Tautomeric equilibrium and spectroscopic properties of 8-azaguanine revealed by quantum chemistry methods.
8-Azaguanine
Nucleobases
Tautomeric equilibrium
Vertical transition energies
Journal
European biophysics journal : EBJ
ISSN: 1432-1017
Titre abrégé: Eur Biophys J
Pays: Germany
ID NLM: 8409413
Informations de publication
Date de publication:
Oct 2023
Oct 2023
Historique:
received:
17
02
2023
accepted:
11
07
2023
revised:
05
07
2023
medline:
1
11
2023
pubmed:
29
7
2023
entrez:
28
7
2023
Statut:
ppublish
Résumé
8-azaguanine is a triazolopyrimidine nucleobase analog possessing potent antibacterial and antitumor activities, and it has been implicated as a lead molecule in cancer and malaria therapy. Its intrinsic fluorescence properties can be utilized for monitoring its interactions with biological polymers like proteins or nucleic acids. In order to better understand these interactions, it is important to know the tautomeric equilibrium of this compound. In this work, the tautomeric equilibrium of all natural neutral and anionic compound forms (except highly improbable imino-enol tautomers) as well as their methyl derivatives and ribosides was revealed by quantum chemistry methods. It was shown that, as expected, tautomers protonated at positions 1 and 9 dominate neutral forms both in gas phase and in aqueous solution. 8-azaguanines methylated at any position of the triazole ring are protonated at position 1. The computed vertical absorption and emission energies are in very good agreement with the experimental data. They confirm the validity of the assumption that replacing the proton with the methyl group does not significantly change the positions of absorption and fluorescence peaks.
Identifiants
pubmed: 37507591
doi: 10.1007/s00249-023-01672-x
pii: 10.1007/s00249-023-01672-x
pmc: PMC10618388
doi:
Substances chimiques
Azaguanine
Q150359I72
Protons
0
Proteins
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
545-557Informations de copyright
© 2023. The Author(s).
Références
J Phys Chem B. 2009 Apr 30;113(17):6140-50
pubmed: 19351126
Phys Rev B Condens Matter. 1988 Jan 15;37(2):785-789
pubmed: 9944570
Mol Biosyst. 2014 Nov;10(11):2756-74
pubmed: 25124808
Biochem J. 1962 Nov;85:313-9
pubmed: 13970782
Neurocirugia (Astur). 2011 Jun;22(3):245-50
pubmed: 21743945
Chem Rev. 2005 Aug;105(8):2999-3093
pubmed: 16092826
J Chem Phys. 2007 Feb 28;126(8):084108
pubmed: 17343441
J Phys Chem A. 2007 Aug 16;111(32):8007-12
pubmed: 17637049
J Chem Inf Model. 2020 Mar 23;60(3):1595-1606
pubmed: 31944095
Biochem Pharmacol. 1982 Aug 1;31(15):2505-11
pubmed: 7126262
Z Naturforsch C J Biosci. 2004 Sep-Oct;59(9-10):713-25
pubmed: 15540606
J Chem Phys. 2012 Mar 14;136(10):104101
pubmed: 22423822
Science. 1971 Feb 19;171(3972):675-7
pubmed: 5540307
J Am Chem Soc. 2006 Jun 7;128(22):7320-8
pubmed: 16734487
Adv Enzyme Regul. 1982;20:351-73
pubmed: 7113801
J Am Chem Soc. 2004 Jan 14;126(1):154-64
pubmed: 14709079
Annu Rev Phys Chem. 2012;63:287-323
pubmed: 22242728
Z Naturforsch C Biosci. 1976 Jul-Aug;31(7-8):361-70
pubmed: 8892
Nucleosides Nucleotides Nucleic Acids. 2017 Apr 3;36(4):256-274
pubmed: 28332916
Nat Commun. 2020 Mar 31;11(1):1614
pubmed: 32235841
Mol Pharmacol. 1965 Sep;1(2):113-25
pubmed: 5835693
Top Curr Chem. 2016;368:347-75
pubmed: 26003564
J Comput Chem. 2004 Jan 15;25(1):83-99
pubmed: 14634996
J Am Chem Soc. 2007 Mar 21;129(11):3426-32
pubmed: 17326637
J Chem Phys. 2008 Apr 7;128(13):134110
pubmed: 18397056
J Am Chem Soc. 1975 Aug 6;97(16):4636-42
pubmed: 1159226
Front Bioeng Biotechnol. 2020 Nov 05;8:603514
pubmed: 33251204
J Biomol Struct Dyn. 2014;32(1):27-35
pubmed: 23384120
J Mol Model. 2020 Apr 21;26(5):107
pubmed: 32318882
J Med Chem. 2006 Dec 14;49(25):7479-86
pubmed: 17149876
J Antibiot (Tokyo). 1961 Nov;14:340-2
pubmed: 14036815
Cancer Res. 1975 Oct;35(10):2872-8
pubmed: 1157053
Biophys Chem. 1995 Aug;55(3):231-7
pubmed: 17020869
Eur Biophys J. 2004 Aug;33(5):377-85
pubmed: 14655027
Phys Rev A Gen Phys. 1988 Sep 15;38(6):3098-3100
pubmed: 9900728
J Phys Chem A. 2019 Apr 11;123(14):3109-3120
pubmed: 30901221
J Chem Theory Comput. 2013 Apr 9;9(4):2072-82
pubmed: 26583553
J Phys Chem A. 2009 Nov 5;113(44):12088-93
pubmed: 19795828
Phys Rev Lett. 1996 Oct 28;77(18):3865-3868
pubmed: 10062328
J Chem Theory Comput. 2020 Apr 14;16(4):2766-2777
pubmed: 32125859
J Am Chem Soc. 2003 Jun 25;125(25):7678-88
pubmed: 12812509
J Chem Theory Comput. 2009 Apr 14;5(4):949-61
pubmed: 26609604
Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):459-64
pubmed: 16247971
J Chem Theory Comput. 2012 Jul 10;8(7):2359-72
pubmed: 26588969
J Phys Chem A. 2013 Feb 21;117(7):1548-59
pubmed: 23347296