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Advances in the Chemistry of Porphyrins and Related Macrocycles

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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 October 2020) | Viewed by 48871

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Special Issue Editors

Dr. Maria Angela Castriciano

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Istituto Per Lo Studio Dei Materiali Nanostrutturati, c/o Dipartimento di Scienze Chimiche, Biologiche, Farmaceutich ed Ambientali, University of Messina, V.le F. Stagno D’Alcontres, 31, 98166 Messina, Italy
Interests: nanomaterials; supramolecular chemistry; self-assembly; porphyrins; expression and transmission of chirality at nano and mesoscopic scale; spectroscopy
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Prof. Dr. Luigi Monsù Scolaro

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Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, University of Messina, Messina, Italy
Interests: supramolecular chemistry; porphyrins; nanostructured materials; self-assembling; aggregation kinetics; chirality; symmetry-breaking; homochirality
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Prof. Dr. Andrea Romeo

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Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, University of Messina, Messina, Italy
Interests: nanoaggregates; porphyrins; polymers; expression and transmission of chirality at nano and mesoscopic scale; disassembling; kinetics; spectroscopy
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Porphyrins and related macrocycles possess widely tunable physico-chemical properties controlled by peripheral substitution or metal coordination in the inner core. Recent progress in their synthesis and the fundamental understanding of their properties has led to significant advances in nanomaterial-based porphyrins for manifold applications.

To this end, it is essential to design and synthesize novel systems with optimized structure and properties or to achieve a complex system through non-conventional approaches. Supramolecular self-assembly through non-covalent interactions, such as hydrogen bonding, stacking, and electrostatic interactions, offers an easy way to access well-defined arrays.

In this respect, nanostructured materials with peculiar optical properties are attracting increasing interest since their optical response, in terms of electronic absorption, emission fluorescence, optical activity, photocurrent generation and so on, can be largely influenced by slight changes in the micro-environments and in the presence of specific analytes.

This Special Issue welcomes the submission of original research papers or comprehensive reviews that demonstrate or summarize significant advances in the porphyrin chemistry in terms of synthesis and application of novel functional nanostructures with potential applications in sensors, optoelectronic devices, and/or nanomedicine.

Dr. Maria Angela Castriciano
Prof. Dr. Luigi Monsù Scolaro
Prof. Dr. Andrea Romeo
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.

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Keywords

• Synthesis
• Properties
• Aggregation
• Supramolecular chemistry
• Sensors
• Chirality
• Artificial light harvesting
• Biomimetic systems
• Optical devices
• Functional nanostructures

Published Papers (13 papers)

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Editorial

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4 pages, 208 KiB

Open AccessEditorial

Advances in the Chemistry of Porphyrins and Related Macrocycles

by Andrea Romeo, Maria Angela Castriciano and Luigi Monsù Scolaro

Int. J. Mol. Sci. 2021, 22(14), 7487; https://doi.org/10.3390/ijms22147487 - 13 Jul 2021

Cited by 1 | Viewed by 1637

Abstract

Porphyrins and their analogues feature remarkably in nature, being prosthetic groups in a wide variety of primary metabolites playing a pivotal role in many biological processes [...] Full article

(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles)

Research

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20 pages, 2531 KiB

Open AccessArticle

Oxidation of Hydrogen Sulfide by Quinones: How Polyphenols Initiate Their Cytoprotective Effects

by Kenneth R. Olson, Yan Gao and Karl D. Straub

Int. J. Mol. Sci. 2021, 22(2), 961; https://doi.org/10.3390/ijms22020961 - 19 Jan 2021

Cited by 16 | Viewed by 2572

Abstract

We have shown that autoxidized polyphenolic nutraceuticals oxidize H₂S to polysulfides and thiosulfate and this may convey their cytoprotective effects. Polyphenol reactivity is largely attributed to the B ring, which is usually a form of hydroxyquinone (HQ). Here, we examine the effects of HQs on sulfur metabolism using H₂S- and polysulfide-specific fluorophores (AzMC and SSP4, respectively) and thiosulfate sensitive silver nanoparticles (AgNP). In buffer, 1,4-dihydroxybenzene (1,4-DB), 1,4-benzoquinone (1,4-BQ), pyrogallol (PG) and gallic acid (GA) oxidized H₂S to polysulfides and thiosulfate, whereas 1,2-DB, 1,3-DB, 1,2-dihydroxy,3,4-benzoquinone and shikimic acid did not. In addition, 1,4-DB, 1,4-BQ, PG and GA also increased polysulfide production in HEK293 cells. In buffer, H₂S oxidation by 1,4-DB was oxygen-dependent, partially inhibited by tempol and trolox, and absorbance spectra were consistent with redox cycling between HQ autoxidation and H₂S-mediated reduction. Neither 1,2-DB, 1,3-DB, 1,4-DB nor 1,4-BQ reduced polysulfides to H₂S in either 21% or 0% oxygen. Epinephrine and norepinephrine also oxidized H₂S to polysulfides and thiosulfate; dopamine and tyrosine were ineffective. Polyphenones were also examined, but only 2,5-dihydroxy- and 2,3,4-trihydroxybenzophenones oxidized H₂S. These results show that H₂S is readily oxidized by specific hydroxyquinones and quinones, most likely through the formation of a semiquinone radical intermediate derived from either reaction of oxygen with the reduced quinones, or from direct reaction between H₂S and quinones. We propose that polysulfide production by these reactions contributes to the health-promoting benefits of polyphenolic nutraceuticals. Full article

(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles)

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12 pages, 2479 KiB

Open AccessArticle

Conformation of the Intermediates in the Reaction Catalyzed by Protoporphyrinogen Oxidase: An In Silico Analysis

by Abigail L. Barker, Hamlin Barnes and Franck E. Dayan

Int. J. Mol. Sci. 2020, 21(24), 9495; https://doi.org/10.3390/ijms21249495 - 14 Dec 2020

Cited by 4 | Viewed by 1905

Abstract

Protoporphyrinogen oxidase (PPO) is a critical enzyme across life as the last common step in the synthesis of many metalloporphyrins. The reaction mechanism of PPO was assessed in silico and the unstructured loop near the binding pocket was investigated. The substrate, intermediates, and product were docked in the catalytic domain of PPO using a modified Autodock method, introducing flexibility in the macrocycles. Sixteen PPO protein sequences across phyla were aligned and analyzed with Phyre2 and ProteinPredict to study the unstructured loop from residue 204–210 in the H. sapiens structure. Docking of the substrate, intermediates, and product all resulted in negative binding energies, though the substrate had a lower energy than the others by 40%. The α-H of C10 was found to be 1.4 angstroms closer to FAD than the β-H, explaining previous reports of the reaction occurring on the meso face of the substrate. A lack of homology in sequence or length in the unstructured loop indicates a lack of function for the protein reaction. This docking study supports a reaction mechanism proposed previously whereby all hydride abstractions occur on the C10 of the tetrapyrrole followed by tautomeric rearrangement to prepare the intermediate for the next reaction. Full article

(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles)

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33 pages, 14635 KiB

Open AccessArticle

Photodynamic Inactivation of Bacteria with Porphyrin Derivatives: Effect of Charge, Lipophilicity, ROS Generation, and Cellular Uptake on Their Biological Activity In Vitro

by Adam Sułek, Barbara Pucelik, Marcin Kobielusz, Agata Barzowska and Janusz M. Dąbrowski

Int. J. Mol. Sci. 2020, 21(22), 8716; https://doi.org/10.3390/ijms21228716 - 18 Nov 2020

Cited by 48 | Viewed by 4619

Abstract

Resistance of microorganisms to antibiotics has led to research on various therapeutic strategies with different mechanisms of action, including photodynamic inactivation (PDI). In this work, we evaluated a cationic, neutral, and anionic meso-tetraphenylporphyrin derivative’s ability to inactivate the Gram-negative and Gram-positive bacteria in a planktonic suspension under blue light irradiation. The spectroscopic, physicochemical, redox properties, as well as reactive oxygen species (ROS) generation capacity by a set of photosensitizers varying in lipophilicity were investigated. The theoretical calculations were performed to explain the distribution of the molecular charges in the evaluated compounds. Moreover, logP partition coefficients, cellular uptake, and phototoxicity of the photosensitizers towards bacteria were determined. The role of a specific microbial efflux pump inhibitor, verapamil hydrochloride, in PDI was also studied. The results showed that E. coli exhibited higher resistance to PDI than S. aureus (3–5 logs) with low light doses (1–10 J/cm²). In turn, the prolongation of irradiation (up to 100 J/cm²) remarkably improved the inactivation of pathogens (up to 7 logs) and revealed the importance of photosensitizer photostability. The PDI potentiation occurs after the addition of KI (more than 3 logs extra killing). Verapamil increased the uptake of photosensitizers (especially in E. coli) due to efflux pump inhibition. This effect suggests that PDI is mediated by ROS, the electrostatic charge interaction, and the efflux of photosensitizers (PSs) regulated by multidrug-resistance (MDR) systems. Thus, MDR inhibition combined with PDI gives opportunities to treat more resistant bacteria. Full article

(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles)

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19 pages, 5595 KiB

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Hybrid Materials Based on Silica Matrices Impregnated with Pt-Porphyrin or PtNPs Destined for CO₂ Gas Detection or for Wastewaters Color Removal

by Diana Anghel, Anca Lascu, Camelia Epuran, Ion Fratilescu, Catalin Ianasi, Mihaela Birdeanu and Eugenia Fagadar-Cosma

Int. J. Mol. Sci. 2020, 21(12), 4262; https://doi.org/10.3390/ijms21124262 - 15 Jun 2020

Cited by 20 | Viewed by 2726

Abstract

Multifunctional hybrid materials with applications in gas sensing or dye removal from wastewaters were obtained by incorporation into silica matrices of either Pt(II)-5,10,15,20-tetra-(4-allyloxy-phenyl)-porphyrin (PtTAOPP) or platinum nanoparticles (PtNPs) alone or accompanied by 5,10,15,20-tetra-(4-allyloxy-phenyl)-porphyrin (TAOPP). The tetraethylorthosilicate (TEOS)-based silica matrices were obtained by using the sol-gel method performed in two step acid-base catalysis. Optical, structural and morphological properties of the hybrid materials were determined and compared by UV-vis, fluorescence and FT-IR spectroscopy techniques, by atomic force microscopy (AFM) and high resolution transmission electron microscopy (HRTEM) and by Brunauer–Emmett–Teller (BET) analysis. PtTAOPP-silica hybrid was the most efficient material both for CO₂ adsorption (0.025 mol/g) and for methylene blue adsorption (7.26 mg/g) from wastewaters. These results were expected due to both the ink-bottle mesopores having large necks that exist in this hybrid material and to the presence of the porphyrin moiety that facilitates chemical interactions with either CO₂ gas or the dye molecule. Kinetic studies concerning the mechanism of dye adsorption demonstrated a second order kinetic model, thus it might be attributed to both physical and chemical processes. Full article

(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles)

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16 pages, 2953 KiB

Open AccessArticle

Controlling J-Aggregates Formation and Chirality Induction through Demetallation of a Zinc(II) Water Soluble Porphyrin

by Ilaria Giuseppina Occhiuto, Maria Angela Castriciano, Mariachiara Trapani, Roberto Zagami, Andrea Romeo, Robert F. Pasternack and Luigi Monsù Scolaro

Int. J. Mol. Sci. 2020, 21(11), 4001; https://doi.org/10.3390/ijms21114001 - 03 Jun 2020

Cited by 18 | Viewed by 2699

Abstract

Under acidic conditions and at high ionic strength, the zinc cation is removed from its metal complex with 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin (TPPS₄) thus leading to the diacid free porphyrin, that subsequently self-organize into J-aggregates. The kinetics of the demetallation step and the successive supramolecular assembly formation have been investigated as a function of pH and ionic strength (controlled by adding ZnSO₄). The demetallation kinetics obey to a rate law that is first order in [ZnTPPS₄] and second order in [H⁺], according to literature, with k₂ = 5.5 ± 0.4 M⁻² s⁻¹ at 298 K (IS = 0.6 M, ZnSO₄). The aggregation process has been modeled according to an autocatalytic growth, where after the formation of a starting seed containing m porphyrin units, the rate evolves as a power of time. A complete analysis of the extinction time traces at various wavelengths allows extraction of the relevant kinetic parameters, showing that a trimer or tetramer should be involved in the rate-determining step of the aggregation. The extinction spectra of the J-aggregates evidence quite broad bands, suggesting an electronic coupling mechanism different to the usual Frenkel exciton coupling. Resonance light scattering intensity in the aggregated samples increases with increasing both [H⁺] and [ZnSO₄]. Symmetry breaking occurs in these samples and the J-aggregates show circular dichroism spectra with unusual bands. The asymmetry g-factor decreases in its absolute value with increasing the catalytic rate k_c, nulling and eventually switching the Cotton effect from negative to positive. Some inferences on the role exerted by zinc cations on the kinetics and structural features of these nanostructures have been discussed. Full article

(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles)

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13 pages, 2788 KiB

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Photodegradation of Antibiotics by Noncovalent Porphyrin-Functionalized TiO₂ in Water for the Bacterial Antibiotic Resistance Risk Management

by Massimiliano Gaeta, Giuseppe Sanfilippo, Aurore Fraix, Giuseppe Sortino, Matteo Barcellona, Gea Oliveri Conti, Maria Elena Fragalà, Margherita Ferrante, Roberto Purrello and Alessandro D’Urso

Int. J. Mol. Sci. 2020, 21(11), 3775; https://doi.org/10.3390/ijms21113775 - 27 May 2020

Cited by 26 | Viewed by 3509

Abstract

Antibiotics represent essential drugs to contrast the insurgence of bacterial infections in humans and animals. Their extensive use in livestock farming, including aquaculture, has improved production performances and food safety. However, their overuse can implicate a risk of water pollution and related antimicrobial resistance. Consequently, innovative strategies for successfully removing antibiotic contaminants have to be advanced to protect human health. Among them, photodegradation TiO₂-driven under solar irradiation appears not only as a promising method, but also a sustainable pathway. Hence, we evaluated several composite TiO₂ powders with H₂TCPP, CuTCPP, ZnTCPP, and SnT4 porphyrin for this scope in order to explore the effect of porphyrins sensitization on titanium dioxide. The synthesis was realized through a fully non-covalent functionalization in water at room conditions. The efficacy of obtained composite materials was also tested in photodegrading oxolinic acid and oxytetracycline in aqueous solution at micromolar concentrations. Under simulated solar irradiation, TiO₂ functionalized with CuTCPP has shown encouraging results in the removal of oxytetracycline from water, by opening the way as new approaches to struggle against antibiotic’s pollution and, finally, to represent a new valuable tool of public health. Full article

(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles)

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24 pages, 3718 KiB

Open AccessArticle

Novel Phenothiazine-Bridged Porphyrin-(Hetero)aryl dyads: Synthesis, Optical Properties, In Vitro Cytotoxicity and Staining of Human Ovarian Tumor Cell Lines

by Eva Molnar, Emese Gal, Luiza Gaina, Castelia Cristea, Eva Fischer-Fodor, Maria Perde-Schrepler, Patriciu Achimas-Cadariu, Monica Focsan and Luminita Silaghi-Dumitrescu

Int. J. Mol. Sci. 2020, 21(9), 3178; https://doi.org/10.3390/ijms21093178 - 30 Apr 2020

Cited by 10 | Viewed by 3138

Abstract

We report here the synthetic procedure applied for the preparation of new AB₃-type and trans-A₂B₂ type meso-halogenophenothiazinyl-phenyl-porphyrin derivatives, their metal core complexation and their peripheral modification using Suzuki–Miyaura cross coupling reactions with various (hetero)aryl (phenothiazinyl, 7-formyl-phenothiazinyl, (9-carbazolyl)-phenyl and 4-formyl-phenyl, phenyl) boronic acid derivatives. The meso-phenothiazinyl-phenyl-porphyrin (MPP) dyes family was thus extended by a series of novel phenothiazine-bridged porphyrin-(hetero)aryl dyads characterized by UV–Vis absorption/emission properties typical to the porphyrin chromophore, slightly modulated by increasing the size of peripheral substituents. Three phenothiazine-bridged porphyrin-heteroaryl dyads with fluorescence emission above 655 nm were selected as fluorophores in red spectral region for applications in cellular staining of human ovarian tumors. In vitro experiments of cell metabolic activity displayed a moderate toxicity on human ovarian tumor cell lines (OVCAR-3, cisplatin-sensitive A2780 and cisplatin-resistant A2780cis respectively). Visualization of the stained living cells was performed both by fluorescence microscopy imaging and by fluorescence lifetime imaging under two photon excitation (TPE-FLIM), confirming their cellular uptake and the capability of staining the cell nucleus. Full article

(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles)

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11 pages, 1915 KiB

Open AccessArticle

Relaxation Dynamics of Chlorophyll b in the Sub-ps Ultrafast Timescale Measured by 2D Electronic Spectroscopy

by Elisa Fresch and Elisabetta Collini

Int. J. Mol. Sci. 2020, 21(8), 2836; https://doi.org/10.3390/ijms21082836 - 18 Apr 2020

Cited by 4 | Viewed by 2572

Abstract

A thorough characterization of the early time sub-100 fs relaxation dynamics of biologically relevant chromophores is of crucial importance for a complete understanding of the mechanisms regulating the ultrafast dynamics of the relaxation processes in more complex multichromophoric light-harvesting systems. While chlorophyll a has already been the object of several investigations, little has been reported on chlorophyll b, despite its pivotal role in many functionalities of photosynthetic proteins. Here the relaxation dynamics of chlorophyll b in the ultrafast regime have been characterized using 2D electronic spectroscopy. The comparison of experimental measurements performed at room temperature and 77 K allows the mechanisms and the dynamics of the sub-100 fs relaxation dynamics to be characterized, including spectral diffusion and fast internal conversion assisted by a specific set of vibrational modes. Full article

(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles)

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18 pages, 5580 KiB

Open AccessArticle

Enhanced Cellular Uptake and Photodynamic Effect with Amphiphilic Fluorinated Porphyrins: The Role of Sulfoester Groups and the Nature of Reactive Oxygen Species

by Barbara Pucelik, Adam Sułek, Agnieszka Drozd, Grażyna Stochel, Mariette M. Pereira, Sara M. A. Pinto, Luis G. Arnaut and Janusz M. Dąbrowski

Int. J. Mol. Sci. 2020, 21(8), 2786; https://doi.org/10.3390/ijms21082786 - 16 Apr 2020

Cited by 25 | Viewed by 3297

Abstract

A class of amphiphilic photosensitizers for photodynamic therapy (PDT) was developed. Sulfonate esters of modified porphyrins bearing—F substituents in the ortho positions of the phenyl rings have adequate properties for PDT, including absorption in the red, increased cellular uptake, favorable intracellular localization, low cytotoxicity, and high phototoxicity against A549 (human lung adenocarcinoma) and CT26 (murine colon carcinoma) cells. Moreover, the role of type I and type II photochemical processes was assessed by fluorescent probes specific for various reactive oxygen species (ROS). The photodynamic effect is improved not only by enhanced cellular uptake but also by the high generation of both singlet oxygen and oxygen-centered radicals. All of the presented results support the idea that the rational design of photosensitizers for PDT can be further improved by better understanding the determinants affecting its therapeutic efficiency and explain how smart structural modifications can make them suitable photosensitizers for application in PDT. Full article

(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles)

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Review

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27 pages, 8274 KiB

Open AccessReview

Recent Advances in Porphyrin-Based Materials for Metal Ions Detection

by Zhen-Li Qi, Yun-Hui Cheng, Zhou Xu and Mao-Long Chen

Int. J. Mol. Sci. 2020, 21(16), 5839; https://doi.org/10.3390/ijms21165839 - 14 Aug 2020

Cited by 61 | Viewed by 7264

Abstract

Porphyrins have planar and conjugated structures, good optical properties, and other special functional properties. Owing to these excellent properties, in recent years, porphyrins and their analogues have emerged as a multifunctional platform for chemical sensors. The rich chemistry of these molecules offers many possibilities for metal ions detection. This review mainly discusses two types of molecular porphyrin and porphyrin composite sensors for metal ions detection, because porphyrins can be functionalized to improve their functional properties, which can introduce more chemical and functional sites. According to the different application materials, the section of porphyrin composite sensors is divided into five sub-categories: (1) porphyrin film, (2) porphyrin metal complex, (3) metal–organic frameworks, (4) graphene materials, and (5) other materials, respectively. Full article

(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles)

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24 pages, 2472 KiB

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Recent Advances in Porphyrin-Based Inorganic Nanoparticles for Cancer Treatment

by Hanieh Montaseri, Cherie Ann Kruger and Heidi Abrahamse

Int. J. Mol. Sci. 2020, 21(9), 3358; https://doi.org/10.3390/ijms21093358 - 09 May 2020

Cited by 54 | Viewed by 7144

Abstract

The application of porphyrins and their derivatives have been investigated extensively over the past years for phototherapy cancer treatment. Phototherapeutic Porphyrins have the ability to generate high levels of reactive oxygen with a low dark toxicity and these properties have made them robust photosensitizing agents. In recent years, Porphyrins have been combined with various nanomaterials in order to improve their bio-distribution. These combinations allow for nanoparticles to enhance photodynamic therapy (PDT) cancer treatment and adding additional nanotheranostics (photothermal therapy—PTT) as well as enhance photodiagnosis (PDD) to the reaction. This review examines various porphyrin-based inorganic nanoparticles developed for phototherapy nanotheranostic cancer treatment over the last three years (2017 to 2020). Furthermore, current challenges in the development and future perspectives of porphyrin-based nanomedicines for cancer treatment are also highlighted. Full article

(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles)

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20 pages, 4324 KiB

Open AccessReview

Photoacoustic Imaging Probes Based on Tetrapyrroles and Related Compounds

by Jean Michel Merkes, Leiming Zhu, Srishti Ballabh Bahukhandi, Magnus Rueping, Fabian Kiessling and Srinivas Banala

Int. J. Mol. Sci. 2020, 21(9), 3082; https://doi.org/10.3390/ijms21093082 - 27 Apr 2020

Cited by 17 | Viewed by 4444

Abstract

Photoacoustic imaging (PAI) is a rapidly evolving field in molecular imaging that enables imaging in the depths of ultrasound and with the sensitivity of optical modalities. PAI bases on the photoexcitation of a chromophore, which converts the absorbed light into thermal energy, causing an acoustic pressure wave that can be captured with ultrasound transducers, in generating an image. For in vivo imaging, chromophores strongly absorbing in the near-infrared range (NIR; > 680 nm) are required. As tetrapyrroles have a long history in biomedical applications, novel tetrapyrroles and inspired mimics have been pursued as potentially suitable contrast agents for PAI. The goal of this review is to summarize the current state of the art in PAI applications using tetrapyrroles and related macrocycles inspired by it, highlighting those compounds exhibiting strong NIR-absorption. Furthermore, we discuss the current developments of other absorbers for in vivo photoacoustic (PA) applications. Full article

(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles)

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