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Aromatic pentaamide macrocycles bind anions with high affinity for transport across biomembranes.
Cao, Ruikai; Rossdeutcher, Robert B; Zhong, Yulong; Shen, Yi; Miller, Daniel P; Sobiech, Thomas A; Wu, Xiangxiang; Buitrago, Laura Sánchez; Ramcharan, Karishma; Gutay, Mark I; Figueira, Miriam Frankenthal; Luthra, Pia; Zurek, Eva; Szyperski, Thomas; Button, Brian; Shao, Zhifeng; Gong, Bing.
Afiliação
  • Cao R; Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY, USA.
  • Rossdeutcher RB; Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY, USA.
  • Zhong Y; Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY, USA.
  • Shen Y; State Key Laboratory of Systems Medicine for Cancer, School of Biomedical Engineering, Shanghai Jiao Tong University, Shanghai, China.
  • Miller DP; Department of Chemistry, Hofstra University, Hempstead, NY, USA.
  • Sobiech TA; Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY, USA.
  • Wu X; Academy of Chinese Medical Science, Henan University of Chinese Medicine, Zhengzhou, Henan, China.
  • Buitrago LS; Department of Chemistry, Hofstra University, Hempstead, NY, USA.
  • Ramcharan K; Department of Chemistry, Hofstra University, Hempstead, NY, USA.
  • Gutay MI; Marsico Lung Institute, University of North Carolina School of Medicine, Chapel Hill, NC, USA.
  • Figueira MF; Marsico Lung Institute, University of North Carolina School of Medicine, Chapel Hill, NC, USA.
  • Luthra P; Department of Chemistry, Hofstra University, Hempstead, NY, USA.
  • Zurek E; Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY, USA.
  • Szyperski T; Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY, USA.
  • Button B; Marsico Lung Institute, University of North Carolina School of Medicine, Chapel Hill, NC, USA.
  • Shao Z; State Key Laboratory of Systems Medicine for Cancer, School of Biomedical Engineering, Shanghai Jiao Tong University, Shanghai, China. zfshao@sjtu.edu.cn.
  • Gong B; Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY, USA. bgong@buffalo.edu.
Nat Chem ; 15(11): 1559-1568, 2023 Nov.
Article em En | MEDLINE | ID: mdl-37814114
ABSTRACT
The convergent positioning of functional groups in biomacromolecules leads to good binding, catalytic and transport capabilities. Synthetic frameworks capable of convergently locking functional groups with minimized conformational uncertainty-leading to similar properties-are highly desirable but rare. Here we report C5-symmetric aromatic pentaamide macrocycles synthesized in one pot from the corresponding monomers. Their crystal structures reveal a star-shaped, fully constrained backbone that causes ten alternating NH/CH hydrogen-bond donors and five large amide dipoles to orient towards the centre of the macrocycle. With a highly electropositive cavity in a high-energy unbound state, the macrocycles bind anions in a 11 stoichiometry in solution, with high affinity for halides and very high affinity for oxoanions. We demonstrate that such macrocycles are able to transport anions across lipid bilayers with a high chloride selectivity and restore the depleted airway surface liquid of cystic fibrosis airway cell cultures.
Assuntos

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Compostos Macrocíclicos Idioma: En Ano de publicação: 2023 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Compostos Macrocíclicos Idioma: En Ano de publicação: 2023 Tipo de documento: Article