PSMA ligand conjugated PCL-PEG polymeric micelles targeted to prostate cancer cells

PLoS ONE

Volumn 9, Issue 11, 2014, Pages

  Jin, Jian ^a   Sui, Bowen ^a   Gou, Jingxin ^b   Liu, Jingshuo ^a   Tang, Xing ^b   Xu, Hui ^b   Zhang, Yu ^b   Jin, Xiangqun ^a  

^a JILIN UNIVERSITY   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COPOLYMER; DOCETAXEL; MACROGOL; POLYCAPROLACTONE; PROSTATE SPECIFIC MEMBRANE ANTIGEN; GLUTAMATE CARBOXYPEPTIDASE II; GLUTAMATE CARBOXYPEPTIDASE II, HUMAN; MEMBRANE ANTIGEN; MICELLE;

ARTICLE; DIALYSIS; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; DYNAMIC LIGHT SCATTERING; HUMAN; HUMAN CELL; HYDROPHILICITY; HYDROPHOBICITY; IC50; IN VITRO STUDY; INCUBATION TIME; LIGHT SCATTERING; LNCAP CELL LINE; MICELLE; MTT ASSAY; PARTICLE SIZE; POLYMERIZATION; PROCESS OPTIMIZATION; PROSTATE ADENOCARCINOMA; PROSTATE CANCER; STRUCTURE ANALYSIS; SUSTAINED DRUG RELEASE; TRANSMISSION ELECTRON MICROSCOPY; DRUG EFFECTS; MALE; PATHOLOGY; PROSTATE; PROSTATIC NEOPLASMS; TUMOR CELL LINE;

ANTIGENS, SURFACE; CELL LINE, TUMOR; DRUG DELIVERY SYSTEMS; GLUTAMATE CARBOXYPEPTIDASE II; HUMANS; MALE; MICELLES; PROSTATE; PROSTATIC NEOPLASMS;

EID: 84911441206     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0112200     Document Type: Article

References (41)

1. Branco MC, Schneider JP (2009) Self-assembling materials for therapeutic delivery. Acta Biomaterialia 5: 817-831.
2. Haag R (2004) Supramolecular drug-delivery systems based on polymeric coreshell architectures. Angew Chem Int Ed Engl 43: 278-282.
3. Huang W, Wang W, Wang P, Tian Q, Zhang C, et al. (2010) Glycyrrhetinic acid-modified poly(ethylene glycol)-b-poly(gamma-benzyl l-glutamate) micelles for liver targeting therapy. Acta Biomater 6: 3927-3935.
4. Saxena V, Hussain MD (2013) Polymeric Mixed Micelles for Delivery of Curcumin to Multidrug Resistant Ovarian Cancer. J Biomed Nanotechnol 9: 1146-1154.
5. Li J, He Z, Yu S, Li S, Ma Q, et al. (2012) Micelles Based on Methoxy Poly(Ethylene Glycol)Cholesterol Conjugate for Controlled and Targeted Drug Delivery of a Poorly Water Soluble Drug. J Biomed Nanotechnol 8: 809-817.
6. Savic R, Eisenberg A, Maysinger D (2006) Block copolymer micelles as delivery vehicles of hydrophobic drugs: micelle-cell interactions. J Drug Target 14: 343-355.
7. Kazunori K, Glenn S K, Masayuki Y, Teruo O, Yasuhisa S (1993) Block copolymer micelles as vehicles for drug delivery. J Control Release 24: 119-132.
8. Gu PF, Xu H, Sui BW, Gou JX, Meng LK, et al. (2012) Polymeric micelles based on poly(ethylene glycol) block poly(racemic amino acids) hybrid polypeptides: conformation-facilitated drug-loading behavior and potential application as effective anticancer drug carriers. Int J Nanomedicine 7: 109-122.
9. Wang Y, Xu H, Liu H, Wang Y, Sun J, et al. (2012) Efficacy and Biodistribution of Tocopheryl Polyethylene Glycol Succinate Noncovalent Functionalized Single Walled Nanotubes Loading Doxorubicin in Sarcoma Bearing Mouse Model. J Biomed Nanotechnol 8: 450-457.
10. Maresca K, Hillier S, Femia F, Keith D, Barone C, et al. (2008) A series of halogenated heterodimeric inhibitors of prostate specific membrane antigen (PSMA) as radiolabeled probes for targeting prostate cancer. J Med Chem 52: 347-357.
11. Murphy GP, Elgamal AAA, Su SL, Bostwick DG, Holmes EH (1998) Current evaluation of the tissue localization and diagnostic utility of prostate specific membrane antigen. Cancer 83: 2259-2269.
12. Israeli RS, Powell CT, Corr JG, Fair WR, Heston WD (1994) Expression of the prostate-specific membrane antigen. Cancer Res 54: 1807-1811.
13. Chang SS, O'Keefe DS, Bacich DJ, Reuter VE, Heston WD, et al. (1999) Prostate-specific membrane antigen is produced in tumor-associated neovasculature. Clin Cancer Res 5: 2674-2681.
14. Ghosh A, Heston WD (2004) Tumor target prostate specific membrane antigen (PSMA) and its regulation in prostate cancer. J Cell Biochem 91: 528-539.
15. Colombatti M, Grasso S, Porzia A, Fracasso G, Scupoli MT, et al. (2009) The Prostate Specific Membrane Antigen Regulates the Expression of IL-6 and CCL5 in Prostate Tumour Cells by Activating the MAPK Pathways1. PloS one 4: e4608.
16. Wolf P, Freudenberg N, Bu?hler P, Alt K, Schultze-Seemann W, et al. (2010) Three conformational antibodies specific for different PSMA epitopes are promising diagnostic and therapeutic tools for prostate cancer. The Prostate 70: 562-569.
17. Sanna V, Pintus G, Bandiera P, Anedda R, Punzoni S, et al. (2011) Development of polymeric microbubbles targeted to prostate-specific membrane antigen as prototype of novel ultrasound contrast agents. Mol Pharm 8: 748-757.
18. Hrkach J, Von Hoff D, Ali MM, Andrianova E, Auer J, et al. (2012) Preclinical development and clinical translation of a PSMA-targeted docetaxel nanoparticle with a differentiated pharmacological profile. Sci Transl Med 4: 128ra139- 128ra139.
19. Bae SJ, Suh JM, Sohn YS, Bae YH, Kim SW, et al. (2005) Thermogelling poly (caprolactone-b-ethylene glycol-b-caprolactone) aqueous solutions. Macromolecules 38: 5260-5265.
20. Chung Y-M, Simmons KL, Gutowska A, Jeong B (2002) Sol-gel transition temperature of PLGA-g-PEG aqueous solutions. Biomacromolecules 3: 511-516.
21. Zamani S, Khoee S (2012) Preparation of core-shell chitosan/PCL-PEG triblock copolymer nanoparticles with ABA and BAB morphologies: Effect of intraparticle interactions on physicochemical properties. Polymer 53: 5723-5736.
22. Liu C, Gong C, Pan Y, Zhang Y, Wang J, et al. (2007) Synthesis and characterization of a thermosensitive hydrogel based on biodegradable amphiphilic PCL-Pluronic (L35)-PCL block copolymers. Colloids and Surfaces A: Physicochem Eng Aspects 302: 430-438.
23. Li J, Li X, Ni X, Wang X, Li H, et al. (2006) Self-assembled supramolecular hydrogels formed by biodegradable PEO-PHB-PEO triblock copolymers and alpha-cyclodextrin for controlled drug delivery. Biomaterials 27: 4132-4140.
24. Gaucher G, Dufresne M-H, Sant VP, Kang N, Maysinger D, et al. (2005) Block copolymer micelles: preparation, characterization and application in drug delivery. J Control Release 109: 169-188.
25. Gou M, Zheng X, Men K, Zhang J, Zheng L, et al. (2009) Poly (εcaprolactone)/ poly (ethylene glycol)/poly (ε-caprolactone) nanoparticles: preparation, characterization, and application in doxorubicin delivery. J Phy Chem B 113: 12928-12933.
26. Qi R, Hu X, Yan L, Chen X, Huang Y, et al. (2011) Synthesis of biodegradable cationic triblock copolymer mPEG-PCL-PLL for siRNA delivery. J Control Release 152: e167-e168.
27. Farokhzad OC, Cheng J, Teply BA, Sherifi I, Jon S, et al. (2006) Targeted nanoparticle-aptamer bioconjugates for cancer chemotherapy in vivo. Proc Natl Acad Sci U S A 103: 6315-6320.
28. Dhar S, Liu Z, Thomale J, Dai H, Lippard SJ (2008) Targeted single-wall carbon nanotube-mediated Pt (IV) prodrug delivery using folate as a homing device. J Am Chem Soc 130: 11467-11476.
29. Hinterwirth H, Lindner W, Lammerhofer M (2012) Bioconjugation of trypsin onto gold nanoparticles: effect of surface chemistry on bioactivity. Anal Chim Acta 733: 90-97.
30. Torchilin V (2011) Tumor delivery of macromolecular drugs based on the EPR effect. Adv Drug Deliv Rev 63: 131-135.
31. Davis ME, Chen ZG, Shin DM (2008) Nanoparticle therapeutics: an emerging treatment modality for cancer. Nat Rev Drug Discov 7: 771-782.
32. Alexis F, Pridgen E, Molnar LK, Farokhzad OC (2008) Factors affecting the clearance and biodistribution of polymeric nanoparticles. Mol Pharm 5: 505-515.
33. Hu Y, Zhang L, Cao Y, Ge H, Jiang X, et al. (2004) Degradation Behavior of Poly(&epsi-caprolactone)-b-poly(ethylene glycol)-b-poly(ε-caprolactone) Micelles in Aqueous Solution. Biomacromolecules 5: 1756-1762.
34. Nie S, Hsiao WL, Pan W, Yang Z (2011) Thermoreversible Pluronic F127-based hydrogel containing liposomes for the controlled delivery of paclitaxel: in vitro drug release, cell cytotoxicity, and uptake studies. Int J Nanomedicine 6: 151-166.
35. Rofstad EK, Mathiesen B, Kindem K, Galappathi K (2006) Acidic extracellular pH promotes experimental metastasis of human melanoma cells in athymic nude mice. Cancer Res 66: 6699-6707.
36. Samarajeewa S, Shrestha R, Elsabahy M, Karwa A, Li A, et al. (2013) In vitro efficacy of paclitaxel-loaded dual-responsive shell cross-linked polymer nanoparticles having orthogonally degradable disulfide cross-linked corona and polyester core domains. Mol Pharm 10: 1092-1099.
37. Yamamichi F, Matsuoka T, Shigemura K, Kawabata M, Shirakawa T, et al. (2012) Potential establishment of lung metastatic xenograft model of androgen receptor-positive and androgen-independent prostate cancer (C4-2B). Urology 80: 951 e951-957.
38. Denmeade SR, Sokoll LJ, Dalrymple S, Rosen DM, Gady AM, et al. (2003) Dissociation between androgen responsiveness for malignant growth vs. expression of prostate specific differentiation markers PSA, hK2, and PSMA in human prostate cancer models. The Prostate 54: 249-257.
39. Esmaeili F, Dinarvand R, Ghahremani MH, Amini M, Rouhani H, et al. (2009) Docetaxel-albumin conjugates: preparation, in vitro evaluation and biodistribution studies. J Pharm Sci 98: 2718-2730.
40. Farokhzad OC, Jon S, Khademhosseini A, Tran T-NT, LaVan DA, et al. (2004) Nanoparticle-aptamer bioconjugates a new approach for targeting prostate cancer cells. Cancer Res 64: 7668-7672.
41. Conner SD, Schmid SL (2003) Regulated portals of entry into the cell. Nature 422: 37-44.