Raman spectra of putrescine, spermidine and spermine polyamines and their <i>N</i>‐deuterated and <i>N</i>‐ionized derivatives

Costa, A. M. Amorim da; Marques, M. P. M.; Carvalho, Luís A. E. Batista de

doi:10.1002/jrs.1001

Cited by 24 publications

(22 citation statements)

References 40 publications

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“…31 These chelates, containing the biogenic polyamines spermidine (H 2 N(CH 2 ) 3 NH(CH 2 ) 4 NH 2 ) and spermine (H 2 N(CH 2 ) 3 NH(CH 2 ) 4 NH(CH 2 ) 3 NH 2 ) as bridging linkers, differ in the metal coordination pattern, as well as in the number and geometry of their leaving groups. This is intended as an interactive structureactivity research work, the structural characteristics of the compounds tested (determined in a concurrent study through physical-chemical methods [32][33][34][35][36] ) being changed according to their antitumor activity evaluation. Thus, the results obtained from these studies may hopefully contribute to a better understanding of the molecular basis of toxicity (i.e., of the biochemical processes underlying the antiproliferative effect of these kinds of compounds), which is fundamental in order to design new cytostatic agents with improved therapeutical properties.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Activity of Metal Complexes of Biogenic Polyamines: Polynuclear Platinum(II) Chelates

et al. 2004

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Several polynuclear Pt(II) chelates with biogenic polyamines were synthesized and screened for their potential antiproliferative and cytotoxic activity in different human cancer cell lines. To gather information regarding the structure-activity relationships underlying their biological activity, the complexes studied were designed to differ in geometrical parameters such as the nature of the ligand and the number and chemical environment of the metal centers. Distinct effects were found for different cell lines and different structural characteristics of the complexes; chelates II, III, and IV displayed specificity toward the HeLa and HSC-3 epithelial-type cells, while V, VI, and VII were clearly more effective against the THP-1, MOLT-3, and CCRF-CEM leukemia cell lines. The toxicity of these Pt(II) complexes on noncancer cells was, in all cases, found to be reversed upon drug removal.

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Section: Introductionmentioning

confidence: 99%

Cytotoxic Activity of Metal Complexes of Biogenic Polyamines: Polynuclear Platinum(II) Chelates

et al. 2004

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“…In fact, to the best of the authors' knowledge, only two studies can be found in the literature on the ab initio assignment of the Raman spectra of such molecules, and even these are restricted to the NÀH and CÀH stretching modes. [38,39] The present work is aimed at the study of the homologous series of a,w-diamine dihydrochlorides of general formula [H 3 N(CH 2 ) n NH 3 )] 2 + ·2Cl À (n = 2-10 and n = 12) in the solid state. In the absence of any theoretical report on these polycationic molecules, the primary concern was the selection of an adequate molecular model for the representation of such systems.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic and Theoretical Studies on Solid 1,2‐Ethylenediamine Dihydrochloride Salt

Amado¹,

Otero²,

Marques³

et al. 2004

ChemPhysChem

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A structural study of [H3N(CH2)2NH3)]2+⋅2Cl−, the smallest element of the homologous series of the α,ω‐diamine dihydrochlorides, was carried out by means of Raman and FTIR spectroscopy coupled to ab initio molecular orbital (MO) calculations. As a primary concern, an adequate molecular model for the representation of these solid amine salts was chosen. Thus, several models, varying in the number and position of the counterions as well as in the number of diamine units, were considered. It was found that the best molecular system (i.e., that yielding the best compromise between accuracy and computational requirements) consists of one ethylenediamine cation surrounded by six chloride ions in an arrangement based on the crystal structure reported in the literature for [H3N(CH2)2NH3)]2+⋅2Cl−. This conclusion will hopefully allow for a better understanding of the conformational preferences, in the solid state, of these biologically relevant linear polyamines.

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“…The homologous series of the linear α,ω-diamines [H 2 N(CH 2 ) n NH 2 ] (n = 2-10, n = 12) and the tri-and tetramines spermidine and spermine ( Figures 1A-1C) were studied in order to achieve a thorough knowledge of their structural preferences, both for their unprotonated and Nprotonated forms [24][25][26][27][28][29][30][31][32][33]. Several theoretical molecular models were proposed for an accurate representation of these linear polyamines, yielding the best possible agreement with the experimental data (both vibrational spectroscopy results and reported X-ray structures).…”

Section: Aliphatic Linear Polyaminesmentioning

confidence: 99%

Vibrational spectroscopy studies on linear polyamines

Marques

Carvalho

2007

Biochemical Society Transactions

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Vibrational spectroscopy [both Raman and INS (inelastic neutron scattering)], coupled to quantum mechanical calculations, was used in order to perform a thorough structural analysis of linear polyamines and polynuclear polyamine metal chelates [e.g. with Pt(II) and Pd(II)] with potential anticancer activity. The complementarity of the Raman and INS spectroscopies was exploited in order to gain a better knowledge of the conformational behaviour of these systems. Moreover, the conjugation of the experimental spectroscopic data to the theoretical results allows us to obtain valuable information on the structural preferences of this kind of system, which may lead to the establishment of SARs (structure-activity relationships) ruling their biological activity. Some of the most significant results obtained by the 'Molecular Physical-Chemistry' Research Group of the University of Coimbra (Portugal) are reviewed here.

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Raman spectra of putrescine, spermidine and spermine polyamines and their N‐deuterated and N‐ionized derivatives

Cited by 24 publications

References 40 publications

Cytotoxic Activity of Metal Complexes of Biogenic Polyamines: Polynuclear Platinum(II) Chelates

Cytotoxic Activity of Metal Complexes of Biogenic Polyamines: Polynuclear Platinum(II) Chelates

Spectroscopic and Theoretical Studies on Solid 1,2‐Ethylenediamine Dihydrochloride Salt

Vibrational spectroscopy studies on linear polyamines

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