Effects of amide side chains on nanoassembly formation and gelation of Fmoc–valine conjugates

Romanelli, Steven M.; Hartnett, Joseph W.; Banerjee, Ipsita A.

doi:10.1016/j.powtec.2014.10.028

Cited by 8 publications

(4 citation statements)

References 62 publications

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“…In previous work, we reported the preparation of Fmoc-valyl-bis-boc protected spermidine based nanoassemblies [32]. The chemical structure of the formed product is shown in Figure 1.…”

Section: A N U S C R I P Tmentioning

confidence: 99%

Supramolecular Fmoc-valyl based nanoassemblies for delivery of mitoxantrone into HeLa cells

Romanelli

Fath

Davidov

et al. 2015

Journal of Drug Delivery Science and Technology

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“…In previous work, we reported the preparation of Fmoc-valyl-bis-boc protected spermidine based nanoassemblies [32]. The chemical structure of the formed product is shown in Figure 1.…”

Section: A N U S C R I P Tmentioning

confidence: 99%

Supramolecular Fmoc-valyl based nanoassemblies for delivery of mitoxantrone into HeLa cells

Romanelli

Fath

Davidov

et al. 2015

Journal of Drug Delivery Science and Technology

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“…For example, KLD-12 peptides formed interweaving nanofibers due to the presence of alternating lysine and aspartic acid residues [52]. Short peptide sequences with the protecting group FMOC were found to self-assemble due to π-π stacking interactions between aromatic FMOC functionalized amino acids [53,54].…”

Section: Self-assembly Of Cga-amp and Preparation Of Scaffoldsmentioning

confidence: 99%

Development of Multilayered Chlorogenate-Peptide Based Biocomposite Scaffolds for Potential Applications in Ligament Tissue Engineering - An <i>In Vitro</i> Study

Pajovich

Brown

Smith

et al. 2017

JBBBE

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In this work, for the first time, chlorogenic acid, a natural phytochemical, was conjugated to a lactoferrin derived antimicrobial peptide sequence RRWQWRMKKLG to develop a self-assembled template. To mimic the components of extracellular matrix, we then incorporated Type I Collagen, followed by a sequence of aggrecan peptide (ATEGQVRVNSIYQDKVSL) onto the self-assembled templates for potential applications in ligament tissue regeneration. Mechanical properties and surface roughness were studied and the scaffolds displayed a Young’s Modulus of 169 MP and an average roughness of 72 nm respectively. Thermal phase changes were studied by DSC analysis. Results showed short endothermic peaks due to water loss and an exothermic peak due to crystallization of the scaffold caused by rearrangement of the components. Biodegradability studies indicated a percent weight loss of 27.5 % over a period of 37 days. Furthermore, the scaffolds were found to adhere to fibroblasts, the main cellular component of ligament tissue. The scaffolds promoted cell proliferation and displayed actin stress fibers indicative of cell motility and attachment. Collagen and proteoglycan synthesis were also promoted, demonstrating increased expression and deposition of collagen and proteoglycans. Additionally, the scaffolds exhibited antimicrobial activity against Staphylococcus epidermis bacteria, which is beneficial for minimizing biofilm formation if potentially used as implants. Thus, we have developed a novel biocomposite that may open new avenues to enhance ligament tissue regeneration.

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“…Fmoc-Valyl-Cetylamide (FVC) was prepared according to previously established methods [38]. To prepare the fibrous assemblies, the product (1 mM) was allowed to self-assemble at pH 7 for a period of 3-4 weeks.…”

Section: Preparation Of Fmoc-valyl-cetylamide (Fvc) Fibrous Assembliesmentioning

confidence: 99%

“…In previous work, we reported the formation of Fmoc derived peptides covalently linked to cetyl amine (FVC) and demonstrated their ability to form a nanofibrous matrix and support growth and proliferation of mouse pre-osteoblasts [38,39]. Herein, we have developed two new hybrid peptide-glycosaminoglycan based constructs using FVC as a template and examined their ability to promote proliferation and attachment of chondrocytes as well as promote chondrogenesis (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Comparison of Engineered Peptide-Glycosaminoglycan Microfibrous Hybrid Scaffolds for Potential Applications in Cartilage Tissue Regeneration

Romanelli

Knoll

Santora

et al. 2015

Fibers

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Advances in tissue engineering have enabled the ability to design and fabricate biomaterials at the nanoscale that can actively mimic the natural cellular environment of host tissue. Of all tissues, cartilage remains difficult to regenerate due to its avascular nature. Herein we have developed two new hybrid polypeptide-glycosaminoglycan microfibrous scaffold constructs and compared their abilities to stimulate cell adhesion, proliferation, sulfated proteoglycan synthesis and soluble collagen synthesis when seeded with chondrocytes. Both constructs were designed utilizing self-assembled Fmoc-protected valyl cetylamide nanofibrous templates. The peptide components of the constructs were varied. For Construct I a short segment of dentin sialophosphoprotein followed by Type I collagen were attached to the templates using the layer-by-layer approach. For Construct II, a short peptide segment derived from the integrin subunit of Type II collagen binding protein expressed by chondrocytes was attached to the templates followed by Type II collagen. To both constructs, we then attached the natural polymer N-acetyl glucosamine, chitosan. Subsequently, the glycosaminoglycan chondroitin sulfate was then attached as the final layer. The scaffolds were characterized by Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), atomic force microscopy and scanning electron microscopy. In vitro culture studies were carried out in the presence of chondrocyte cells for OPEN ACCESSFibers 2015, 3 266 both scaffolds and growth morphology was determined through optical microscopy and scanning electron microscopy taken at different magnifications at various days of culture. Cell proliferation studies indicated that while both constructs were biocompatible and supported the growth and adhesion of chondrocytes, Construct II stimulated cell adhesion at higher rates and resulted in the formation of three dimensional cell-scaffold matrices within 24 h. Proteoglycan synthesis, a hallmark of chondrocyte cell differentiation, was also higher for Construct II compared to Construct I. Soluble collagen synthesis was also found to be higher for Construct II. The results of the above studies suggest that scaffolds designed from Construct II be superior for potential applications in cartilage tissue regeneration. The peptide components of the constructs play an important role not only in the mechanical properties in developing the scaffolds but also control cell adhesion, collagen synthesis and proteoglycan synthesis capabilities.

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Effects of amide side chains on nanoassembly formation and gelation of Fmoc–valine conjugates

Cited by 8 publications

References 62 publications

Supramolecular Fmoc-valyl based nanoassemblies for delivery of mitoxantrone into HeLa cells

Supramolecular Fmoc-valyl based nanoassemblies for delivery of mitoxantrone into HeLa cells

Development of Multilayered Chlorogenate-Peptide Based Biocomposite Scaffolds for Potential Applications in Ligament Tissue Engineering - An <i>In Vitro</i> Study

Comparison of Engineered Peptide-Glycosaminoglycan Microfibrous Hybrid Scaffolds for Potential Applications in Cartilage Tissue Regeneration

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