摘要
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).
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).
引文
[1]F.A.Beland,W.R.Benson,P.W.Mellick,et al.,Food Chem.Toxicol.43(2005)1-19.
[2]S.W.Cha,H.K.Gu,K.P.Lee,et al.,Toxicol.Lett.115(2000)173-181.
[3]X.Zhao,G.Du,H.Zou,et al.,Trends Food Sci.Technol.32(2013)97-107.
[4]Z.Ajtony,N.Szoboszlai,L.Bencs,et al.,Food Chem.141(2013)1301-1305.
[5]R.Baan,K.Straif,Y.Grosse,et al.,Lancet Oncol.8(2007)292-293.
[6]J.V.Weber,V.I.Sharypov,Environ.Chem.Lett.7(2009)233-247.
[7]A.Armnda,O.Beatriz,H.Paulo,Anal.Bioanal.Chem.382(2005)498-503.
[8]http://down.foodmate.net/standard/sort/4/36211.html.
[9]Z.H.Jiao,Y.C.Dong,Q.H.Chen,Compr.Rev.Food Sci.Food 13(2014)611-626.
[10]B.D.Smith,Synthetic Receptors for Biomolecules:Design Principles and Applications,The Royal Society of Chemistry,Cambridge,U.K,2015.
[11]H.H.L.Lee,J.W.Lee,Y.Jang,et al.,Angew.Chem.Int.Ed.55(2016)8249-8253.
[12]A.P.Davis,S.Kubik,A.D.Cort,Org.Biomol.Chem.13(2015)2499-2500.
[13]Y.Zhang,Y.Fang,N.Z.Zhang,et al.,Chin.Chem.Lett.27(2016)1673-1678.
[14]X.Nie,X.Ning,Y.Y.Zhao,et al.,Chin.Chem.Lett.28(2017)619-624.
[15]W.Wu,S.Song,X.W.Cui,et al.,Chin.Chem.Lett.29(2018)95-98.
[16]M.G.Zhou,S.Y.Qin,Z.Z.Feng,et al.,Chin.Chem.Lett.29(2018)973-976.
[17]F.Jia,Z.F.He,L.P.Yang,et al.,Chem.Sci.6(2015)6731-6738.
[18]L.P.Yang,S.B.Lu,A.Valkonen,et al.,Beilstein J.Org.Chem.14(2018)1570-1577.
[19]Z.F.He,G.Ye,W.Jiang,Chem.-Eur.J.21(2015)3005-3012.
[20]G.Huang,A.Valkonen,K.Rissanen,W.Jiang,Chem.Commun.52(2016)9078-9081.
[21]Y.L.Ma,H.Ke,A.Valkonen,et al.,Angew.Chem.Int.Ed.57(2018)709-713.
[22]J.S.Cui,Q.K.Ba,H.Ke,et al.,Angew.Chem.Int.Ed.57(2018)7809-7814.
[23]G.B.Huang,W.E.Liu,A.Valkonen,et al.,Chin.Chem.Lett.29(2018)91-94.
[24]H.X.Chai,L.P.Yang,H.Ke,et al.,Chem.Commun.54(2018)7677-7680.
[25]G.B.Huang,S.H.Wang,H.Ke,et al.,J.Am.Chem.Soc.138(2016)14550-14553.
[26]L.L.Wang,Z.Chen,W.E.Liu,et al.,J.Am.Chem.Soc.139(2017)8436-8439.
[27]H.Yao,H.Ke,X.B.Zhang,et al.,J.Am.Chem.Soc.140(2018)13466-13477.