Metal coordinated pyrrole-based macrocycles as contrast agents for magnetic resonance imaging technologies: Synthesis and applications

Peripherally Metalated Porphyrins with Applications in Catalysis, Molecular Electronics and Biomedicine

“…Improving the r 1 value with porphyrin macrocycles wasf irst investigated. [85] However,t he inner cavity of porphyrins is too small to accommodate Gd III adequately,a nd Gd III porphyrins are too unstablef or safe in vivo applications. The use of porphyrins bearing peripheral and thermodynamically stable Gd III complexes was ab etter option to combine within the same framework PDT,f luorescencei maging and MRI.…”

“…Among the Gd III porphyrin conjugates reported in the literature, [85][86][87][88][89][90] only those with four Gd III at the porphyrin periphery (like those represented in Scheme 30) at 25 8Ca nd 20 MHz are discussed for better comparison. The tetranuclearG d III complex 69 is af ree-base porphyrin bearing four meso DOTA-like Gd III complexes.…”

A New Tool in the Quest for Biocompatible Phthalocyanines: Palladium Catalyzed Aminocarbonylation for Amide Substituted Phthalonitriles and Illustrative Phthalocyanines Thereof

“…Molecules of the tetrapyrrole family (e.g., porphyrin and phthalocyanine derivatives) are probably the most appealing chromophores for a vast array of photoactivated processes, such as phototherapy [1][2][3], photodiagnosis [4][5][6], photocatalysis [7,8], solar energy conversion [9,10], and also as photomaterials [11][12][13]. In particular, phthalocyanines largely fulfil a crucial optical requisite, necessary for photomedicinal applications, which is a strong absorption in near-infrared (NIR) spectral region (600-900 nm), as light in this region affords the deepest penetration in soft tissue.…”

“…In particular, phthalocyanines largely fulfil a crucial optical requisite, necessary for photomedicinal applications, which is a strong absorption in near-infrared (NIR) spectral region (600-900 nm), as light in this region affords the deepest penetration in soft tissue. These highly stable compounds, possessing high molar absorptivity, high quantum yields of fluorescence and structural versatility [4,13,14], can be conveniently modified to grant suitable biological solubility [15][16][17][18], by introduction of hydrophilic moieties in the structure. The majority of the moieties used so far are negatively charged, such as sulfonates or carboxylates [15,19] or positively charged, like quaternized amines [15,20].…”

β-Formyl- and β-Vinylporphyrins: Magic Building Blocks for Novel Porphyrin Derivatives

“…The contributions of Hans Fischer to the final structure elucidation of protoporphyrin-IX and hemin reported in 1929 and of Woodward in the synthesis of chlorophyll a in 1960 are important highlights in the extraordinary evolution observed afterwards with these molecules [ 1 , 2 , 3 ]. Today, natural and synthetic porphyrin derivatives are recognized as excellent systems to be explored in the development of novel catalysts [ 4 , 5 , 6 , 7 , 8 ], electronic devices [ 9 , 10 , 11 , 12 ], sensors [ 13 , 14 , 15 , 16 ], dyes for photovoltaic solar cells [ 17 , 18 , 19 , 20 , 21 , 22 ] and as therapeutic agents [ 23 , 24 , 25 , 26 , 27 ]. In medicine, porphyrin derivatives are being used as photosensitisers in the treatment of oncologic and non-oncologic diseases by photodynamic therapy (PDT) [ 28 , 29 , 30 , 31 , 32 , 33 ].…”