The antitumor activity of di-n-butyltin(IV) glycylglycinate, and the correlation with the structure of dialkyltin(IV) glycylglycinates in solution

Ruisi, Gìuseppe; Silvestri, Arturo; GIUDICE, M. T. LO; Barbieri, Renato; Atassi, Ghanem; Huber, F.; Grätz, K.; Lamartina, Liliana

doi:10.1016/0162-0134(85)80023-4

Cited by 79 publications

(30 citation statements)

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“…Studies of structureactivity relationships have shown that the factors influencing activity may be very subtle differences in bond lengths or bond angles, reinforcing the value of structural investigations in this field (10)(11)(12)(13). Recent reports of the activity of certain diorganotin derivatives of pyridine 2,6-dicarboxylic acid and some related compounds (14,15) against the P388 lymphocytic leukemia tumour, both in vitro and in vivo, led us to report the synthesis and characterization of a series of diorganotin iminodiacetates (16) and diorganotin(1V)-N-arylidene-a-amino acid complexes (17). In line with these developments, we now report the synthesis and characterization of diphenyl(2-oxidonaphthylmethyliminoacetato)tin(IV), including the results of a full X-ray structural analysis.…”

Section: Introductionmentioning

confidence: 99%

The synthesis, and molecular and crystal structure of diphenyl(2-oxidonaphthylmethyl-iminoacetato)tin(IV)

Smith¹,

Khoo²,

Goh³

et al. 1996

Can. J. Chem.

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Abstract:The new diorganotin complex ((C6HS),Sn(OC,,H6CH=NCH2COO)) was prepared and characterized by 'H NMR, IR, elemental analysis, and a single crystal X-ray diffraction study. The crystals are monoclinic, space group P2,la with a = 16.9167(9) A, b = 19.1276(16) A, c = 26.538(2) A, P = 100.534(6)", V = 8442.5(11) A3, Z = 16, and DCaIc = 1.574 Mg m-3. The final discrepancy factors are R, = 0.030, and Rw = 0.02 1 for 6524 significant reflections. The tin atom has a distorted trigonal bipyramidal coordination, with no short intermolecular contacts. The two axial Sn-0 bonds of 2.12 A and 2.09 A and the equatorial Sn-N bond of 2.14 8, are among the shortest found in related complexes.Key words: diorganotin(IV), bicycloazastannoxide, trigonal bipyramidal, antitumour.

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Section: Introductionmentioning

confidence: 99%

The synthesis, and molecular and crystal structure of diphenyl(2-oxidonaphthylmethyl-iminoacetato)tin(IV)

Smith¹,

Khoo²,

Goh³

et al. 1996

Can. J. Chem.

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“…3a) which reaches T/C values of about 150% in the P388leukaemia (T/C: median survival time of treated animals vs. median survival time of untreated control animals· 100). Only marginal activity was found in other tumor systems [63][64][65].…”

Section: Tinmentioning

confidence: 99%

Non-Platinum Antitumor Compounds

Pieper

Borsky

Keppler

1999

Metallopharmaceuticals I

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Non-platinum antitumor compounds have gained increasing interest during the last decade. A variety of antitumor active agents, from early transition to main -group metal or metalloid compounds, has been found and evaluated. Due to their different chemical characteristics, the mode of action and spectrum of activity of these compounds differ from each other. Antitumor activity in vitro is known for many compounds. Some compounds, like the ruthenium complexes, also exhibit promising in vivo activity. Two early transition metal complexes show interesting activity especially in experimental colon tumor models and are under evaluation in clinical trials: titanocene dichloride and budotitane. The two germanium complexes spirogermanium and germanium-132 have been evaluated but, despite their moderate toxicity, no encouraging results have been obtained. Gallium nitrate and gallium chloride are active against lymphomas and bladder cancer, and show a positive effeet on hypocalcaemias caused by tumors. They have undergone a number of clinical trials and are being investigated in promising combination regimens. Arsenic trioxide was found to be active against a rare blood cancer in clinical studies in China.

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“…The spectra were acquired at room temperature (298 K) unless otherwise specified; 13 C spectra are broadband proton decoupled. The chemical shifts were reported in ppm with respect to the references and were stated relative to external tetramethylsilane (TMS) for 1 H and 13 C NMR, and to neat tetramethyltin for 119 Sn NMR. Elemental analyses were performed with a PE-2400II apparatus.…”

Section: Materials and Instrumentationmentioning

confidence: 99%

“…1 H, 13 C, and 119 Sn NMR spectra were recorded on a Bruker AMX-300 spectrometer operating at 300, 75.3, and 111.9 MHz, respectively. The spectra were acquired at room temperature (298 K) unless otherwise specified; 13 C spectra are broadband proton decoupled.…”

Section: Materials and Instrumentationmentioning

confidence: 99%

“…To widen the scope of investigations on the coordination behavior of ligands in biological systems toward organotins, here we report the synthesis of five diorganotin(IV) derivatives of L-cysteine, and they have been characterized by elemental analyses, 1 H, 13 C, 119 Sn NMR, and IR spectroscopy. Moreover, the crystal structure of [(CH 3 ) 2 Sn(L-C 3 H 5 NO 2 S)·H 2 O] (1) has been determined by X-ray diffraction, showing that the structural distortion for tin is a displacement from the tetragonal toward a trigonal bipyramidal.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Syntheses and characterizations of diorganotin(IV) complexes with L‐cysteine: Crystal structure of [(CH₃)₂Sn(L‐C₃H₅NO₂S)· H₂O]

Zhang

2003

Heteroatom Chemistry

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Five diorganotin(IV) derivatives of L‐cysteine have been synthesized and characterized by 1H, 13C, 119Sn NMR, and IR spectroscopies along with elemental analyses. The diorganotin(IV) complexes were readily obtained from the reactions of diorganotin(IV) dichlorides and L‐cysteine. The crystal structure of [(CH3)2Sn(L‐C3H5NO2S)·H2O] contains a one dimensional infinite “S” conformation polymeric chain, with the L‐cysteine acting as a bridged tridentate ligand. The tin(IV) atom, bonding to two methyl carbons, amino nitrogen atom, thiol sulfur atom, and carboxylate oxygen atom, has a five‐coordinated trigonal bipyramid environment. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:636–641, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10218

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The antitumor activity of di-n-butyltin(IV) glycylglycinate, and the correlation with the structure of dialkyltin(IV) glycylglycinates in solution

Cited by 79 publications

References 22 publications

The synthesis, and molecular and crystal structure of diphenyl(2-oxidonaphthylmethyl-iminoacetato)tin(IV)

The synthesis, and molecular and crystal structure of diphenyl(2-oxidonaphthylmethyl-iminoacetato)tin(IV)

Non-Platinum Antitumor Compounds

Syntheses and characterizations of diorganotin(IV) complexes with L‐cysteine: Crystal structure of [(CH₃)₂Sn(L‐C₃H₅NO₂S)· H₂O]

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The antitumor activity of di-n-butyltin(IV) glycylglycinate, and the correlation with the structure of dialkyltin(IV) glycylglycinates in solution

Cited by 79 publications

References 22 publications

The synthesis, and molecular and crystal structure of diphenyl(2-oxidonaphthylmethyl-iminoacetato)tin(IV)

The synthesis, and molecular and crystal structure of diphenyl(2-oxidonaphthylmethyl-iminoacetato)tin(IV)

Non-Platinum Antitumor Compounds

Syntheses and characterizations of diorganotin(IV) complexes with L‐cysteine: Crystal structure of [(CH3)2Sn(L‐C3H5NO2S)· H2O]

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Product

Resources

About

Syntheses and characterizations of diorganotin(IV) complexes with L‐cysteine: Crystal structure of [(CH₃)₂Sn(L‐C₃H₅NO₂S)· H₂O]