Docking studies, antitumor and antioxidant evaluation of newly synthesized porphyrin and metalloporphyrin derivatives

Ahmed, Asmaa; Omar, Walaa A. E.; El-Asmy, Hala A.; Abou-Zeid, Laila A.; Fadda, Ahmed A.

doi:10.1016/j.dyepig.2020.108728

Cited by 16 publications

(15 citation statements)

References 72 publications

(111 reference statements)

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“…The observed prooxidant action was also dose-dependent. It has recently been shown that, in some cases, metalloporphyrins exhibit both antioxidant [ 42 , 74 , 75 , 76 ] and prooxidant properties [ 46 , 47 , 77 , 78 ], depending on environmental conditions, such as the presence of the other reagents in the system [ 44 ], the level of reactive oxygen species, the availability of oxygen, etc. [ 47 ].…”

Section: Resultsmentioning

confidence: 99%

Switchable Nanozyme Activity of Porphyrins Intercalated in Layered Gadolinium Hydroxide

Теплоногова

Volostnykh

Yapryntsev

et al. 2022

IJMS

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In this study, organo-inorganic nanohybrids LHGd-MTSPP with enzyme-like activity were prepared by in situ intercalation of anionic 5,10,15,20-tetrakis-(4-sulfonatophenyl)porphyrin and its complexes with Zn(II) and Pd(II) (MTSPP, M = 2H, Zn(II) and Pd(II)) into gadolinium layered hydroxide (LHGd). The combination of powder XRD, CHNS analysis, FT-IR, EDX, and TG confirmed the layered structure of the reaction products. The basal interplanar distances in LHGd-MTSPP samples were 22.3–22.6 Å, corresponding to the size of an intercalated tetrapyrrole molecule. According to SEM data, LHGd-MTSPP hybrids consisted of individual lamellar nanoparticles 20–50 nm in thickness. The enzyme-like activity of individual constituents, LHGd-Cl and sulfoporphyrins TSPP, ZnTSPP and PdTSPP, and hybrid LHGd-MTSPP materials, was studied by chemiluminescence analysis using the ABAP/luminol system in phosphate buffer solution. All the individual porphyrins exhibited dose-dependent antioxidant properties with respect to alkylperoxyl radicals at pH 7.4. The intercalation of free base TSPP porphyrin into the LHGd preserved the radical scavenging properties of the product. Conversely, in LHGd-MTSPP samples containing Zn(II) and Pd(II) complexes, the antioxidant properties of the porphyrins changed to dose-dependent prooxidant activity. Thus, an efficient approach to the design and synthesis of advanced LHGd-MTSPP materials with switchable enzyme-like activity was developed.

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Section: Resultsmentioning

confidence: 99%

Switchable Nanozyme Activity of Porphyrins Intercalated in Layered Gadolinium Hydroxide

Теплоногова

Volostnykh

Yapryntsev

et al. 2022

IJMS

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“…The main problem in porphyrin synthesis is its low yields (6%–20%) although different trials to enhance the yields of porphyrins are reported [24–26]. Recently, Fadda et al [27,28] reported a new methodology, which yields 70%–80% yield. In this case, Fadda et al used DMF “ N , N ‐dimethylformamide” as a solvent and capping reagent.…”

Section: Resultsmentioning

confidence: 99%

“…The intermediate DMF‐pyrrole reacts with another pyrrole moiety to give the corresponding porphyrinogen. When each time pyrrole is added, loss of DMF molecule was appropriate as a good leaving group [27,28]. In this work, we report here the synthesis of free‐base porphyrin 6 in high yields (75%).…”

Section: Resultsmentioning

confidence: 99%

“…In this work, we report here the synthesis of free‐base porphyrin 6 in high yields (75%). Therefore, it was found that 2,7,12,17‐tetranitro‐5,10,15,20‐tetraphenylporphyrin ( 6 ) was synthesized from the reaction of 3‐nitropyrrole ( 5 ) with benzaldehyde according to the reported method by Fadda et al [27,28]. The synthesized porphyrin was well characterized by spectral data.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, biological evaluation, and docking studies of various β‐substituted porphyrin conjugates embedded with N‐containing heterocycles

Masaret

2021

Journal of Heterocyclic Chem

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A new methodology for the synthesis of some new β‐porphyrin heterocyclic compounds containing nitrogen derivatives 10, 12, 13, 15, 17, 19, 21, 22, 25, 27, and 29 was screened for their cytotoxic activities. Both elemental and spectral analyses were used to confirm the structures of new compounds. Compounds 22, 27, and 21 exhibited very strong activity against the HepG2 cell line. Investigation of the binding between porphyrin 22 and the binding site of telomerase was performed by molecular docking.

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“…The meso-substituted porphyrins have gained considerable interest due to their ability to act as ligands for metal ions forming the complexes that have high applicability for therapeutic purposes [104,105]. Recently, Ahmed et al synthesized and evaluated the antioxidant and anticancer activities of porphyrin derivatives 102-106 and their metalloporphyrin counterparts 107-114 ( Figure 17) [106]. All compounds showed radical-scavenging activity.…”

Section: Porphyrinmentioning

confidence: 99%

Macrocycles and Supramolecules as Antioxidants: Excellent Scaffolds for Development of Potential Therapeutic Agents

et al. 2020

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Oxidative stress due to the high levels of reactive oxygen species (ROS) that damage biomolecules (lipids, proteins, DNA) results in acute inflammation. However, without proper intervention, acute inflammation progresses to chronic inflammation and then to several chronic diseases, including cancer, myocardial infarction, cardiovascular diseases, chronic inflammation, atherosclerosis, and more. There has been extensive research on the antioxidants of natural origin. However, there are myriad possibilities for the development of synthetic antioxidants for pharmacological applications. There is an increasing interest in the identification of novel synthetic antioxidants for the modulation of biochemical processes related to ROS. In this regard, derivatives of supramolecules, such as calix[n]arene, resorcinarene, calixtyrosol, calixpyrrole, cucurbit[n]uril, porphyrin etc. are gaining attention for their abilities to scavenge the free radicals. Supramolecular chemistry offers excellent scaffolds for the development of novel antioxidants that can be used to modulate free radical reactions and to improve the disorders related to oxidative stress. This review focuses on the interdisciplinary approach for the design and development of novel synthetic antioxidants based on supramolecular scaffolds, with potentially protective effects against oxidative stress.

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Docking studies, antitumor and antioxidant evaluation of newly synthesized porphyrin and metalloporphyrin derivatives

Cited by 16 publications

References 72 publications

Switchable Nanozyme Activity of Porphyrins Intercalated in Layered Gadolinium Hydroxide

Switchable Nanozyme Activity of Porphyrins Intercalated in Layered Gadolinium Hydroxide

Synthesis, biological evaluation, and docking studies of various β‐substituted porphyrin conjugates embedded with N‐containing heterocycles

Macrocycles and Supramolecules as Antioxidants: Excellent Scaffolds for Development of Potential Therapeutic Agents

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