Poly(ethylene glycol)-b-poly(lysine) copolymer bearing nitroaromatics for hypoxia-sensitive drug delivery

Acta Biomaterialia

Volumn 29, Issue , 2016, Pages 261-270

  Thambi, Thavasyappan ^a   Son, Soyoung ^a   Lee, Doo Sung ^a   Park, Jae Hyung ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

Block copolymer; Cancer; DOX; Drug delivery; Hypoxia

Indexed keywords

AMINO ACIDS; BLOCK COPOLYMERS; CONTROLLED DRUG DELIVERY; ETHYLENE GLYCOL; HYDROPHILICITY; HYDROPHOBICITY; MICELLES; POLYETHYLENE GLYCOLS; POLYOLS; TARGETED DRUG DELIVERY; TUMORS;

BLOCK CO POLYMERS; DOXORUBICIN; HYDROPHILIC BLOCKS; HYDROPHOBIC BLOCKS; HYPOXIA; HYPOXIC CONDITION; L-LYSINE; PATHOLOGICAL CONDITIONS; POLYMERIC MICELLE; RHEUMATOID ARTHRITIS;

DISEASES;

AMPHOPHILE; AROMATIC NITRO COMPOUND; DOXORUBICIN; MACROGOL; NITROBENZENE DERIVATIVE; NITROBENZYL CHLOROFORMATE; POLYLYSINE; UNCLASSIFIED DRUG; DELAYED RELEASE FORMULATION; MACROGOL DERIVATIVE; POLYETHYLENE GLYCOL 1000;

AQUEOUS SOLUTION; ARTICLE; BIOCOMPATIBILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; DRUG DELIVERY SYSTEM; DRUG RELEASE; HYDROPHOBICITY; HYPOXIA; IN VITRO STUDY; MICELLIZATION; OXYGEN CONCENTRATION; PARTICLE SIZE; PHYSICAL CHEMISTRY; POLYMERIZATION; PRIORITY JOURNAL; ZETA POTENTIAL; CELL HYPOXIA; CHEMISTRY; DELAYED RELEASE FORMULATION; HUMAN; PHARMACOKINETICS; PHARMACOLOGY; TUMOR CELL LINE;

CELL HYPOXIA; CELL LINE, TUMOR; DELAYED-ACTION PREPARATIONS; DOXORUBICIN; HUMANS; NITROBENZENES; POLYETHYLENE GLYCOLS; POLYLYSINE;

EID: 84952637529     PISSN: 17427061     EISSN: 18787568     Source Type: Journal    
DOI: 10.1016/j.actbio.2015.10.011     Document Type: Article

References (52)

1. A.L. Harris Hypoxia - a key regulatory factor in tumour growth Nat. Rev. Cancer 2 2002 38 47
2. 2 availability on human cancer Nat. Rev. Cancer 8 2008 967 975
3. D. Neri, and C.T. Supuran Interfering with pH regulation in tumours as a therapeutic strategy Nat. Rev. Drug Discov. 10 2011 767 777
4. M. Takasawa, R.R. Moustafa, and J.-C. Baron Applications of nitroimidazole in vivo hypoxia imaging in ischemic stroke Stroke 39 2008 1629 1637
5. G.H. Gao, J.W. Lee, M.K. Nguyen, G.H. Im, J. Yang, H. Heo, and et al. PH-responsive polymeric micelle based on PEG-poly(β-amino ester)/(amido amine) as intelligent vehicle for magnetic resonance imaging in detection of cerebral ischemic area J. Control. Release 155 2011 11 17
6. A. Gaudin, M. Yemisci, H. Eroglu, S. Lepetre-Mouelhi, O.F. Turkoglu, B. Dönmez-Demir, and et al. Squalenoyl adenosine nanoparticles provide neuroprotection after stroke and spinal cord injury Nat. Nano 9 2014 1054 1062
7. P. Wardman Chemical radiosensitizers for use in radiotherapy Clin. Oncol. 19 2007 397 417
8. W.R. Wilson, and M.P. Hay Targeting hypoxia in cancer therapy Nat. Rev. Cancer 11 2011 393 410
9. L. Cui, Y. Zhong, W. Zhu, Y. Xu, Q. Du, X. Wang, and et al. A new prodrug-derived ratiometric fluorescent probe for hypoxia: high selectivity of nitroreductase and imaging in tumor cell Org. Lett. 13 2011 928 931
10. T. Rhim, D.Y. Lee, and M. Lee Hypoxia as a target for tissue specific gene therapy J. Control. Release 172 2013 484 494
11. W.A. Denny Hypoxia-activated prodrugs in cancer therapy: progress to the clinic Future Oncol. 6 2010 419 428
12. K. Kiyose, K. Hanaoka, D. Oushiki, T. Nakamura, M. Kajimura, M. Suematsu, and et al. Hypoxia-sensitive fluorescent probes for in vivo real-time fluorescence imaging of acute ischemia J. Am. Chem. Soc. 132 2010 15846 15848
13. S. Mura, J. Nicolas, and P. Couvreur Stimuli-responsive nanocarriers for drug delivery Nat. Mater. 12 2013 991 1003
14. V.P. Torchilin Multifunctional, stimuli-sensitive nanoparticulate systems for drug delivery Nat. Rev. Drug Discov. 13 2014 813 827
15. X. Liu, A.L. Miller Ii, M.J. Yaszemski, and L. Lu Biodegradable and crosslinkable PPF-PLGA-PEG self-assembled nanoparticles dual-decorated with folic acid ligands and Rhodamine B fluorescent probes for targeted cancer imaging RSC Adv. 5 2015 33275 33282
16. R. Mo, T. Jiang, R. DiSanto, W. Tai, and Z. Gu ATP-triggered anticancer drug delivery Nat. Commun. 5 2014 3364
17. H. Grüll, and S. Langereis Hyperthermia-triggered drug delivery from temperature-sensitive liposomes using MRI-guided high intensity focused ultrasound J. Control. Release 161 2012 317 327
18. J.M. Shin, S.-H. Kim, T. Thambi, D.G. You, J. Jeon, J.O. Lee, and et al. A hyaluronic acid-methotrexate conjugate for targeted therapy of rheumatoid arthritis Chem. Commun. 50 2014 7632 7635
19. T. Thambi, D.G. You, H.S. Han, V.G. Deepagan, S.M. Jeon, Y.D. Suh, and et al. Bioreducible carboxymethyl dextran nanoparticles for tumor-targeted drug delivery Adv. Healthcare Mater. 3 2014 1829 1838
20. W. Xiao, X. Zeng, H. Lin, K. Han, H.-Z. Jia, and X.-Z. Zhang Dual stimuli-responsive multi-drug delivery system for the individually controlled release of anti-cancer drugs Chem. Commun. 51 2015 1475 1478
21. Y. Dai, H. Xiao, J. Liu, Q. Yuan, Ma Pa, and D. Yang In vivo multimodality imaging and cancer therapy by near-infrared light-triggered trans-platinum pro-drug-conjugated upconverison nanoparticles J. Am. Chem. Soc. 135 2013 18920 18929
22. H. Xiao, G.T. Noble, J.F. Stefanick, R. Qi, T. Kiziltepe, X. Jing, and et al. Photosensitive Pt(IV)-azide prodrug-loaded nanoparticles exhibit controlled drug release and enhanced efficacy in vivo J. Control. Release 173 2014 11 17
23. J. Wang, X. Sun, W. Mao, W. Sun, J. Tang, M. Sui, and et al. Tumor redox heterogeneity-responsive prodrug nanocapsules for cancer chemotherapy Adv. Mater. 25 2013 3670 3676
24. D.H. Kim, Y.K. Seo, T. Thambi, G.J. Moon, J.P. Son, G. Li, and et al. Enhancing neurogenesis and angiogenesis with target delivery of stromal cell derived factor-1α using a dual ionic pH-sensitive copolymer Biomaterials 61 2015 115 125
25. T. Thambi, and J.H. Park Recent advances in shell-sheddable nanoparticles for cancer therapy J. Biomed. Nanotechnol. 10 2014 1841 1862
26. J.M. Brown, and W.R. Wilson Exploiting tumour hypoxia in cancer treatment Nat. Rev. Cancer 4 2004 437 447
27. F. Marcucci, M. Bellone, C.A. Caserta, and A. Corti Pushing tumor cells towards a malignant phenotype: stimuli from the microenvironment, intercellular communications and alternative roads Int. J. Cancer 135 2014 1265 1276
28. M. Upreti, A. Jyoti, and P. Sethi Tumor microenvironment and nanotherapeutics Transl. Cancer Res. 2 2013 309 319
29. P. Vaupel The role of hypoxia-induced factors in tumor progression Oncologist 9 2004 10 17
30. X. Zheng, X. Wang, H. Mao, W. Wu, B. Liu, and X. Jiang Hypoxia-specific ultrasensitive detection of tumours and cancer cells in vivo Nat. Commun. 6 2015 5834
31. T. Thambi, V.G. Deepagan, H.Y. Yoon, H.S. Han, S.-H. Kim, S. Son, and et al. Hypoxia-responsive polymeric nanoparticles for tumor-targeted drug delivery Biomaterials 35 2014 1735 1743
32. W.H. Daly, and D. Poché The preparation of N-carboxyanhydrides of α-amino acids using bis(trichloromethyl)carbonate Tetrahedron Lett. 29 1988 5859 5862
33. T. Thambi, V.G. Deepagan, C.K. Yoo, and J.H. Park Synthesis and physicochemical characterization of amphiphilic block copolymers bearing acid-sensitive orthoester linkage as the drug carrier Polymer 52 2011 4753 4759
34. A. Harada, and K. Kataoka Novel polyion complex micelles entrapping enzyme molecules in the core: preparation of narrowly-distributed micelles from lysozyme and poly(ethylene glycol)-poly(aspartic acid) block copolymer in aqueous medium Macromolecules 31 1998 288 294
35. S.J. Lee, K.H. Min, H.J. Lee, A.N. Koo, H.P. Rim, B.J. Jeon, and et al. Ketal cross-linked poly(ethylene glycol)-poly(amino acid)s copolymer micelles for efficient intracellular delivery of doxorubicin Biomacromolecules 12 2011 1224 1233
36. H.S. Han, T. Thambi, K.Y. Choi, S. Son, H. Ko, M.C. Lee, and et al. Bioreducible shell-cross-linked hyaluronic acid nanoparticles for tumor-targeted drug delivery Biomacromolecules 16 2015 447 456
37. M. Wilhelm, C.L. Zhao, Y. Wang, R. Xu, M.A. Winnik, J.L. Mura, and et al. Poly(styrene-ethylene oxide) block copolymer micelle formation in water: a fluorescence probe study Macromolecules 24 1991 1033 1040
38. T. Thambi, G. Saravanakumar, J.-U. Chu, R. Heo, H. Ko, V. Deepagan, and et al. Synthesis and physicochemical characterization of reduction-sensitive block copolymer for intracellular delivery of doxorubicin Macromol. Res. 21 2013 100 107
39. M. Sivasubramanian, T. Thambi, V.G. Deepagan, G. Saravanakumar, H. Ko, Y.M. Kang, and et al. Carboxymethyl dextran-cyclodextrin conjugate as the carrier of doxorubicin J. Nanosci. Nanotechnol. 13 2013 7271 7278
40. H. Cho, J. Bae, V.K. Garripelli, J.M. Anderson, H.-W. Jun, and S. Jo Redox-sensitive polymeric nanoparticles for drug delivery Chem. Commun. 48 2012 6043 6045
41. T. Thambi, H.Y. Yoon, K. Kim, I.C. Kwon, C.K. Yoo, and J.H. Park Bioreducible block copolymers based on poly(ethylene glycol) and poly(γ-benzyl l-glutamate) for intracellular delivery of camptothecin Bioconjug. Chem. 22 2011 1924 1931
42. T. Thambi, V.G. Deepagan, H. Ko, D.S. Lee, and J.H. Park Bioreducible polymersomes for intracellular dual-drug delivery J. Mater. Chem. 22 2012 22028 22036
43. Y. Zhang, and I. Angelidaki Submersible microbial fuel cell sensor for monitoring microbial activity and BOD in groundwater: focusing on impact of anodic biofilm on sensor applicability Biotechnol. Bioeng. 108 2011 2339 2347
44. T.M. Allen, and P.R. Cullis Drug delivery systems: entering the mainstream Science 303 2004 1818 1822
45. S. Kwon, J.H. Park, H. Chung, I.C. Kwon, S.Y. Jeong, and I.-S. Kim Physicochemical characteristics of self-assembled nanoparticles based on glycol chitosan bearing 5β-cholanic acid Langmuir 19 2003 10188 10193
46. M.R. Horsman, L.S. Mortensen, J.B. Petersen, M. Busk, and J. Overgaard Imaging hypoxia to improve radiotherapy outcome Nat. Rev. Clin. Oncol. 9 2012 674 687
47. K. Okuda, Y. Okabe, T. Kadonosono, T. Ueno, B.G.M. Youssif, S. Kizaka-Kondoh, and et al. 2-Nitroimidazole-tricarbocyanine conjugate as a near-infrared fluorescent probe for in vivo imaging of tumor hypoxia Bioconjug. Chem. 23 2012 324 329
48. Q. Lin, C. Bao, Y. Yang, Q. Liang, D. Zhang, S. Cheng, and et al. Highly discriminating photorelease of anticancer drugs based on hypoxia activatable phototrigger conjugated chitosan nanoparticles Adv. Mater. 25 2013 1981 1986
49. D.I. Edwards Nitroimidazole drugs-action and resistance mechanisms I. Mechanism of action J. Antimicrob. Chemother. 31 1993 9 20
50. J. Bae, L.E. McNamara, M.A. Nael, F. Mahdi, R.J. Doerksen, G.L. Bidwell, and et al. Nitroreductase-triggered activation of a novel caged fluorescent probe obtained from methylene blue Chem. Commun. 51 2015 12787 12790
51. A.B. Mauger, P.J. Burke, H.H. Somani, F. Friedlos, and R.J. Knox Self-immolative prodrugs: candidates for antibody-directed enzyme prodrug therapy in conjunction with a nitroreductase enzyme J. Med. Chem. 37 1994 3452 3458
52. T. Guo, L. Cui, J. Shen, W. Zhu, Y. Xu, and X. Qian A highly sensitive long-wavelength fluorescence probe for nitroreductase and hypoxia: selective detection and quantification Chem. Commun. 49 2013 10820 10822