2011
DOI: 10.1007/s13361-011-0289-3
|View full text |Cite
|
Sign up to set email alerts
|

Noncovalent Complexation of Monoamine Neurotransmitters and Related Ammonium Ions by Tetramethoxy Tetraglucosylcalix[4]arene

Abstract: The noncovalent complexation of monoamine neurotransmitters and related ammonium and quaternary ammonium ions by a conformationally flexible tetramethoxy glucosylcalix[4]arene was studied by electrospray ionization Fourier transform ion cyclotron resonance (ESI-FTICR) mass spectrometry. The glucosylcalixarene exhibited highest binding affinity towards serotonin, norepinephrine, epinephrine, and dopamine. Structural properties of the guests, such as the number, location, and type of hydrogen bonding groups, len… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
3
1
1

Citation Types

0
11
0

Year Published

2012
2012
2024
2024

Publication Types

Select...
8

Relationship

1
7

Authors

Journals

citations
Cited by 17 publications
(12 citation statements)
references
References 72 publications
(96 reference statements)
0
11
0
Order By: Relevance
“…Collision‐induced dissociation (CID) experiments were used to investigate the relative gas‐phase kinetic stability of complexes, which can be expressed as E COM 50% based on a dissociation curve calculated considering the relative intensities of the adduct and of the dissociation products in the mass spectrum at different collision energy values (see Figure S29, S32, S33, S35, S36 and S38‐S43 in the Supporting Information for spectra and dissociation curves) . Since the formation of 1:1 and 2:1 ligand/DNA complexes were observed in most of the cases, the stability of the complexes with different stoichiometry was investigated.…”
Section: Chemical Structures Of Compounds 4a–4fmentioning
confidence: 99%
“…Collision‐induced dissociation (CID) experiments were used to investigate the relative gas‐phase kinetic stability of complexes, which can be expressed as E COM 50% based on a dissociation curve calculated considering the relative intensities of the adduct and of the dissociation products in the mass spectrum at different collision energy values (see Figure S29, S32, S33, S35, S36 and S38‐S43 in the Supporting Information for spectra and dissociation curves) . Since the formation of 1:1 and 2:1 ligand/DNA complexes were observed in most of the cases, the stability of the complexes with different stoichiometry was investigated.…”
Section: Chemical Structures Of Compounds 4a–4fmentioning
confidence: 99%
“…Although p-p and cation-p interactions are considered to provide an essential contribution to the observed binding selectivity for serotonin over norepinephrine, epinephrine and dopamine, the results obtained strongly indicate that the calixarene complexes are mainly stabilised by H-bonds. 55 Diglucosyl-24a and tetraglucosylthioureido calix [4]arene 24b also bind amino acids forming only 1 : 1 complexes with a marked selectivity for aromatic amino acids (stability order: Trp, Tyr c Phe > Ser, Leu, Asp). Computational studies proved the presence of H-bonds between saccharide units and the indole N atom of Trp or the phenolic hydroxyl group of Tyr, at least in the gas-phase.…”
Section: Glycocalixarenes and Multitaskingmentioning
confidence: 99%
“…31 Again, the value of E COM 50% can be directly calculated by using the relative intensities of such complexes and fragmentation products by plotting dissociation curves and using the following formula: E COM = I complex /(I complex + I dissociation products ) (Figure 4). 31,119 This parameter is of great relevance when evaluating small molecules as GQ binders, as GQ stabilization is one of the required properties for triggering biological effects. 31 The issue of complex stability can be also approached by means of ESI-MS from another perspective.…”
Section: ■ Introductionmentioning
confidence: 99%