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Porphyrin and Biomolecules: A Long-Lasting Friendship

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A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Physical Chemistry and Chemical Physics".

Deadline for manuscript submissions: closed (31 July 2023) | Viewed by 6360

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Special Issue Editors

Dr. Alessandro D'Urso

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Guest Editor

Dipartimento di Scienze Chimiche, Università degli Studi di Catania, Viale A. Doria 6, 95125 Catania, Italy
Interests: supramolecular chemistry related to porphyrin self-assembly and chirality; design of chiroptical probes for biomolecules conformations
Special Issues, Collections and Topics in MDPI journals

Prof. Dr. Roberto Purrello

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Guest Editor

Department of Chemical Sciences, Università degli Studi di Catania, Catania, Italy
Interests: supramolecular chemistry; chirality; circular dichroism; porphyrinoids; conformational probe; host-guest chemistry

Dr. Massimiliano Gaeta

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Guest Editor

Department of Chemical Science, University of Catania, 95125 Catania, Italy
Interests: supramolecular chemistry; spectroscopic investigations (UV/Vis, circular dichroism, fluorescence, RLS); porphyrin self-assembly and chiroptical properties; polypeptides; calixarenes; bio-inspired adhesives; hybrid nanomaterials; supramolecular materials

Special Issue Information

Dear Colleagues,

Porphyrins and related macrocycles are fascinating compounds widely employed in supramolecular chemistry as a paradigm to imitate self-assembly in natural systems, i.e., enzymatic reactions, assembling of multiprotein complexes, conformational changes, and many other processes driven by non-covalent interactions. Moreover, their synthetic versatility along with tunable physico-chemical properties has led to significant advances in the field of molecular recognition and conformational probes for numerous biomolecules (amino acids, peptides, DNAs, RNAs, etc.). Nevertheless, the understanding of the spontaneous porphyrin self-assembly through biomolecules offers tremendous potentialities to obtain a wide variety of complex systems, having specific functions and properties.

The aim of the Special Issue “Porphyrin and Biomolecules: A Long-Lasting Friendship” is to explore the more recent advances on the covalent and non-covalent interactions between porphyrins or related macrocycles and biomolecules.

This Special Issue welcomes interdisciplinary original research papers or comprehensive reviews focusing on the wide versatility of the supramolecular interactions between porphyrinoids and biomolecules for potential applications as sensors, conformational probes and in the field of nanomedicine and biotechnology. A paper highlighting the spectroscopic and chiral outcomes of building supramolecular systems or chiroptical probes will also be covered in this Issue.

Dr. Alessandro D'Urso
Prof. Dr. Roberto Purrello
Dr. Massimiliano Gaeta
Guest Editors

Manuscript Submission Information

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. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short 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 thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. There is an Article Processing Charge (APC) for publication in this open access journal. For details about the APC please see here. Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

conformational probes
chiroptical sensor
porphyrinoids
supramolecular chemistry
biomolecules conformations
self-organization
nanomedicine
biotechnology

Published Papers (4 papers)

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Research

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12 pages, 3150 KiB

Open AccessArticle

Interaction of Aggregated Cationic Porphyrins with Human Serum Albumin

by Mario Samperi, Serena Vittorio, Laura De Luca, Andrea Romeo and Luigi Monsù Scolaro

Int. J. Mol. Sci. 2023, 24(3), 2099; https://doi.org/10.3390/ijms24032099 - 20 Jan 2023

Cited by 2 | Viewed by 1213

Abstract

The interaction of an equilibrium mixture of monomeric and aggregated cationic trans-5,15-bis(N-methylpyridinium-4-yl)-10,15-bis-diphenylporphine (t-H₂Pagg) chloride salt with human serum albumin (HSA) has been investigated through UV/Vis absorption, fluorescence emission, circular dichroism and resonant light scattering techniques. The spectroscopic evidence reveals that both the monomeric t-H₂Pagg and its aggregates bind instantaneously to HSA, leading to the formation of a tight adduct in which the porphyrin is encapsulated within the protein scaffold (S₄₃₀) and to clusters of aggregated porphyrins in electrostatic interaction with the charged biomolecules. These latter species eventually interconvert into the final S₄₃₀ species following pseudo-first-order kinetics. Molecular docking simulations have been performed to get some insights into the nature of the final adduct. Analogously to hemin bound to HSA, the obtained model supports favorable interactions of the porphyrin in the same 1B subdomain of the protein. Hydrophobic and van der Waals energy terms are the main contributions to the calculated ΔG_bind value of −117.24 kcal/mol. Full article

(This article belongs to the Special Issue Porphyrin and Biomolecules: A Long-Lasting Friendship)

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12 pages, 2456 KiB

Open AccessArticle

Kinetic Investigations on the Chiral Induction by Amino Acids in Porphyrin J-Aggregates

by Roberto Zagami, Maria Angela Castriciano, Andrea Romeo and Luigi Monsù Scolaro

Int. J. Mol. Sci. 2023, 24(2), 1695; https://doi.org/10.3390/ijms24021695 - 15 Jan 2023

Cited by 3 | Viewed by 1453

Abstract

The self-assembling kinetics of the 5,10,15,20-tetrakis(4-sulfonato-phenyl)porphyrin (TPPS₄) into nano-tubular J-aggregates under strong acidic condition and in the presence of amino acids as templating chiral reagents have been investigated through UV/Vis spectroscopy. The ability of the chiral species to transfer its chiral information to the final J-aggregate has been measured through circular dichroism (CD) spectroscopy and compared to the spontaneous symmetry breaking process usually observed in these nano-aggregates. Under the experimental conditions here selected, including mixing protocol, we have observed a large difference in the observed aggregation rates for the various amino acids, those with a positively charged side group being the most effective. On the contrary, these species are less efficient in transferring their chirality, exhibiting a quite low or modest enhancement in the observed dissymmetry g-factors. On the other side, hydrophobic and some hydrophilic amino acids are revealed to be very active in inducing chirality with a discrete increase of intensity of the detected CD bands with respect to the spontaneous symmetry breaking. Full article

(This article belongs to the Special Issue Porphyrin and Biomolecules: A Long-Lasting Friendship)

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11 pages, 2590 KiB

Open AccessArticle

Enlarging the Scope of 5-Aminolevulinic Acid-Mediated Photodiagnosis towards Breast Cancers

by Martin Kiening and Norbert Lange

Int. J. Mol. Sci. 2022, 23(23), 14900; https://doi.org/10.3390/ijms232314900 - 28 Nov 2022

Cited by 2 | Viewed by 1492

Abstract

Today, most research on treating cancers targets one single cancer, often because of the very specific operation principle of the therapy. For instance, immunotherapies require the expression of a particular antigen, which might not be expressed in all cancers or in all patients. What about metastases? Combination therapies are promising but require treatment personalization and are an expensive approach that many health systems are not willing to pay for. Resection of cancerous tissues may be conducted beforehand. However, the precise location and removal of tumors are in most cases, hurdles that require margins to prevent recurrence. Herein, we further demonstrate the wide application of aminolevulinate-based photodynamic diagnosis and therapy toward breast cancers. By selecting four breast cancer cell lines that represent the main breast tumor subtypes, we investigated their ability to accumulate the fluorescent protoporphyrin IX upon treatment with the marketed 5-aminolevulinic acid hexyl ester (ALA-Hex) or our new and more stable derivative PSI-ALA-Hex. We found that all cell lines were able to accumulate PpIX under a few hours independent of their hormonal status with both treatments. Additionally, this accumulation was less dose-dependent with PSI-ALA-Hex and induced similar or higher fluorescence intensity than ALA-Hex in three out of four cell lines. The toxicity of the two molecules was not different up to 0.33 mM. However, PSI-ALA-Hex was more toxic at 1 mM, even though lower concentrations of PSI-ALA-Hex led to the same PpIX accumulation level. Additional illumination with blue light to induce cell death by generating reactive oxygen species was also considered. The treatments led to a dramatic death of the BT-474 cells under all conditions. In SK-BR-3 and MCF-7, ALA-Hex was also very efficient at all concentrations. However, increasing doses of PSI-ALA-Hex (0.33 and 1 mM) surprisingly led to a higher viability rate. In contrast, the triple-negative breast cancer cells MDA-MB-231 showed a higher death induction with higher concentrations of ALA-Hex or PSI-ALA-Hex. Derivatives of ALA seem promising as fluorescence-guided resection tools and may enable subsequent completion of cancer cell destruction by blue light irradiation. Full article

(This article belongs to the Special Issue Porphyrin and Biomolecules: A Long-Lasting Friendship)

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Review

Jump to: Research

18 pages, 5873 KiB

Open AccessReview

Stereospecific Self-Assembly Processes of Porphyrin-Proline Conjugates: From the Effect of Structural Features and Bulk Solvent Properties to the Application in Stereoselective Sensor Systems

by Manuela Stefanelli, Gabriele Magna, Corrado Di Natale, Roberto Paolesse and Donato Monti

Int. J. Mol. Sci. 2022, 23(24), 15587; https://doi.org/10.3390/ijms232415587 - 09 Dec 2022

Cited by 2 | Viewed by 1530

Abstract

Conjugating the porphyrin ring with an amino acid via amide linkage represents a straightforward way for conferring both amphiphilicity and chirality to the macrocycle. Proline residue is a good choice in this context since its conformational rigidity allows for porphyrin assembling where molecular chirality is efficiently transferred and amplified using properly honed aqueous environments. Herein, we describe the evolution of the studies carried out by our group to achieve chiral systems from some porphyrin-proline derivatives, both in solution and in the solid state. The discussion focuses on some fundamental aspects reflecting on the final molecular architectures obtained, which are related to the nature of the appended group (stereochemistry and charge), the presence of a metal ion coordinated to the porphyrin core and the bulk solvent properties. Indeed, fine-tuning the mentioned parameters enables the achievement of stereospecific structures with distinctive chiroptical and morphological features. Solid films based on these chiral systems were also obtained and their recognition abilities in gaseous and liquid phase are here described. Full article

(This article belongs to the Special Issue Porphyrin and Biomolecules: A Long-Lasting Friendship)

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