DendriPeps: Expanding Dendrimer Functionality by Hybridizing Poly(amidoamine) (PAMAM) Scaffolds with Peptide Segments

Smith, Ryan; Gorman, Christopher B.; Menegatti, Stefano

doi:10.1002/marc.201900325

Cited by 6 publications

(8 citation statements)

References 19 publications

(34 reference statements)

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“…tissue adhesives) are but a few industries that could benefit from electrocuring designs [5][6][7][8][9] . In addition, applications of Voltaglue could also be explored in the fields where PAMAM has been exploited such as-stimuli-responsive biomaterials, electrochemical sensors, conductive polymers, and controlled chemical releaseall applications that can benefit from voltage-activated adhesion [10][11][12][13][14][15][16][17] .…”

Section: Discussionmentioning

confidence: 99%

“…Voltaglue is an example of voltage-activated adhesives, in which aryl-diazirine (electrochemical cross-linker) is grafted onto the surface of a polyamidoamine (PAMAM) dendrimer. PAMAM dendrimers are commercially available in a number of sizes and a choice of surface functionalizations. − Aryl-diazirine is an ambient stable precursor that can be activated by heat (>100 °C), UVA, or voltage.…”

Section: Introductionmentioning

confidence: 99%

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Synergistic Voltaglue Adhesive Mechanisms with Alternating Electric Fields

et al. 2020

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Voltage-activated adhesion is a relatively new discovery that relies on direct currents for initiation of crosslinking. Previous investigations have found that direct currents are linearly correlated to the migration rates of electrocuring, but this is limited by high voltages exceeding 100 V with instances of incomplete curing of voltage-activated adhesives on semiconducting substrates. Practical applications of electrocuring would benefit from lower voltages to mitigate high voltage risks, especially with regard to potential medical applications. Alternative electrocuring strategies based on alternating current (AC), electrolyte ionic radius, and temperature are evaluated herein. Square waveform AC electric fields are hypothesized to initiate a two-sided curing progression of voltage-activated adhesive (PAMAM-g-diazirine aka Voltaglue), where initiation occurs at the cathode terminal. Structure-activity relationships of AC frequency at currents of 1-3 mA are evaluated against direct currents, migration rate, storage modulus, and lap shear adhesion on ex-vivo tissue mimics. Numerous improvements in electrocuring are observed with AC stimulation versus DC, including a 35 % decrease in maximum voltage, 180 % improvement in kinetic rates, and 100 % increase in lap shear adhesion at 2 mA. Li + ion electrolytes and curing at 4 o C shift curing kinetics by +104 % and -22 % with respect to the control ion (Na + ion at 24 o C), suggesting electrolyte migration is the rate limiting step. Li + ion electrolytes and curing at 50 o C improves storage modulus by 110% and 470 % respectively. Further evaluations of electrocured matrices with 19 F NMR, solid-state NMR and infrared spectroscopy provide insights into the probable crosslinking mechanisms.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synergistic Voltaglue Adhesive Mechanisms with Alternating Electric Fields

et al. 2020

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“…In their synthetic process, a range of design parameters such as size, architecture, elemental composition, degree of branching (DB), and functional groups, can be tunable in a statistical (hyperbranched polymer), semi‐controlled (dendrigraft polymer) or controlled (dendron or dendrimer) manner (Gu, Luo, She, Wu, & He, 2010; Smith, Gorman, & Menegatti, 2019; Tomalia, Christensen, & Boas, 2012). Moreover, various methodologies have been applied to characterize the dendritic polymers.…”

Section: Classification and Preparation Of Dendritic Polymersmentioning

confidence: 99%

Recent advances in development of dendritic polymer‐based nanomedicines for cancer diagnosis

Sun

Zhu

et al. 2020

WIREs Nanomed Nanobiotechnol

173

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Dendritic polymers have highly branched three‐dimensional architectures, the fourth type apart from linear, cross‐linked, and branched one. They possess not only a large number of terminal functional units and interior cavities, but also a low viscosity with weak or no entanglement. These features endow them with great potential in various biomedicine applications, including drug delivery, gene therapy, tissue engineering, immunoassay and bioimaging. Most review articles related to bio‐related applications of dendritic polymers focus on their drug or gene delivery, while very few of them are devoted to their function as cancer diagnosis agents, which are essential for cancer treatment. In this review, we will provide comprehensive insights into various dendritic polymer‐based cancer diagnosis agents. Their classification and preparation are presented for readers to have a precise understanding of dendritic polymers. On account of physical/chemical properties of dendritic polymers and biological properties of cancer, we will suggest a few design strategies for constructing dendritic polymer‐based diagnosis agents, such as active or passive targeting strategies, imaging reporters‐incorporating strategies, and/or internal stimuli‐responsive degradable/enhanced imaging strategies. Their recent applications in in vitro diagnosis of cancer cells or exosomes and in vivo diagnosis of primary and metastasis tumor sites with the aid of single/multiple imaging modalities will be discussed in great detail. This article is categorized under: Therapeutic Approaches and Drug Discovery > Nanomedicine for Oncologic Disease Diagnostic Tools > in vivo Nanodiagnostics and Imaging Diagnostic Tools > in vitro Nanoparticle‐Based Sensing

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“…92 Colcom, a French start-up, has commercialized a dendrimer-like structure first discovered by Collet et al and known as "lysine dendrigrafts," which display primary amine functionalities along its backbone and surface ( Figure 11). [77][78][79][80][81][82][83][84][85][86][87][88][89][90][91][92][94][95][96][97][98][99][100][101][102][103][104][105][106][127][128][129][130][131][132][133][134][135][136][137][138] Lysine dendrigrafts are primarily utilized for drug 89 and gene delivery. 107 but have also been investigated for their potential as a coagulant, 108 imaging agent, 95 and substrates for tissue engineering.…”

Section: Hydrophilic Ifdsmentioning

confidence: 99%

“…In recent work, our group reported the synthesis of modular IFDs that feature a hybrid PAMAM‐(di)peptide architecture, wherein dipeptide segments are integrated longitudinally across the PAMAM scaffold (Figure 10). 91 Labeled as “DendriPeps,” these IFDs were synthesized in good yield and purity using an orthogonal protection/deprotecting divergent strategy combined with traditional aza‐Michael and ester amidation reactions associated with PAMAM chemistry. The use of amino acids to introduce any desired functional group in a modular fashion is a distinct advantage of DendriPeps as IFDs, and opens avenues such as cross‐linking, drug and gene delivery, surface coating and functionalization, and catalysis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structure, and function of internally functionalized dendrimers

Smith

Gorman

Menegatti

2020

Journal of Polymer Science

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The past three decades have witnessed an exponential increase in the structural diversity and applications of dendrimers, spanning across drug delivery and diagnostics, protein, and enzyme mimicry, solubility enhancement, coatings, light harvesting, and catalysis. The dendrimer community has recently focused on internally functionalized dendrimers (IFDs) owing to their advanced design and functionality. The synthesis of IFDs relies on advanced orthogonal chemistries and/or (de)protection schemes, as well as careful purification to minimize polydispersity of composition and molecular weight. The studies published on IFDs, however, lay scattered across the chemical literature, and a comprehensive presentation of structural rationale, synthetic procedures, and technologically relevant applications is missing. To address this need, this review presents a comprehensive collection and discussion of all available studies on IFDs, detailing their methods of synthesis and their structure-function correlations. The wide variety of internal functionalities, including hydroxyl, amine, carboxylic acid, allyl, alkyne, and imidazole groups, enables myriad applications in biochemistry, chemical and biomedical engineering, and material science. Particular focus is given to IFDs that are amenable to modular synthetic strategies, which promote higher synthetic yield and scalability, and therefore possess stronger translational and commercial potential. As such, this review guides research groups pursuing the difficult task of IFD rational design and synthesis providing them a concise roadmap to their mission.

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DendriPeps: Expanding Dendrimer Functionality by Hybridizing Poly(amidoamine) (PAMAM) Scaffolds with Peptide Segments

Cited by 6 publications

References 19 publications

Synergistic Voltaglue Adhesive Mechanisms with Alternating Electric Fields

Synergistic Voltaglue Adhesive Mechanisms with Alternating Electric Fields

Recent advances in development of dendritic polymer‐based nanomedicines for cancer diagnosis

Synthesis, structure, and function of internally functionalized dendrimers

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