Cyclic peptide-capped gold nanoparticles as drug delivery systems

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

Research output: Contribution to journalArticle

Abstract

A number of cyclic peptides were synthesized and evaluated as simultaneous reducing and capping agents for generation of cyclic peptide-capped gold nanoparticles (CP-AuNPs). Among them, direct dissolution of cyclic peptides containing alternate arginine and tryptophan [WR]n (n = 3-5) into an aqueous solution of AuCl4 - led to the formation of CP-AuNPs, through the reducing activity of tryptophan residues and attraction of positively charged arginine residues toward chloroaurate anions in the reaction environment. Differential interference contrast microscopy of fluorescence-labeled lamivudine in the presence of [WR]4-capped AuNPs showed significantly higher cellular delivery of antiviral drug versus that of parent drug alone. Flow cytometry studies also showed that the cellular uptake of fluorescence-labeled lamivudine, emtricitabine, and stavudine was significantly enhanced in human ovarian adenocarcinoma (SK-OV-3) cells in the presence of [WR]4-AuNPs. For example, fluorescence labeled lamivudine-loaded [WR]4-AuNPs exhibited approximately 12- and 15-times higher cellular uptake than that of fluorescence labeled lamivudine alone in CCRF-CEM cells and SK-OV-3 cells, respectively. Confocal microscopy revealed that the presence of the [WR]4-AuNPs enhanced the retention and nuclear localization of doxorubicin in SK-OV-3 cells after 24 h. These data suggest that these complexes can be used as potential noncovalent prodrugs for delivery of antiviral and anticancer agents.

Original languageEnglish (US)
Pages (from-to)500-511
Number of pages12
JournalMolecular Pharmaceutics
Volume10
Issue number2
DOIs
StatePublished - Feb 4 2013
Externally publishedYes

Fingerprint

Cyclic Peptides
Lamivudine
Drug Delivery Systems
Gold
Nanoparticles
Fluorescence
Tryptophan
Antiviral Agents
Arginine
Interference Microscopy
Stavudine
Reducing Agents
Prodrugs
Confocal Microscopy
Antineoplastic Agents
Doxorubicin
Anions
Flow Cytometry
Adenocarcinoma
Pharmaceutical Preparations

Keywords

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

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Molecular Medicine
  • Drug Discovery

Cite this

Nasrolahi Shirazi, A., Mandal, D., Tiwari, R. K., Guo, L., Lu, W., & Parang, K. (2013). Cyclic peptide-capped gold nanoparticles as drug delivery systems. Molecular Pharmaceutics, 10(2), 500-511. https://doi.org/10.1021/mp300448k

Cyclic peptide-capped gold nanoparticles as drug delivery systems. / Nasrolahi Shirazi, Amir; Mandal, Dindyal; Tiwari, Rakesh K.; Guo, Liangran; Lu, Wei; Parang, Keykavous.

In: Molecular Pharmaceutics, Vol. 10, No. 2, 04.02.2013, p. 500-511.

Research output: Contribution to journalArticle

Nasrolahi Shirazi, A, Mandal, D, Tiwari, RK, Guo, L, Lu, W & Parang, K 2013, 'Cyclic peptide-capped gold nanoparticles as drug delivery systems', Molecular Pharmaceutics, vol. 10, no. 2, pp. 500-511. https://doi.org/10.1021/mp300448k
Nasrolahi Shirazi A, Mandal D, Tiwari RK, Guo L, Lu W, Parang K. Cyclic peptide-capped gold nanoparticles as drug delivery systems. Molecular Pharmaceutics. 2013 Feb 4;10(2):500-511. https://doi.org/10.1021/mp300448k
Nasrolahi Shirazi, Amir ; Mandal, Dindyal ; Tiwari, Rakesh K. ; Guo, Liangran ; Lu, Wei ; Parang, Keykavous. / Cyclic peptide-capped gold nanoparticles as drug delivery systems. In: Molecular Pharmaceutics. 2013 ; Vol. 10, No. 2. pp. 500-511.
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