67605-65-6Relevant academic research and scientific papers
On selective functionalization of meso-tetraphenylporphyrin derivatives by Vicarious Nucleophilic Substitution of Hydrogen
Ostrowski, Stanislaw,Mikus, Agnieszka,Shim, Young Key,Lee, Jong-Cheol,Seo, Eun-Young,Lee, Kee-In,Olejnik, Marian
, p. 1615 - 1626 (2002)
The studies on selective derivatization of meso-tetraphenylporphyrin (TPP) using nitration and Vicarious Nucleophilic Substitution of Hydrogen (VNS) are reported. TPP, its metal complexes and N,N-dimethyl substituted derivatives do not enter the VNS reaction. On the other hand, meso-substituted TPP results in the mono-nitration of one phenyl ring and the intermediate obtained, after simple transformation to its metal complex, reacts with carbanions bearing leaving groups at the carbanionic center, according to VNS scheme. This gives new opportunities for the peripheral functionalization of porphyrins. In this work the copper and zinc complexes were investigated.
Spectral studies of protonated and anionic forms of porphyrins with an asymmetric substitution system
Ivanova, Yulia B.,Lyubimtsev, Alexey V.,Plotnikova, Anna O.,Pukhovskaya, Svetlana G.,Syrbu, Sergei A.
, (2022/01/26)
The directed synthesis of asymmetrically substituted porphyrins—tetraphenylporphyrine derivatives containing amino acid residues as a functional group, which can be used as “anchor” groups, for incorporation into the structure of a protein molecule, was c
Photosensitizer-peptoid conjugates for photoinactivation of Gram-negative bacteria: structure-activity relationship and mechanistic studies
Choi, Jieun,Lee, Hohjai,Lee, Seongsoo,Lee, Yunho,Lee, Yunjee,Oh, Hyeongyeol,Seo, Jiwon,Shin, Sujin,Yang, Woojin,Yoon, Younggun
supporting information, p. 6546 - 6557 (2021/08/03)
Multitarget engagement is considered an effective strategy to overcome the threat of bacterial infection, and antimicrobials with multiple mechanisms of action have been successful as natural chemical weaponry. Here, we synthesized a library of photosensitizer-peptoid conjugates (PsPCs) as novel antimicrobial photodynamic therapy (aPDT) agents. The peptoids, linkers, and photosensitizers were varied, and their structure-antimicrobial activity relationships againstEscherichia coliwere evaluated; PsPC9was indicated to be the most promising photoresponsive antimicrobial agent among the synthesized PsPCs. Spectroscopic analyses indicated that9generated singlet oxygen upon absorption of visible light (420 nm) while maintaining the weakly helical conformation of the peptoid. Mechanistic studies suggested that damage to the bacterial membrane and cleavage of DNA upon light irradiation were the main causes of bactericidal activity, which was supported by flow cytometry and DNA gel electrophoresis experiments. We demonstrated that the optimal combination of membrane-active peptoids and photosensitizers can generate an efficient aPDT agent that targets multiple sites of bacterial components and kills bacteria by membrane disruption and reactive oxygen species generation.
Tetraphenylporphyrin covalent functionalized titanium disulfide nonlinear nanometer hybrid material and preparation thereof
-
Paragraph 0041-0042; 0045-0046, (2021/12/07)
The invention relates to a tetraphenylporphyrin covalent functionalized titanium disulfide nonlinear nanometer hybrid material and a preparation method thereof, wherein the hybrid material is prepared from tetraphenylporphyrin diazonium salt TPP-N. 2
Poly(L-Glutamic Acid)-Drug Conjugates for Chemo- and Photodynamic Combination Therapy
Yu, Haiyang,Bao, Yanli,Xu, Caina,Chen, Li,Tang, Zhaohui
, (2020/10/14)
Despite the polymeric vascular disrupting agent (poly(L-glutamic acid)-graft-methoxy poly(ethylene glycol)/combretastatin A4) nanoparticles can efficiently inhibit cancer growth, their further application is still a challenge owing to the tumor
A kind of porphyrin maleimide derivative covalent functionalized molybdenum disulfide nanosheet nonlinear hybrid material and its preparation and application
-
Paragraph 0042-0043; 0045, (2022/01/10)
The present invention relates to a porphyrin maleimide derivative covalent functionalized molybdenum disulfide nanosheet nonlinear hybrid material and its preparation and application, the porphyrin by maleimide and molybdenum disulfide sulfur atom click r
Synthesis and Acid-Base Properties of Tetraphenylporphine Derivatives with Amino Acid “Anchor” Groups
Ivanova, Yu. B.,Khrushkova, Yu. V.,Lyubimtsev, A. V.,Plotnikova, A. O.,Pukhovskaya, S. G.,Shorokhova, T. V.,Syrbu, S. A.
, p. 799 - 806 (2021/06/26)
Abstract: Asymmetrically substituted 5,10,15,20-tetraphenylporphyrin derivatives such as5-(4-aminophenyl)10,15,20-triphenylporphine,5-[4-(tyrosinylamino)phenyl]-10,15,20-triphenylporphine and 5-{4-[(N-tert-butoxycarbonyltyrosinyl)amino]phenyl}-10,15,20-tr
Porphyrin phthalocyanine covalent bifunctional graphene nonlinear nano hybrid material and preparation method thereof
-
Paragraph 0048; 0061, (2021/10/02)
The invention relates to a porphyrin phthalocyanine covalent bifunctional graphene nonlinear nanometer hybrid material and a preparation method thereof. The electron porphyrin and the electron-withdrawing phthalocyanine with the strong electron group are bonded to the surface of the graphene through radical addition reaction, charge is obtained through bridging of graphene, and third-order nonlinear performance of the organic - inorganic hybrid material is enhanced. In the invention, amino-substituted tetraphenylporphyrin and amino-substituted pull electron phthalocyanine are reacted through azo salt, so that a novel bifunctional organic-inorganic covalent functionalized nano hybrid material is successfully prepared. , The prepared material has more enhanced nonlinear optical performance in the nanosecond visible light field compared with the traditional materials, and has very strong reference significance.
An Artificial Hemoprotein with Inducible Peroxidase- and Monooxygenase-Like Activities
Kariyawasam, Kalani,Di Meo, Thibault,Hammerer, Fabien,Valerio-Lepiniec, Marie,Sciortino, Giuseppe,Maréchal, Jean-Didier,Minard, Philippe,Mahy, Jean-Pierre,Urvoas, Agathe,Ricoux, Rémy
supporting information, p. 14929 - 14937 (2020/10/19)
A novel inducible artificial metalloenzyme obtained by covalent attachment of a manganese(III)-tetraphenylporphyrin (MnTPP) to the artificial bidomain repeat protein, (A3A3′)Y26C, is reported. The protein is part of the αRep family. The biohybrid was fully characterized by MALDI-ToF mass spectrometry, circular dichroism and UV/Vis spectroscopies. The peroxidase and monooxygenase activities were evaluated on the original and modified scaffolds including those that have a) an additional imidazole, b) a specific αRep bA3-2 that is known to induce the opening of the (A3A3′) interdomain region and c) a derivative of the αRep bA3-2 inducer extended with a His6-Tag (His6-bA3-2). Catalytic profiles are highly dependent on the presence of co-catalysts with the best activity obtained with His6-bA3-2. The entire mechanism was rationalized by an integrative molecular modeling study that includes protein–ligand docking and large-scale molecular dynamics. This constitutes the first example of an entirely artificial metalloenzyme with inducible peroxidase and monooxygenase activities, reminiscent of allosteric regulation of natural enzymatic pathways.
Peroxynitrite (ONOO-) generation from the HA-TPP@NORM nanoparticles based on synergistic interactions between nitric oxide and photodynamic therapies for elevating anticancer efficiency
Jiang, Dawei,Yue, Tao,Wang, Guichen,Wang, Chaochao,Cao, Hongliang,Gao, Yun,Chen, Chao
supporting information, p. 162 - 170 (2019/12/26)
Due to biological safety and negligible toxicity, nitric oxide (NO) therapy has gained increasing interest in the field of cancer therapy during the past few years. However, individual NO cancer therapy normally exhibited limited therapeutic efficiency. In order to acquire satisfactory therapeutic outcomes, the NO therapy is usually combined with other therapeutic treatments, mostly chemotherapy. Herein, we constructed HA-TPP@NORM nanoparticles based on the co-assembly of an NO donor (NORM) and tetraphenylporphyrin (TPP)-modified hyaluronic acid, which can efficiently generate a highly biocidal molecule of peroxynitrite (ONOO-) via the synergistic interactions of the nitric oxide (NO) therapy and photodynamic therapy (PDT) to enhance the cancer therapeutic efficiency. In addition, MTT results exhibited that without light irradiation, the HA-TPP@NORM nanoparticles have favourable biocompatibility with the cell viability above 95% at the maximum TPP concentration (20 μg mL-1). Under simultaneous irradiation with 365 nm and 650 nm light, ONOO- can be efficiently produced in cancer cells via the direct coupling reaction of the generated NO and superoxide anion radical (O2-), which significantly enhanced the anticancer effect, when compared with individual NO therapy or PDT therapy. Therefore, the HA-TPP@NORM nanoparticles may provide a new insight into the design of efficiently NO-related cancer therapeutic systems.
