Review
Chemistry, Multidisciplinary
Pravin Pathak, Mohammad Amin Zarandi, Xiao Zhou, Janarthanan Jayawickramarajah
Summary: This review provides a detailed overview of synthetic strategies and applications for conjugating porphyrinoids with nucleic acids and peptides/proteins. Tailored synthetic approaches are crucial for attaching porphyrins to different types of biomacromolecules, highlighting the importance of fine-tuning in the field of porphyrinoid-biomacromolecule conjugation.
FRONTIERS IN CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yue Wu, Ho-Fai Chau, Yik-Hoi Yeung, Waygen Thor, Hei-Yui Kai, Wai-Lun Chan, Ka-Leung Wong
Summary: In this study, a novel synthetic method for the efficient preparation of prefunctionalized core porphyrins and the controllable construction of various valent porphyrin-peptide conjugates was reported. Compared to traditional methods, this approach is faster, greener, and requires only one final-stage purification.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Nanoscience & Nanotechnology
Hyungkyu Moon, Suyeon Jeong, T. Sheshashena Reddy, Hae Dong Lee, Myung-Seok Choi
Summary: A series of tetraphenylethylene-porphyrin conjugates were synthesized and their photophysical and electrochemical properties were analyzed. The results showed that the porphyrin band gaps slightly decreased with the increase of tetraphenylethylene moieties, accompanied by a red shift in absorption and emission wavelengths. Additionally, TEM observations revealed that the wall thickness of nanotubes increased with the number of tetraphenylethylene moieties.
SCIENCE OF ADVANCED MATERIALS
(2022)
Article
Chemistry, Physical
Louis-Gabriel Bronstein, Paul Cressey, Wasim Abuillan, Oleg Konovalov, Maciej Jankowski, Veronique Rosilio, Ali Makky
Summary: This study investigated the interfacial behavior of phospholipid-porphyrin (Pl-Por) conjugates and their dependence on the porphyrin type and alkyl chain length. The results showed that Pl-Por conjugates can form stable monolayers at the air/water interface, and the packing of the monolayer is influenced by the porphyrin type. The length of the alkyl chain determines the structure of the formed domains.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2022)
Article
Chemistry, Multidisciplinary
Kais Dhbaibi, Paola Matozzo, Laura Abella, Marion Jean, Nicolas Vanthuyne, Jochen Autschbach, Ludovic Favereau, Jeanne Crassous
Summary: Enantiopure helicene-porphyrin conjugates exhibit strong changes in their circular dichroic response, showing highly intense bisignate Exciton Coupling signal and Delta epsilon values up to 680 M-1 cm(-1) for the Soret band. They also display circularly polarized fluorescence in the (far-)red region, with dissymmetry factors of up to 7 x 10(-4).
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Tawfik A. Saleh, Asma M. Elsharif, Osamah A. Bin-Dahman
Summary: Carbon nanotubes were functionalized with amine groups and conjugated with prophyrine derivatives to increase active sites. Compound 3 showed better adsorption efficiency for methylene blue at different pH values, achieving high efficiency when the adsorbent dosage increased. The adsorption mechanism involved non-electrostatic and electrostatic interactions, making the material effective for simultaneous adsorption of MB and toxic metal ions.
JOURNAL OF MOLECULAR LIQUIDS
(2021)
Article
Biochemistry & Molecular Biology
Janet Ocampo-Hernandez, Jose de Jesus Gomez-Guzman, Marisela Cruz-Ramirez, Juan Pablo F Rebolledo-Chavez, Angel Mendoza, Rafael Moreno-Esparza, Luis Ortiz-Frade
Summary: In this study, we investigated the interaction between a model complex [Cu-iota iota(Bztpen)](2+) and transport proteins, such as Bovine Serum Albumin (BSA), using electrochemical, spectroscopic and spectro-electrochemical methods. The results showed a weak interaction between the copper complex and BSA, with no adsorption of the protein on the electrode surface.
JOURNAL OF INORGANIC BIOCHEMISTRY
(2022)
Article
Chemistry, Organic
Jose Almeida, Guanyu Zhang, Maodie Wang, Carla Queiros, Ana F. R. Cerqueira, Augusto C. Tome, Giampaolo Barone, M. Graca H. Vicente, Evamarie Hey-Hawkins, Ana M. G. Silva, Maria Rangel
Summary: Indomethacin is a potent NSAID selective inhibitor towards COX-2, while porphyrins and chlorins are promising PSs for PDT. The conjugates P2-Ind and C2-Ind showed high yield and singlet oxygen generation capacity, with C2 being the best PS. Cytotoxicity studies revealed C2-Ind had lower cellular uptake but was detected in small aggregates.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ayman M. K. Sweed, Sherif S. Ragab, Yasser M. Shaker
Summary: In this study, a series of novel asymmetric A(3)B porphyrin molecules with oxyacetamide linkers were successfully synthesized. The synthesized porphyrin conjugates exhibited high extension coefficient values in methanol, indicating their potential applications in photomedicine.
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
(2022)
Article
Chemistry, Multidisciplinary
Christian Fiankor, James Nyakuchena, Rebecca Shu Hui Khoo, Xu Zhang, Yuchen Hu, Sizhuo Yang, Jier Huang, Jian Zhang
Summary: This study presents the design and synthesis of a highly porous and photoactive mixed-ligand MOF, showcasing the potential of MOFs as an ideal platform for studying energy transfer processes and the possibility of directly utilizing EnT processes in photocatalytic applications.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Emmanouil Nikoloudakis, Maria Pigiaki, Maria N. Polychronaki, Alexandra Margaritopoulou, Georgios Charalambidis, Efthymis Serpetzoglou, Anna Mitraki, Panagiotis A. Loukakos, Athanassios G. Coutsolelos
Summary: In this research, diphenylalanine dipeptide was covalently attached to a tripyridyl porphyrin macrocycle, imparting self-assembling properties to the resulting hybrid used for non-noble metal photocatalytic hydrogen evolution studies. The self-assembling nanostructures of the hybrid were found to enhance hydrogen production in the photocatalytic system. This was supported by fluorescence and transient absorption experiments shedding light on electron transfer processes during photocatalysis.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Pharmacology & Pharmacy
Kseniya A. A. Zhdanova, Anastasia V. V. Ivantsova, Fedor Yu. Vyalba, Maxim N. N. Usachev, Margarita A. A. Gradova, Oleg V. V. Gradov, Natalia Yu. Karpechenko, Natal'ya A. Bragina
Summary: This paper presents the design and synthesis of new multifunctional porphyrin-based therapeutic agents, which have potential applications in therapy and diagnosis. The zinc complexes of A3B-type meso-arylporphyrins were modified with chelating ligands based on 4'-(4-methylphenyl)-2,2':6',2''-terpyridine derivatives to obtain novel complexes with Gd(III) and Fe(III). The aggregation behavior, photophysical properties, and photochemical properties of these porphyrins were studied, and the micellar Pluronic F127 formulation was found to be the most effective solubilizer. In vitro cytotoxicity studies showed that the compounds had significant toxic effects under irradiation, but no toxicity without irradiation.
Article
Electrochemistry
Yee-Seul Kim, Sebastien Kriegel, Alla Bessmertnykh-Lemeune, Kenneth D. Harris, Benoit Limoges, Veronique Balland
Summary: The study investigates the catalytic reduction of O-2 by a manganese(III) porphyrin immobilized in a nanostructured semiconductive transparent TiO2 electrode, revealing the presence of two faradaic electrochemical processes between TiO2 and the immobilized catalyst. The competition between irreversible interfacial electron transfer triggering catalysis and reversible proton-coupled electrochemical reduction of TiO2 leads to a fascinating phenomenon where catalysis transitions to charge storage when O-2 is locally depleted, impacting applications utilizing metal oxide-based photoelectrodes in aqueous media.
Article
Pharmacology & Pharmacy
Toni Todorovski, Diogo A. Mendonca, Lorena O. Fernandes-Siqueira, Christine Cruz-Oliveira, Giuseppina Guida, Javier Valle, Marco Cavaco, Fernanda I. Limas, Vera Neves, Iris Cadima-Couto, Sira Defaus, Ana Salome Veiga, Andrea T. Da Poian, Miguel A. R. B. Castanho, David Andreu
Summary: Viral disease outbreaks pose a serious threat to global health, particularly the Zika virus, which can cause severe complications during pregnancy. There is currently no effective treatment, but peptide-porphyrin conjugation shows promise as a strategy for filling this treatment gap.
Review
Chemistry, Organic
Dileep Kumar Singh
Summary: Among the various approaches in organic synthesis, the click chemistry protocol, also known as CuAAC reaction, is commonly used to connect different moieties in a single framework. This review focuses on the synthesis and photophysical studies of porphyrin conjugates with meso-substituted and 1,2,3-triazole-fused structures. The triazole ring serves as a spacer and an electron transfer bridge between the attached chromophores and the porphyrin.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Changjiang Yu, Jiazhu Li, Erhong Hao, Yingzhu Sun, Xingbao Fang, Qinghua Wu, Weibin Bu, Xing Guo, Hua Wang, Lijuan Jiao
Summary: A series of aromatic-ring-fused BOPPY dyes with excellent photophysical properties and fluorescence quantum yields have been developed, and they can selectively light up subcellular organelles at ultralow concentration.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhong-Yuan Li, Jin-Ping Zhang, Yun-Yi Ying, Dong Yan, Lijuan Jiao, Erhong Hao
Summary: A novel protocol for the rhodium-catalyzed tandem C-H annulation of aldehyde and aniline with diazonaphthalen-1(2H)-one via transient directing group strategy and sequential nucleophilic substitution has been demonstrated, leading to the synthesis of 6-aryl-6H-benzo[c]chromene derivatives in moderate to excellent yields.
Article
Chemistry, Multidisciplinary
Wei Miao, Xing Guo, Xi Yan, Yingjian Shang, Changjiang Yu, En Dai, Ting Jiang, Erhong Hao, Lijuan Jiao
Summary: In this study, a series of 3-pyrrolylBODIPY derivatives and 3,5-dipyrrolylBODIPY derivatives were synthesized by a simple regioselective nucleophilic aromatic substitution reaction. The introduction of a pyrrolic unit onto the 3-position of the BODIPY chromophore resulted in a significant red shift in both absorption and emission. Further functionalization at the 5-position fine-tuned their photophysical properties, and these derivatives exhibited strong absorption and intense near-infrared fluorescence emission. One of the derivatives, pyrrolylBODIPY 6 a, containing a mitochondrion-targeting cationic species, showed selective localization in mitochondria with low cytotoxicity and intense red fluorescence emission.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Fan Lv, Xing Guo, Zhong-Yuan Li, Qinghua Wu, Juanjie Chen, Changjiang Yu, Lijuan Jiao, Erhong Hao
Summary: A copper-catalyzed direct acylation of BODIPYs with aldehydes via C-H bond activation was developed, where acyl radicals were formed from aldehydes using TBHP as the radical initiator and selectively reacted with BODIPYs at the alpha-positions. This reaction showed excellent tolerance towards different functional groups, allowing for effective reaction between heteroaromatic and aliphatic aldehydes with BODIPYs. The alpha-acylated BODIPYs exhibited red-shifted absorption and emission, as well as decreased HOMO and LUMO energies compared to the starting BODIPYs due to the introduction of electron-deficient carbonyl groups. Moreover, removal of the BF2 protecting groups from the alpha-acylated BODIPY provided a efficient access to alpha-acylated dipyrrin, which showed sensitive and selective turn-on fluorescence response towards Zn2+ ion in aqueous buffer solution and living cells.
Article
Chemistry, Applied
Hua Wang, Xing Guo, Weibin Bu, Zhengxin Kang, Changjiang Yu, Qinghua Wu, Lijuan Jiao, Erhong Hao
Summary: A series of boronic acid derived salicylidenehydrazinopyridine complexes were synthesized and characterized. These complexes display a tetrahedral geometry due to the boron atoms and exhibit stereochemistry and molecular chirality. The curved nonplanar structure and axial-substituted groups of the complexes provide solubility and steric protection. The complexes also show strong absorption, weak emission, and large Stoke shifts, as well as aggregation-induced emission activities, making them potential bioimaging dyes.
Article
Chemistry, Multidisciplinary
Jun Wang, Huiquan Zuo, Qinghua Wu, Erhong Hao, Lijuan Jiao
Summary: In this study, two novel phenylenes bridged dimeric BOBPY were designed and synthesized. The resulting dyes showed high photostability, intense absorption and emission properties, and the electronic interactions were related to the length of the linker.
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
(2023)
Article
Chemistry, Multidisciplinary
Qingbao Gong, Xinfu Zhang, Wanwan Li, Xing Guo, Qinghua Wu, Changjiang Yu, Lijuan Jiao, Yi Xiao, Erhong Hao
Summary: This study describes a new class of long-wavelength photoconvertible fluorophores that can be activated by visible light, producing stable products with bright fluorescence properties, offering potential applications in biological imaging.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Zhaoyun Wang, Xing Guo, Zhengxin Kang, Qinghua Wu, Heng Li, Cheng Cheng, Changjiang Yu, Lijuan Jiao, Erhong Hao
Summary: An efficient procedure is developed for synthesizing aryl-boron-substituted BODIPY and aza-BODIPY derivatives through functional-nucleophiles in the presence of aluminum chloride. These derivatives exhibit bright emission in aqueous solution, with enhanced aggregation-induced emission and high solid-state emission due to restricted rotation and the formation of J-type aggregates.
Article
Spectroscopy
Wanle Sheng, Xing Guo, Bing Tang, Weibin Bu, Fan Zhang, Erhong Hao, Lijuan Jiao
Summary: The optical properties and aggregation-induced emission (AIE) activities of BODIPYs with TPA groups were studied systematically, and the dynamic behaviors of lipid droplets and lysosomes in living cells were successfully tracked through organelle-specific imaging.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2023)
Article
Chemistry, Multidisciplinary
Zhengxin Kang, Long Wang, Zhongxin Li, Qinghua Wu, Ying Wei, Huiquan Zuo, Erhong Hao, Lijuan Jiao
Summary: The reaction of dipyrrolomethane and acetone in the presence of acid and oxidant yields a mixture of 5,15-calixphyrin and 5,10-calixphyrin. The 5,10-calixphyrin forms a Pd(II) complex when treated with Pd(OAc)(2) in acetonitrile and refluxed. The introduction of palladium metal to 5,10-calixphyrin has significant effects on its structure and properties, such as absorption bands and electron density.
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
(2023)
Article
Chemistry, Organic
Zhongxin Li, Lei Zhang, Wei Miao, Yingjian Shang, Long Wang, Changjiang Yu, Lijuan Jiao, Erhong Hao
Summary: Linear pi-conjugated oligopyrroles are attractive precursors for the synthesis of expanded porphyrinoids, chemosensors, and supramolecular motifs. A new method for the synthesis of a set of linear pyrrolyltripyrrins and dipyrrolyltripyrrins through a regioselective S(N)Ar reaction on alpha,alpha '-dibromotripyrrins using various pyrroles or indoles is demonstrated. A representative calixsmaragdyrin was prepared via the 2-fold SNAr reaction between alpha,alpha '-dibromotripyrrin and dipyrromethene through a convergent [3 + 2] strategy. These oligopyrroles showed intense deep red absorptions with an interesting pH response.
Article
Chemistry, Organic
Changjiang Yu, Yingzhu Sun, Lijuan Jiao, Erhong Hao
Summary: In recent years, several series of novel diboron compounds with tunable structures and outstanding spectroscopic properties have been developed as valuable fluorophores. This article mainly focuses on the synthetic strategies and superior properties of the fluorophores BOPHY, BOPPY, and BOAPY developed by our group. It also includes significant photophysical data of these fluorophores in solution and solid states. The facile functionalization of these fluorophores allows for practical structural modifications to generate versatile dyes with excellent chemical and photophysical properties. We believe that these fluorophores have the potential to make important contributions in a wide range of applications.
Review
Chemistry, Inorganic & Nuclear
Zhongxin Li, Qingbao Gong, Erhong Hao, Lijuan Jiao
Summary: In recent years, subporphyrazines and subporphyrins, fascinating ring-contracted porphyrinoids containing boron, have been developed as promising functional dyes due to their interesting structural, photophysical and electrochemical properties. This review provides an overview of their synthesis and summarizes the main structural modification methods, as well as discusses related analogues, dimers and oligomers, and stable subporphyrin radicals. Special attention is given to outstanding free base triphyrin(1.1.1) and free base subporphyrin, as well as hybrid subporphyrinoids.
COORDINATION CHEMISTRY REVIEWS
(2023)
Article
Chemistry, Applied
Xiangmin Wang, Xiaofan Fu, Weibin Bu, Changjian Yu, Erhong Hao, Lijuan Jiao, Qinghua Wu, Rentian Wang, Jinjun Wang, Jiazhu Li
Summary: Fusion of thiophene to BODIPY allows for the development of novel symmetric bisbenzothieno[b]-fused BODIPYs (BTBs) with absorption maxima in the range of 643-665 nm, large molar extinction coefficients, and high singlet oxygen generation. Theoretical calculations show that the smaller singlet-triplet energy gap and larger spin-orbit coupling contribute to efficient intersystem crossing and increased singlet oxygen generation yield. Interestingly, a methyl diphenyl substituted BTB exhibits good reactive oxygen species generation efficiency (0.41) and remarkable photo-cytotoxicity (IC50 = 83.5 nM) in HeLa cells, demonstrating its potential in low-dose photodynamic therapy.
Article
Chemistry, Organic
Long Wang, Qinghua Wu, Zhengxin Kang, Xing Guo, Wei Miao, Zhongxin Li, Huiquan Zuo, Hua Wang, Hongwei Si, Lijuan Jiao, Erhong Hao
Summary: A family of directly β,β-linked BODIPY dimers with amino groups at α-positions were selectively prepared by oxidative coupling reaction of α-amino-substituted BODIPYs. The structure of one representative dimer was elucidated by X-ray diffraction analysis, showing a twisted orientation of two BODIPY units with a dihedral angle of 49°. Compared with the corresponding monomers, these dimers exhibited red-shifted absorptions and emissions along with efficient intersystem crossing, with a quantum yield Φ(Δ) of 43% for dimer 4b in toluene, indicating their potential use as heavy-atom-free photosensitizers.