Cyclic peptide-capped gold nanoparticles as drug delivery systems

Molecular Pharmaceutics

Volumn 10, Issue 2, 2013, Pages 500-511

  Nasrolahi Shirazi, Amir ^a   Mandal, Dindyal ^a   Tiwari, Rakesh K ^a   Guo, Liangran ^a   Lu, Wei ^a   Parang, Keykavous ^a  

^a UNIVERSITY OF RHODE ISLAND   (United States)

Author keywords

arginine; cellular delivery; cyclic peptide; gold nanoparticle; tryptophan

Indexed keywords

ANION; ARGININE; CYCLIC PEPTIDE CAPPED GOLD NANOPARTICLE; CYCLOPEPTIDE; DOXORUBICIN; EMTRICITABINE; GOLD NANOPARTICLE; LAMIVUDINE; STAVUDINE; TRYPTOPHAN; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CARCINOMA CELL; CONCENTRATION (PARAMETERS); CONFOCAL MICROSCOPY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG DISTRIBUTION; DRUG RELEASE; DRUG RETENTION; DRUG UPTAKE; FEMALE; FLOW CYTOMETRY; FLUORESCENCE; HUMAN; HUMAN CELL; OVARY ADENOCARCINOMA; PHASE CONTRAST MICROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

CELL LINE, TUMOR; CELL SURVIVAL; DRUG DELIVERY SYSTEMS; FLOW CYTOMETRY; GOLD; HUMANS; METAL NANOPARTICLES; MICROSCOPY, CONFOCAL; MICROSCOPY, FLUORESCENCE; PEPTIDES, CYCLIC;

EID: 84873357426     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp300448k     Document Type: Article

References (28)

1. Sepúlveda, B.; Angelomé, P. C.; Lechuga, L. M.; Liz-Marzán, L. M. LSPR-based nanobiosensors Nano Today 2009, 4, 244-251
2. Hu, M.; Chen, J.; Zhi-Yuan, L.; Leslie, A.; Hartland, G. V.; Li, X.; Marquez, M.; Xia, Y. Gold nanostructures: engineering their plasmonic properties for biomedical applications Chem. Soc. Rev. 2006, 35, 1084-1094 (Pubitemid 44611721)
3. Ghosha, P.; Hana, G.; Dea, M.; Kima, C. K.; Rotello, V. M. Gold nanoparticles in delivery applications Adv. Drug Delivery Rev. 2008, 60, 1307-1315
4. Huang, X. H.; Jain, P. K.; El-Sayed, I. H.; El-Sayed, M. A. Gold nanoparticles: interesting optical properties and recent applications in cancer diagnostics and therapy Nanomedicine 2007, 2, 681-693 (Pubitemid 350268247)
5. Jain, P. K.; El-Sayed, I. H.; El-Sayed, M. A. Au nanoparticles target cancer Nano Today 2007, 2, 18-29 (Pubitemid 46196541)
6. Dykman, L.; Khlebtsov, N. Gold nanoparticles in biomedical applications: recent advances and perspectives Chem. Soc. Rev. 2012, 41, 2256-2282
7. De, M.; Ghosh, P. S.; Rotello, V. M. Applications of nanoparticles in biology Adv. Mater. 2008, 20, 4225-4241
8. Lévy, R. Peptide-capped gold nanoparticles: towards artificial proteins ChemBioChem 2006, 7, 1141-1145 (Pubitemid 44230832)
9. Mandal, D.; Nasrolahi Shirazi, A.; Parang, K. Cell-penetrating homochiral cyclic peptides as nuclear-targeting molecular transporters Angew. Chem., Int. Ed. 2011, 50, 9633-9637
10. Satyabrata, S.; Mandal, T. K. Tryptophan-based peptides to synthesize gold and silver nanoparticles: a mechanistic and kinetic study Chem.-Eur. J. 2007, 13, 3160-3168 (Pubitemid 46941841)
11. Selvakannan, P. R.; Mandal, S.; Phadtare, S.; Gole, A.; Pasricha, R.; Adyanthaya, S. D.; Sastry, M. Water-dispersible tryptophan-protected gold nanoparticles prepared by the spontaneous reduction of aqueous chloroaurate ions by the amino acid J. Colloid Interface Sci. 2004, 269, 97-102 (Pubitemid 37490999)
12. Bhargava, S. K.; Booth, J. M.; Agrawal, S.; Coloe, P.; Kar, G. Gold nanoparticle formation during bromoaurate reduction by amino acids Langmuir 2005, 21, 5949-5956 (Pubitemid 40925844)
13. Tan, Y. N.; Lee, J. Y.; Wang, D. I. C. Uncovering the design rules for peptide synthesis of metal nanoparticles J. Am. Chem. Soc. 2010, 132, 5677-5686
14. Ye, G.; Nam, N. H.; Saleh, A.; Kumar, A.; Sun, G.; Shenoy, D. B.; Amiji, M. M.; Lin, X.; Sun, G.; Parang, K. Synthesis and evaluation of tripodal peptide analogues for cellular delivery of phosphopeptides J. Med. Chem. 2007, 50, 3604-3617 (Pubitemid 47195467)
15. Ye, G.; Gupta, A.; DeLuca, R.; Parang, K.; Bothun, G. D. Bilayer disruption and liposome restructuring by a homologous series of small Arg-rich synthetic peptides Colloids Surf., B 2010, 76, 76-81
16. Katsara, M.; Tselios, T.; Deraos, S.; Deraos, G.; Matsoukas, M. T.; Lazoura, E.; Matsoukas, J.; Apostolopoulos, V. Round and round we go: cyclic peptides in disease Curr. Med. Chem. 2006, 13, 2221-2232 (Pubitemid 44184648)
17. Massard, J.; Benhamou, Y. Treatment of chronic hepatitis B in HIV co-infected patients Gastroenterol. Clin. Biol. 2008, 32, 20-24
18. Agarwal, H. K.; Chhikara, B. S.; Hanley, M. J.; Ye, G.; Doncel, G. F.; Parang, K. Synthesis and biological evaluation of fatty acyl ester derivatives of (-)-2′,3′-dideoxy-3′-thiacytidine J. Med. Chem. 2012, 55, 4861-4871
19. Agarwal, H. K.; Loethan, K.; Mandal, D.; Doncel, G. F.; Parang, K. Synthesis and biological evaluation of fatty acyl ester derivatives of 2′,3′-didehydro-2′,3′-dideoxythymidine Bioorg. Med. Chem. Lett. 2011, 21, 1917-1921
20. Alivisatos, A. P.; Johnsson, K. P.; Peng, X. G.; Wilson, T. E.; Loweth, C. J.; Bruchez, M. P. Organization of 'nanocrystal molecules' using DNA Nature 1996, 382, 609-611 (Pubitemid 26268950)
21. Mirkin, C. A.; Letsinger, R. L.; Mucic, R. C.; Storhoff, J. J. A DNA-based method for rationally assembling nanoparticles into macroscopic materials Nature 1996, 382, 607-609 (Pubitemid 26268949)
22. Levy, R.; Thanh, N. T. K.; Doty, R. C.; Hussain, I.; Nichols, R. J.; Schiffrin, D. J. Rational and combinatorial design of peptide capping ligands for gold nanoparticles J. Am. Chem. Soc. 2004, 126, 10076-10084 (Pubitemid 39079430)
23. Skidmore, M. A.; Patey, S. J.; Thanh, N. T. K.; Fernig, D. G.; Turnbull, J. E.; Yates, E. A. Attachment of glycosaminoglycan oligosaccharides to thiol-derivatised gold surfaces Chem. Commun. 2004, 23, 2700-2701 (Pubitemid 40029543)
24. Wang, S.; Lu, W.; Tovmachenko, O.; Rai, U. S.; Yu, H.; Ray, P. C. Challenge in understanding size and shape dependent toxicity of gold nanomaterials in human skin keratinocytes Chem. Phys. Lett. 2008, 463, 145-149
25. Alkilany, A. M.; Nagaria, P.; Hexel, C. R.; Shaw, T. J.; Murphy, C. J. Cellular uptake and cytotoxicity of gold nanorods: molecular origin of cytotoxicity and surface effects Small 2009, 5, 701-708
26. Murphy, C. J.; Gole, A. M.; Stone, J. W.; Sisco, P. N.; Alkilany, A. M.; Goldsmith, E. C.; Baxter, S. C. Gold nanoparticles in biology: beyond toxicity to cellular imaging Acc. Chem. Res. 2008, 41, 1721-1730
27. Kim, C. K.; Ghosh, P.; Pagliuca, C.; Zhu, Z. J.; Menichetti, S.; Rotello, V. M. Entrapment of hydrophobic drugs in nanoparticle monolayers with efficient release into cancer cells J. Am. Chem. Soc. 2009, 131, 1360-1361
28. Duncan, B.; Kim, C.; Rotello, V. M. Gold nanoparticle platforms as drug and biomacromolecule delivery systems J. Controlled Release 2010, 148, 122-127