Design and Synthesis of Near-Infrared Mechanically Interlocked Molecules for Specific Targeting of Mitochondria

Rabi Sankar Das; Pranab Chandra Saha; Nayim Sepay; Ayan Mukherjee; Sudipta Chatterjee; Samit Guha

doi:10.1021/acs.orglett.0c01922

Design and Synthesis of Near-Infrared Mechanically Interlocked Molecules for Specific Targeting of Mitochondria

Rabi Sankar Das, Pranab Chandra Saha, Nayim Sepay, Ayan Mukherjee, Sudipta Chatterjee, Samit Guha

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

The entrapment of squaraine (SQ) within a molecular container to form rotaxane has been shown to improve the dye stability and the fluorescence proficiency inside the mitochondria. The macrocycle provides shelter and protects the near-infrared (NIR) SQ chromophore from nucleophilic attacks made by the exposed thiol of Cys-containing mitochondrial proteins and mitochondrial glutathione. Herein a microwave-assisted template-directed clipping reaction on low-loading 2-chlorotrityl chloride resin is used to develop an NIR unsymmetrical squaraine rotaxane in high quantum yield.

Original language	English
Pages (from-to)	5839-5843
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.0c01922
State	Published - 7 Aug 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
Copyright © 2020 American Chemical Society.

Funding

This work is supported by DST-SERB, Govt. of India (file no. ECR/2017/001405). This work is supported by DST-SERB Govt. of India (file no. ECR/2017/001405).

Funders	Funder number
DST-SERB	ECR/2017/001405

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10.1021/acs.orglett.0c01922

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abstract = "The entrapment of squaraine (SQ) within a molecular container to form rotaxane has been shown to improve the dye stability and the fluorescence proficiency inside the mitochondria. The macrocycle provides shelter and protects the near-infrared (NIR) SQ chromophore from nucleophilic attacks made by the exposed thiol of Cys-containing mitochondrial proteins and mitochondrial glutathione. Herein a microwave-assisted template-directed clipping reaction on low-loading 2-chlorotrityl chloride resin is used to develop an NIR unsymmetrical squaraine rotaxane in high quantum yield.",

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AU - Saha, Pranab Chandra

AU - Sepay, Nayim

AU - Mukherjee, Ayan

AU - Chatterjee, Sudipta

AU - Guha, Samit

PY - 2020/8/7

Y1 - 2020/8/7

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AB - The entrapment of squaraine (SQ) within a molecular container to form rotaxane has been shown to improve the dye stability and the fluorescence proficiency inside the mitochondria. The macrocycle provides shelter and protects the near-infrared (NIR) SQ chromophore from nucleophilic attacks made by the exposed thiol of Cys-containing mitochondrial proteins and mitochondrial glutathione. Herein a microwave-assisted template-directed clipping reaction on low-loading 2-chlorotrityl chloride resin is used to develop an NIR unsymmetrical squaraine rotaxane in high quantum yield.

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Design and Synthesis of Near-Infrared Mechanically Interlocked Molecules for Specific Targeting of Mitochondria

Abstract

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