3-Substituted xanthines as promising candidates for quadruplex formation: Computational, synthetic and analytical studies

János Szolomájer; Gábor Paragi; Gyula Batta; Célia Fonseca Guerra; F. Matthias Bickelhaupt; Zoltán Kele; Petra Pádár; Zoltán Kupihár; Lajos Kovács

doi:10.1039/c0nj00612b

3-Substituted xanthines as promising candidates for quadruplex formation: Computational, synthetic and analytical studies

János Szolomájer
, Gábor Paragi
, Gyula Batta
, Célia Fonseca Guerra
, F. Matthias Bickelhaupt
, Zoltán Kele
, Petra Pádár
, Zoltán Kupihár
, Lajos Kovács

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

Our computational studies suggest that 3-substituted xanthines are good candidates for tetrad and quadruplex structures. 3-Methylxanthine (3MX) has been synthesized from 7-benzylxanthine, and the existence of tetrameric and octameric aggregates of 3MX with NH₄⁺, Na⁺ and K⁺ ions in the gas phase (MS) and in DMSO-d₆ solution (NMR) has been observed. The "internal" H-bonds (N1H⋯O6) are stronger than the "external" ones (N7H⋯O2) in these clusters (NMR).

Original language	English
Pages (from-to)	476-482
Number of pages	7
Journal	New Journal of Chemistry
Volume	35
Issue number	2
DOIs	https://doi.org/10.1039/c0nj00612b
Publication status	Published - Feb 2011
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Materials Chemistry

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10.1039/c0nj00612b

Cite this

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title = "3-Substituted xanthines as promising candidates for quadruplex formation: Computational, synthetic and analytical studies",

abstract = "Our computational studies suggest that 3-substituted xanthines are good candidates for tetrad and quadruplex structures. 3-Methylxanthine (3MX) has been synthesized from 7-benzylxanthine, and the existence of tetrameric and octameric aggregates of 3MX with NH4+, Na+ and K+ ions in the gas phase (MS) and in DMSO-d6 solution (NMR) has been observed. The {"}internal{"} H-bonds (N1H⋯O6) are stronger than the {"}external{"} ones (N7H⋯O2) in these clusters (NMR).",

author = "J{\'a}nos Szolom{\'a}jer and G{\'a}bor Paragi and Gyula Batta and Guerra, \{C{\'e}lia Fonseca\} and Bickelhaupt, \{F. Matthias\} and Zolt{\'a}n Kele and Petra P{\'a}d{\'a}r and Zolt{\'a}n Kupih{\'a}r and Lajos Kov{\'a}cs",

year = "2011",

month = feb,

doi = "10.1039/c0nj00612b",

language = "English",

volume = "35",

pages = "476--482",

journal = "New Journal of Chemistry",

issn = "1144-0546",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - 3-Substituted xanthines as promising candidates for quadruplex formation

T2 - Computational, synthetic and analytical studies

AU - Szolomájer, János

AU - Paragi, Gábor

AU - Batta, Gyula

AU - Guerra, Célia Fonseca

AU - Bickelhaupt, F. Matthias

AU - Kele, Zoltán

AU - Pádár, Petra

AU - Kupihár, Zoltán

AU - Kovács, Lajos

PY - 2011/2

Y1 - 2011/2

N2 - Our computational studies suggest that 3-substituted xanthines are good candidates for tetrad and quadruplex structures. 3-Methylxanthine (3MX) has been synthesized from 7-benzylxanthine, and the existence of tetrameric and octameric aggregates of 3MX with NH4+, Na+ and K+ ions in the gas phase (MS) and in DMSO-d6 solution (NMR) has been observed. The "internal" H-bonds (N1H⋯O6) are stronger than the "external" ones (N7H⋯O2) in these clusters (NMR).

AB - Our computational studies suggest that 3-substituted xanthines are good candidates for tetrad and quadruplex structures. 3-Methylxanthine (3MX) has been synthesized from 7-benzylxanthine, and the existence of tetrameric and octameric aggregates of 3MX with NH4+, Na+ and K+ ions in the gas phase (MS) and in DMSO-d6 solution (NMR) has been observed. The "internal" H-bonds (N1H⋯O6) are stronger than the "external" ones (N7H⋯O2) in these clusters (NMR).

UR - https://www.scopus.com/pages/publications/79551589424

U2 - 10.1039/c0nj00612b

DO - 10.1039/c0nj00612b

M3 - Article

AN - SCOPUS:79551589424

SN - 1144-0546

VL - 35

SP - 476

EP - 482

JO - New Journal of Chemistry

JF - New Journal of Chemistry

IS - 2

ER -

3-Substituted xanthines as promising candidates for quadruplex formation: Computational, synthetic and analytical studies

Abstract

ASJC Scopus subject areas

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