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Special Issue "Bioconjugations"

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Synthesis".

Deadline for manuscript submissions: closed (31 January 2015)

Special Issue Editor

Guest Editor
Prof. Dr. Scott Reed (Website)

Department of Chemistry, University of Colorado Denver, Campus Box 194, P.O. Box 173364, Denver, Colorado 80217, USA
Interests: nanoparticle-lipid conjugates as membrane mimics; nanomaterials for phototherapeutic applications; biosensors; aptamers

Special Issue Information

Dear Colleagues,

This special issue of Molecules is dedicated to Bioconjugations. Contributions that describe methods for performing selective bioconjugations, materials used for bioconjugations, and methods for characterizing bioconjugates are welcome. This field continues to grow as the variety of biomolecules used for bioconjugation increases. Furthermore, as new materials are explored as biological probes and modifiers, novel methods are needed to link these materials to biomolecules and to characterize the resulting conjugates. I encourage authors to submit research papers and comprehensive reviews for this Special Issue. I hope that the topics covered will reflect the intrinsically interdisciplinary nature of this field.

Dr. Scott Reed
Guest Editor

Submission

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. Papers will be published continuously (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are refereed through a peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed Open Access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs).

Keywords

  • fluorescent probes
  • photoactive probes
  • glycoconjugates
  • labels for multimodal imaging
  • bioorthogonal chemistry
  • theranostic agents
  • cross-linkers
  • modified oligonucleotides
  • click chemistry
  • peptide and nucleic acid analogs
  • polymer/dendrimer bioconjugates
  • nanoparticle bioconjugates
  • native chemical ligation

Published Papers (8 papers)

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Research

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Open AccessArticle Synthesis of S-Layer Conjugates and Evaluation of Their Modifiability as a Tool for the Functionalization and Patterning of Technical Surfaces
Molecules 2015, 20(6), 9847-9861; doi:10.3390/molecules20069847
Received: 26 January 2015 / Accepted: 20 May 2015 / Published: 27 May 2015
Cited by 1 | PDF Full-text (1349 KB) | HTML Full-text | XML Full-text
Abstract
Chemical functional groups of surface layer (S-layer) proteins were chemically modified in order to evaluate the potential of S-layer proteins for the introduction of functional molecules. S-layer proteins are structure proteins that self-assemble into regular arrays on surfaces. One general feature of [...] Read more.
Chemical functional groups of surface layer (S-layer) proteins were chemically modified in order to evaluate the potential of S-layer proteins for the introduction of functional molecules. S-layer proteins are structure proteins that self-assemble into regular arrays on surfaces. One general feature of S-layer proteins is their high amount of carboxylic and amino groups. These groups are potential targets for linking functional molecules, thus producing reactive surfaces. In this work, these groups were conjugated with the amino acid tryptophan. In another approach, SH-groups were chemically inserted in order to extend the spectrum of modifiable groups. The amount of modifiable carboxylic groups was further evaluated by potentiometric titration in order to evaluate the potential efficiency of S-layer proteins to work as matrix for bioconjugations. The results proved that S-layer proteins can work as effective matrices for the conjugation of different molecules. The advantage of using chemical modification methods over genetic methods lies in its versatile usage enabling the attachment of biomolecules, as well as fluorescent dyes and inorganic molecules. Together with their self-assembling properties, S-layer proteins are suitable as targets for bioconjugates, thus enabling a nanostructuring and bio-functionalization of surfaces, which can be used for different applications like biosensors, filter materials, or (bio)catalytic surfaces. Full article
(This article belongs to the Special Issue Bioconjugations)
Open AccessCommunication Site-Specific Bioconjugation of an Organometallic Electron Mediator to an Enzyme with Retained Photocatalytic Cofactor Regenerating Capacity and Enzymatic Activity
Molecules 2015, 20(4), 5975-5986; doi:10.3390/molecules20045975
Received: 8 February 2015 / Revised: 20 March 2015 / Accepted: 25 March 2015 / Published: 7 April 2015
Cited by 2 | PDF Full-text (1686 KB) | HTML Full-text | XML Full-text
Abstract
Photosynthesis consists of a series of reactions catalyzed by redox enzymes to synthesize carbohydrates using solar energy. In order to take the advantage of solar energy, many researchers have investigated artificial photosynthesis systems mimicking the natural photosynthetic enzymatic redox reactions. These redox [...] Read more.
Photosynthesis consists of a series of reactions catalyzed by redox enzymes to synthesize carbohydrates using solar energy. In order to take the advantage of solar energy, many researchers have investigated artificial photosynthesis systems mimicking the natural photosynthetic enzymatic redox reactions. These redox reactions usually require cofactors, which due to their high cost become a key issue when constructing an artificial photosynthesis system. Combining a photosensitizer and an Rh-based electron mediator (RhM) has been shown to photocatalytically regenerate cofactors. However, maintaining the high concentration of cofactors available for efficient enzymatic reactions requires a high concentration of the expensive RhM; making this process cost prohibitive. We hypothesized that conjugation of an electron mediator to a redox enzyme will reduce the amount of electron mediators necessary for efficient enzymatic reactions. This is due to photocatalytically regenerated NAD(P)H being readily available to a redox enzyme, when the local NAD(P)H concentration near the enzyme becomes higher. However, conventional random conjugation of RhM to a redox enzyme will likely lead to a substantial loss of cofactor regenerating capacity and enzymatic activity. In order to avoid this issue, we investigated whether bioconjugation of RhM to a permissive site of a redox enzyme retains cofactor regenerating capacity and enzymatic activity. As a model system, a RhM was conjugated to a redox enzyme, formate dehydrogenase obtained from Thiobacillus sp. KNK65MA (TsFDH). A RhM-containing azide group was site-specifically conjugated to p-azidophenylalanine introduced to a permissive site of TsFDH via a bioorthogonal strain-promoted azide-alkyne cycloaddition and an appropriate linker. The TsFDH-RhM conjugate exhibited retained cofactor regenerating capacity and enzymatic activity. Full article
(This article belongs to the Special Issue Bioconjugations)
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Open AccessArticle A Facile Route to Tailoring Peptide-Stabilized Gold Nanoparticles Using Glutathione as a Synthon
Molecules 2014, 19(5), 6754-6775; doi:10.3390/molecules19056754
Received: 3 March 2014 / Revised: 20 May 2014 / Accepted: 21 May 2014 / Published: 23 May 2014
Cited by 3 | PDF Full-text (1095 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The preparation of gold nanoparticles (AuNPs) of high purity and stability remains a major challenge for biological applications. This paper reports a simple synthetic strategy to prepare water-soluble peptide-stabilized AuNPs. Reduced glutathione, a natural tripeptide, was used as a synthon for the [...] Read more.
The preparation of gold nanoparticles (AuNPs) of high purity and stability remains a major challenge for biological applications. This paper reports a simple synthetic strategy to prepare water-soluble peptide-stabilized AuNPs. Reduced glutathione, a natural tripeptide, was used as a synthon for the growth of two peptide chains directly on the AuNP surface. Both nonpolar (tryptophan and methionine) and polar basic (histidine and dansylated arginine) amino acids were conjugated to the GSH-capped AuNPs. Ultracentrifugation concentrators with polyethersulfone (PES) membranes were used to purify precursor materials in each stage of the multi-step synthesis to minimize side reactions. Thin layer chromatography, transmission electron microscopy, UV-Visible, 1H-NMR, and fluorescence spectroscopies demonstrated that ultracentrifugation produces high purity AuNPs, with narrow polydispersity, and minimal aggregation. More importantly, it allows for more control over the composition of the final ligand structure. Studies under conditions of varying pH and ionic strength revealed that peptide length, charge, and hydrophobicity influence the stability as well as solubility of the peptide-capped AuNPs. The synthetic and purification strategies used provide a facile route for developing a library of tailored biocompatible peptide-stabilized AuNPs for biomedical applications. Full article
(This article belongs to the Special Issue Bioconjugations)
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Open AccessCommunication Development of Multi-Functional Chelators Based on Sarcophagine Cages
Molecules 2014, 19(4), 4246-4255; doi:10.3390/molecules19044246
Received: 17 February 2014 / Revised: 30 March 2014 / Accepted: 1 April 2014 / Published: 3 April 2014
Cited by 7 | PDF Full-text (306 KB) | HTML Full-text | XML Full-text
Abstract A new class of multifunctionalized sarcophagine derivatives was synthesized for 64Cu chelation. The platform developed in this study could have broad applications in 64Cu-radiopharmaceuticals. Full article
(This article belongs to the Special Issue Bioconjugations)
Open AccessArticle Synthesis of PNA Oligoether Conjugates
Molecules 2014, 19(3), 3135-3148; doi:10.3390/molecules19033135
Received: 21 January 2014 / Revised: 1 March 2014 / Accepted: 4 March 2014 / Published: 13 March 2014
Cited by 2 | PDF Full-text (346 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Several different approaches have been explored for conjugation of oligoethers to PNA with internally or N-terminal placed diaminopropionic acid residues. Single and double conjugation of 2-(2-(2-aminoethoxy)ethoxy)ethanol was obtained using carbonyldimidazole. Using a post PNA-assembly coupling procedure the building block 2-(2-(2-(benzoyloxy)ethoxy)ethoxy)acetic acid multiple [...] Read more.
Several different approaches have been explored for conjugation of oligoethers to PNA with internally or N-terminal placed diaminopropionic acid residues. Single and double conjugation of 2-(2-(2-aminoethoxy)ethoxy)ethanol was obtained using carbonyldimidazole. Using a post PNA-assembly coupling procedure the building block 2-(2-(2-(benzoyloxy)ethoxy)ethoxy)acetic acid multiple attachment of 2-(2-(2-hydroxyethoxy)ethoxy)acetyl groups to both N-terminal and β-amino groups of inserted diaminopropionic acids residues was achieved. Use of a new oligoether functionalized amino acid allows inclusion of oligoether conjugates during on-line machine assisted synthesis which also allowed combination of methods for attachment of different oligoethers and co-conjugation of neocuproine as well as conjugation of an aminosugar. Full article
(This article belongs to the Special Issue Bioconjugations)

Review

Jump to: Research

Open AccessReview Exploiting Protected Maleimides to Modify Oligonucleotides, Peptides and Peptide Nucleic Acids
Molecules 2015, 20(4), 6389-6408; doi:10.3390/molecules20046389
Received: 12 February 2015 / Revised: 27 March 2015 / Accepted: 31 March 2015 / Published: 10 April 2015
Cited by 4 | PDF Full-text (382 KB) | HTML Full-text | XML Full-text
Abstract
This manuscript reviews the possibilities offered by 2,5-dimethylfuran-protected maleimides. Suitably derivatized building blocks incorporating the exo Diels-Alder cycloadduct can be introduced at any position of oligonucleotides, peptide nucleic acids, peptides and peptoids, making use of standard solid-phase procedures. Maleimide deprotection takes place [...] Read more.
This manuscript reviews the possibilities offered by 2,5-dimethylfuran-protected maleimides. Suitably derivatized building blocks incorporating the exo Diels-Alder cycloadduct can be introduced at any position of oligonucleotides, peptide nucleic acids, peptides and peptoids, making use of standard solid-phase procedures. Maleimide deprotection takes place upon heating, which can be followed by either Michael-type or Diels-Alder click conjugation reactions. However, the one-pot procedure in which maleimide deprotection and conjugation are simultaneously carried out provides the target conjugate more quickly and, more importantly, in better yield. This procedure is compatible with conjugates involving oligonucleotides, peptides and peptide nucleic acids. A variety of cyclic peptides and oligonucleotides can be obtained from peptide and oligonucleotide precursors incorporating protected maleimides and thiols. Full article
(This article belongs to the Special Issue Bioconjugations)
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Open AccessReview Development of Bioorthogonal Reactions and Their Applications in Bioconjugation
Molecules 2015, 20(2), 3190-3205; doi:10.3390/molecules20023190
Received: 5 January 2015 / Revised: 19 January 2015 / Accepted: 2 February 2015 / Published: 16 February 2015
Cited by 10 | PDF Full-text (1053 KB) | HTML Full-text | XML Full-text
Abstract
Biomolecule labeling using chemical probes with specific biological activities has played important roles for the elucidation of complicated biological processes. Selective bioconjugation strategies are highly-demanded in the construction of various small-molecule probes to explore complex biological systems. Bioorthogonal reactions that undergo fast [...] Read more.
Biomolecule labeling using chemical probes with specific biological activities has played important roles for the elucidation of complicated biological processes. Selective bioconjugation strategies are highly-demanded in the construction of various small-molecule probes to explore complex biological systems. Bioorthogonal reactions that undergo fast and selective ligation under bio-compatible conditions have found diverse applications in the development of new bioconjugation strategies. The development of new bioorthogonal reactions in the past decade has been summarized with comments on their potentials as bioconjugation method in the construction of various biological probes for investigating their target biomolecules. For the applications of bioorthogonal reactions in the site-selective biomolecule conjugation, examples have been presented on the bioconjugation of protein, glycan, nucleic acids and lipids. Full article
(This article belongs to the Special Issue Bioconjugations)
Open AccessReview Hyaluronic Acid Conjugates as Vectors for the Active Targeting of Drugs, Genes and Nanocomposites in Cancer Treatment
Molecules 2014, 19(3), 3193-3230; doi:10.3390/molecules19033193
Received: 20 January 2014 / Revised: 7 March 2014 / Accepted: 11 March 2014 / Published: 17 March 2014
Cited by 21 | PDF Full-text (583 KB) | HTML Full-text | XML Full-text
Abstract
Hyaluronic acid (HA) is a naturally-occurring glycosaminoglycan and a major component of the extracellular matrix. Low levels of the hyaluronic acid receptor CD44 are found on the surface of epithelial, hematopoietic, and neuronal cells; it is overexpressed in many cancer cells, and [...] Read more.
Hyaluronic acid (HA) is a naturally-occurring glycosaminoglycan and a major component of the extracellular matrix. Low levels of the hyaluronic acid receptor CD44 are found on the surface of epithelial, hematopoietic, and neuronal cells; it is overexpressed in many cancer cells, and in particular in tumor-initiating cells. HA has recently attracted considerable interest in the field of developing drug delivery systems, having been used, as such or encapsulated in different types of nanoassembly, as ligand to prepare nano-platforms for actively targeting drugs, genes, and diagnostic agents. This review describes recent progress made with the several chemical strategies adopted to synthesize conjugates and prepare novel delivery systems with improved behaviors. Full article
(This article belongs to the Special Issue Bioconjugations)

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