Microwave-Assisted Synthesis of Triazole-Linked Phthalocyanine-Peptide Conjugates as Potential Photosensitizers for Photodynamic Therapy

Sokolova, N. V.; Schotten, Theo; Berthold, Herwig J.; Thiem, Joachim; Nenajdenko, Valentine G.

doi:10.1055/s-0032-1316845

Cited by 6 publications

(1 citation statement)

References 9 publications

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“…Hence, CuAAC has become an ideal option when considering the ligation of porphyrin photosensitizers to peptides. Indeed, researchers have used CuAAC facilitated porphyrin-peptidic chimeras for applications like PDT (Ke et al, 2012;Sokolova et al, 2013;Acherar et al, 2015;Bryden et al, 2015;Ladomenou et al, 2016;Gazzali et al, 2017), PACT (Feese et al, 2019), and tumor imaging or targeting (Bakleh et al, 2009). Ikawa et al, in 2009 synthesized a derivative of N-fused porphyrin (NFP) and conjugated this porphyrin with a nona-arginine (R9) peptide tail by "click" chemistry for the first time.…”

Section: Copper Catalyzed Alkyne-azide Cycloadditionmentioning

confidence: 99%

Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates

et al. 2021

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With potential applications in materials and especially in light-responsive biomedicine that targets cancer tissue selectively, much research has focused on developing covalent conjugation techniques to tether porphyrinoid units to various biomacromolecules. This review details the key synthetic approaches that have been employed in the recent decades to conjugate porphyrinoids with oligonucleotides and peptides/proteins. In addition, we provide succinct discussions on the subsequent applications of such hybrid systems and also give a brief overview of the rapidly progressing field of porphyrin-antibody conjugates. Since nucleic acid and peptide systems vary in structure, connectivity, functional group availability and placement, as well as stability and solubility, tailored synthetic approaches are needed for conjugating to each of these biomacromolecule types. In terms of tethering to ONs, porphyrins are typically attached by employing bioorthogonal chemistry (e.g., using phosphoramidites) that drive solid-phase ON synthesis or by conducting post-synthesis modifications and subsequent reactions (such as amide couplings, hydrazide-carbonyl reactions, and click chemistry). In contrast, peptides and proteins are typically conjugated to porphyrinoids using their native functional groups, especially the thiol and amine side chains. However, bioorthogonal reactions (e.g., Staudinger ligations, and copper or strain promoted alkyne-azide cycloadditions) that utilize de novo introduced functional groups onto peptides/proteins have seen vigorous development, especially for site-specific peptide-porphyrin tethering. While the ON-porphyrin conjugates have largely been explored for programmed nanostructure self-assembly and artificial light-harvesting applications, there are some reports of ON-porphyrin systems targeting clinically translational applications (e.g., antimicrobial biomaterials and site-specific nucleic acid cleavage). Conjugates of porphyrins with proteinaceous moieties, on the other hand, have been predominantly used for therapeutic and diagnostic applications (especially in photodynamic therapy, photodynamic antimicrobial chemotherapy, and photothermal therapy). The advancement of the field of porphyrinoid-bioconjugation chemistry from basic academic research to more clinically targeted applications require continuous fine-tuning in terms of synthetic strategies and hence there will continue to be much exciting work on porphyrinoid-biomacromolecule conjugation.

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Section: Copper Catalyzed Alkyne-azide Cycloadditionmentioning

confidence: 99%

Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates

et al. 2021

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Chiral Heteroditopic Baskets Designed from Triazolated Calixarenes and Short Peptides

Горбунов

Sokolova

Kudryashova

et al. 2016

Chemistry A European J

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Cone calix[4]arenes and calix[6]arenes bearing two, three, and four short peptide units each having two chiral carbon atoms were prepared. The syntheses were performed by using an efficient modular approach that includes the Ugi preparation of the azido-peptide followed by its reactions with the propargylated calixarenes under CuAAC (Cu(I) -catalyzed azide-alkyne cycloaddition) conditions. The three novel multitopic hosts were probed for their ability to bind metal ions by UV titration, and showed the highest complexation efficiency towards copper(II) and lead(II). These two cations possessed quite different complexation modes with copper(II) bound predominantly by multiple-triazole sites, in contrast to lead(II), which is stabilized mainly by multiple interactions with amide groups of the peptide units. Circular dichroism data for the free chiral hosts, their equimolar mixtures with copper(II) perchlorate and lead(II) perchlorate, and for tertiary mixtures of all three compounds showed the formation of mono- and binuclear complexes, or a switching behavior, depending on the structure of the host and the addition order of the cations.

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