG TRANSPORT; HUMAN; HUMAN CELL; IN VITRO STUDY; INTRACELLULAR TRANSPORT; MIAPACA 2 CELL LINE; MICELLE; NANOMICELLE; PANCREATIC CANCER CELL LINE; PRIORITY JOURNAL; SUSTAINED DRUG RELEASE; ANALOGS AND DERIVATIVES; NANOTECHNOLOGY; PANCREATIC NEOPLASMS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CURCUMIN; HUMANS; MICELLES; NANOTECHNOLOGY; PANCREATIC NEOPLASMS;

EID: 84930677214     PISSN: 09277765     EISSN: 18734367     Source Type: Journal    
DOI: 10.1016/j.colsurfb.2015.05.007     Document Type: Article

References (52)

1. Rahib L., Smith B.D., Aizenberg R., Rosenzweig A.B., Fleshman J.M., Matrisian L.M. Projecting cancer incidence and deaths to 2030: the unexpected burden of thyroid, liver, and pancreas cancers in the United States. Cancer Res. 2014, 74:2913-2921.
2. Cancer Facts & Figures 2014 2014, American Cancer Society, Atlanta.
3. Smith B.D., Smith G.L., Hurria A., Hortobagyi G.N., Buchholz T.A. Future of cancer incidence in the United States: burdens upon an aging, changing nation. J. Clin. Oncol. 2009, 27:2758-2765.
4. Whatcott C., Han H., Posner R.G., Von Hoff D.D. Tumor-stromal interactions in pancreatic cancer. Crit. Rev. Oncog. 2013, 18:135-151.
5. Mimeault M., Brand R.E., Sasson A.A., Batra S.K. Recent advances on the molecular mechanisms involved in pancreatic cancer progression and therapies. Pancreas 2005, 31:301-316.
6. Mimeault M., Batra S.K. Potential applications of curcumin and its novel synthetic analogs and nanotechnology-based formulations in cancer prevention and therapy. Chin. Med. 2011, 6:31.
7. Padhye S., Banerjee S., Chavan D., Pandye S., Swamy K.V., Ali S., Li J., Dou Q.P., Sarkar F.H. Fluorocurcumins as cyclooxygenase-2 inhibitor: molecular docking, pharmacokinetics and tissue distribution in mice. Pharm. Res. 2009, 26:2438-2445.
8. Ali S., Ahmad A., Banerjee S., Padhye S., Dominiak K., Schaffert J.M., Wang Z., Philip P.A., Sarkar F.H. 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, 70:3606-3617.
9. Wang Z., Zhang Y., Banerjee S., Li Y., Sarkar F.H. Notch-1 down-regulation by curcumin is associated with the inhibition of cell growth and the induction of apoptosis in pancreatic cancer cells. Cancer 2006, 106:2503-2513.
10. Anand P., Sundaram C., Jhurani S., Kunnumakkara A.B., Aggarwal B.B. Curcumin and cancer: an old-age disease with an age-old solution. Cancer Lett. 2008, 267:133-164.
11. Aggarwal S., Ichikawa H., Takada Y., Sandur S.K., Shishodia S., Aggarwal B.B. Curcumin (diferuloylmethane) down-regulates expression of cell proliferation and antiapoptotic and metastatic gene products through suppression of IkappaBalpha kinase and Akt activation. Mol. Pharm. 2006, 69:195-206.
12. Shishodia S., Chaturvedi M.M., Aggarwal B.B. Role of curcumin in cancer therapy, Curr. Probl. Cancer 2007, 31:243-305.
13. Orr W.S., Denbo J.W., Saab K.R., Myers A.L., Ng C.Y., Zhou J., Morton C.L., Pfeffer L.M., Davidoff A.M. Liposome-encapsulated curcumin suppresses neuroblastoma growth through nuclear factor-kappa B inhibition. Surgery 2012, 151:736-744.
14. Wang D., Veena M.S., Stevenson K., Tang C., Ho B., Suh J.D., Duarte V.M., Faull K.F., Mehta K., Srivatsan E.S., Wang M.B. Liposome-encapsulated curcumin suppresses growth of head and neck squamous cell carcinoma in vitro and in xenografts through the inhibition of nuclear factor kappaB by an AKT-independent pathway. Clin. Cancer Res. 2008, 14:6228-6236.
15. Li L., Braiteh F.S., Kurzrock R. Liposome-encapsulated curcumin: in vitro and in vivo effects on proliferation, apoptosis, signaling, and angiogenesis. Cancer 2005, 104:1322-1331.
16. Gou Q., Liu L., Wang C., Wu Q., Sun L., Yang X., Xie Y., Li P., Gong C. Polymeric nanoassemblies entrapping curcumin overcome multidrug resistance in ovarian cancer. Colloids Surf. B: Biointerfaces 2014, 126C:26-34.
17. Song Z., Feng R., Sun M., Guo C., Gao Y., Li L., Zhai G. Curcumin-loaded PLGA-PEG-PLGA triblock copolymeric micelles: preparation, pharmacokinetics and distribution in vivo. J. Colloid Interface Sci. 2011, 354:116-123.
18. Gou M., Men K., Shi H., Xiang M., Zhang J., Song J., Long J., Wan Y., Luo F., Zhao X., Qian Z. Curcumin-loaded biodegradable polymeric micelles for colon cancer therapy in vitro and in vivo. Nanoscale 2011, 3:1558-1567.
19. Chuah L.H., Roberts C.J., Billa N., Abdullah S., Rosli R. Cellular uptake and anticancer effects of mucoadhesive curcumin-containing chitosan nanoparticles. Colloids Surf. B: Biointerfaces 2014, 116:228-236.
20. Shaikh J., Ankola D.D., Beniwal V., Singh D., Kumar M.N. Nanoparticle encapsulation improves oral bioavailability of curcumin by at least 9-fold when compared to curcumin administered with piperine as absorption enhancer. Eur. J. Pharm. Sci. 2009, 37:223-230.
21. Ma Z., Shayeganpour A., Brocks D.R., Lavasanifar A., Samuel J. High-performance liquid chromatography analysis of curcumin in rat plasma: application to pharmacokinetics of polymeric micellar formulation of curcumin. Biomed. Chromatogr. 2007, 21:546-552.
22. Kim T.H., Jiang H.H., Youn Y.S., Park C.W., Tak K.K., Lee S., Kim H., Jon S., Chen X., Lee K.C. Preparation and characterization of water-soluble albumin-bound curcumin nanoparticles with improved antitumor activity. Int. J. Pharm. 2011, 403:285-291.
23. Gao X., Zheng F.J., Guo G., Liu X.X., Fan R.R., Qian Z.Y., Huang N., Wei Y.Q. Improving the anti-colon cancer activity of curcumin with biodegradable nano-micelles. J. Mater. Chem. B 2013, 1:5778-5790.
24. Gou M.L., Men K., Shi H.S., Xiang M.L., Zhang J.A., Song J., Long J.L., Wan Y., Luo F., Zhao X., Qian Z.Y. Curcumin-loaded biodegradable polymeric micelles for colon cancer therapy in vitro and in vivo. Nanoscale 2011, 3:1558-1567.
25. Padhye S., Yang H., Jamadar A., Cui Q.C., Chavan D., Dominiak K., McKinney J., Banerjee S., Dou Q.P., Sarkar F.H. New difluoro Knoevenagel condensates of curcumin, their Schiff bases and copper complexes as proteasome inhibitors and apoptosis inducers in cancer cells. Pharm. Res. 2009, 26:1874-1880.
26. Dandawate P.R., Vyas A., Ahmad A., Banerjee S., Deshpande J., Swamy K.V., Jamadar A., Dumhe-Klaire A.C., Padhye S., Sarkar F.H. Inclusion complex of novel curcumin analogue CDF and beta-cyclodextrin (1:2) and its enhanced in vivo anticancer activity against pancreatic cancer. Pharm. Res. 2012, 29:1775-1786.
27. Daruwalla J., Greish K., Malcontenti-Wilson C., Muralidharan V., Iyer A., Maeda H., Christophi C. Styrene maleic acid-pirarubicin disrupts tumor microcirculation and enhances the permeability of colorectal liver metastases. J. Vasc. Res. 2009, 46:218-228.
28. Iyer A.K., Greish K., Fang J., Murakami R., Maeda H. High-loading nanosized micelles of copoly(styrene-maleic acid)-zinc protoporphyrin for targeted delivery of a potent heme oxygenase inhibitor. Biomaterials 2007, 28:1871-1881.
29. Iyer A.K., Greish K., Seki T., Okazaki S., Fang J., Takeshita K., Maeda H. Polymeric micelles of zinc protoporphyrin for tumor targeted delivery based on EPR effect and singlet oxygen generation. J. Drug Target. 2007, 15:496-506.
30. Daruwalla J., Greish K., Nikfarjam M., Millar I., Malcontenti-Wilson C., Iyer A.K., Christophi C. Evaluation of the effect of SMA-pirarubicin micelles on colorectal cancer liver metastases and of hyperbaric oxygen in CBA mice. J. Drug Target. 2007, 15:487-495.
31. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65:55-63.
32. Greish K., Sawa T., Fang J., Akaike T., Maeda H. SMA-doxorubicin, a new polymeric micellar drug for effective targeting to solid tumours. J. Control. Release 2004, 97:219-230.
33. Greish K., Nagamitsu A., Fang J., Maeda H. Copoly(styrene-maleic acid)-pirarubicin micelles: high tumor-targeting efficiency with little toxicity. Bioconjugate Chem. 2005, 16:230-236.
34. Lin W., He Y., Zhang J., Wang L., Wang Z., Ji F., Chen S. Highly hemocompatible zwitterionic micelles stabilized by reversible cross-linkage for anti-cancer drug delivery. Colloids Surf. B: Biointerfaces 2014, 115:384-390.
35. Seymour L.W., Olliff S.P., Poole C.J., De Takats P.G., Orme R., Ferry D.R., Maeda H., Konno T., Kerr D.J. A novel dosage approach for evaluation of SMANCS [poly-(styrene-co-maleyl-half-n-butylate) - neocarzinostatin] in the treatment of primary hepatocellular carcinoma. Int. J. Oncol. 1998, 12:1217-1223.
36. Jinno K., Moriwaki S., Tanada M., Wada T., Mandai K., Okada Y. Clinicopathological study on combination therapy consisting of arterial infusion of lipiodol-dissolved SMANCS and transcatheter arterial embolization for hepatocellular carcinoma. Cancer Chemother. Pharmacol. 1992, 31(Suppl):S7-S12.
37. Nakaba H., Hashimoto T., Sunada S., Akamatsu D., Ito A., Teramoto S., Ohara S., Katayama S. Results of SMANCS/Lipiodol injection therapy for multiple intrahepatic recurrence of hepatocellular carcinoma. Gan to kagaku ryoho 1998, 25(Suppl 1):46-50.
38. Konno T., Tabaru K., Isogai M., Nagamitsu A., Oda T. Targeted chemotherapy of hepatocellular carcinoma with SMANCS/Lipiodol - how to use SMANCS/Lipiodol. Gan to kagaku ryoho 1998, 25(Suppl 1):10-18.
39. Maeda H. SMANCS/lipiodol. Gan to kagaku ryoho 1994, 21:907-913.
40. Maeda H., Konno T., Iwai K., Maki S., Tashiro S. Tumor selective drug delivery with lipid contrast medium (smancs/lipiodol): sustained antitumor effect, enhanced diagnostic value and quantification of dosage regimen. Gan to kagaku ryoho 1984, 11:814-826.
41. Duncan R. Polymer conjugates as anticancer nanomedicines. Nat. Rev. Cancer 2006, 6:688-701.
42. Juliano R.L., Stamp D. The effect of particle size and charge on the clearance rates of liposomes and liposome encapsulated drugs. Biochem. Biophys. Res. Commun. 1975, 63:651-658.
43. Iyer A.K., Khaled G., Fang J., Maeda H. Exploiting the enhanced permeability and retention effect for tumor targeting. Drug Discov. Today 2006, 11:812-818.
44. Kesharwani P., Iyer A.K. Recent advances in dendrimer-based nanovectors for tumor-targeted drug and gene delivery. Drug Discov. Today 2014, [Epub ahead of print]. 10.1016/j.drudis.2014.12.012.
45. Lee S.C., Huh K.M., Lee J., Cho Y.W., Galinsky R.E., Park K. Hydrotropic polymeric micelles for enhanced paclitaxel solubility: in vitro and in vivo characterization. Biomacromolecules 2007, 8:202-208.
46. Kobayashi A., Oda T., Maeda H. Protein binding of macromolecular anticancer agent SMANCS: characterization of poly(styrene-co-maleic acid) derivatives as an albumin binding ligand. J. Bioact. Compat. Polym. 1988, 3:319-333.
47. Larson N., Greish K., Bauer H., Maeda H., Ghandehari H. Synthesis and evaluation of poly(styrene-co-maleic acid) micellar nanocarriers for the delivery of tanespimycin. Int. J. Pharm. 2011, 420:111-117.
48. Kim S., Shi Y.Z., Kim J.Y., Park K., Cheng J.X. Overcoming the barriers in micellar drug delivery: loading efficiency, in vivo stability, and micelle-cell interaction. Expert Opin. Drug Deliv. 2010, 7:49-62.
49. Smith P.J., Giroud M., Wiggins H.L., Gower F., Thorley J.A., Stolpe B., Mazzolini J., Dyson R.J., Rappoport J.Z. Cellular entry of nanoparticles via serum sensitive clathrin-mediated endocytosis, and plasma membrane permeabilization. Int. J. Nanomed. 2012, 7:2045-2055.
50. Hao X., Wu J., Shan Y., Cai M., Shang X., Jiang J., Wang H. Caveolae-mediated endocytosis of biocompatible gold nanoparticles in living Hela cells. J. Phys.: Condens. Matter 2012, 24:164207.
51. Gan Q., Dai D., Yuan Y., Qian J., Sha S., Shi J., Liu C. Effect of size on the cellular endocytosis and controlled release of mesoporous silica nanoparticles for intracellular delivery. Biomed. Microdevices 2012, 14:259-270.
52. Zhang S., Li J., Lykotrafitis G., Bao G., Suresh S. Size-Dependent Endocytosis of Nanoparticles. Adv. Mater. 2009, 21:419-424.