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Hydrogen bond dynamics of histamine monocation in aqueous solution: Car-Parrinello molecular dynamics and vibrational spectroscopy study.
J Phys Chem B. 2011 May 19; 115(19):5999-6010.JP

Abstract

Hydration of histamine was examined by infrared spectroscopy and Car-Parrinello molecular dynamics simulation. Histamine is a neurotransmitter and inflammation mediator, which at physiological pH conditions is present mainly in monocationic form. Our focus was on the part of vibrational spectra that corresponds to histamine N-H stretching, since these degrees of freedom are essential for its interactions with either water molecules or transporters and receptors. Assignment of the experimental spectra revealed a broad feature between 3350 and 2300 cm(-1), being centered at 2950 cm(-1), which includes a mixed contribution from the ring N-H and the aminoethyl N-H stretching vibrations. Computational analysis was performed in two ways: first, by making Fourier transformation on the autocorrelation function of all four N-H bond distances recorded during CPMD run, and second, and most importantly, by incorporating quantum effects through applying an a posteriori quantization of all N-H stretching motions utilizing our snapshot analysis of the fluctuating proton potential. The one-dimensional vibrational Schrödinger equation was solved numerically for each snapshot, and the N-H stretching envelopes were calculated as a superposition of the 0→1 transitions. The agreement with the experiment was much better in the case of the second approach. Our calculations clearly demonstrated that the ring amino group absorbs at higher frequencies than the remaining three amino N-H protons of the protonated aminoethyl group, implying that the chemical bonding in the former group is stronger than in the three amino N-H bonds, thus forming weaker hydrogen bonding with the surrounding solvent molecules. In this way the results of the simulation complemented the experimental spectrum that cannot distinguish between the two sets of protons. The effects of deuteration were also considered. The resulting N-D absorption is narrower and red-shifted. The presented methodology is of general applicability to strongly correlated systems, and it is particularly tuned to provide computational support to vibrational spectroscopy. Perspectives are given for its future applications in computational studies of tunneling in enzyme reactive centers and for receptor activation.

Authors+Show Affiliations

National Institute of Chemistry, Hajdrihova 19, SI-1000 Ljubljana, Slovenia.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21517054

Citation

Stare, Jernej, et al. "Hydrogen Bond Dynamics of Histamine Monocation in Aqueous Solution: Car-Parrinello Molecular Dynamics and Vibrational Spectroscopy Study." The Journal of Physical Chemistry. B, vol. 115, no. 19, 2011, pp. 5999-6010.
Stare J, Mavri J, Grdadolnik J, et al. Hydrogen bond dynamics of histamine monocation in aqueous solution: Car-Parrinello molecular dynamics and vibrational spectroscopy study. J Phys Chem B. 2011;115(19):5999-6010.
Stare, J., Mavri, J., Grdadolnik, J., Zidar, J., Maksić, Z. B., & Vianello, R. (2011). Hydrogen bond dynamics of histamine monocation in aqueous solution: Car-Parrinello molecular dynamics and vibrational spectroscopy study. The Journal of Physical Chemistry. B, 115(19), 5999-6010. https://doi.org/10.1021/jp111175e
Stare J, et al. Hydrogen Bond Dynamics of Histamine Monocation in Aqueous Solution: Car-Parrinello Molecular Dynamics and Vibrational Spectroscopy Study. J Phys Chem B. 2011 May 19;115(19):5999-6010. PubMed PMID: 21517054.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Hydrogen bond dynamics of histamine monocation in aqueous solution: Car-Parrinello molecular dynamics and vibrational spectroscopy study. AU - Stare,Jernej, AU - Mavri,Janez, AU - Grdadolnik,Jože, AU - Zidar,Jernej, AU - Maksić,Zvonimir B, AU - Vianello,Robert, Y1 - 2011/04/25/ PY - 2011/4/27/entrez PY - 2011/4/27/pubmed PY - 2011/9/21/medline SP - 5999 EP - 6010 JF - The journal of physical chemistry. B JO - J Phys Chem B VL - 115 IS - 19 N2 - Hydration of histamine was examined by infrared spectroscopy and Car-Parrinello molecular dynamics simulation. Histamine is a neurotransmitter and inflammation mediator, which at physiological pH conditions is present mainly in monocationic form. Our focus was on the part of vibrational spectra that corresponds to histamine N-H stretching, since these degrees of freedom are essential for its interactions with either water molecules or transporters and receptors. Assignment of the experimental spectra revealed a broad feature between 3350 and 2300 cm(-1), being centered at 2950 cm(-1), which includes a mixed contribution from the ring N-H and the aminoethyl N-H stretching vibrations. Computational analysis was performed in two ways: first, by making Fourier transformation on the autocorrelation function of all four N-H bond distances recorded during CPMD run, and second, and most importantly, by incorporating quantum effects through applying an a posteriori quantization of all N-H stretching motions utilizing our snapshot analysis of the fluctuating proton potential. The one-dimensional vibrational Schrödinger equation was solved numerically for each snapshot, and the N-H stretching envelopes were calculated as a superposition of the 0→1 transitions. The agreement with the experiment was much better in the case of the second approach. Our calculations clearly demonstrated that the ring amino group absorbs at higher frequencies than the remaining three amino N-H protons of the protonated aminoethyl group, implying that the chemical bonding in the former group is stronger than in the three amino N-H bonds, thus forming weaker hydrogen bonding with the surrounding solvent molecules. In this way the results of the simulation complemented the experimental spectrum that cannot distinguish between the two sets of protons. The effects of deuteration were also considered. The resulting N-D absorption is narrower and red-shifted. The presented methodology is of general applicability to strongly correlated systems, and it is particularly tuned to provide computational support to vibrational spectroscopy. Perspectives are given for its future applications in computational studies of tunneling in enzyme reactive centers and for receptor activation. SN - 1520-5207 UR - https://www.unboundmedicine.com/medline/citation/21517054/Hydrogen_bond_dynamics_of_histamine_monocation_in_aqueous_solution:_Car_Parrinello_molecular_dynamics_and_vibrational_spectroscopy_study_ L2 - https://dx.doi.org/10.1021/jp111175e DB - PRIME DP - Unbound Medicine ER -