2,060
Views
23
CrossRef citations to date
0
Altmetric
Review Article

[60]Fullerene-peptides: bio-nano conjugates with structural and chemical diversity

Pages 164-176 | Received 15 Mar 2016, Accepted 06 Apr 2016, Published online: 10 May 2016

References

  • Kroto HW, Heath JR, O'Brien SC, et al. C60: Buckminsterfullerene. Nature 1985;318:162–3
  • Dresselhaus MS, Dresselhaus G, Eklund PC. Science of fullerenes and carbon nanotubes: their properties and applications. Cambridge: Academic Press; 1996
  • Zichi DA, Rossky PJ. Solvent molecular dynamics in regions of hydrophobic hydration. J Chem Phys 1986;84:2814–22
  • Lecoanet HF, Bottero J-Y, Wiesner MR. Laboratory assessment of the mobility of nanomaterials in porous media. Environ Sci Technol 2004;38:5164–9
  • Yang Y, Arias F, Echegoyen L, et al. Reversible fullerene electrochemistry: correlation with the HOMO-LUMO energy difference for C60, C70, C76, C78, and C84. J Am Chem Soc 1995;117:7801–4
  • Bosi S, Da Ros T, Spalluto G, Prato M. Fullerene derivatives: an attractive tool for biological applications. Eur J Med Chem 2003;38:913–23
  • Jensen W, Wilson SR, Schuster DI. Biological applications of fullerenes. Bioorg Med Chem 1996;4:767–79
  • Bakry R, Vallant RM, Najam-ul-Haq M, et al. Medicinal applications of fullerenes. Int J Nanomedicine 2007;2:639–49
  • Djordjevic A, Srdjenovic B, Seke M, et al. Review of synthesis and antioxidant potential of fullerenol nanoparticles. J Nanomater 2015;2015:567073
  • Sun Y-P, Lawson GE, Huang W, et al. Preparation and characterization of highly water-soluble pendant fullerene polymers. Macromolecules 1999;32:8747–52
  • An Y-Z, Anderson JL, Rubin Y. Synthesis of α-amino acid derivatives of C60 from 1,9-(4-hydroxycyclohexano)buckminsterfullerene. J Org Chem 1993;58:4799–801
  • Skiebe A, Hirsch A. A facile method for the synthesis of amino acid and amido derivatives of C60. J Chem Soc Chem Commun 1994;335–6
  • Gan L, Zhou D, Luo C, et al. Synthesis of fullerene amino acid derivatives by direct interaction of amino acid ester with C60. J Org Chem 1996;61:1954–61
  • Pellarini F, Pantarotto D, Da Ros T, et al. A novel [60]fullerene amino acid for use in solid-phase peptide synthesis. Org Lett 2001;3:1845–8
  • Yang J, Barron AR. A new route to fullerene substituted phenylalanine derivatives. Chem Commun 2004;2884–5
  • Strom TA, Barron AR. A simple quick route to fullerene amino acid derivatives. Chem Commun 2010;46:4764–6
  • Burley GA, Keller PA, Pyne SG. [60]Fullerene amino acids and related derivatives. Fullerene. Sci Techn 1999;7:973–1001
  • Bianco A, da Ros T, Prato M, Toniolo C. Fullerene-based amino acids and peptides. J Pept Sci 2001;7:208–19
  • Pantarotto D, Tagmatarchis N, Bianco A, Prato M. Synthesis and biological properties of fullerene-containing amino acids and peptides. Mini Rev Med Chem 2004;4:805–14
  • Jennepalli S, Pyne SG, Keller PA. [60]Fullerenyl amino acids and peptides: a review of their synthesis and applications. RSC Adv 2014;4:46383–98
  • Romanova VS, Tsyryapkin VA, Lyakhovetsky YI, et al. Addition of amino acids and dipeptides to fullerene C60 giving rise to monoadducts. Russ Chem Bull 1994;43:1090–1
  • Wang N, Li J, Zhu D, Chan TH. A C60-derivatized dipeptide. Tetrahedron Lett 1995;36:431–4
  • Prato M, Bianco A, Maggini M, et al. Synthesis and characterization of the first fullerene-peptide. J Org Chem 1993;58:5578–80
  • Toniolo C, Bianco A, Maggini M, et al. A bioactive fullerene peptide. J Med Chem 1994;37:4558–62
  • Bianco A, Bertolini T, Crisma M, et al. Beta-turn induction by C60-based fulleroproline: synthesis and conformational characterization of Fpr/Pro small peptides. J Peptide Sci 1997;50:159–70
  • Bianco A, Maggini M, Scorrano G, et al. Synthesis, chiroptical properties, and configurational assignment of fulleroproline derivatives and peptides. J Am Chem Soc 1996;118:4072–80
  • Xu Y, Zhu J, Xiang K, et al. Synthesis and immunomodulatory activity of [60]fullerene–tuftsin conjugates. Biomaterials 2011;32:9940–9
  • Jennepalli S, Hammer KA, Riley TV, et al. Synthesis of mono and bis[60]fullerene-based dicationic peptoids. Eur J Org Chem 2015;2015:195–201
  • Bjelaković MS, Kop TJ, Vlajić M, et al. Design, synthesis, and characterization of fullerene-peptide-steroid covalent hybrids. Tetrahedron 2014;70:8564–70
  • Sofou P, Elemes Y, Panou-Pomonis E, et al. Synthesis of a proline-rich [60]fullerene peptide with potential biological activity. Tetrahedron 2004;60:2823–8
  • Yang Y, Alemany LB, Driver J, et al. Fullerene-derivatized amino acids: synthesis, characterization, antioxidant properties, and solid phase peptide synthesis. Chem Eur J 2007;3:2530–45
  • Aroua S, Schweizer WB, Yamakoshi Y. C60 Pyrrolidine bis-carboxylic acid derivative as a versatile precursor for biocompatible fullerenes. Org Lett 2014;16:1688–91
  • Innocenti A, Durdagi S, Doostdar N, et al. Nanoscale enzyme inhibitors: fullerenes inhibit carbonic anhydrase by occluding the active site entrance. Biorg Med Chem 2010;18:2822–8
  • Pantarotto D, Bianco A, Pellarini F, et al. Solid-phase synthesis of fullerene-peptides. J Am Chem Soc 2002;124:12543–9
  • Watanabe LA, Bhuiyan MPI, Jose B, et al. Synthesis of novel fullerene amino acids and their multifullerene peptides. Tetrahedron Lett 2004;45:7137–40
  • Yang J, Wang K, Driver J, et al. The use of fullerene substituted phenylalanine derivatives as a passport through cell membranes. Org Biomol Chem 2007;5:260–6
  • Strom TA, Durdagi S, Ersoz SS, et al. Fullerene-based inhibitors of HIV-1 protease. J Pept Sci 2015;21:862–70
  • Strom TA, Barron AR. Attempts towards the bucky-amino acid acylation of the phospho-cytidine-phospho-adenosine (pdCpA) subunit. All Res J Nano 2015;1:4–9
  • Klemenkova ZS, Romanova VS, Tsyryapkin VA, et al. Infrared spectra of amino acid and peptide monoderivatives of [60]fullerene and their methyl esters. Mendeleev Commun 1996;6:60–2
  • Pacor S, Giangaspero A, Bacac M, et al. Analysis of the cytotoxicity of synthetic antimicrobial peptides on mouse leucocytes: implications for systemic use. J Antimicrob Chemother 2002;50:339–48
  • Zhang LW, Yang J, Barron AR, Monteiro-Riviere NA. Endocytic mechanisms and toxicity of a functionalized fullerene in human cells. Toxicol Lett 2009;191:149–57
  • Rouse JG, Yang J, Barron AR, Monteiro-Riviere NA. Fullerene-based amino acid nanoparticle interactions with human epidermal keratinocytes. Toxicol in Vitro 2006;20:1313–20
  • Doostdar N. In-vitro model system for calcific band keratopathy and inhibitory effects of C60 fullerene derivatives. PhD Thesis. Houston (TX): Rice University; 2010
  • Friedman SH, De Camp DL, Sijbesma RP, et al. Inhibition of the HIV-1 protease by fullerene derivatives: model building studies and experimental verification. J Am Chem Soc 1993;115:6506–9
  • Durdagi S, Supuran CT, Strom TA, et al. In silico drug screening approach to designing magic bullets: A successful example with anti-HIV fullerene derivatized amino acids. J Chem Inf Model 2009;49:1139–43
  • Saleh NA. The QSAR and docking calculations of fullerene derivatives as HIV-1 protease inhibitors. Spectrochim Acta A Mol Biomol Spectrosc 2015;136:1523–9
  • Ryman-Rasmussen JP, Riviere JE, Monteiro-Riviere NA. Penetration of intact skin by quantum dots with diverse physicochemical properties. Toxicol Sci 2006;91:159–65
  • Prow TW, Monteiro-Riviere NA, Inman AO, et al. Quantum dot penetration into viable human skin. Nanotoxicology 2012;6:173–85
  • Rouse JG, Ryman-Rasmussen JP, Yang J, et al. Effects of mechanical flexion on the penetration of fullerene amino acid-derivatized peptide nanoparticles through skin. Nano Lett 2007;7:155–60
  • van der Merwe D, Brooks JD, Gehring R, et al. A physiologically based pharmacokinetic model of organophosphate dermal absorption. Toxicol Sci 2006;89:188–204

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.