Stable, six coordinated Bu2SnLA type complexes have been prepared [where LH =
<mml:math alttext="${\text{RCOC:C}}\left( {{\text{OH}}} \right){\text{N}}\left( {{\text{C}}_{\text{6}} {\text{H}}_{\text{5}} } \right){\text{N:CCH}}_{\text{3}}$" id="E1" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mtext>RCO</mml:mtext><mml:mover accent="true"><mml:mrow><mml:mtext>C:C</mml:mtext><mml:mrow><mml:mo>(</mml:mo><mml:mrow><mml:mtext>OH</mml:mtext></mml:mrow><mml:mo>)</mml:mo></mml:mrow><mml:mtext>N</mml:mtext><mml:mrow><mml:mo>(</mml:mo><mml:mrow><mml:msub><mml:mtext>C</mml:mtext><mml:mtext>6</mml:mtext></mml:msub><mml:msub><mml:mtext>H</mml:mtext><mml:mtext>5</mml:mtext></mml:msub></mml:mrow><mml:mo>)</mml:mo></mml:mrow><mml:mtext>N:</mml:mtext></mml:mrow><mml:mo stretchy="true">︹</mml:mo></mml:mover><mml:msub><mml:mtext>CCH</mml:mtext><mml:mtext>3</mml:mtext></mml:msub></mml:math>; R = -4-F-C6H4-(L1H), R = -4-Cl-C6H4-(L2H), R= -4-Br-C6H4-(L3H), R=
-CF3(L4H) and <mml:math alttext="${\text{AH = C}}\left( {\text{O}} \right){\text{C}}_{\text{6}} {\text{H}}_{\text{4}} {\text{C}}\left( {\text{O}} \right){\text{NCHR'COOH}}$" id="E2" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mtext>AH</mml:mtext><mml:mo>=</mml:mo><mml:mover accent="true"><mml:mrow><mml:mtext>C</mml:mtext><mml:mrow><mml:mo>(</mml:mo><mml:mtext>O</mml:mtext><mml:mo>)</mml:mo></mml:mrow><mml:msub><mml:mtext>C</mml:mtext><mml:mtext>6</mml:mtext></mml:msub><mml:msub><mml:mtext>H</mml:mtext><mml:mtext>4</mml:mtext></mml:msub><mml:mtext>C</mml:mtext><mml:mrow><mml:mo>(</mml:mo><mml:mtext>O</mml:mtext><mml:mo>)</mml:mo></mml:mrow></mml:mrow><mml:mo stretchy="true">︹</mml:mo></mml:mover><mml:msup><mml:mtext>NCHR</mml:mtext><mml:mo>′</mml:mo></mml:msup><mml:mtext>COOH</mml:mtext></mml:math>; R'= -H(A1H), -CH3(A2H), -CH(CH3)2(A3H)] by the
interaction of 1:1:1 molar ratios of di-n-butyltin(IV) dichloride with corresponding organic moieties in
refluxing benzene using two moles of Et3N as a base. In these complexes LH and AH behave as bidentate
and coordination is taking place through oxygen, this is inferred from IR and 13C NMR studies. These
complexes possess tin atoms in skew trapezoidal bipyramidal geometry with the C-Sn-C angles ranging from
149.88° to 156.84°. Some of these complexes with their corresponding organic moieties (LH, AH) were
tested for their antimicrobial activities.

Anurag Joshi

Shashi Verma

R. B. Gaurb

R. R. Sharma

Di-n-butyltin(IV) Complexes Derived from Heterocyclic β-diketones and N-Phthaloyl Amino Acids: Preparation,
Biological Evaluation, Structural Elucidation Based
upon Spectral [IR, NMR (1H, 13C, 19F and 119Sn)] Studies

The study of inorganic tin (SnCl2, SnCl4) and methyltin compounds (MeSnCl3, Me2SnCI2, Me3SnCl)
effects on the enzymatic activity of alcohol dehydrogenase (ADH) in the reaction of ethanol oxidation has
been carried out. The experimental results of the study show that inorganic tin and methyltin substances
induce slight inhibition of the catalytic activity of horse liver alcohol dehydrogenase (HLADH), unable to be
improved during pre-incubation with the enzyme. The conditions for carrying out the kinetic investigation of
the mentioned phenomenon were optimized and as it turned out the mechanism of methyltin trichloride
action, as the most effective methyltin inhibitor, is more complex than the proposed interaction of the metal
atom with SH-groups of the enzyme protein. It was demonstrated that the tin compounds act in the same
manner as methylmercury compounds and might serve as oxidative agents towards the co-enzyme NADH.
Kinetic data on MeSnCl3 were calculated. Data acquired on NAD-dependent ADH from horse liver and those
regarding NAD-dependent LDH from sturgeon liver were compared.

Pavel V. Bychkov

Tatyana N. Shekhovtsova

Elena R. Milaeva

Inhibition of Horse Liver Alcohol Dehydrogenase by
Methyltin Compounds

In order to develop platinum complexes with selective activity in primary and secondary bone
malignancies and with the aim to optimize antitumor activity, platinum(II) complexes with
aminotris(methylenephosphonic acid) as bone-seeking (osteotropic) ligand have been synthesized,
characterized and tested in the cisplatin-sensitive ovarian carcinoma cell line CH1. As non-leaving diamine
ligands, which are decisive for the cellular processing of DNA adducts, cis-R,S-cyclohexane-1,2-diamine,
trans-S,S-cyclohexane-1,2-diamine and trans-R,R-cyclohexane-1,2-diamine have been used, resulting in
complexes 1, 2, and 3, respectively. The cytotoxicity of the complexes under investigation decreases in the
order 3 <mml:math alttext="$\gt$" id="E1" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mo>&gt;</mml:mo></mml:math> 2 <mml:math alttext="$\gt$" id="E2" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mo>&gt;</mml:mo></mml:math> 1 which is in accord with structure-activity relationships with other (cyclohexane-1,2-
diamine)platinum(II) and platinum(IV) complexes: Both trans complexes (2 and 3) display a higher in vitro
potency than the corresponding cis isomer (I), with the trans-R,R isomer (3) being the most active in this
series. In comparison to the analogous (cyclohexane-1,2-diamine)platinum(II) complexes with
bis(phosphonomethyl)aminoacetic acid as osteotropic carrier ligand, the cytotoxicity of 1-3 was found to be
1.5 – 2 fold higher, which is explainable by a different coordination mode of the phosphonic acid ligands
(acetato versus phosphonato).

Markus Galanski

Susanna Slaby

Michael A. Jakupec

Bernhard K. Keppler

Synthesis and in vitro Antitumor Potency of
(Cyclohexane-1,2-Diamine)Platinum(II) Complexes
with Aminotris(Methylenephosphonic Acid) as Bone-Seeking Ligand

Fourteen to eighteen membered tetraazamacrocyclic ligands N4TTD1–N4TTD4 have been synthesized by
the condensation of aliphatic diamines. H2N–(CH2)y–NH2 (y = 2 or 3) and dicarboxylic acids, HOOC-
(CH2)x–COOH (x = 1 or 2) in the presence of condensing reagents dicyclohexylcarbodiimide (DCHC) and 4-
dimethylaminopyridine (DMAP). On reduction these macrocyclic ligands give N4TTD5-N4TTD8, which form
complexes with manganese(II) acetate. The new products with octahedral geometry have been characterized
by elemental analyses, molecular weight determinations, magnetic moment and spectral studies viz., infrared,
electronic, mass and X-ray. On the basis of the spectral studies the binding sites are proposed as the nitrogen
atom of the macrocycles. The formulation of the complexes as [Mn(CH3COO)2(N4TTDn)] (where n = 1 - 8)
has been established on the basis of chemical composition. To assess the growth inhibiting potential of the
ligands and their manganese (II) complexes biological screening have been undertaken. The testicular
morphology, testicular sperm density, sperm motility, density of cauda epididymal spermatozoa and fertility
in mating trials and biochemical parameters of reproductive organs with ligands and their corresponding
complexes, in vivo have also been described in the this communication.

Ashu Chaudhary

Anita Phor

R. V. Singh

Potentially Biodynamic Tetraaza Macrocycles and their
Manganese Complexes: Antiandrogen, Antimicrobial
and PDI Studies

The reactions of bis(cyclopentadienyl)titanium(IV) dichloride with a new class of thiosemicarbazone
(LH2), derived by condensing isatin with different N(4)-substituted thiosemicarbazides, have been studied
and products of type [Cp2Ti(L)] have been isolated. On the basis of various physico-chemical and spectral
studies, five coordinate structures have been assigned to these derivatives. Toxicity studies of titanocene
complexes at tbur different concentrations have been carried out against snail Lymnaea acuminata. The
effect of most potent compounds on the activity of acetylcholinesterase enzyme, which inhibits the activity of
enzyme, possibly by the formation of enzyme-inhibitor complex, was also studied.

Garima Vatsa

O. P. Pandey

S. K. Sengupta

Synthesis, Spectroscopic and Toxicity Studies of
Titanocene Chelates of Isatin-3-Thiosemicarbazones

Industrial water systems often suffer from undesirable inorganic deposits, such as calcium carbonate,
calcium phosphates, calcium sulfate, magnesium silicate, and others. Synthetic water additives, such as
phosphonates and phosphonocarboxylates, are the most important and widely utilized scale inhibitors in a plethora of industrial applications including cooling water, geothermal drilling, desalination, etc. The design
of efficient and cost-effective inhibitors, as well as the study of their structure and function at the molecular
level are important areas of research. This study reports various physicochemical aspects of the chemistry of
PBTC (PBTC = 2-phosphonobutane-1,2,4-tricarboxylic acid), one of the most widely used scale inhibitors in
the cooling water treatment industry. These aspects include its CaCO3 crystal growth inhibition and
modification properties under severe conditions of high CaCO3 supersaturation, stability towards oxidizing
microbiocides and tolerance towards precipitation with Ca2+. Results show that 15 ppm of PBTC can inhibit
the formation of by &#8764;35 &#37;, 30 ppm by &#8764;40 &#37;, and 60 ppm by &#8764;44 &#37;. PBTC is virtually stable to the effects
of a variety of oxidizing microbiocides, including chlorine, bromine and others. PBTC shows excellent
tolerance towards precipitation as its Ca salt. Precipitation in a 1000 ppm Ca2+ (as CaCO3) occurs after 185
ppm PBTC are present.

Konstantinos D. Demadis

Panos  Lykoudis

Chemistry of Organophosphonate Scale Growth
lnhibitors: 3. Physicochemical Aspects of 2-Phosphonobutane-1,2,4-Tricarboxylate (PBTC) And Its
Effect on C<small.letters>a</small.letters>CO3 Crystal Growth

Industrial water systems often suffer from undesirable inorganic deposits, such as calcium carbonate,
calcium phosphate(s), magnesium silicate, and others. Synthetic water additives such as phosphonates and
phosphonocarboxylates are the most important and widely utilized scale inhibitors in a plethora of industrial
applications. The design of efficient and cost-effective inhibitors, as well as the study of their structure and
function at the molecular level are important areas of research. This study reports the crystal and molecular
structure of PBTC (PBTC = 2-phosphonobutane-1,2,4-tricarboxylic acid), one of the most widely used scale
inhibitors in the cooling water treatment industry. Triclinic PBTC monohydrate crystallizes in the P 1 space
group with cell dimesions, a =7.671(1) &#xC5;, b = 8.680(1) &#xC5;, c = 9.886(1) &#xC5;, &#x3B1; = 65.518(2) deg, &#x3B2; = 71.683(2) deg, &#x3B3; = 76.173(2) deg, V = 564.20(11) &#xC5;3, and Z = 2. Bond distances in the -PO3 moiety are 1.4928(10) &#xC5; for the P=O double bond and 1.5294(10) &#xC5; and 1.5578(10) &#xC5; for the two -P-O(H) groups. P-C and C-O bond lengths fall in the normal range. A network of hydrogen bonds are formed between the water molecule of crystallization, the -P-OH and the -COOH groups.

Raphael G. Raptis

Peter Baran

Chemistry of Organophosphonate Scale Growth Inhibitors: 2. Structural Aspects of 2-Phosphonobutane-1,2,4-Tricarboxylic Acid Monohydrate (PBTC.H2O)

Batch and column experiments were performed to determine the Cu(II) binding capacity of silica-immobilized humin biomass. For column studies, 500 bed volumes of a 0.1 mM Cu(II) solution were passed through humin packed columns at the flow rates of 1, 1.5, 2, and 3 mL/min. The biopolymer showed an average Cu binding capacity of 12 ± 1.5 mg/g and a Cu recovery of about 96.5 % ± 1.5. The breakthrough points for Cu(II) alone were approximately 420, 390, 385, and 300 bed volumes for the flow rates of 1, 1.5, 2 and 3 mL/min, respectively. The interference studies demonstrated that at low concentrations, the hard cations Ca(II) and Mg(II) did not seem to represent a major interference on Cu(II) binding to the humin biopolymer. The selectivity showed by this biopolymer was Cu(II)&gt;Ca(II)&gt;Mg(II). On the other hand, batch experiments showed that Ca(II) + Mg(II) at 100mM each reduced the Cu(II) binding to 73 %. However, 1000 mM concentrations of Ca(II) and Mg(II), separately and in mixture, reduced the Cu(II) binding to 47 %, 44 % and 31 %, respectively. The results of this study showed that immobilized humin in a silica matrix could represent an inexpensive bio-source for Cu removal from contaminated water, even in the presence of low concentrations of the hard cations Ca(II) and Mg(II).

Jorge L. Gardea-Torresdey

Carolina Contreras

Guadalupe de la Rosa

Jose R. Peralta-Videa

Flow Rate and Interference Studies for Copper Binding
to a Silica-Immobilized Humin Polymer Matrix:
Column and Batch Experiments

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Bioinorganic Chemistry and Applications publishes research in all aspects of bioinorganic chemistry, including bioorganometallic chemistry and applied bioinorganic chemistry, and applications in fields such as medicine and immunology.

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Chief Editor, Professor Fanizzi, is based at the Università del Salento. His research interests and current projects are related to the study of transition metals (Platinum in particular), coordination organometallic and bioinorganic chemistry, and the applications of high field NMR Spectroscopy.

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Bioinorganic Chemistry and Applications

Table of Contents

Table of Contents: 2005

Di-n-butyltin(IV) Complexes Derived from Heterocyclic β-diketones and N-Phthaloyl Amino Acids: Preparation, Biological Evaluation, Structural Elucidation Based upon Spectral [IR, NMR (¹H, ¹³C, ¹⁹F and ¹¹⁹Sn)] Studies

Inhibition of Horse Liver Alcohol Dehydrogenase by Methyltin Compounds

Synthesis and in vitro Antitumor Potency of (Cyclohexane-1,2-Diamine)Platinum(II) Complexes with Aminotris(Methylenephosphonic Acid) as Bone-Seeking Ligand

Potentially Biodynamic Tetraaza Macrocycles and their Manganese Complexes: Antiandrogen, Antimicrobial and PDI Studies

Synthesis, Spectroscopic and Toxicity Studies of Titanocene Chelates of Isatin-3-Thiosemicarbazones

Chemistry of Organophosphonate Scale Growth lnhibitors: 3. Physicochemical Aspects of 2-Phosphonobutane-1,2,4-Tricarboxylate (PBTC) And Its Effect on CaCO₃ Crystal Growth

Chemistry of Organophosphonate Scale Growth Inhibitors: 2. Structural Aspects of 2-Phosphonobutane-1,2,4-Tricarboxylic Acid Monohydrate (PBTC.H₂O)

Flow Rate and Interference Studies for Copper Binding to a Silica-Immobilized Humin Polymer Matrix: Column and Batch Experiments