Nucleoside sites for transition metal ion binding

Martin, R. Bruce

doi:10.1021/ar00110a001

Cited by 341 publications

(239 citation statements)

References 28 publications

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“…A chemical shift change at pH 4.5 is ascribed to the protonation of a non-platinated N3 of cytosine [29] and is comparable with the value observed for 5'CMP [30]. Platination of the N3 of thymine does not occur, the pK, of 9.9 is the same as the value previously reported by Martin [31]. The change in the chemical shift of H8 at pH 8.5 is characteristic for an N1-protonation of an N7-platinated guanine [32 -341.…”

Section: Identification Of the Reaction Productssupporting

confidence: 78%

Alterations in the d(CpGpT) structure in solution as a result of [PtCl(diethylenetriamine)]⁺ binding

Garderen

Altona

Reedijk

1988

European Journal of Biochemistry

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The trinucleotide d(CpGpT) reacts with [PtClidien)lCl (dien = diethylenetriamine) to yield as a single adduct Pt(dien)[d(CpGpT)-N7(2)]. The structure of this adduct in solution has been analysed with the aid of NMR spectroscopy and compared with that of the unmodified trinucleotide. A change in the population of the S conformer of the guanosine deoxyribose ring and a syn preference of the guanine residue are the most important changes occurring upon platination. As a result the dC-dG stack disappears, whereas the dG-dT stack is hardly affected. The CD spectra of both platinated and free d(CpGpT) confirm the different nature of the two molecules.DNA is believed to be the major target for the tumorinhibiting agent cis-diamminedichloroplatinum(I1) [

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Section: Identification Of the Reaction Productssupporting

confidence: 78%

Alterations in the d(CpGpT) structure in solution as a result of [PtCl(diethylenetriamine)]⁺ binding

Garderen

Altona

Reedijk

1988

European Journal of Biochemistry

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“…Or to put it differently: upon phosphate deprotonation (Eqn 9) a significant downfield shift of the resonance of H-8 occurs. This so-called 'wrongway' downfield shift [44] has been observed before 12, 19,47,48] and several interpretations have been offered including the postulation of a hydrogen bond between N-7 and the -P03H-group. In this connection it is interesting to view the results of Fig.…”

Section: Deuterated) and Free Forms Of 2'-amp 3'-amp S'-amp And 5'-mentioning

confidence: 62%

“…This is the only possibility, as the species H2(5'-AMP)' has already one proton at N-1 and one at the phosphate group, the latter still carrying a negative charge. It must be emphasized that the N-7 of 5'-AMP is not protonated under these conditions; its affinity for H + is very low: pK, = -1.6 [44]. Indeed, that at this low pD protonation of the -P03H-group occurs is confirmed by the considerable downfield shifts of H-5' and H-5" (see Fig.…”

Section: Chemical Shifts For Adenosine D-ribose 5'-monophosphate Andmentioning

confidence: 89%

Self‐association and protonation of adenosine 5′‐monophosphate in comparison with its 2′‐ and 3′‐analogues and tubercidin 5′‐monophosphate (7‐deaza‐AMP)

Tribolet

Sigel

1987

European Journal of Biochemistry

160

237

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The concentration dependence of the chemical shifts of the protons H-2, H-8 and H-1' for 2'-, 3'-and 5'-AMP2-and of the protons H-2, H-7, H-8 and H-1' for tubercidin 5'-monophosphate (= 7-deaza-AMP2-; TuMP2-) has been measured in D 2 0 at 27°C to elucidate the self-association of the nucleoside monophosphates (NMPs). The results are consistent with the isodesmic model of indefinite non-cooperative stacking; the association constants for all four NMPs are very similar: K w 2 M -l . These 'H-NMR measurements and those on the dependence of the chemical shifts on the pD of the solutions indicate that the NMP2-species exist predominately in the anti conformation. Comparison of the shift data for 5'-TuMP and 5'-AMP shows that no hydrogen bonding between N-7 and -P03H-occurs; hence, the previously observed and confirmed 'wrongway' chemical shift [Martin, R. B. (1985) Acc. Chem. Res 18, 321 connected with the deprotonation of the -P03Hp group most probably results from the anisotropic properties of the phosphate group which is in the anti conformation close to N-7. From the dependence between the chemical shift and the pD of the solutions the acidity constants were calculated for the four protonated NMPs, and for adenosine and D-ribose 5'-monophosphate. The measurements also allow an estimation of the first acidity constant of H3(5'-AMP)+ = 0.9 and pKHH,(AMp) = 0.4). The values for pK&(NMP) and pK:(NMP) were also determined from potentiometric pH titrations in aqueous solution ( I = 0.1 M, NaN03; 25°C). The agreement of the results obtained by the two methods is excellent. The position of the phosphate group at the ribose moiety and the presence of N-7 in the base moiety influence somewhat the acid-base properties of the mentioned NMPs. Measurements with 5'-AMP in 50% (v/v) aqueous dioxane show that lowering of the solvent polarity facilitates removal of the proton from the H+(N-I) site while the -PO:-group becomes more basic; this increases the pH range in which the monoprotonated H(S'-AMP)-species is stable and which is now also extended into the physiological pH region. Some consequences of this observation for biological systems are indicated.About one sixth of all enzyme systems need ATP or a related adenine cofactor [l]. With this fact in mind, it is not surprising that the properties of adenine nucleotides are receiving much attention. One of their most fascinating qualities is the self-association via base-stacking [2] which, for example, is thought to be important in the storage of some neurotransmitters [3 -51, possibly playing a role in stabilizing the aggregates.The self-stacking of adenine nucleotides occurs clearly beyond the dimer stage, so that oligomers are formed [6 -131. 'Head-to-tail' stacking, with the five-membered and sixmembered rings alternating in the stack, has been suggested [14], but other geometries are also possible [2, 10, 151. Due to electrostatic repulsion of the negatively charged phosphate residues the tendency for self-association decreases within the series, adenosine > 5'-AMPZ-> 5-...

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“…Out of the numerous biomolecules that can interact with metal ions, DNA and nucleotides have been extensively studied since they can bind to various metal ions via both the hard phosphate ligand and the more soft DNA bases. [6][7][8][9][10][11][12] In particular, adenine and its derivatives are very attractive ligands as they contain multiple high affinity metal binding sites. [13][14][15] For example, Wei et al…”

mentioning

confidence: 99%

Light-Activated Metal-Coordinated Supramolecular Complexes with Charge-Directed Self-Assembly

Lopez

Liu

2013

J. Phys. Chem. C

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Metal coordinated materials are attractive for many applications including catalysis, sensing, and controlled release. Adenine and its derivatives have been widely used to generate many coordination complexes, polymers, and nanoparticles. However, few of these materials display fluorescence. Herein, we report fluorescent gold complexes and nanoclusters formed with adenosine, deoxyadenosine, AMP and ATP, where the former two produced micrometer-sized particles and the latter two produced molecular clusters. Only weak fluorescence was produced with adenine, while no emission was observed with uridine, cytidine or guanosine. We found that adding citrate and light exposure are two key factors to generate fluorescence and their mechanistic roles have been explored. In all the products, the ratio between gold and adenine was determined to be 1:1 using UV-vis spectroscopy. Mass spectrometry showed clusters containing 2, 4, and 6 gold atoms in the gas phase.The fluorescence peak is around 470 nm for the AMP and ATP complex and 480 nm for the (deoxy)adenosine complexes. This work has provided a systematic approach to obtain fluorescent metal coordinated polymers and materials with tunable sizes, which will find applications in analytical chemistry, drug delivery and imaging. The fundamental physical chemistry of these materials has been systematically explored.

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Nucleoside sites for transition metal ion binding

Cited by 341 publications

References 28 publications

Alterations in the d(CpGpT) structure in solution as a result of [PtCl(diethylenetriamine)]⁺ binding

Alterations in the d(CpGpT) structure in solution as a result of [PtCl(diethylenetriamine)]⁺ binding

Self‐association and protonation of adenosine 5′‐monophosphate in comparison with its 2′‐ and 3′‐analogues and tubercidin 5′‐monophosphate (7‐deaza‐AMP)

Light-Activated Metal-Coordinated Supramolecular Complexes with Charge-Directed Self-Assembly

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Nucleoside sites for transition metal ion binding

Cited by 341 publications

References 28 publications

Alterations in the d(CpGpT) structure in solution as a result of [PtCl(diethylenetriamine)]+ binding

Alterations in the d(CpGpT) structure in solution as a result of [PtCl(diethylenetriamine)]+ binding

Self‐association and protonation of adenosine 5′‐monophosphate in comparison with its 2′‐ and 3′‐analogues and tubercidin 5′‐monophosphate (7‐deaza‐AMP)

Light-Activated Metal-Coordinated Supramolecular Complexes with Charge-Directed Self-Assembly

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Alterations in the d(CpGpT) structure in solution as a result of [PtCl(diethylenetriamine)]⁺ binding

Alterations in the d(CpGpT) structure in solution as a result of [PtCl(diethylenetriamine)]⁺ binding