Synthesis of 2-morpholinetetraphenylporphyrins and their photodynamic activities

Liao, Ping-Yong; Wang, Xinrong; Zhang, Xianghua; Hu, Tai‐Shan; Min, Zheng; Gao, Yan; Yan, Yuan; Chen, Zhilong

doi:10.1016/j.bioorg.2017.02.015

Cited by 7 publications

(2 citation statements)

References 22 publications

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“…36 In another study, a range of morpholine linked porphyrins have been synthesized by Chen et al for biological purposes and the experiments revealed that some of the synthesized compounds exhibited potent photodynamic antitumor efficacy in BALB/c nude mice at lower concentration. 37…”

Section: Introductionmentioning

confidence: 99%

New AB₃-type porphyrins with piperidine and morpholine motifs; synthesis and photo-physicochemical and biological properties

Harmandar

Giray²,

Önal

et al. 2023

Dalton Trans.

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Section: Introductionmentioning

confidence: 99%

New AB₃-type porphyrins with piperidine and morpholine motifs; synthesis and photo-physicochemical and biological properties

Harmandar

Giray²,

Önal

et al. 2023

Dalton Trans.

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“…Cancer is one of the deadliest diseases in the world [1]. Compared to the traditional cancer treatments including surgery, chemotherapy and radiation therapy, photodynamic therapy (PDT) has been widely utilized in clinical oncology due to their non-invasiveness, selectivity, repeatability and low side-effects [2][3][4][5][6][7][8]. The PSs were excited by suitable wavelength of light to undergo an energy level transition, which led to the PSs to transform from the ground state to the singlet excited state, and then partial excited-state molecules convert into triplet excited state through the intersystem crossing, which finally caused the destruction of tumor cells by three photochemical reactions such as type I, type II and type III [8,9].…”

Section: Introductionmentioning

confidence: 99%

The bromoporphyrins as promising anti-tumor photosensitizers in vitro

Namulinda

et al. 2022

Photochem Photobiol Sci

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The synthesis of ideal photosensitizers (PSs) is considered to be the most significant bottleneck in photodynamic therapy (PDT). To discover novel PSs with excellent photodynamic anti-tumor activities, a series of novel photosensitizers 5,15-diaryl-10,20-dibromoporphyrins (I 1-6 ) were synthesized by a facile method. Compared with hematoporphyrin monomethyl ether (HMME) as the representative porphyrin-based photosensitizers, it is found that not only the longest absorption wavelength of all compounds was red-shifted to therapeutic window (660 nm) of photodynamic therapy, but also the singlet oxygen quantum yields were significantly increased. Furthermore, all compounds exhibited lower dark toxicity (except I 2 ) and stronger phototoxicity (except I 4 ) against Eca-109 tumor cells than HMME. Among them, I 3 possessed the highest singlet oxygen quantum yield (Φ Δ = 0.205), the lower dark toxicity and the strongest phototoxicity (IC 50 = 3.5 μM) in vitro. The findings indicated the compounds I 3 had the potential to become anti-tumor agents for PDT.

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Nucleophilic Aromatic Substitution (S_NAr) and Related Reactions of Porphyrinoids: Mechanistic and Regiochemical Aspects

Sample

Senge

2020

Eur J Org Chem

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The nucleophilic substitution of aromatic moieties (SNAr) has been known for over 150 years and found wide use for the functionalization of (hetero)aromatic systems. Currently, several “types” of SNAr reactions have been established and notably the area of porphyrinoid macrocycles has seen many uses thereof. Herein, we detail the SNAr reactions of seven types of porphyrinoids with differing number and type of pyrrole units: subporphyrins, norcorroles, corroles, porphyrins, azuliporphyrins, N‐confused porphyrins, and phthalocyanines. For each we analyze the substitution dependent upon: a) the type of nucleophile and b) the site of substitution (α, β, or meso). Along with this we evaluate this route as a synthetic strategy for the generation of unsymmetrical porphyrinoids. Distinct trends can be identified for each type of porphyrinoid discussed, regardless of nucleophile. The use of nucleophilic substitution on porphyrinoids is found to often be a cost‐effective procedure with the ability to yield complex substituent patterns, which can be conducted in non‐anhydrous solvents with easily accessible simple porphyrinoids.

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Synthesis of 2-morpholinetetraphenylporphyrins and their photodynamic activities

Cited by 7 publications

References 22 publications

New AB₃-type porphyrins with piperidine and morpholine motifs; synthesis and photo-physicochemical and biological properties

New AB₃-type porphyrins with piperidine and morpholine motifs; synthesis and photo-physicochemical and biological properties

The bromoporphyrins as promising anti-tumor photosensitizers in vitro

Nucleophilic Aromatic Substitution (S_NAr) and Related Reactions of Porphyrinoids: Mechanistic and Regiochemical Aspects

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Synthesis of 2-morpholinetetraphenylporphyrins and their photodynamic activities

Cited by 7 publications

References 22 publications

New AB3-type porphyrins with piperidine and morpholine motifs; synthesis and photo-physicochemical and biological properties

New AB3-type porphyrins with piperidine and morpholine motifs; synthesis and photo-physicochemical and biological properties

The bromoporphyrins as promising anti-tumor photosensitizers in vitro

Nucleophilic Aromatic Substitution (SNAr) and Related Reactions of Porphyrinoids: Mechanistic and Regiochemical Aspects

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New AB₃-type porphyrins with piperidine and morpholine motifs; synthesis and photo-physicochemical and biological properties

New AB₃-type porphyrins with piperidine and morpholine motifs; synthesis and photo-physicochemical and biological properties

Nucleophilic Aromatic Substitution (S_NAr) and Related Reactions of Porphyrinoids: Mechanistic and Regiochemical Aspects