Photoswitchable Antimicrobial Metallohelices

Changhao Liu; Mi Li; Xinyu Wang; Guoqing Li; Xue Zhao; Xuebin Wang; Siying Qin; Xuejian Zhang; Nicola J. Rogers; Xin Zhang; Qianshuo Dong; Guy J. Clarkson; Yuji Wang; Xinyi Yang; Peter Scott; Rubing Wang; Hualong Song

doi:10.1002/anie.202508959

Photoswitchable Antimicrobial Metallohelices

Changhao Liu, Mi Li, Xinyu Wang, Guoqing Li, Xue Zhao, Xuebin Wang, Siying Qin, Xuejian Zhang, Nicola J. Rogers, Xin Zhang, Qianshuo Dong, Guy J. Clarkson, Yuji Wang, Xinyi Yang, Peter Scott, Rubing Wang, Hualong Song^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

Abstract

Chiral subcomponent self-assembly is used to access optically pure, metallo-helical species based on Zn and Fe(II) and incorporating three trans-azobenzene units. UV-visible, circular dichroism and NMR spectroscopies, alongside X-ray crystallographic and DFT computational studies are used to unambiguously characterize a highly reversible stepwise photochemical transformation to an all-cis state in which structural integrity and optical purity have been retained. While the all-trans state of the water-soluble enantiomers exhibited low or moderate activity against Gram-positive strains, irradiation at 365 nm led to up to eight-fold reduction in MIC. Electron microscopy and a cell permeability assay indicate a membrane disruption mechanism; the higher activity of the photochemically-generated all-cis state is consistent with its more compact supramolecular fold.

Original language	English
Article number	e202508959
Number of pages	8
Journal	Angewandte Chemie. International Edition
Volume	64
Issue number	31
Early online date	26 May 2025
DOIs	https://doi.org/10.1002/anie.202508959
Publication status	Published - 28 Jul 2025

User-Defined Keywords

Metallohelices
Self-assembly
Photoswitch
Antimicrobial agent

Access to Document

10.1002/anie.202508959

Cite this

@article{34783bd1ddad40f698e86bee289632de,

title = "Photoswitchable Antimicrobial Metallohelices",

abstract = "Chiral subcomponent self-assembly is used to access optically pure, metallo-helical species based on Zn and Fe(II) and incorporating three trans-azobenzene units. UV-visible, circular dichroism and NMR spectroscopies, alongside X-ray crystallographic and DFT computational studies are used to unambiguously characterize a highly reversible stepwise photochemical transformation to an all-cis state in which structural integrity and optical purity have been retained. While the all-trans state of the water-soluble enantiomers exhibited low or moderate activity against Gram-positive strains, irradiation at 365 nm led to up to eight-fold reduction in MIC. Electron microscopy and a cell permeability assay indicate a membrane disruption mechanism; the higher activity of the photochemically-generated all-cis state is consistent with its more compact supramolecular fold.",

keywords = "Metallohelices, Self-assembly, Photoswitch, Antimicrobial agent",

author = "Changhao Liu and Mi Li and Xinyu Wang and Guoqing Li and Xue Zhao and Xuebin Wang and Siying Qin and Xuejian Zhang and Rogers, {Nicola J.} and Xin Zhang and Qianshuo Dong and Clarkson, {Guy J.} and Yuji Wang and Xinyi Yang and Peter Scott and Rubing Wang and Hualong Song",

note = "H.L.S. and R.B.W. thank the National Natural Science Foundation of China (No. 22307087, 82073739, and 22477140) and Beijing Natural Science Foundation (No. 7232244) for ﬁnancial support. Y.J.W. thanks Chinese Institutes for Medical Research, Beijing under the CIMR Organized Scientiﬁc Research Program (CX23YZ06) and Beijing Hospitals Authority Clinical medicine Development of special funding support (ZLRK202308). Y.X.Y. and G.Q.L. thank National Natural Science Foundation of China (No. 82330110), the National Key Research and Development Program of China (No. 2024YFC2309300), the CAMS Innovation Fund for Medical Sciences (CIFMS; 2021-I2M-1–039), and the National Science and Technology Infrastructure of China (National Pathogen Resource Center-NPRC-32) for ﬁnancial support. Publisher copyright: {\textcopyright} 2025 Wiley-VCH GmbH",

year = "2025",

month = jul,

day = "28",

doi = "10.1002/anie.202508959",

language = "English",

volume = "64",

journal = "Angewandte Chemie. International Edition",

issn = "1433-7851",

publisher = "John Wiley & Sons Ltd",

number = "31",

}

TY - JOUR

T1 - Photoswitchable Antimicrobial Metallohelices

AU - Liu, Changhao

AU - Li, Mi

AU - Wang, Xinyu

AU - Li, Guoqing

AU - Zhao, Xue

AU - Wang, Xuebin

AU - Qin, Siying

AU - Zhang, Xuejian

AU - Rogers, Nicola J.

AU - Zhang, Xin

AU - Dong, Qianshuo

AU - Clarkson, Guy J.

AU - Wang, Yuji

AU - Yang, Xinyi

AU - Scott, Peter

AU - Wang, Rubing

AU - Song, Hualong

N1 - H.L.S. and R.B.W. thank the National Natural Science Foundation of China (No. 22307087, 82073739, and 22477140) and Beijing Natural Science Foundation (No. 7232244) for ﬁnancial support. Y.J.W. thanks Chinese Institutes for Medical Research, Beijing under the CIMR Organized Scientiﬁc Research Program (CX23YZ06) and Beijing Hospitals Authority Clinical medicine Development of special funding support (ZLRK202308). Y.X.Y. and G.Q.L. thank National Natural Science Foundation of China (No. 82330110), the National Key Research and Development Program of China (No. 2024YFC2309300), the CAMS Innovation Fund for Medical Sciences (CIFMS; 2021-I2M-1–039), and the National Science and Technology Infrastructure of China (National Pathogen Resource Center-NPRC-32) for ﬁnancial support. Publisher copyright: © 2025 Wiley-VCH GmbH

PY - 2025/7/28

Y1 - 2025/7/28

N2 - Chiral subcomponent self-assembly is used to access optically pure, metallo-helical species based on Zn and Fe(II) and incorporating three trans-azobenzene units. UV-visible, circular dichroism and NMR spectroscopies, alongside X-ray crystallographic and DFT computational studies are used to unambiguously characterize a highly reversible stepwise photochemical transformation to an all-cis state in which structural integrity and optical purity have been retained. While the all-trans state of the water-soluble enantiomers exhibited low or moderate activity against Gram-positive strains, irradiation at 365 nm led to up to eight-fold reduction in MIC. Electron microscopy and a cell permeability assay indicate a membrane disruption mechanism; the higher activity of the photochemically-generated all-cis state is consistent with its more compact supramolecular fold.

AB - Chiral subcomponent self-assembly is used to access optically pure, metallo-helical species based on Zn and Fe(II) and incorporating three trans-azobenzene units. UV-visible, circular dichroism and NMR spectroscopies, alongside X-ray crystallographic and DFT computational studies are used to unambiguously characterize a highly reversible stepwise photochemical transformation to an all-cis state in which structural integrity and optical purity have been retained. While the all-trans state of the water-soluble enantiomers exhibited low or moderate activity against Gram-positive strains, irradiation at 365 nm led to up to eight-fold reduction in MIC. Electron microscopy and a cell permeability assay indicate a membrane disruption mechanism; the higher activity of the photochemically-generated all-cis state is consistent with its more compact supramolecular fold.

KW - Metallohelices

KW - Self-assembly

KW - Photoswitch

KW - Antimicrobial agent

UR - http://www.scopus.com/inward/record.url?scp=105006930392&partnerID=8YFLogxK

U2 - 10.1002/anie.202508959

DO - 10.1002/anie.202508959

M3 - Journal article

SN - 1433-7851

VL - 64

JO - Angewandte Chemie. International Edition

JF - Angewandte Chemie. International Edition

IS - 31

M1 - e202508959

ER -

Photoswitchable Antimicrobial Metallohelices

Abstract

User-Defined Keywords

Access to Document

Other files and links

Embargoed Document

Fingerprint

Cite this