Porphyrin-based covalent organic polymer by inverse electron demand Diels-Alder reaction

Çetinkaya, Ahmet; Sadak, Ali Enis; Ayhan, Mehmet Menaf; Zorlu, Yunus; Kahveci, Muhammet U.

doi:10.1016/j.eurpolymj.2021.110664

Cited by 6 publications

(5 citation statements)

References 71 publications

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“…FT-IR spectra of PTPPF 16 -EDA and PZnTPPF 16 -EDA showed the presence of amine groups, with characteristic bands between 3600 and 3100 cm −1 (Figure S2) [47]. These bands are assigned to the N-H stretching vibrations of aliphatic primary amine groups and aromatic secondary amine groups.…”

Section: Synthesis Of Ptppf 16 -Eda and Pzntppf 16 -Edamentioning

confidence: 99%

Porphyrin Polymers Bearing N,N′-Ethylene Crosslinkers as Photosensitizers against Bacteria

et al. 2022

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The appearance of microbes resistant to antibiotics requires the development of alternative therapies for the treatment of infectious diseases. In this work two polymers, PTPPF16-EDA and PZnTPPF16-EDA, were synthesized by the nucleophilic aromatic substitution of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin and its Zn(II) complex with ethylenediamine, respectively. In these structures, the tetrapyrrolic macrocycles were N,N′-ethylene crosslinked, which gives them greater mobility. The absorption spectra of the polymers showed a bathochromic shift of the Soret band of ~10 nm with respect to the monomers. This effect was also found in the red fluorescence emission peaks. Furthermore, both polymeric materials produced singlet molecular oxygen with high quantum yields. In addition, they were capable of generating superoxide anion radicals. Photodynamic inactivation sensitized by these polymers was tested in Staphylococcus aureus and Escherichia coli bacteria. A decrease in cell viability greater than 7 log (99.9999%) was observed in S. aureus incubated with 0.5 μM photosensitizer upon 30 min of irradiation. Under these conditions, a low inactivation of E. coli (0.5 log) was found. However, when the cells were treated with KI, the elimination of the Gram-negative bacteria was achieved. Therefore, these polymeric structures are interesting antimicrobial photosensitizing materials for the inactivation of pathogens.

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Section: Synthesis Of Ptppf 16 -Eda and Pzntppf 16 -Edamentioning

confidence: 99%

Porphyrin Polymers Bearing N,N′-Ethylene Crosslinkers as Photosensitizers against Bacteria

et al. 2022

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“…The IEDDA click reaction was chosen for the conjugation of the glycopolymer and the PBAE due to its kinetics and orthogonality. IEDDA has been intensively and effectively employed in live-cell imaging, − diagnostics, , chemical biology, , biomaterials, − material science, , and polymer science. ,− First, the pH-responsive hydrophobic PBAE segment was synthesized via Michael addition polymerization of relatively hydrophobic monomers, namely, BDA and AP. At the final stage of the polymerization, the addition of excess BDA yielded acrylate end-capped PBAE, then, it was converted to norbornene end functional PBAE via reacting the terminal acrylates with amino norbornene (Scheme -A).…”

Section: Resultsmentioning

confidence: 99%

“…The IEDDA click reaction was chosen for the conjugation of the glycopolymer and the PBAE due to its kinetics and orthogonality. IEDDA has been intensively and effectively employed in live-cell imaging, 66 − 68 diagnostics, 69 , 70 chemical biology, 71 , 72 biomaterials, 73 − 75 material science, 76 , 77 and polymer science. 58 , 78 − 80 First, the pH-responsive hydrophobic PBAE segment was synthesized via Michael addition polymerization of relatively hydrophobic monomers, namely, BDA and AP.…”

Section: Resultsmentioning

confidence: 99%

Glycopolymer and Poly(β-amino ester)-Based Amphiphilic Block Copolymer as a Drug Carrier

Kahveci

Celebi

et al. 2022

Biomacromolecules

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Glycopolymers are synthetic macromolecules having pendant sugar moieties and widely utilized to target cancer cells. They are usually considered as a hydrophilic segment of amphiphilic block copolymers to fabricate micelles as drug carriers. A novel amphiphilic block copolymer, namely, poly(2-deoxy-2-methacrylamido-d-glucose-co-2-hydroxyethyl methacrylate)-b-poly(β-amino ester) [P(MAG-co-HEMA)-b-PBAE], with active cancer cell targeting potential and pH responsivity was prepared. Tetrazine end functional P(MAG-co-HEMA) and norbornene end functional PBAE blocks were separately synthesized through reversible addition fragmentation chain transfer polymerization and Michael addition-based poly-condensation, respectively, and followed by end-group transformation. Then, inverse electron demand Diels Alder reaction between the tetrazine and the norbornene groups was performed by simply mixing to obtain the amphiphilic block copolymer. After characterization of the block copolymer in terms of chemical structure, pH responsivity, and drug loading/releasing, pH-responsive micelles were obtained with or without doxorubicin (DOX), a model anticancer drug. The micelles exhibited a sharp protonated/deprotonated transition on tertiary amine groups around pH 6.75 and the pH-specific release of DOX below this value. Eventually, the drug delivery potential was evaluated by cytotoxicity assays on both the noncancerous human umbilical vein endothelial cell (HUVEC) cell line and glioblastoma cell line, U87-MG. While the DOX-loaded polymeric micelles were not toxic in noncancerous HUVEC cells, being toxic only to the cancer cells indicates that it is a potential specific cell targeting strategy in the treatment of cancer.

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“…A variety of MOPs derived from a porphyrin and its metal derivatives exhibit high microporosities and superior gas sorption capacities, thus making them promising candidates for gas adsorption/separation applications. In general, PMOP networks are typically fabricated using a variety of reactions, including multifunctional aromatic aldehyde with pyrrole, 15,[20][21][22] Friedel-Crafts alkylation reactions, 23,24 Diels-Alder reaction, 25 Schiff-base reactions, [26][27][28][29][30][31] metal-catalysis/oxidative coupling reactions, [32][33][34][35] the Zincke reaction, 16 and cyanate ester trimerization. 6 Compared with these strategies, aromatic multifunctional aldehydes with pyrrole have garnered attention because of their inherent advantages, including a metal-free catalysis procedure, a cost-effective monomer, and a short polymerization time.…”

Section: Introductionmentioning

confidence: 99%

A facile one-pot preparation of porphyrin-based microporous organic polymers for adsorption of carbon dioxide, ethane, and methane

et al. 2022

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Porphyrin-based covalent organic polymer by inverse electron demand Diels-Alder reaction

Cited by 6 publications

References 71 publications

Porphyrin Polymers Bearing N,N′-Ethylene Crosslinkers as Photosensitizers against Bacteria

Porphyrin Polymers Bearing N,N′-Ethylene Crosslinkers as Photosensitizers against Bacteria

Glycopolymer and Poly(β-amino ester)-Based Amphiphilic Block Copolymer as a Drug Carrier

A facile one-pot preparation of porphyrin-based microporous organic polymers for adsorption of carbon dioxide, ethane, and methane

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