Towards multiporphyrinic α‐helices with a polypeptidic backbone as system endowed with light harvesting capabilities

Solladié, Nathalie; Hamel, Arnaud; Gross, Maurice

doi:10.1002/chir.10008

Cited by 9 publications

(6 citation statements)

References 14 publications

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“…An active area of research is where porphyrin-biomacromolecule conjugates have applications in artificial light harvesting. Towards this goal, the Solladie group has developed model systems using peptides attached to multiple porphyrins prepared via amide coupling ( Solladié et al, 2000 , 2001 ; Aubert et al, 2002 ; Aziat et al, 2008 ). Their synthetic strategy has focused on in-situ carbodiimide-based activation of a carboxylic acid functionality on porphyrins to build a monomer, and subsequent oligomerization via further amide couplings.…”

Section: Porphyrin-peptide Conjugatesmentioning

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: Porphyrin-peptide Conjugatesmentioning

confidence: 99%

Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates

et al. 2021

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“…For the last few years, we have focussed on cofacial bis-porphyrin tweezers for host/guest interactions and investigated the possibility to obtain self-coordinated molecular systems with predictable spectral and redox characteristics [40]. We report here the synthesis of a di-nucleotide bearing pendant porphyrins dedicated to adopt a pre-organized coformation with face-to-face porphyrins, and capable to self-organize in a stable sandwich type complexe with bidentate base such as DABCO.…”

Section: Introductionmentioning

confidence: 98%

Pre-organized dinucleosides with pendant porphyrins for the formation of sandwich type complexes with DABCO with high association constants

Merkaš

Bouatra

Rein

et al. 2015

J. Porphyrins Phthalocyanines

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We report herein the synthesis of a dinucleotide bearing pendant porphyrins dedicated to adopt a pre-organized coformation with face-to-face porphyrins, and capable to self-organize in a stable sandwich type complexe with bidentate base such as DABCO. Earlier studies demonstrated that a peptidic linker does not provide sufficient pre-organization to enhance significantly the association constant with bidentate bases such as DABCO on the contrary of some other flexible linkers such as uridine or 2′-deoxyuridine. We document herein that the gain in stability for the formation of sandwich type host-guest complex with DABCO can be even greater when a dinucleotide linker is used. Such preorganization increases the association constants by one to two orders of magnitude when compared to the association constants of the same bidentate ligands with a reference Zn(II) porphyrin. Comparison of these results with those obtained for rigid tweezers shows a better efficiency of the flexible nucleosidic dimers. We thus document the fact that the choice of rigid spacers is not the only way to pre-organize bisporphyrins, and that some well-chosen nucleosidic linkers offer an interesting option for the synthesis of such devices. Furthermore, the chirality and enantio-purity of the nucleosidic linkers paves the way toward the selective complexation of enantio-pure bidentate guests and the resolution of racemates. tel: +33 (0)5-6133-3202, fax: +33 (0)5-6155-3003 J. Porphyrins Phthalocyanines 2015.19:535-546. Downloaded from www.worldscientific.com by PURDUE UNIVERSITY on 04/12/15. For personal use only.

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“…For the last few years, we have focused on cofacial bis-porphyrin tweezers for host–guest interactions and investigated the possibility of obtaining self-coordinated molecular systems with predictable spectral and redox characteristics [ 40 ]. We report here the synthesis of a di-nucleotide bearing pendant porphyrins dedicated to adopting a pre-organized conformation with face-to-face porphyrins, and capable of self-organizing in a stable sandwich type complex with a bidentate base such as 1,4-diazabicyclo[2.2.2]octane (DABCO).…”

Section: Introductionmentioning

confidence: 99%

Efficiency of Dinucleosides as the Backbone to Pre-Organize Multi-Porphyrins and Enhance Their Stability as Sandwich Type Complexes with DABCO

et al. 2017

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Flexible linkers such as uridine or 2′-deoxyuridine pre-organize bis-porphyrins in a face-to-face conformation, thus forming stable sandwich complexes with a bidentate base such as 1,4-diazabicyclo[2.2.2]octane (DABCO). Increased stability can be even greater when a dinucleotide linker is used. Such pre-organization increases the association constant by one to two orders of magnitude when compared to the association constant of DABCO with a reference porphyrin. Comparison with rigid tweezers shows a better efficiency of nucleosidic dimers. Thus, the choice of rigid spacers is not the only way to pre-organize bis-porphyrins, and well-chosen nucleosidic linkers offer an interesting option for the synthesis of such devices.

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Towards multiporphyrinic α‐helices with a polypeptidic backbone as system endowed with light harvesting capabilities

Abstract: Starting from a porphyrin functionalized derivative of the L-lysine, three peptides, bearing, respectively, two, four, and eight chromophores, were synthesized using an iterative synthetic strategy based on the choice of mild conditions for the deprotection steps.

Cited by 9 publications

References 14 publications

Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates

Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates

Pre-organized dinucleosides with pendant porphyrins for the formation of sandwich type complexes with DABCO with high association constants

Efficiency of Dinucleosides as the Backbone to Pre-Organize Multi-Porphyrins and Enhance Their Stability as Sandwich Type Complexes with DABCO

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