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Keywords:

  • amines;
  • coordination;
  • macrocycles;
  • molecular recognition;
  • supramolecular chemistry

Abstract

Synthesis and characterization of three new polyamine receptors, composed of a cyclam unit (cyclam=1,4,8,11-tetraazacyclotetradecane) linked by a 2,6-dimethylpyridinyl spacer to the linear polyamines 1,4,8,11-tetraazaundecane (L1py), 1,4,7-triazaheptane (L2py), and to a quaternary ammonium group (L3 py+), are reported. All receptors form highly charged polyammonium cations at neutral pH, suitable for anion recognition studies. ATP recognition was analyzed by using potentiometric, calorimetric, 1H and 31P NMR measurements in aqueous solution. All receptors form 1:1 adducts with ATP in aqueous solution, stabilized by charge–charge and hydrogen-bonding interactions between their ammonium groups and the anionic triphosphate chain of ATP. The binding ability of the three receptors for ATP increases in the order of L3 py+<L2py<L1py. These adducts are stabilized by largely favourable entropic contributions, probably due to the large desolvation of the host and guest species upon complexation. The sequence observed for the binding affinity is explained in terms of the different ability of the three receptors to wrap around the phosphate chain of ATP.

Featured Compounds

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  1. 1 - 13
Compound L1py
Molecular Weight:463.7062
Molecular Formula:C24H49N9
InChIKey:SRFXMSJACLHDTK-UHFFFAOYSA-N
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Compound L2py
Molecular Weight:406.6118
Molecular Formula:C21H42N8
InChIKey:LNZRRCDEOLEDDE-UHFFFAOYSA-N
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Compound L3py
Molecular Weight:405.6436
Molecular Formula:C23H45N6
InChIKey:JWYNBOISLDAXAZ-UHFFFAOYSA-N
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Compound 1
Molecular Weight:244.2737
Molecular Formula:C10H21N4OP
InChIKey:UIOLWVCJNVYXRU-UHFFFAOYSA-N
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Compound 2
Molecular Weight:176.043
Molecular Formula:C7H7Cl2N
InChIKey:IWQNFYRJSVJWQA-UHFFFAOYSA-N
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Compound 3
Molecular Weight:383.856
Molecular Formula:C17H27ClN5OP
InChIKey:KSTGXZOWLCOYEX-UHFFFAOYSA-N
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Compound 4
Molecular Weight:182.266
Molecular Formula:C9H18N4
InChIKey:DAVLXWLUGZJMOK-KYZUINATSA-N
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Compound 5
Molecular Weight:295.1823
Molecular Formula:C8H11F6N3O2
InChIKey:RUXQXYHBGKXTHQ-UHFFFAOYSA-N
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Compound 6a
Molecular Weight:529.661
Molecular Formula:C26H44N9OP
InChIKey:UIPVUIHCLOMUSF-GWGYQYQUSA-N
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Compound 6b
Molecular Weight:507.6555
Molecular Formula:C24H46N9OP
InChIKey:UOVYVTGFJWSQPX-UHFFFAOYSA-N
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Compound 7a
Molecular Weight:642.5773
Molecular Formula:C25H37F6N8O3P
InChIKey:RYMRMFOQCBFXIA-UHFFFAOYSA-N
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Compound 7b
Molecular Weight:450.5611
Molecular Formula:C21H39N8OP
InChIKey:PXPOAROGDKRRLJ-UHFFFAOYSA-N
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Compound 8
Molecular Weight:485.046
Molecular Formula:C23H42ClN6OP
InChIKey:LEQKSPZMWMGSGG-UHFFFAOYSA-M
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  1. 1 - 13