Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates

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 app...

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Autores principales:	Pravin Pathak, Mohammad Amin Zarandi, Xiao Zhou, Janarthanan Jayawickramarajah
Formato:	article
Lenguaje:	EN
Publicado:	Frontiers Media S.A. 2021
Materias:	bioconjugation porphyrin bioconjugates DNA-porphyrin peptide-porphyrin protein-porphyrin antibody-porphyrin Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/d4dde2fb224c4f92aaaf0eed2271190f
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spelling	oai:doaj.org-article:d4dde2fb224c4f92aaaf0eed2271190f2021-11-08T07:22:04ZSynthesis and Applications of Porphyrin-Biomacromolecule Conjugates2296-264610.3389/fchem.2021.764137https://doaj.org/article/d4dde2fb224c4f92aaaf0eed2271190f2021-11-01T00:00:00Zhttps://www.frontiersin.org/articles/10.3389/fchem.2021.764137/fullhttps://doaj.org/toc/2296-2646With 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.Pravin PathakMohammad Amin ZarandiXiao ZhouJanarthanan JayawickramarajahJanarthanan JayawickramarajahFrontiers Media S.A.articlebioconjugationporphyrin bioconjugatesDNA-porphyrinpeptide-porphyrinprotein-porphyrinantibody-porphyrinChemistryQD1-999ENFrontiers in Chemistry, Vol 9 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	bioconjugation porphyrin bioconjugates DNA-porphyrin peptide-porphyrin protein-porphyrin antibody-porphyrin Chemistry QD1-999
spellingShingle	bioconjugation porphyrin bioconjugates DNA-porphyrin peptide-porphyrin protein-porphyrin antibody-porphyrin Chemistry QD1-999 Pravin Pathak Mohammad Amin Zarandi Xiao Zhou Janarthanan Jayawickramarajah Janarthanan Jayawickramarajah Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates
description	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.
format	article
author	Pravin Pathak Mohammad Amin Zarandi Xiao Zhou Janarthanan Jayawickramarajah Janarthanan Jayawickramarajah
author_facet	Pravin Pathak Mohammad Amin Zarandi Xiao Zhou Janarthanan Jayawickramarajah Janarthanan Jayawickramarajah
author_sort	Pravin Pathak
title	Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates
title_short	Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates
title_full	Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates
title_fullStr	Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates
title_full_unstemmed	Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates
title_sort	synthesis and applications of porphyrin-biomacromolecule conjugates
publisher	Frontiers Media S.A.
publishDate	2021
url	https://doaj.org/article/d4dde2fb224c4f92aaaf0eed2271190f
work_keys_str_mv	AT pravinpathak synthesisandapplicationsofporphyrinbiomacromoleculeconjugates AT mohammadaminzarandi synthesisandapplicationsofporphyrinbiomacromoleculeconjugates AT xiaozhou synthesisandapplicationsofporphyrinbiomacromoleculeconjugates AT janarthananjayawickramarajah synthesisandapplicationsofporphyrinbiomacromoleculeconjugates AT janarthananjayawickramarajah synthesisandapplicationsofporphyrinbiomacromoleculeconjugates
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Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates

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