Raman spectroscopy study of the interaction between biogenic polyamines and an alternating AT oligodeoxyribonucleotide

Ruiz-Chica, J.

doi:10.1016/s0167-4781(03)00098-8

Cited by 30 publications

(30 citation statements)

References 59 publications

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“…2)-are ubiquitous in cells of higher organisms, and result from the decarboxylation of ornithine. Under physiological conditions, these linear amines (PAs) are totally protonated and behave as natural polycations, capable of interacting with both DNA and RNA, therefore inducing conformational transitions and affecting nucleic acid function (Ouameur and Tajmir-Riahi 2004;Ruiz-Chica et al 2003;N'soukpoKossi et al 2008;Wallace 2003). Actually, it has been shown that biogenic polyamines cause DNA condensation in both isolated DNA (Patel and Anchoroquy 2006) and chromatin (Todd et al 2008).…”

Section: Polyamines As Essential Biomoleculesmentioning

confidence: 99%

Polyamines: fundamental characters in chemistry and biology

et al. 2009

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Polyamines are small cationic molecules required for cellular proliferation and are detected at higher concentrations in most tumour tissues, compared to normal tissues. Agmatine (AGM), a biogenic amine, is able to arrest proliferation in cell lines by depleting intracellular polyamine levels. It enters mammalian cells via the polyamine transport system. Agmatine is able to induce oxidative stress in mitochondria at low concentrations (10 or 100 lM), while at higher concentrations (e.g. 1-2 mM) it does not affect mitochondrial respiration and is ineffective in inducing any oxidative stress. As this effect is strictly correlated with the mitochondrial permeability transition induction and the triggering of the pro-apoptotic pathway, AGM may be considered as a regulator of this type of cell death. Furthermore, polyamine transport is positively correlated with the rate of cellular proliferation. By increasing the expression of antizyme, a protein that inhibits polyamine biosynthesis and transport, AGM also exhibits a regulatory effect on cell proliferation. Methylglyoxal bis(guanylhydrazone) (MGBG), a competitive inhibitor of S-adenosyl-L-methionine decarboxylase, displaying anticancer activity, is a structural analogue of the natural polyamine spermidine. MGBG has been extensively studied, preclinically as well as clinically, and its anticancer activity has been attributed to the inhibition of polyamine biosynthesis and also to its effect on mitochondrial function. Numerous findings have suggested that MGBG might be used as a chemotherapeutic agent against cancer.

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Section: Polyamines As Essential Biomoleculesmentioning

confidence: 99%

Polyamines: fundamental characters in chemistry and biology

et al. 2009

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“…Several models involving the binding of spermidine in the minor groove of dsDNA have been proposed recently (24,25). In these models, the authors showed an interstrand contact between polyamine amino groups and T(O 2 ), A(N3), and PO 2 Ϫ groups.…”

Section: Preferred Binding Models For Polyamine⅐dna Complexes and Thementioning

confidence: 99%

“…Thus, diverse binding models could be considered for spermine, because the interactions with the bases are sequence-dependent. Recent Raman studies (24,25) propose the interactions along and across the major grooves involving contacts between the inner amino groups and purine-N7 and thymine-O4 atoms, which also permit hydrophobic contact between CH 2 group of thymine and methylene group of spermine. These models correlate well with our infrared data, because interactions with the purine-N7 atoms and hydrophobic contacts are observed.…”

Section: Preferred Binding Models For Polyamine⅐dna Complexes and Thementioning

confidence: 99%

“…Their bindings have been reported to promote the conversion of the right-handed to a left-handed Z-DNA (16 -19) or to an alternative form of right-handed helix, A-DNA (20 -22). However, polyamines can also bind B-DNA, thus inducing no major biopolymer conformational changes (23)(24)(25).Another consequence of polyamine binding is the condensation of DNA occurring with both naked DNA (26 -30) and chromatin (31,32). Immunocytochemical studies of spermidine and spermine have shown that these polyamines are associated with highly compacted mitotic chromosomes (33, 34), inducing more stabilizing than regulating effects on the chromatin structure during the cell cycle (35).…”

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Structural Analysis of DNA Interactions with Biogenic Polyamines and Cobalt(III)hexamine Studied by Fourier Transform Infrared and Capillary Electrophoresis

Ouameur

Tajmir-Riahi

2004

Journal of Biological Chemistry

286

234

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Biogenic polyamines, such as putrescine, spermidine, and spermine are small organic polycations involved in numerous diverse biological processes. These compounds play an important role in nucleic acid function due to their binding to DNA and RNA. It has been shown that biogenic polyamines cause DNA condensation and aggregation similar to that of inorganic cobalt(III)hexamine cation, which has the ability to induce DNA conformational changes. However, the nature of the polyamine⅐DNA binding at the molecular level is not clearly established and is the subject of much controversy. In the present study the effects of spermine, spermidine, putrescine, and cobalt(III)hexamine on the solution structure of calf-thymus DNA were investigated using affinity capillary electrophoresis, Fourier transform infrared, and circular dichroism spectroscopic methods. At low polycation concentrations, putrescine binds preferentially through the minor and major grooves of double strand DNA, whereas spermine, spermidine, and cobalt(III)hexamine bind to the major groove. At high polycation concentrations, putrescine interaction with the bases is weak, whereas strong base binding occurred for spermidine in the major and minor grooves of DNA duplex. However, major groove binding is preferred by spermine and cobalt(III)hexamine cations. Electrostatic attractions between polycation and the backbone phosphate group were also observed. No major alterations of B-DNA were observed for biogenic polyamines, whereas cobalt(III)hexamine induced a partial B 3 A transition. DNA condensation was also observed for cobalt(III)hexamine cation, whereas organic polyamines induced duplex stabilization. The binding constants calculated for biogenic polyamines are K Spm ‫؍‬ 2.3 ؋ 10 5 M ؊1 , K Spd ‫؍‬ 1.4 ؋ 10 5 M ؊1 , and K Put ‫؍‬ 1.02 ؋ 10 5 M ؊1 . Two binding constants have been found for cobalt(III)hexamine with K 1 ‫؍‬ 1.8 ؋ 10 5 M ؊1 and K 2 ‫؍‬ 9.2 ؋ 10 4 M ؊1 . The Hill coefficients indicate a positive cooperativity binding for biogenic polyamines and a negative cooperativity for cobalt(III)hexamine.The biogenic polyamines putrescine [NH 2 (CH 2 ) 4 NH 2 ], spermidine [NH 2 (CH 2 ) 4 NH(CH 2 ) 3 NH 2 ], and spermine [NH 2 (C-H 2 ) 3 NH(CH 2 ) 4 NH(CH 2 ) 3 NH 2 ] (Structure 1) are the most prevalent polyamines in mammalian cells. They are small aliphatic polycations involved in numerous diverse biological processes, such as the ability to modulate gene expression and enzyme activities, activation of DNA synthesis, cell proliferation and differentiation, and others (1-8). Other functions of polyamines have been related to DNA protection from external agents (9, 10) and against radiation damage (11, 12). In general, spermidine and spermine are present in millimolar concentrations in vivo, whereas putrescine levels are slightly lower (13-15). However, the most important characteristic of polyamines within the cells is to bind nucleic acids and DNA in particular (1, 6).Polyamines also have the ability to induce DNA conformational transitions. Their bindi...

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Cyclometalated Iridium(III)–Polyamine Complexes with Intense and Long‐Lived Multicolor Phosphorescence: Synthesis, Crystal Structure, Photophysical Behavior, Cellular Uptake, and Transfection Properties

Tang

Yiu

et al. 2012

Chemistry A European J

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A new class of phosphorescent cyclometalated iridium(III)-polyamine complexes [{Ir(N^C)(2)}(n)(bPEI)](PF(6))(n)(bPEI=branched poly(ethyleneimine), average M(w =25 kDa, n=15.6-27.4; HN^C=2-phenylpyridine Hppy (1a), 2-((1,1'-biphenyl)-4-yl)pyridine Hpppy (2a), 2-phenylquinoline Hpq (3a), 2-phenylbenzothiazole Hbt (4a), 2-(1-naphthyl)benzothiazole Hbsn (5a)) and [Ir(N^C)(2)(en)](PF(6)) (en=ethylenediamine; HN^C=Hppy (1b), Hpppy (2b), Hpq (3b), Hbt (4b), Hbsn (5b)) have been synthesized and characterized. The X-ray crystal structure of complex 5b was also determined. All of these complexes showed a reversible iridium(IV/III) oxidation couple at +1.01 to +1.26 V and a quasi-reversible ligand-based reduction couple at -1.54 to -2.08 V (versus SCE). Upon photoexcitation, the complexes displayed intense and long-lived green to orange-red emission in fluid solutions at room temperature and in low-temperature glass. Lipophilicity measurements indicated that bPEI played a dominant role in the polar nature of complexes 1a-5a, thus rendering them very soluble in aqueous solutions. Inductively coupled plasma-mass spectrometry (ICP-MS) and confocal laser scanning microscopy (CLSM) data indicated that an energy-requiring process, such as endocytosis, was involved in the cellular uptake of all of the complexes. In addition, the cytotoxicity of the complexes toward human cervix epithelioid carcinoma (HeLa) and human embryonic kidney 293T (HEK293T) cell-lines has been evaluated by the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyltetrazolium bromide (MTT) assay. The DNA-binding properties of complex 5a have been investigated by gel-retardation assays and the polyplexes that were formed from this complex with plasmid DNA (pDNA) were studied by zeta-potential measurements and particle-size estimation. Furthermore, complex 5a was grafted with poly(ethylene glycol) (PEG, average M(w)=2 kDa) to different extents, thereby yielding the phosphorescent copolymers PEG(12.3)-g-5a, PEG(25.4)-g-5a, and PEG(62.1)-g-5a. Interestingly, these copolymers showed enhanced transfection activity, as revealed by in vitro transfection experiments with tissue-culture-based luciferase assays.

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Raman spectroscopy study of the interaction between biogenic polyamines and an alternating AT oligodeoxyribonucleotide

Cited by 30 publications

References 59 publications

Polyamines: fundamental characters in chemistry and biology

Polyamines: fundamental characters in chemistry and biology

Structural Analysis of DNA Interactions with Biogenic Polyamines and Cobalt(III)hexamine Studied by Fourier Transform Infrared and Capillary Electrophoresis

Cyclometalated Iridium(III)–Polyamine Complexes with Intense and Long‐Lived Multicolor Phosphorescence: Synthesis, Crystal Structure, Photophysical Behavior, Cellular Uptake, and Transfection Properties

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