Riboflavin-targeted polymer conjugates for breast tumor delivery

Pharmaceutical Research

Volumn 30, Issue 7, 2013, Pages 1799-1812

  Bareford, Lisa M ^a   Avaritt, Brittany R ^a   Ghandehari, Hamidreza ^a,b   Nan, Anjan ^a   Swaan, Peter W ^a  

^a UNIVERSITY OF MARYLAND   (United States)

^b UNIVERSITY OF UTAH   (United States)

Author keywords

breast cancer; nanomedicine; receptor mediated endocytosis; riboflavin; targeted delivery

Indexed keywords

CARRIER PROTEIN; COPOLYMER; MITOMYCIN; N (2 HYDROXYPROPYL)METHACRYLAMIDE; POLYMER; RIBOFLAVIN;

ARTICLE; BREAST CANCER; CELL STRAIN MCF 7; CONFOCAL MICROSCOPY; CYTOTOXICITY; DISEASE COURSE; DRUG DELIVERY SYSTEM; DRUG STRUCTURE; DRUG TARGETING; ENDOCYTOSIS; HUMAN; IC 50; IMMUNOFLUORESCENCE; INTERNALIZATION; LYSOSOME; PRIORITY JOURNAL;

ACRYLAMIDES; ANTIBIOTICS, ANTINEOPLASTIC; BREAST; BREAST NEOPLASMS; CELL LINE, TUMOR; DRUG DELIVERY SYSTEMS; ENDOCYTOSIS; FEMALE; HUMANS; MITOMYCIN; RIBOFLAVIN;

EID: 84878828777     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-013-1024-5     Document Type: Article

References (52)

1. Andersson L, Davies J, Duncan R, Ferruti P, Ford J, Kneller S, et al. Poly(ethylene glycol)-poly(ester-carbonate) block copolymers carrying PEG-peptidyl-doxorubicin pendant side chains: synthesis and evaluation as anticancer conjugates. Biomacromolecules. 2005;6:914-26. (Pubitemid 40467837)
2. Duncan R. The dawning era of polymer therapeutics. Nat Rev Drug Discov. 2003;2:347-60. (Pubitemid 37361705)
3. Tanaka T, Shiramoto S, Miyashita M, Fujishima Y, Kaneo Y. Tumor targeting based on the effect of enhanced permeability and retention (EPR) and the mechanism of receptor-mediated endocytosis (RME). Int J Pharm. 2004;277:39-61. (Pubitemid 38670420)
4. Mamot C, Drummond DC, Hong K, Kirpotin DB, Park JW. Liposome-based approaches to overcome anticancer drug resistance. Drug Resist Updat. 2003;6:271-9. (Pubitemid 37493783)
5. Reddy JA, Westrick E, Vlahov I, Howard SJ, Santhapuram HK, Leamon CP. Folate receptor specific anti-tumor activity of folate-mitomycin conjugates. Cancer Chemother Pharmacol. 2006;58:229-36.
6. Duncan R. Designing polymer conjugates as lysosomotropic nanomedicines. Biochem Soc Trans. 2007;35:56-60.
7. Russell-Jones G, McTavish K, McEwan J, Rice J, Nowotnik D. Vitamin-mediated targeting as a potential mechanism to increase drug uptake by tumours. J Inorg Biochem. 2004;98:1625-33. (Pubitemid 39349188)
8. Bareford LM, Swaan PW. Endocytic mechanisms for targeted drug delivery. Adv Drug Deliv Rev. 2007;59:748-58. (Pubitemid 47320813)
9. Parker N, Turk MJ, Westrick E, Lewis JD, Low PS, Leamon CP. Folate receptor expression in carcinomas and normal tissues determined by a quantitative radioligand binding assay. Anal Biochem. 2005;338:284-93. (Pubitemid 40312593)
10. Garnett MC. Targeted drug conjugates: principles and progress. Adv Drug Deliv Rev. 2001;53:171-216. (Pubitemid 33135563)
11. Qian ZM, Li H, Sun H, Ho K. Targeted drug delivery via the transferrin receptor-mediated endocytosis pathway. Pharmacol Rev. 2002;54:561-87. (Pubitemid 35351196)
12. Paulos CM, Reddy JA, Leamon CP, Turk MJ, Low PS. Ligand binding and kinetics of folate receptor recycling in vivo: impact on receptor-mediated drug delivery. Mol Pharmacol. 2004;66:1406-14. (Pubitemid 39564767)
13. Salazarand MD, Ratnam M. The folate receptor: what does it promise in tissue-targeted therapeutics? Cancer Metastasis Rev. 2007;26:141-52. (Pubitemid 46452188)
14. Castrellonand AB, Gluck S. Chemoprevention of breast cancer. Expert Rev Anticancer Ther. 2008;8:443-52. (Pubitemid 351836291)
15. Karande AA, Sridhar L, Gopinath KS, Adiga PR. Riboflavin carrier protein: a serum and tissue marker for breast carcinoma. Int J Cancer. 2001;95:277-81. (Pubitemid 32847035)
16. Vaidya SM, Kamlakar PL, Kamble SM. Molybdenum, xanthine oxidase and riboflavin levels in tamoxifen treated postmenopausal women with breast cancer. Indian J Med Sci. 1998;52:244-7.
17. Mason CW, D'Souza VM, Bareford LM, Phelps MA, Ray A, Swaan PW. Recognition, co-internalization, and recycling of an avian riboflavin carrier protein in human placental trophoblasts. J Pharmacol Exp Ther. 2006;317:465-72.
18. Yonezawa A, Masuda S, Katsura T, Inui KI. Identification and functional characterization of a novel human and rat riboflavin transporter, RFT1. Am J Physiol Cell Physiol. 2008;295:C632-41.
19. Huangand SN, Swaan PW. Involvement of a receptor-mediated component in cellular translocation of riboflavin. J Pharmacol Exp Ther. 2000;294:117-25. (Pubitemid 30434677)
20. Bareford LM, Phelps MA, Foraker AB, Swaan PW. Intracellular processing of riboflavin in human breast cancer cells. Mol Pharm. 2008;5:839-48.
21. D'Souza VM, Foraker AB, Free RB, Ray A, Shapiro PS, Swaan PW. cAMP-Coupled riboflavin trafficking in placental trophoblasts: a dynamic and ordered process. Biochemistry. 2006;45:6095-104. (Pubitemid 43727102)
22. Kopecek J, Kopeckova P, Minko T, Lu Z. HPMA copolymer-anticancer drug conjugates: design, activity, and mechanism of action. Eur J Pharm Biopharm. 2000;50:61-81. (Pubitemid 30326689)
23. Noriand A, Kopecek J. Intracellular targeting of polymer-bound drugs for cancer chemotherapy. Adv Drug Deliv Rev. 2005;57:609-36. (Pubitemid 40267695)
24. Rihovaand B, Kubackova K. Clinical implications of N-(2-hydroxypropyl) methacrylamide copolymers. Curr Pharm Biotechnol. 2003;4:311-22. (Pubitemid 37220863)
25. Bradner WT. Mitomycin C: a clinical update. Cancer Treat Rev. 2001;27:35-50. (Pubitemid 32229684)
26. Strohalmand J, Kopecek J. Poly N-(2-hydroxypropyl) methacrylamide. 4. Heterogeneous polymerization. Makromol Chem. 1978;70:109-18.
27. Kopeček J, Rejmanová P, Strohalm J, Ulbrich K, Říhová B, Chytrý V, Lloyd JB, Duncan R. Synthetic polymeric drugs. US Patent. 5, 037, 883. Aug 6, 1991. p. 883.
28. Rejmanova P, Labsky J, Kopecek J. Aminolyses of monomeric and polymeric p-nitrophenyl esters of methacryloylated amino acids. Makromol Chem. 1977;178:2159-68.
29. Omelyanenko V, Kopeckova P, Gentry C, Kopecek J. Targetable HPMA copolymer-adriamycin conjugates. Recognition, internalization, and subcellular fate. J Control Release. 1998;53:25-37. (Pubitemid 28218687)
30. Mitra A, Nan A, Ghandehari H, McNeill E, Mulholland J, Line BR. Technetium-99m-Labeled N-(2-hydroxypropyl) methacrylamide copolymers: synthesis, characterization, and in vivo biodistribution. Pharm Res. 2004;21:1153-9. (Pubitemid 38954199)
31. Luo J, Smith MD, Lantrip DA, Wang S, Fuchs PL. Efficient syntheses of pyrofolic acid and pteroyl azide, reagents for the production of carboxyl-differentiated derivatives of folic acid. J Am Chem Soc. 1997;119:10004-13. (Pubitemid 27478789)
32. Phelps MA, Foraker AB, Gao W, Dalton JT, Swaan PW. A novel rhodamine-riboflavin conjugate probe exhibits distinct fluorescence resonance energy transfer that enables riboflavin trafficking and subcellular localization studies. Mol Pharm. 2004;1:257-66.
33. Apodaca G, Katz LA, Mostov KE. Receptor-mediated transcytosis of IgA in MDCK cells is via apical recycling endosomes. J Cell Biol. 1994;125:67-86. (Pubitemid 24100040)
34. Demarre A, Soyez H, Schacht E, Shoaibi MA, Seymour LW, Rihova B. Synthesis and evaluation of macromolecular prodrugs of Mitomycin-C. J Control Release. 1995;36:87-97.
35. Pan SS, Iracki T, Bachur NR. DNA alkylation by enzyme-activated mitomycin C. Mol Pharmacol. 1986;29:622-8. (Pubitemid 16064858)
36. D'Souza VM, Bareford LM, Ray A, Swaan PW. Cytoskeletal scaffolds regulate riboflavin endocytosis and recycling in placental trophoblasts. J Nutr Biochem. 2006;17:821-9. (Pubitemid 44738515)
37. Foraker AB, Ray A, Da Silva TC, Bareford LM, Hillgren KM, Schmittgen TD, et al. Dynamin 2 regulates riboflavin endocytosis in human placental trophoblasts. Mol Pharmacol. 2007;72:553-62. (Pubitemid 47347290)
38. Guoand W, Lee RL. Receptor-targeted gene delivery via folate-conjugated polyethylenimine. AAPS Pharm Sci. 1999;1:E19.
39. Rachmilewitz B, Sulkes A, Rachmilewitz M, Fuks Z. Serum transcobalamin II levels in breast carcinoma patients. Isr J Med Sci. 1981;17:874-8. (Pubitemid 12239585)
40. Auvinen P, Tammi R, Parkkinen J, Tammi M, Agren U, Johansson R, et al. Hyaluronan in peritumoral stroma and malignant cells associates with breast cancer spreading and predicts survival. Am J Pathol. 2000;156:529-36. (Pubitemid 30643808)
41. Nichifor M, Schacht EH, Seymour LW. Macromolecular prodrugs of 5-fluorouracil.2. Enzymatic degradation. J Control Release. 1996;39:79-92. (Pubitemid 26139813)
42. Hoste K, De Winne K, Schacht E. Polymeric prodrugs. Int J Pharm. 2004;277:119-31. (Pubitemid 38670427)
43. Winski SL, Swann E, Hargreaves RH, Dehn DL, Butler J, Moody CJ, et al. Relationship between NAD(P)H:quinone oxidoreductase 1 (NQO1) levels in a series of stably transfected cell lines and susceptibility to antitumor quinones. Biochem Pharmacol. 2001;61:1509-16. (Pubitemid 32476905)
44. Cheung RY, Rauth AM, Ronaldson PT, Bendayan R, Wu XY. In vitro toxicity to breast cancer cells of microsphere-delivered mitomycin C and its combination with doxorubicin. Eur J Pharm Biopharm. 2006;62:321-31. (Pubitemid 43356582)
45. Chen R, Yue Z, Eccleston ME, Williams S, Slater NK. Modulation of cell membrane disruption by pH-responsive pseudo-peptides through grafting with hydrophilic side chains. J Control Release. 2005;108:63-72. (Pubitemid 41476675)
46. Mukherjee S, Ghosh RN, Maxfield FR. Endocytosis. Physiol Rev. 1997;77:759-803. (Pubitemid 27328740)
47. Maalmi M, Strieder W, Varma A. Ligand diffusion and receptor mediated internalization: Michaelis-Menten kinetics. Chem Eng Sci. 2001;56:5609-16. (Pubitemid 32978625)
48. King AC, Hernaez-Davis L, Cuatrecasas P. Lysomotropic amines cause intracellular accumulation of receptors for epidermal growth factor. Proc Natl Acad Sci U S A. 1980;77:3283-7. (Pubitemid 10016934)
49. Watts PL, Plumb JA, Courtney JM, Scott R. Sensitivity of cell lines to mitomycin C. Br J Urol. 1996;77:363-6. (Pubitemid 26090970)
50. Mahoney BP, Raghunand N, Baggett B, Gillies RJ. Tumor acidity, ion trapping and chemotherapeutics. I. Acid pH affects the distribution of chemotherapeutic agents in vitro. Biochem Pharmacol. 2003;66:1207-18. (Pubitemid 37130296)
51. Nomura T, Saikawa A, Morita S, Sakaeda Kakutani T, Yamashita F, Honda K, et al. Pharmacokinetic characteristics and therapeutic effects of mitomycin C-dextran conjugates after intratumoural injection. J Control Release. 1998;52:239-52. (Pubitemid 28135253)
52. David A, Kopeckova P, Minko T, Rubinstein A, Kopecek J. Design of a multivalent galactoside ligand for selective targeting of HPMA copolymer-doxorubicin conjugates to human colon cancer cells. Eur J Cancer. 2004;40:148-57. (Pubitemid 37542327)