Benjamin M. Long
Deakin University
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Publication
Featured researches published by Benjamin M. Long.
RSC Advances | 2015
Rui Li; Conor C. Horgan; Benjamin M. Long; Alexandra L. Rodriguez; Lauren Mather; Colin J. Barrow; David R. Nisbet; Richard J. Williams
Hydrogels formed by the self-assembly of peptides are promising biomaterials. The bioactive and biocompatible molecule Fmoc-FRGDF has been shown to be an efficient hydrogelator via a π-β self-assembly mechanism. Herein, we show that the mechanical properties and morphology of Fmoc-FRGDF hydrogels can be effectively and easily manipulated by tuning both the final ionic strength and the rate of pH change. The increase of ionic strength, and consequent increase in rate of gelation and stiffness, does not interfere with the underlying π-β assembly of this Fmoc-protected peptide. However, by tuning the changing rate of the systems pH through the use of glucono-δ-lactone to form a hydrogel, as opposed to the previously reported HCl methodology, the morphology (nano- and microscale) of the scaffold can be manipulated.
Chemical Communications | 2013
Adam J. Lowe; Benjamin M. Long; Frederick M. Pfeffer
Norbornane and fused [n]polynorbornane frameworks are readily synthesised, can be tailored to a variety of predictable geometries and can be functionalised regiospecifically. As such, these highly preorganised scaffolds offer the supramolecular chemist an excellent starting point when designing hosts for specific guests. This feature article will highlight the evolution of our research from relatively simple norbornane based anion receptors to more sophisticated tetrathioureido functionalised fused [n]polynorbornane hosts.
Journal of Organic Chemistry | 2012
Adam J. Lowe; Benjamin M. Long; Frederick M. Pfeffer
A family of conformationally preorganized, [n]polynorbornane-based anion hosts 1a,b-6a,b have been synthesized. The series includes receptors with 4, 8, and 12 H-bond donors. Using (1)H NMR titration techniques, evaluation of the new hosts against a series of alkyl and aryl dicarboxylates as well as a range of phosphoanionic species has revealed that the tris(thioureido) hosts (in particular 3a) are capable of regioselectively binding dicarboxylates and pyrophosphate (H(2)PPi(2-)).
Nanomedicine: Nanotechnology, Biology and Medicine | 2016
Rui Li; Sivapriya Pavuluri; Kiara F. Bruggeman; Benjamin M. Long; Andrew J. Parnell; Anne Martel; Steven R. Parnell; Frederick M. Pfeffer; Andrew J. C. Dennison; Kevin R. Nicholas; Colin J. Barrow; David R. Nisbet; Richard J. Williams
The local inflammatory environment of the cell promotes the growth of epithelial cancers. Therefore, controlling inflammation locally using a material in a sustained, non-steroidal fashion can effectively kill malignant cells without significant damage to surrounding healthy cells. A promising class of materials for such applications is the nanostructured scaffolds formed by epitope presenting minimalist self-assembled peptides; these are bioactive on a cellular length scale, while presenting as an easily handled hydrogel. Here, we show that the assembly process can distribute an anti-inflammatory polysaccharide, fucoidan, localized to the nanofibers within the scaffold to create a biomaterial for cancer therapy. We show that it supports healthy cells, while inducing apoptosis in cancerous epithelial cells, as demonstrated by the significant down-regulation of gene and protein expression pathways associated with epithelial cancer progression. Our findings highlight an innovative material approach with potential applications in local epithelial cancer immunotherapy and drug delivery.
Supramolecular Chemistry | 2015
Benjamin M. Long; Frederick M. Pfeffer
The use of modified Job plot methodology provides a quick and easy means for evaluating host–guest stoichiometry and requires less material than the original method. In this short paper, the results of a recent anion recognition study using thiourea-functionalised norbornanes and [n]polynorbornanes are presented. A significant difference between the plots constructed using the original and modified method was observed and, as such, caution is advised when the modified Jobs method is solely used for the determination of host–guest stoichiometry.
Scientific Reports | 2017
Rui Li; Mitchell Boyd-Moss; Benjamin M. Long; Anne L. Martel; Andrew J. Parnell; Andrew J. C. Dennison; Colin J. Barrow; David R. Nisbet; Richard J. Williams
Enabling control over macromolecular ordering and the spatial distribution of structures formed via the mechanisms of molecular self-assembly is a challenge that could yield a range of new functional materials. In particular, using the self-assembly of minimalist peptides, to drive the incorporation of large complex molecules will allow a functionalization strategy for the next generation of biomaterial engineering. Here, for the first time, we show that co-assembly with increasing concentrations of a highly charged polysaccharide, fucoidan, the microscale ordering of Fmoc-FRGDF peptide fibrils and subsequent mechanical properties of the resultant hydrogel can be easily and effectively manipulated without disruption to the nanofibrillar structure of the assembly.
Polymers | 2018
Rui Li; Mitchell Boyd-Moss; Benjamin M. Long; Sivapriya Pavuluri; Kiara F. Bruggeman; Yi Wang; Colin R Barrow; David R. Nisbet; Richard J. Williams
Self-assembling peptides (SAPs) are a relatively new class of low molecular weight gelators which immobilize their solvent through the spontaneous formation of (fibrillar) nanoarchitectures. As peptides are derived from proteins, these hydrogels are ideal for use as biocompatible scaffolds for regenerative medicine. Importantly, due to the propensity of peptide sequences to act as signals in nature, they are easily functionalized to be cell instructive via the inclusion of bioactive epitopes. In nature, the fibronectin peptide sequence, arginine-glycine-aspartic acid (RGD) synergistically promotes the integrin α5β1 mediated cell adhesion with another epitope, proline-histidine-serine-arginine-asparagine (PHSRN); however most functionalization strategies focus on RGD alone. Here, for the first time, we discuss the biomimetic inclusion of both these sequences within a self-assembled minimalistic peptide hydrogel. Here, based on our work with Fmoc-FRGDF (N-flourenylmethyloxycarbonyl phenylalanine-arginine-glycine-aspartic acid-phenylalanine), we show it is possible to present two epitopes simultaneously via the assembly of the epitopes by the coassembly of two SAPs, and compare this to the effectiveness of the signals in a single peptide; Fmoc-FRGDF: Fmoc-PHSRN (N-flourenylmethyloxycarbonyl-proline-histidine-serine-arginine-asparagine) and Fmoc-FRGDFPHSRN (N-flourenylmethyloxycarbonyl-phenylalanine-arginine-glycine-asparticacid-phenylalanine-proline-histidine-serine-arginine-asparagine). We show both produced self-supporting hydrogel underpinned by entangled nanofibrils, however, the stiffness of coassembled hydrogel was over two orders of magnitude higher than either Fmoc-FRGDF or Fmoc-FRGDFPHSRN alone. In-vitro three-dimensional cell culture of human mammary fibroblasts on the hydrogel mixed peptide showed dramatically improved adhesion, spreading and proliferation over Fmoc-FRGDF. However, the long peptide did not provide effective cell attachment. The results demonstrated the selective synergy effect of PHSRN with RGD is an effective way to augment the robustness and functionality of self-assembled bioscaffolds.
Supramolecular Chemistry | 2015
Benjamin M. Long; Frederick M. Pfeffer
Vancomycin is currently used as last-line therapy against many Gram-positive bacterial pathogens. Herein, we report a series of peptidomimetic norbornene-based anion receptors that were designed as simple vancomycin mimics New hosts were evaluated for their affinity to both acetate and acetyl D-Ala by 1H NMR titration. Modest binding to both anions was observed in DMSO-d6 (Log Ka 1–2 for TBA Acetyl D-Alanine) in the anticipated 1:1 mode of binding.
Current Medicinal Chemistry | 2011
Jagat R. Kanwar; Benjamin M. Long; Rupinder K. Kanwar
Tetrahedron Letters | 2012
Jarrad M. Altimari; Joshua P. Delaney; Linden Servinis; Jennifer S. Squire; Megan T. Thornton; Simren K. Khosa; Benjamin M. Long; Mark D. Johnstone; Cassandra L. Fleming; Frederick M. Pfeffer; Shane M. Hickey; Matthew P. Wride; Trent D. Ashton; Bronwyn Fox; Nolene Byrne; Luke C. Henderson