A Modular Approach for the Synthesis of Diverse Heterobifunctional Cyanine Dyes

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Abstract

Herein, we present a straightforward synthetic route for the design and synthesis of diverse heterobifunctional cyanine 5 dyes. We optimized the workup by harnessing the pH- and functional group-dependent solubility of the asymmetric cyanine 5 dyes. Therefore, purification through chromatography is deferred until the last synthesis step. Demonstrating successful large-scale synthesis, our modular approach prevents functional group degradation by introducing them in the last synthesis step. These modifiable heterobifunctional dyes offer significant utility in advancing biological studies.

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Most cited references 55

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Simple Method for the Esterification of Carboxylic Acids

Bernhard Neises, Wolfgang Steglich (1978)

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A review of NIR dyes in cancer targeting and imaging.

Shenglin Luo, Erlong Zhang, Yongping Su … (2011)

The development of multifunctional agents for simultaneous tumor targeting and near infrared (NIR) fluorescence imaging is expected to have significant impact on future personalized oncology owing to the very low tissue autofluorescence and high tissue penetration depth in the NIR spectrum window. Cancer NIR molecular imaging relies greatly on the development of stable, highly specific and sensitive molecular probes. Organic dyes have shown promising clinical implications as non-targeting agents for optical imaging in which indocyanine green has long been implemented in clinical use. Recently, significant progress has been made on the development of unique NIR dyes with tumor targeting properties. Current ongoing design strategies have overcome some of the limitations of conventional NIR organic dyes, such as poor hydrophilicity and photostability, low quantum yield, insufficient stability in biological system, low detection sensitivity, etc. This potential is further realized with the use of these NIR dyes or NIR dye-encapsulated nanoparticles by conjugation with tumor specific ligands (such as small molecules, peptides, proteins and antibodies) for tumor targeted imaging. Very recently, natively multifunctional NIR dyes that can preferentially accumulate in tumor cells without the need of chemical conjugation to tumor targeting ligands have been developed and these dyes have shown unique optical and pharmaceutical properties for biomedical imaging with superior signal-to-background contrast index. The main focus of this article is to provide a concise overview of newly developed NIR dyes and their potential applications in cancer targeting and imaging. The development of future multifunctional agents by combining targeting, imaging and even therapeutic routes will also be discussed. We believe these newly developed multifunctional NIR dyes will broaden current concept of tumor targeted imaging and hold promise to make an important contribution to the diagnosis and therapeutics for the treatment of cancer. Copyright © 2011 Elsevier Ltd. All rights reserved.

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Targeted protein degradation by PROTACs.

Taavi Neklesa, James D Winkler, Craig M Crews (2017)

Targeted protein degradation using the PROTAC technology is emerging as a novel therapeutic method to address diseases driven by the aberrant expression of a disease-causing protein. PROTAC molecules are bifunctional small molecules that simultaneously bind a target protein and an E3-ubiquitin ligase, thus causing ubiquitination and degradation of the target protein by the proteasome. Like small molecules, PROTAC molecules possess good tissue distribution and the ability to target intracellular proteins. Herein, we highlight the advantages of protein degradation using PROTACs, and provide specific examples where degradation offers therapeutic benefit over classical enzyme inhibition. Foremost, PROTACs can degrade proteins regardless of their function. This includes the currently "undruggable" proteome, which comprises approximately 85% of all human proteins. Other beneficial aspects of protein degradation include the ability to target overexpressed and mutated proteins, as well as the potential to demonstrate prolonged pharmacodynamics effect beyond drug exposure. Lastly, due to their catalytic nature and the pre-requisite ubiquitination step, an exquisitely potent molecules with a high degree of degradation selectivity can be designed. Impressive preclinical in vitro and in vivo PROTAC data have been published, and these data have propelled the development of clinically viable PROTACs. With the molecular weight falling in the 700-1000Da range, the delivery and bioavailability of PROTACs remain the largest hurdles on the way to the clinic. Solving these issues and demonstrating proof of concept clinical data will be the focus of many labs over the next few years.

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Author and article information

Journal

Journal ID (nlm-ta): J Org Chem

Journal ID (iso-abbrev): J Org Chem

Journal ID (publisher-id): jo

Journal ID (coden): joceah

Title: The Journal of Organic Chemistry

Publisher: American Chemical Society

ISSN (Print): 0022-3263

ISSN (Electronic): 1520-6904

Publication date (Electronic): 27 February 2024

Publication date Collection: 15 March 2024

Volume: 89

Issue: 6

Pages: 3844-3856

Affiliations

[† ]Signalling Research Centres BIOSS and CIBSS, University of Freiburg , Freiburg 79104, Germany

[‡ ]Faculty of Chemistry and Pharmacy, University of Freiburg , Freiburg 79104, Germany

[§ ]Faculty of Biology, University of Freiburg , Freiburg 79104, Germany

[∥ ]Spermann Graduate School of Biology and Medicine (SGBM), University of Freiburg , Freiburg 79104, Germany

Author notes

[* ]Email: maja.koehn@ 123456bioss.uni-freiburg.de .

Author information

Corina Maller https://orcid.org/0000-0003-3271-7690

Franziska Schedel https://orcid.org/0009-0009-3473-0478

Maja Köhn https://orcid.org/0000-0001-8142-3504

Article

DOI: 10.1021/acs.joc.3c02673

PMC ID: 10949230

PubMed ID: 38413005

SO-VID: c968603b-06e3-4823-b048-b7fc8e0f133c

License:

Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works ( https://creativecommons.org/licenses/by-nc-nd/4.0/).

History

Date received : 20 November 2023

Date accepted : 13 February 2024

Date revision received : 07 February 2024

Funding

Funded by: H2020 European Research Council, doi 10.13039/100010663;

Award ID: 865119

Funded by: Deutsche Forschungsgemeinschaft, doi 10.13039/501100001659;

Award ID: EXC-2189 390939984

Funded by: Deutsche Forschungsgemeinschaft, doi 10.13039/501100001659;

Award ID: EXC 294

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document-id-old-9 jo3c02673

document-id-new-14 jo3c02673

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ScienceOpen disciplines: Organic & Biomolecular chemistry

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ScienceOpen disciplines: Organic & Biomolecular chemistry

A Modular Approach for the Synthesis of Diverse Heterobifunctional Cyanine Dyes

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Abstract

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Most cited references 55

Simple Method for the Esterification of Carboxylic Acids

A review of NIR dyes in cancer targeting and imaging.

Targeted protein degradation by PROTACs.

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