Development of Quinic Acid-Conjugated Nanoparticles as a Drug Carrier to Solid Tumors
Open accessAbstract
Nanometer-sized drug carriers including polymeric nanoparticles (NPs) have been used to increase biodistribution of a drug in tumors, thereby reducing the effective dose of chemotherapy. NPs increase drug delivery to tumors to a certain extent, but the amount reaching tumors is only a small fraction of the total administered NPs because they depend on passive accumulation via the leaky vasculature surrounding tumors. In an attempt to further increase the drug delivery to tumors, we develop a polymeric NP system that interacts with an endothelial tumor marker. The NPs are decorated with quinic acid, a synthetic mimic of sialyl Lewis-x, which binds to E-selectin, overexpressed on the surface of endothelial cells surrounding solid tumors. The NPs selectively bind to endothelial cells activated with tumor necrosis factor-α, with weak affinity at a relatively high shear stress. These properties may help NPs reach tumors by increasing the encounter of NPs with the peritumoral endothelium without hindering subsequent transport of the NPs.
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Cites
Nanocarriers as an emerging platform for cancer therapy
Peer, D., Karp, J. M., Hong, S., Farokhzad, O. C., Margalit, R., & Langer, R. (2007) · Nature Nanotechnology · doi:10.1038/nnano.2007.387 · Cited by 8,710 · see citing works
Matsumura, Y., & Maeda, H. (1986) · PubMed · Cited by 6,771 · see citing works
Poly Lactic-co-Glycolic Acid (PLGA) as Biodegradable Controlled Drug Delivery Carrier
Makadia, H. K., & Siegel, S. J. (2011) · Polymers · doi:10.3390/polym3031377 · Cited by 4,816 · see citing works
Hemodynamic shear stress and its role in atherosclerosis
Malek, A. M. (1999) · JAMA · doi:10.1001/jama.282.21.2035 · Cited by 3,650 · see citing works
Lawrence, M. B., & Springer, T. A. (1991) · Cell · doi:10.1016/0092-8674(91)90393-d · Cited by 2,157 · see citing works
Novel Modulator for Endothelial Adhesion Molecules
Ouchi, N., Kihara, S., Arita, Y., Maeda, K., Kuriyama, H., Okamoto, Y., Hotta, K., Nishida, M., Takahashi, M., Nakamura, T., et al. (1999) · Circulation · doi:10.1161/01.cir.100.25.2473 · Cited by 2,139 · see citing works
Targeted drug delivery to tumors: Myths, reality and possibility
Bae, Y. H., & Park, K. (2011) · Journal of Controlled Release · doi:10.1016/j.jconrel.2011.06.001 · Cited by 1,947 · see citing works
Gref, R., Lück, M., Quellec, P., Marchand, M., Dellacherie, E., Harnisch, S., Blunk, T., & Müller, R. H. (2000) · Colloids and Surfaces B Biointerfaces · doi:10.1016/s0927-7765(99)00156-3 · Cited by 1,725 · see citing works
Facile Conjugation of Biomolecules onto Surfaces via Mussel Adhesive Protein Inspired Coatings
Lee, H., Rho, J., & Messersmith, P. B. (2009) · Advanced Materials · doi:10.1002/adma.200801222 · Cited by 1,495 · see citing works
T-Cell Function and Migration — Two Sides of the Same Coin
von Andrian, U. H., & Mackay, C. R. (2000) · New England Journal of Medicine · doi:10.1056/nejm200010053431407 · Cited by 1,429 · see citing works
Selectins and their ligands: Current concepts and controversies
Kansas, G. (1996) · Blood · doi:10.1182/blood.v88.9.3259.bloodjournal8893259 · Cited by 1,415 · see citing works
Kirpotin, D. B., Drummond, D. C., Shao, Y., Shalaby, M. R., Hong, K., Nielsen, U. B., Marks, J. D., Benz, C. C., & Park, J. W. (2006) · Cancer Research · doi:10.1158/0008-5472.can-05-4199 · Cited by 1,129 · see citing works
Self-citationBevilacqua, M. P., & Nelson, R. M. (1993) · Journal of Clinical Investigation · doi:10.1172/jci116210 · Cited by 876 · see citing works
Bartlett, D. W., Su, H. C., Hildebrandt, I. J., Weber, W., & Davis, M. E. (2007) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0707461104 · Cited by 808 · see citing works
Mechanism of Amide Formation by Carbodiimide for Bioconjugation in Aqueous Media
Nakajima, N., & Ikada, Y. (1995) · Bioconjugate Chemistry · doi:10.1021/bc00031a015 · Cited by 780 · see citing works
Yamaoka, T., Tabata, Y., & Ikada, Y. (1994) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.2600830432 · Cited by 751 · see citing works
Miller, R. A., Brady, J. M., & Cutright, D. E. (1977) · Journal of Biomedical Materials Research · doi:10.1002/jbm.820110507 · Cited by 722 · see citing works
An Inducible Endothelial Cell Surface Glycoprotein Mediates Melanoma Adhesion
Rice, G. E., & Bevilacqua, M. P. (1989) · Science · doi:10.1126/science.2588007 · Cited by 650 · see citing works
Angiogenesis mediated by soluble forms of E-selectin and vascular cell adhesion molecule-1
Koch, A. E., Halloran, M. M., Haskell, C. J., Shah, M. R., & Polverini, P. J. (1995) · Nature · doi:10.1038/376517a0 · Cited by 600 · see citing works
(2005) · PubMed · Cited by 567 · see citing works
Takada, A., Ohmori, K., Yoneda, T., Tsuyuoka, K., Hasegawa, A., Kiso, M., & Kannagi, R. (1993) · PubMed · Cited by 544 · see citing works
Efficient Conversion of Aromatic Amines into Azides: A One-Pot Synthesis of Triazole Linkages
Barral, K., Moorhouse, A. D., & Moses, J. E. (2007) · Organic Letters · doi:10.1021/ol070527h · Cited by 413 · see citing works
Targeting selectins and selectin ligands in inflammation and cancer
Barthel, S. R., Gavino, J. D., Descheny, L., & Dimitroff, C. J. (2007) · Expert Opinion on Therapeutic Targets · doi:10.1517/14728222.11.11.1473 · Cited by 397 · see citing works
Mamot, C., Drummond, D. C., Noble, C. O., Kallab, V., Guo, Z., Hong, K., Kirpotin, D. B., & Park, J. W. (2005) · Cancer Research · doi:10.1158/0008-5472.can-05-1093 · Cited by 383 · see citing works
Self-citationKimura, H., Braun, R. D., Ong, E. T., Hsu, R., Secomb, T. W., Papahadjopoulos, D., Hong, K., & Dewhirst, M. W. (1996) · PubMed · Cited by 368 · see citing works
PEGylated Proteins: Evaluation of Their Safety in the Absence of Definitive Metabolism Studies
Webster, R., Didier, E., Harris, P., Siegel, N., Stadler, J., Tilbury, L., & Smith, D. (2007) · Drug Metabolism and Disposition · doi:10.1124/dmd.106.012419 · Cited by 337 · see citing works
In vivo fate of folate-targeted polyethylene-glycol liposomes in tumor-bearing mice.
Gabizón, A., Horowitz, A. T., Goren, D., et al. (2003) · PubMed · Cited by 295 · see citing works
Pros and Cons of the Liposome Platform in Cancer Drug Targeting
Gabizón, A., Shmeeda, H., & Zalipsky, S. (2006) · Journal of Liposome Research · doi:10.1080/08982100600848769 · Cited by 272 · see citing works
Endothelial Cell Adhesion Molecules and Cancer Progression
Kobayashi, H., Boelte, K. C., & Lin, P. C. (2007) · Current Medicinal Chemistry · doi:10.2174/092986707779941032 · Cited by 246 · see citing works
Intracellular Drug Delivery by Poly(lactic-co-glycolic acid) Nanoparticles, Revisited
Xu, P., Gullotti, E., Tong, L., Highley, C. B., Errabelli, D. R., Hasan, T. G., Cheng, J., Kohane, D. S., & Yeo, Y. (2008) · Molecular Pharmaceutics · doi:10.1021/mp800137z · Cited by 234 · see citing works
Self-citationNonnatural Amino Acids for Site-Specific Protein Conjugation
de Graaf, A. J., Kooijman, M., Hennink, W. E., et al. (2009) · Bioconjugate Chemistry · doi:10.1021/bc800294a · Cited by 205 · see citing works
E-selectin as a target for drug delivery and molecular imaging
Jubeli, E., Moine, L., Vergnaud, J., et al. (2011) · Journal of Controlled Release · doi:10.1016/j.jconrel.2011.09.084 · Cited by 135 · see citing works
Guo, Y., Jacobs, S. C., & Kyprianou, N. (1997) · International Journal of Cancer · doi:10.1002/(sici)1097-0215(19970516)71:4 · Cited by 129 · see citing works
CD44v4 Is a Major E-Selectin Ligand that Mediates Breast Cancer Cell Transendothelial Migration
Zen, K., Liu, D.-Q., Guo, Y.-L., Wang, C., Shan, J., Fang, M. L., Zhang, C., & Liu, Y. (2008) · PLoS ONE · doi:10.1371/journal.pone.0001826 · Cited by 128 · see citing works
Fox, S. B., Turner, G. D. H., Gatter, K. C., et al. (1995) · The Journal of Pathology · doi:10.1002/path.1711770407 · Cited by 124 · see citing works
DeFrees, S. A., Phillips, L., Guo, L., & Zalipsky, S. (1996) · Journal of the American Chemical Society · doi:10.1021/ja954122g · Cited by 115 · see citing works
Jarowicki, K., & Kocieński, P. (2001) · Journal of the Chemical Society Perkin Transactions 1 · doi:10.1039/b103282h · Cited by 112 · see citing works
Rao, B. N., Anderson, M. B., Musser, J. H., Gilbert, J. H., Schaefer, M. E., Foxall, C., & Brandley, B. K. (1994) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)32068-9 · Cited by 100 · see citing works
Role of Tumor Cell Adhesion and Migration in Organ-Specific Metastasis Formation
Gaßmann, P., Enns, A., & Haier, J. (2004) · Oncology Research and Treatment · doi:10.1159/000081343 · Cited by 95 · see citing works
Eniola‐Adefeso, O., & Hammer, D. A. (2005) · Biomaterials · doi:10.1016/j.biomaterials.2005.05.005 · Cited by 93 · see citing works
Temporal changes in pO2 of R3230Ac tumors in fischer-344 rats
Dewhirst, M. W., Braun, R. D., & Lanzen, J. L. (1998) · International Journal of Radiation Oncology*Biology*Physics · doi:10.1016/s0360-3016(98)00304-6 · Cited by 68 · see citing works
Synthesis of Biologically Active Sialyl Lewis X Mimetics
Huang, H., & Wong, C. (1995) · The Journal of Organic Chemistry · doi:10.1021/jo00115a027 · Cited by 68 · see citing works
E-selectin up-regulation allows for targeted drug delivery in prostate cancer.
Bhaskar, V., Law, D. A., Ibsen, E. M., et al. (2003) · PubMed · Cited by 65 · see citing works
Nguyen, M. T. N., Corless, C. L., Kräling, B. M., et al. (1997) · PubMed · Cited by 63 · see citing works
Gupta, A. S., Wang, S., Link, E., Anderson, E. H., Hofmann, C., Lewandowski, J. J., Kottke‐Marchant, K., & Marchant, R. E. (2006) · Biomaterials · doi:10.1016/j.biomaterials.2006.01.002 · Cited by 62 · see citing works
Yu, C., Shih, J., Lee, Y.-C., Shun, C., Yuan, A., & Yang, P. (2004) · Lung Cancer · doi:10.1016/j.lungcan.2004.05.018 · Cited by 52 · see citing works
Zeisig, R., Stahn, R., Wenzel, K., et al. (2003) · Biochimica et Biophysica Acta (BBA) - Biomembranes · doi:10.1016/j.bbamem.2003.10.014 · Cited by 51 · see citing works
Stahn, R., Schafer, H., Kernchen, F., & Schreiber, J. (1998) · Glycobiology · doi:10.1093/glycob/8.4.311 · Cited by 48 · see citing works
Kaila, N., Somers, W. S., Thomas, B. E., et al. (2005) · Journal of Medicinal Chemistry · doi:10.1021/jm050049l · Cited by 47 · see citing works
Ozawa, M. G., Zurita, A. J., Dias‐Neto, E., Nunes, D. N., Sidman, R. L., Gelovani, J. G., Arap, W., & Pasqualini, R. (2008) · Trends in Cardiovascular Medicine · doi:10.1016/j.tcm.2008.03.001 · Cited by 45 · see citing works
Evaluation of leukocyte adhesion on polyurethanes: the effects of shear stress and blood proteins
Kao, W. J. (2000) · Biomaterials · doi:10.1016/s0142-9612(00)00156-3 · Cited by 32 · see citing works
Tsuruta, W., Tsurushima, H., Yamamoto, T., Suzuki, K., Yamazaki, N., & Matsumura, A. (2008) · Biomaterials · doi:10.1016/j.biomaterials.2008.09.009 · Cited by 30 · see citing works
Aoki, M., Kanamori, M., Yudoh, K., et al. (2001) · Tumor Biology · doi:10.1159/000050622 · Cited by 27 · see citing works
Synthesis of novel 6-amido-6-deoxy-l-galactose derivatives as sialyl Lewis X mimetics
Cappi, M. W., Moree, W. J., Qiao, L., et al. (1997) · Bioorganic & Medicinal Chemistry · doi:10.1016/s0968-0896(96)00236-2 · Cited by 25 · see citing works
Design and synthesis of sialyl lewis x mimics as e-selectin inhibitors
Kaila, N., Thomas, B. E., Thakker, P., et al. (2001) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/s0960-894x(00)00623-5 · Cited by 22 · see citing works
Sialyl Lewisx analogs based on a quinic acid scaffold as the fucose mimic
Girard, C., Dourlat, J., Savarin, A., et al. (2005) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2005.05.004 · Cited by 20 · see citing works
Tailored PEG for rh-G-CSF Analogue Site-Specific Conjugation
Salmaso, S., Bersani, S., Scomparin, A., et al. (2009) · Bioconjugate Chemistry · doi:10.1021/bc9000432 · Cited by 19 · see citing works
Makondo, K. J., Kimura, K., Kitamura, T., Yamaji, D., Jung, B.-D., Shibata, H., & Saito, M. (2003) · Biochimica et Biophysica Acta (BBA) - Molecular Cell Research · doi:10.1016/j.bbamcr.2003.10.006 · Cited by 18 · see citing works
Paprocka, M., Duś, D., Mitterrand, M., et al. (2008) · Microvascular Research · doi:10.1016/j.mvr.2008.03.004 · Cited by 14 · see citing works
Yoshida, M., Chien, L.-J., Yasukochi, Y., et al. (2000) · Annals of the New York Academy of Sciences · doi:10.1111/j.1749-6632.2000.tb06328.x · Cited by 13 · see citing works
Gene Expression of E-Selectin in Tissue and its Protein Level in Serum of Breast Cancer Patients
Shaker, O. G., El-Deen, M. A. A., El-Rahim, M. T. A., et al. (2006) · Tumori Journal · doi:10.1177/030089160609200610 · Cited by 12 · see citing works
New sialyl Lewisx mimic containing an α-substituted β3-amino acid spacer
Pedatella, S., Nisco, M. D., Ernst, B., Guaragna, A., Wagner, B., Woods, R. J., & Palumbo, G. (2007) · Carbohydrate Research · doi:10.1016/j.carres.2007.10.001 · Cited by 8 · see citing works
Rostovtsev, V. V., Green, L. G., Fokin, V. V., & Sharpless, K. B. (2002) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20020715)41:14
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Cancer cells induce metastasis-supporting neutrophil extracellular DNA traps
Park, J., Wysocki, R. W., Amoozgar, Z., Maiorino, L., Fein, M. R., Jorns, J., Schott, A. F., Kinugasa-Katayama, Y., Lee, Y., Won, N. H., et al. (2016) · Science Translational Medicine · doi:10.1126/scitranslmed.aag1711 · Cited by 984 · see citing works
Self-citation
- Authors
- Amoozgar, Z., Park, J., Lin, Q., Weidle, J. H., & Yeo, Y.
- Affiliations
- Purdue University West Lafayette (US)
- Corresponding author
- Yeo, Yoon
- Venue
- Biomacromolecules
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-06-05
- Volume
- 14
- Issue
- 7
- Pages
- 2389-2395
- ISSN
- 1525-7797 (ISSN-L)
- 1526-4602
- PMC
- PMC3717395
- OpenAlex
- W2116088841
- Cited by
- 27
- References
- 63
- Citations by year
- 2026: 1 · 2025: 1 · 2024: 3 · 2023: 1 · 2021: 2 · 2020: 3 · 2019: 1 · 2018: 2 · 2017: 3 · 2016: 4 · 2015: 2 · 2014: 4
- FWCI
- 1.27
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Biomacromolecules (publishedVersion)
- PubMed (publishedVersion)
- Europe PMC (PubMed Central) (acceptedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Cancer Institute (P30CA023168, CA23168, R21CA135130)
- Topics
- Physical Sciences › Materials Science › Biomaterials › Nanoparticle-Based Drug Delivery
- Physical Sciences › Materials Science › Polymers and Plastics › Dendrimers and Hyperbranched Polymers
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmaceutical Science › Advanced Drug Delivery Systems
- Keywords
- quinic acid, polymeric nanoparticles, drug carriers, solid tumors, E-selectin, tumor endothelium, TNF-α, passive tumor targeting, nanoparticle drug delivery, shear stress
- MeSH terms
- Antineoplastic Agents, Drug Carriers, Humans, Neoplasms, Quinic Acid, HL-60 Cells, E-Selectin, Cell Line, Tumor, Nanoparticles, Human Umbilical Vein Endothelial Cells
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