Molecular recognition and fluorescent sensing of Group 2A carcinogen-urethane was achieved in aqueous solution. The molecular sensors are the endo-functionalized molecular tubes with amide protons in the hydrophobic c...Molecular recognition and fluorescent sensing of Group 2A carcinogen-urethane was achieved in aqueous solution. The molecular sensors are the endo-functionalized molecular tubes with amide protons in the hydrophobic cavity.~1H NMR, fluorescence, and ITC titrations and single crystal X-ray crystallography reveal the binding stoichiometry, the binding affinities, and the driving forces. The binding is mainly driven by the hydrophobic effect through releasing the "high-energy" cavity water with minor contribution from hydrogen bonding. In addition, the syn-configured molecular tube was found to be a good fluorescent sensor for urethane in water(concentration range: 6.2–60 mmol/L) and in beer(concentration range: 22.9–60 mmol/L).展开更多
Molecular recognition in water is the basis of numerous biological functions.The key for efficient and selective recognition of an organic drug molecule is to bind both its polar and nonpolar groups.This is achieved b...Molecular recognition in water is the basis of numerous biological functions.The key for efficient and selective recognition of an organic drug molecule is to bind both its polar and nonpolar groups.This is achieved by bioreceptors for which specific noncovalent interactions are efficiently used in a hydrophobic pocket.In contrast,most synthetic receptors cannot efficiently bind the neutral,polar groups of drug molecules and,thus,often exhibit poor binding selectivity and affinity.In this research,we report a systematic study on the binding behaviors of three types of macrocyclic hosts(amide naphthotubes,cucurbit[7]uril,andβ-cyclodextrin)to 18 model compounds and 13 drug molecules.Our results show that the high desolvation penalty of polar groups of guests is the reason for the relatively low binding affinity of cucurbit[7]uril andβ-cyclodextrin.However,amide naphthotubes with a biomimetic cavity bind efficiently and selectively to organic guests through hydrophobic effects and hydrogen bonding.Drug molecules with multiple polar groups can be better accommodated by these naphthotubes.The anti-configured naphthotube show good biocompatibility according to preliminary cell experiments and is capable of enhancing the water solubility of two poorly soluble drug molecules.Therefore,they may have practical applications in pharmaceutical sciences.展开更多
基金financially supported by the National Natural Science Foundation of China (Nos. 21572097, 21772083 and 21822104)the SZSTI (Nos. JCYJ20170307105848463 and KQJSCX20170728162528382)
文摘Molecular recognition and fluorescent sensing of Group 2A carcinogen-urethane was achieved in aqueous solution. The molecular sensors are the endo-functionalized molecular tubes with amide protons in the hydrophobic cavity.~1H NMR, fluorescence, and ITC titrations and single crystal X-ray crystallography reveal the binding stoichiometry, the binding affinities, and the driving forces. The binding is mainly driven by the hydrophobic effect through releasing the "high-energy" cavity water with minor contribution from hydrogen bonding. In addition, the syn-configured molecular tube was found to be a good fluorescent sensor for urethane in water(concentration range: 6.2–60 mmol/L) and in beer(concentration range: 22.9–60 mmol/L).
基金This research was financially supported by the National Natural Science Foundation of China(nos.21772083 and 21822104)the Shenzhen Special Funds(KQJSCX20170728162528382 and JCYJ20180504165810828)+3 种基金the Guangdong Provincial Key Laboratory of Catalysis(2020B121201002)the China Postdoctoral Science Foundation(grant no.2019M652183)the University of Macao(MYRG2019-00059-ICMS)the Shenzhen Nobel Prize Scientists Laboratory Project(C17213101)。
文摘Molecular recognition in water is the basis of numerous biological functions.The key for efficient and selective recognition of an organic drug molecule is to bind both its polar and nonpolar groups.This is achieved by bioreceptors for which specific noncovalent interactions are efficiently used in a hydrophobic pocket.In contrast,most synthetic receptors cannot efficiently bind the neutral,polar groups of drug molecules and,thus,often exhibit poor binding selectivity and affinity.In this research,we report a systematic study on the binding behaviors of three types of macrocyclic hosts(amide naphthotubes,cucurbit[7]uril,andβ-cyclodextrin)to 18 model compounds and 13 drug molecules.Our results show that the high desolvation penalty of polar groups of guests is the reason for the relatively low binding affinity of cucurbit[7]uril andβ-cyclodextrin.However,amide naphthotubes with a biomimetic cavity bind efficiently and selectively to organic guests through hydrophobic effects and hydrogen bonding.Drug molecules with multiple polar groups can be better accommodated by these naphthotubes.The anti-configured naphthotube show good biocompatibility according to preliminary cell experiments and is capable of enhancing the water solubility of two poorly soluble drug molecules.Therefore,they may have practical applications in pharmaceutical sciences.
