Complexes of diorganotin(IV) with aminoacids and a dipeptide. Synthesis and structural investigations.

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Abstract

The aim of this work is to synthesize complexes of Arginine, effector of recognition, with organotin(IV) ions (R2Sn2+, R =Me, nBu) which are known to possess antitumour, antimicrobial, anti-inflammatory activities. The complexes were investigated by FT-IR and 119Sn Můssbauer.While identical stoichiometries are present for Me2Sn(Arg)2 and Me2Sn(Boc-Arg)2 complexes, 119Sn Můssbauer spectra give a clear evidence of different coordination modes. L-Arginine appears to behave as a chelating ligand through carboxylate and a-NH2 groups in the former, while in Nα-Boc-L-Arginine complex, the Nα-protected amino group being exempted from coordination, only the carboxylate groups are effectors of bonding to the organometallic moieties. The L-Ala-L-Arg dipeptide complex appears to adopt a trigonal-bipyramidal geometry at tin, the organometallic moiety being coordinated by α-amino, deprotonated peptide nitrogen and terminal carboxylate groups. FT-IR spectra give a clear indication that guanidino groups in all the complexes are not involved in coordination, since ν(C=N-H) frequency of the terminal guanidino group is fairly constant and unshifted relative to the free ligand.
Lingua originaleEnglish
pagine (da-a)129-138
Numero di pagine10
RivistaATTI DELLA ACCADEMIA DI SCIENZE, LETTERE E ARTI DI PALERMO, PARTE PRIMA: SCIENZE
VolumeSerieQuinta/Volume XXIV
Stato di pubblicazionePublished - 2008

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Dipeptides
Arginine
Organometallics
Ligands
Tin
Chelation
Anti-Inflammatory Agents
Ions

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title = "Complexes of diorganotin(IV) with aminoacids and a dipeptide. Synthesis and structural investigations.",
abstract = "The aim of this work is to synthesize complexes of Arginine, effector of recognition, with organotin(IV) ions (R2Sn2+, R =Me, nBu) which are known to possess antitumour, antimicrobial, anti-inflammatory activities. The complexes were investigated by FT-IR and 119Sn Můssbauer.While identical stoichiometries are present for Me2Sn(Arg)2 and Me2Sn(Boc-Arg)2 complexes, 119Sn Můssbauer spectra give a clear evidence of different coordination modes. L-Arginine appears to behave as a chelating ligand through carboxylate and a-NH2 groups in the former, while in Nα-Boc-L-Arginine complex, the Nα-protected amino group being exempted from coordination, only the carboxylate groups are effectors of bonding to the organometallic moieties. The L-Ala-L-Arg dipeptide complex appears to adopt a trigonal-bipyramidal geometry at tin, the organometallic moiety being coordinated by α-amino, deprotonated peptide nitrogen and terminal carboxylate groups. FT-IR spectra give a clear indication that guanidino groups in all the complexes are not involved in coordination, since ν(C=N-H) frequency of the terminal guanidino group is fairly constant and unshifted relative to the free ligand.",
keywords = "Diorganotin (IV) complexes, aminoacids and dipeptide",
author = "Girasolo, {Maria Assunta} and Simona Rubino",
year = "2008",
language = "English",
volume = "SerieQuinta/Volume XXIV",
pages = "129--138",
journal = "ATTI DELLA ACCADEMIA DI SCIENZE, LETTERE E ARTI DI PALERMO, PARTE PRIMA: SCIENZE",
issn = "0365-0448",

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TY - JOUR

T1 - Complexes of diorganotin(IV) with aminoacids and a dipeptide. Synthesis and structural investigations.

AU - Girasolo, Maria Assunta

AU - Rubino, Simona

PY - 2008

Y1 - 2008

N2 - The aim of this work is to synthesize complexes of Arginine, effector of recognition, with organotin(IV) ions (R2Sn2+, R =Me, nBu) which are known to possess antitumour, antimicrobial, anti-inflammatory activities. The complexes were investigated by FT-IR and 119Sn Můssbauer.While identical stoichiometries are present for Me2Sn(Arg)2 and Me2Sn(Boc-Arg)2 complexes, 119Sn Můssbauer spectra give a clear evidence of different coordination modes. L-Arginine appears to behave as a chelating ligand through carboxylate and a-NH2 groups in the former, while in Nα-Boc-L-Arginine complex, the Nα-protected amino group being exempted from coordination, only the carboxylate groups are effectors of bonding to the organometallic moieties. The L-Ala-L-Arg dipeptide complex appears to adopt a trigonal-bipyramidal geometry at tin, the organometallic moiety being coordinated by α-amino, deprotonated peptide nitrogen and terminal carboxylate groups. FT-IR spectra give a clear indication that guanidino groups in all the complexes are not involved in coordination, since ν(C=N-H) frequency of the terminal guanidino group is fairly constant and unshifted relative to the free ligand.

AB - The aim of this work is to synthesize complexes of Arginine, effector of recognition, with organotin(IV) ions (R2Sn2+, R =Me, nBu) which are known to possess antitumour, antimicrobial, anti-inflammatory activities. The complexes were investigated by FT-IR and 119Sn Můssbauer.While identical stoichiometries are present for Me2Sn(Arg)2 and Me2Sn(Boc-Arg)2 complexes, 119Sn Můssbauer spectra give a clear evidence of different coordination modes. L-Arginine appears to behave as a chelating ligand through carboxylate and a-NH2 groups in the former, while in Nα-Boc-L-Arginine complex, the Nα-protected amino group being exempted from coordination, only the carboxylate groups are effectors of bonding to the organometallic moieties. The L-Ala-L-Arg dipeptide complex appears to adopt a trigonal-bipyramidal geometry at tin, the organometallic moiety being coordinated by α-amino, deprotonated peptide nitrogen and terminal carboxylate groups. FT-IR spectra give a clear indication that guanidino groups in all the complexes are not involved in coordination, since ν(C=N-H) frequency of the terminal guanidino group is fairly constant and unshifted relative to the free ligand.

KW - Diorganotin (IV) complexes, aminoacids and dipeptide

UR - http://hdl.handle.net/10447/35207

M3 - Article

VL - SerieQuinta/Volume XXIV

SP - 129

EP - 138

JO - ATTI DELLA ACCADEMIA DI SCIENZE, LETTERE E ARTI DI PALERMO, PARTE PRIMA: SCIENZE

JF - ATTI DELLA ACCADEMIA DI SCIENZE, LETTERE E ARTI DI PALERMO, PARTE PRIMA: SCIENZE

SN - 0365-0448

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