6-Benzylaminopurine

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Min Xia - One of the best experts on this subject based on the ideXlab platform.

  • Crystal structures and spectroscopic analyses of two Co(II) N 6-Benzylaminopurine supramolecules
    Journal of Coordination Chemistry, 2012
    Co-Authors: Min Xia, Tian-tian Chen, Bu-shun Shan, Chun-li Wei
    Abstract:

    Two mononuclear Co(II) N 6-Benzylaminopurine compounds, [Co(6-BA-H2)2(H2O)4] · (R)2 · 4.5H2O (1) and [Co(6-BA-H)2(H2O)Cl3]Cl · H2O (2) (6-BA = N 6-Benzylaminopurine (C5H2N3NH)(NH)CH2(C6H5), H3R = 5-sulfosalicylic acid (C6H3)CO2H(OH)SO3H), are reported. Compound 1 possesses a 3-D supramolecular structure built via H-bond and π–π stacking interactions that contains a mononuclear six-coordinate [Co(6-BA-H2)2(H2O)4]6+. Compound 2 also exhibits a 3-D supramolecular framework with mononuclear six-coordinate cation [Co(6-BA-H)2(H2O)Cl3]+. Luminescence studies at room temperature show that 1 (λ ex = 268 nm) displays two strong fluorescent emissions centered at 326.8 nm and 356.9 nm, while 2 (λ ex = 233 nm) exhibits a weaker peak emitted at 342.8 nm upon 6-BA-complexation of two different second ligands H3R/Cl− with Co(II).

  • Crystal and molecular structure of adduct of 6-Benzylaminopurine and 5-sulfosalicylic acid
    Crystallography Reports, 2010
    Co-Authors: Min Xia
    Abstract:

    The crystal structure of adduct of 6-Benzylaminopurine and 5-sulfosalicylic acid C19H25N5O10S 1 is studied using single-crystal diffraction (R = 0.0482 for 2852 reflections with I > 2σ(I)). The asymmetric unit of 1 contains one 6-Benzylaminopurine molecule and one 5-sulfosalicylic acid molecule, as well as four lattice water molecules. Hydrogen bonds, formed by 6-Benzylaminopurine and 5-sulfosalicylic acid, link the two molecules into one-dimensional chain (omitting four water molecules), further joined to two-dimensional layer network. Short ring-interactions with intra-chain π-π stacking are observed. The data of IR spectroscopy confirm the formation of the two-dimensional supramolecular layer structure. At last, a 3D supramolecular network constructs via hydrogen bonds.

  • Synthesis and Crystal Structure of Hydrate Adduct of 6-Benzylaminopurine and 5-Sulfosalicylic Acid [(C12H12N5)(C7H5O6S)·H2O]
    Journal of Chemical Crystallography, 2010
    Co-Authors: Min Xia, Yulan Zhu
    Abstract:

    The crystal structure of hydrate adduct of 6-Benzylaminopurine and 5-sulfosalicylic acid [(C12H12N5)(C7H5O6S)·H2O] 1 is studied. It crystallizes in monoclinic system space group P21/n with a = 6.2128(9) A, b = 20.762(3) A, c = 15.675(2) A, β = 92.040(2)°, V = 2,020.6(5) A3, Z = 4, R gt(F) = 0.0494, wR ref(F 2) = 0.1112, and T = 173(2) K. Single-crystal X-ray diffraction analysis reveals that the asymmetric unit of 1 contains one 6-Benzylaminopurine molecule and one 5-sulfosalicylic acid molecule, as well as one lattice water molecule. In 1, hydrogen bonds link the two monomers into one-dimensional double chain, two-dimensional layer network, and further a 3-D supramolecular network. Short ring-interactions with intra-chain π–π stacking are observed (distances between ring centroids are 3.964, 3.796 and 3.571 A, and the dihedral angle between planes are 6.97°, 5.55°, and 5.66°, respectively). A novel hydrate adduct [(C12H12N5)(C7H5O6S)·H2O] 1, has been synthesized and consists of 6-Benzylaminopurine and 5-sulfosalicylic acid molecules with one lattice water molecule. The monomers connect with each other via intermolecular hydrogen bonds C(N, O)–H···O(N) to form double chain, further two-dimensional layer, at last 3-D supramolecular structure network, along with π–π interactions within 4 A.

Libuše Trnková - One of the best experts on this subject based on the ideXlab platform.

  • Copper complexes of 6-aminopurine and 6-Benzylaminopurine inaqueous methanol solutions
    2015
    Co-Authors: Iveta Pilařová, Libuše Trnková, Rudolf Navrátil, Přemysl Lubal
    Abstract:

    In order to follow many biological processes it is important to understand the interactions between nucleic acids and their constituents with metal ions. It is known that adenine shows various probabilities of coordination with transition metal ions due to its potential donor sites. Electronically favoured coordination sites N(1) and N(3) for the metals were added by the nitrogens N(3) and N(9) due to tautomerization of the imidazole hydrogen atom between N(7) and N(9). In this contribution the protonation and stability constants of 6-aminopurine )adenine) or 6-Benzylaminopurine (BAP) and their copper complexes were determined potentiometrically by using the titrator Titrando 835 controlled by tiamo 1.2 (Metrohm, Switzerland). The experiemnts were hampered by BAP solubility and all the potentiometric experimets were conducted in aqueous methanol solutions (10% v/v CH3OH in water). The stability constants of the copper complexes were calculated for different ligand (purine):metal (copper) ratios according to the Sigel procedure. Potentiometric titrations at different temperature and at the same ionic strength (0.1 M NaCl) enabled the thermodynamic evaluation of changes in enthalpy and entropy of the complexation process. The temperature icrease leads to a decrease in the values of the stability constants suggesting an exothermic behaviour for the complexation process. On the base of thermodynamic data obtained for adenine and BAP the differences were attributed to the effect of the benzyl moiety.

  • Oxidation of 6‐Benzylaminopurine‐Copper(I) Complex on Pencil Graphite Electrode
    Electroanalysis, 2012
    Co-Authors: Núria Serrano, Arístides Alberich, Libuše Trnková
    Abstract:

    A voltammetric study of the 6-Benzylaminopurine (BAP)/Cu(I) system is performed. BAP is an adenine-type cytokinin that elicits cell division in plants and presents antitumor activity when forming complexes with different transition metal ions as copper(I). In the frame of this research field, an analysis of linear sweep voltammetry (LSV), adsorptive stripping voltammetry (AdSV), and elimination voltammetry with linear scan (EVLS) data obtained with a pencil graphite electrode (PeGE), allows us to propose the stoichiometry of the possible complexes formed and the mechanism for total electrode reactions of the BAP/Cu(I) system.

  • Potentiometric and Voltammetric Study of 6-Benzylaminopurine and Its Derivatives
    Electroanalysis, 2012
    Co-Authors: Iveta Pilarova, Přemysl Lubal, Libuše Trnková
    Abstract:

    The protonation-deprotonation equilibrium of 6–benzylaminopurine (6–BAP) and its derivatives was studied by potentiometry and voltammetry. The effect of Cl or OCH3 group position in 2', 3' and 4' of the benzene ring of 6–BAP on both pKa values was investigated. To determine the enthalpy and entropy, the temperature dependence of pKa was employed. It was found that with increasing temperature the pKa decreased. In comparison with 6–BAP the chloro- or methoxy- group on the benzene ring resulted in pKa increase, and in the case of both derivatives the pKa values decreased with increasing distance of the chloro- or methoxy- moiety from the aminopurine structure. The first pKa values were also determined by linear sweep voltammetry (LSV) and elimination voltammetry with linear scan (EVLS). New approaches were shown not only for the determination of pKa from voltammetric titration curves but also for the evaluation of the reduction processes of benzylaminopurines.

  • Diffusion Characteristics of Chlorine and Methoxy Derivativesof 6-Benzylaminopurine Studied by Voltammetric Methods
    2012
    Co-Authors: Iveta Pilařová, Libuše Trnková
    Abstract:

    The metal complexes of chlorinated and methoxylated derivatives of 6 - benzylaminopurine (6-BAP) can be used as potential antineoplastic agents. From this point of view, the knowledge of the ability of these substances to diffuse into the intracellular area is very important. This property is characterized by the diffusion coefficient. The aim of our research is to determine the diffusion coefficients D of 6-BAP and its derivatives in buffered solutions (pH 3.21) containing 10% v/v CH3OH for two ionic strengths. Using the Delahay equation involving the reduction peaks of BAP derivatives on mercury electrode we calculated D and the charge transfer coefficient alpha we obtained from the elimination functions E1 and E4. The effect of some experimental parameters on D values was monitored.

  • The effect of methanol and ionic strength on the reductionprocess of 6-Benzylaminopurine
    2012
    Co-Authors: Iveta Pilařová, Přemysl Lubal, Libuše Trnková
    Abstract:

    The reduction process of 6-Benzylaminopurine (6-BAP), known as an adenine type of cytokinin, was investigated on mercury electrode by DC polarography [1, 2], cyclic and differential pulse voltammetry [2]. The aim of our contribution was the study of the effect of methanol content (1-20% v/v) and ionic strength (0.1- 1 M NaCl) on the reduction behavior of 6-BAP on a hanging mercury drop electrode (HMDE). It was found that the reduction of 6-BAP on HMDE proceeds in a protonated form, and therefore the research was devoted also to the study of protonation equilibria using potentiometry. Potentiometric titration provided the determination of protonation constants (pKa). The increase of methanol concentration causes pKa decrease of 6-BAP, and a significant and non-linear influence of ionic strength on protonation equilibrium was observed. In the ionic strength range from 0.1 to 0.5 M pKa decreases, at I = 0.5 M pKa reaches a minimum, and above this ionic strength value a pKa increase was observed. Linear sweep voltammetry (LSV) in connection with elimination voltammetry with linear scan (EVLS) [3,4] allows to determine not only the reduction potentials of 6-BAP and the effect of the two above-mentioned parameters but also prediction of the mechanism of the 6-BAP reduction process. Voltammetric experiments were carried out in buffered solutions (pH 3.21) at scan rate range 100 - 800 mV/s. From the LSV and EVLS experiments it follows that the new process is indicated in more negative potentials. This new process, taking place in adsorbed state, is sensitively revealed by EVLS in the form of a peak–counterpeak signal. Finally, in dependence on ionic strength and methanol content the kinetic parameters of the 6-BAP reduction process were determined and discussed [5].

Gao Sheng-li - One of the best experts on this subject based on the ideXlab platform.

  • Thermochemistry of copper complex of 6-Benzylaminopurine
    Journal of Thermal Analysis and Calorimetry, 2008
    Co-Authors: Y. Xuwu, Z. Hang-guo, S. Wu-juan, W. Xiao-yan, Gao Sheng-li
    Abstract:

    The copper(II) complex of 6-Benzylaminopurine (6-BAP) has been prepared with dihydrated cupric chloride and 6-Benzylaminopurine. Infrared spectrum and thermal stabilities of the solid complex have been discussed. The constant-volume combustion energy, ΔcU, has been determined as −12566.92±6.44 kJ mol−1 by a precise rotating-bomb calorimeter at 298.15 K. From the results and other auxiliary quantities, the standard molar enthalpy of combustion, ΔcHmθ, and the standard molar of formation of the complex, ΔfHmθ, were calculated as −12558.24±6.44 and −842.50±6.47 kJ mol−1, respectively.

Zdeněk Trávníček - One of the best experts on this subject based on the ideXlab platform.

  • Palladium(II) complexes containing cytokinins derived from 6-Benzylaminopurine
    Journal of Coordination Chemistry, 2005
    Co-Authors: Zdeněk Trávníček, Michal Šipl, Igor Popa
    Abstract:

    A series of palladium(II) complexes of general formula [Pd(LH+)Cl3] (1–12) containing 6-Benzylaminopurine derivatives has been prepared [L = 6-(2-methoxybenzylamino)purine (1), 6-(3-methoxybenzylamino)purine (2), 6-(4-methoxybenzylamino)purine (3), 6-(2-hydroxy-benzylamino)purine (4), 6-(3-hydroxybenzylamino)purine (5), 6-(4-hydroxybenzylamino) purine (6), 6-(2-fluorobenzylamino)purine (7), 6-(3-fluorobenzylamino)purine (8), 6-(4-fluorobenzylamino)purine (9), 6-(2-chlorobenzylamino)purine (10), 6-(3-chlorobenzylamino) purine (11) and 6-(4-chlorobenzylamino)purine (12)]. The compounds have been characterized by elemental analysis, IR, ES+ MS and 1H- and 13C-NMR spectroscopy, and two of them, 6 and 12, also by TG/DSC analyses. The complexes have been screened in vitro against the four human tumour cell lines G-361, HOS, K-562 and MCF7.

  • Synthesis, spectral study and cytotoxicity of platinum(II)complexes with 2,9-disubstituted-6-Benzylaminopurines
    Journal of inorganic biochemistry, 2005
    Co-Authors: Michal Maloň, Zdeněk Trávníček, Radek Marek, Miroslav Strnad
    Abstract:

    Abstract A series of platinum(II) complexes with 2,9-disubstituted-6-Benzylaminopurines has been prepared. The complexes have the following composition: cis -[Pt(Boh) 2 Cl 2 ] ( 1 ), cis -[Pt(Oc) 2 Cl 2 ] ( 2 ), cis -[Pt(Ros) 2 Cl 2 ] ( 3 ), cis -[Pt( i -PrOc) 2 Cl 2 ] ( 4 ), cis -[Pt(BohH + ) 2 Cl 2 ]Cl 2 ( 5 ), cis -[Pt(OcH + ) 2 Cl 2 ]Cl 2 ( 6 ), cis -[Pt(RosH + ) 2 Cl 2 ]Cl 2 ( 7 ) and cis -[Pt( i -PrOcH + ) 2 Cl 2 ]Cl 2 ( 8 ), where Boh = 2-(3-hydroxypropylamino)-6-benzylamino-9-isopropylpurine, Oc = 2-(2-hydroxyethylamino)-6-benzylamino-9-methylpurine, Ros = 2-(R)-(1-ethyl-2-hydroxyethylamino)-6-benzylamino-9-isopropylpurine and i -PrOc = 2-(2-hydroxyethylamino)-6-benzylamino-9-isopropylpurine. The complexes have been characterized by elemental analyses, conductivity measurements and their infrared, ES + mass (electrospray mass spectra in the positive ion mode) and NMR ( 1 H, 13 C, 15 N and 195 Pt) spectra. The results obtained from the physical studies, particularly from multinuclear NMR spectroscopy, show that in all the investigated complexes ( 1 – 8 ), two molecules of purine derivative are coordinated to platinum via the N(7) atom of the imidazole ring in a cis -configuration. The prepared compounds have been screened for their in vitro cytotoxicity against G-361 (human malignant melanoma), HOS (human osteogenic sarcoma), K-562 (human chronic myelogenous leukemia) and MCF-7 (human breast adenocarcinoma) cell lines. All complexes are significantly more active than the initial 2,9-disubstituted-6-Benzylaminopurine derivatives. In the case of some tumour cell lines, IC 50 values for the complexes ( 1 , 3 , 4 , 5 , 8 ) are significantly lower than those obtained for cisplatin and oxaliplatin . The best cytotoxicity was achieved for the complex ( 3 ) for which IC 50 values range from 1 to 2 μM.

  • Preparation and cytotoxic activity of nickel(II) complexes with 6-Benzylaminopurine derivatives
    Transition Metal Chemistry, 2002
    Co-Authors: Zdeněk Trávníček, Michal Maloň, Igor Popa, Karel Doležal, Miroslav Strnad
    Abstract:

    Nickel(II) complexes with 6-Benzylaminopurine (BAP) derivatives, namely 6-(3-chlorobenzylamino)purine (HL1), 6-(4-chlorobenzylamino)purine (HL2) and 6-(4-fluorobenzylamino)purine (HL3), have been prepared and characterized by elemental analyses, i.r., u.v.–v.i.s., ES+ and FAB+ mass spectroscopy, magnetic susceptibility and conductivity measurements, and by thermal analysis. The complexes are: [Ni(L1(H2O)2Cl] · H2O, [Ni(L1)(H2O)-(NO3)] · H2O, [Ni(L2)(H2O)2Cl], [Ni(L2)(H2O)2(NO3)] · H2O, [Ni(HL2)(H2O)Cl2] · EtOH and [Ni(L3)(H2O)2Cl]. They have been tested in vitro for their possible cytotoxic activity against G-361 (human malignant melanoma), HOS (human osteogenic sarcoma), K-562 (human chronic myelogenous leukemia) and MCF-7 (human breast adenocarcinoma) cell lines.

Chun-li Wei - One of the best experts on this subject based on the ideXlab platform.

  • Crystal structures and spectroscopic analyses of two Co(II) N 6-Benzylaminopurine supramolecules
    Journal of Coordination Chemistry, 2012
    Co-Authors: Min Xia, Tian-tian Chen, Bu-shun Shan, Chun-li Wei
    Abstract:

    Two mononuclear Co(II) N 6-Benzylaminopurine compounds, [Co(6-BA-H2)2(H2O)4] · (R)2 · 4.5H2O (1) and [Co(6-BA-H)2(H2O)Cl3]Cl · H2O (2) (6-BA = N 6-Benzylaminopurine (C5H2N3NH)(NH)CH2(C6H5), H3R = 5-sulfosalicylic acid (C6H3)CO2H(OH)SO3H), are reported. Compound 1 possesses a 3-D supramolecular structure built via H-bond and π–π stacking interactions that contains a mononuclear six-coordinate [Co(6-BA-H2)2(H2O)4]6+. Compound 2 also exhibits a 3-D supramolecular framework with mononuclear six-coordinate cation [Co(6-BA-H)2(H2O)Cl3]+. Luminescence studies at room temperature show that 1 (λ ex = 268 nm) displays two strong fluorescent emissions centered at 326.8 nm and 356.9 nm, while 2 (λ ex = 233 nm) exhibits a weaker peak emitted at 342.8 nm upon 6-BA-complexation of two different second ligands H3R/Cl− with Co(II).