Bioinorganic Chemistry and Applications

Volume 2006, Article ID 32896, 10 pages

http://dx.doi.org/10.1155/BCA/2006/32896

## New Dihydro OO'Bis(Salicylidene) 2,2' Aminobenzothiazolyl Borate Complexes: Kinetic and Voltammetric Studies of Dimethyltin Copper Complex with Guanine, Adenine, and Calf Thymus DNA

Department of Chemistry, Faculty of Science, Aligarh Muslim University, Aligarh 202 002, India

Received 17 January 2005; Revised 21 March 2005; Accepted 29 March 2005

Copyright © 2006 Farukh Arjmand et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

#### Linked References

- J D Roberts, J Peroutka, and N Farrell, “Cellular pharmacology of polynuclear platinum anti-cancer agents,”
*Journal of Inorganic Biochemistry*, vol. 77, no. 1-2, pp. 51–57, 1999. View at Publisher · View at Google Scholar - N Farrell, Y Qu, U Bierbach, M Valsecchi, and E Menta, “Structure-activity relationship within di- and trinuclear platinum phase I clinical agents,” in
*Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug*, B Lippert, Ed., pp. 479–496, Wiley-VCH, Weinheim, Germany, 1999. View at Google Scholar - M Coluccia, A Nassi, A Boccarelli et al., “In vitro antitumour activity and cellular pharmacological properties of the platinum-iminoether complex trans-$[{\text{PtCl}}_{2}{[\text{E}-\text{HN}=\text{C}(\text{OMe})\text{Me}]}_{2}]$,”
*International Journal of Oncology*, vol. 15, no. 5, pp. 1039–1044, 1999. View at Google Scholar - W Peti, T Pieper, M Sommer, B K Keppler, and G Giester, “Synthesis of tumor-inhibiting complex salts containing the anion
*trans*-tetrachlorobis(indazole)ruthenate(III) and crystal structure of the tetraphenylphosphonium salt,”*European Journal of Inorganic Chemistry*, vol. 1999, no. 9, pp. 1551–1555, 1999. View at Publisher · View at Google Scholar - S T Sullivan, A Ciccarese, F P Fanizzi, and L G Marzilli, “Cisplatin—DNA cross-link models with an unusual type of chirality-neutral chelate amine carrier ligand,
*N,N*${}^{\prime}$dimethylpiperazine (${\text{Me}}_{2}$ppz): ${\text{Me}}_{2}$ppzPt${(\text{guanosine monophosphate})}_{2}$ adducts that exhibit novel properties,”*Inorganic Chemistry*, vol. 39, no. 4, pp. 836–842, 2000. View at Publisher · View at Google Scholar - R Vijayalakshmi, M Kanthimathi, V Subramanian, and B U Nair, “Interaction of DNA with [Cr(Schiff base)${({\text{H}}_{2}\text{O})}_{2}$]${\text{CIO}}_{4}$,”
*Biochimica et Biophysica Acta (BBA)—General Subjects*, vol. 1475, no. 2, pp. 157–162, 2000. View at Google Scholar - B Juskowiak, M Ohba, M Sato, S Takenaka, M Takagi, and H Kondo, “Photoisomerizable DNA ligands. Spectral and electrochemical properties and base-pair selectivity of binding of bis[2-(1-alkylpyridinium-4-yl)vinyl]benzene dyes,”
*Bulletin of the Chemical Society of Japan*, vol. 72, no. 2, pp. 265–277, 1999. View at Publisher · View at Google Scholar - A Rodger, K K Patel, K J Sanders, M Datt, C Sacht, and M J Hannon, “Anti-tumour platinum acylthiourea complexes and their interactions with DNA,”
*Journal of the Chemical Society, Dalton Transactions*, no. 19, pp. 3656–3663, 2002. View at Publisher · View at Google Scholar - F Athar, F Arjmand, and S Tabassum, “New asymmetric N2S2 macrocycles, their metal chelates and the photokinetics of DNA-complex interaction,”
*Transition Metal Chemistry*, vol. 26, no. 4-5, pp. 426–429, 2001. View at Publisher · View at Google Scholar - M Chauhan and F Arjmand, “Synthesis, characterization and interaction of a new chiral trinuclear complex
trinuclear complex [bis(aquodiaminotryptophanato)${\text{Cu}}^{\text{II}}-{\text{Sn}}_{2}^{\text{IV}}$] chloride with calf thymus DNA,”
*Transition Metal Chemistry*, vol. 30, pp. 481–487, 2005. View at Publisher · View at Google Scholar - M-H Baik, R A Friesner, and S J Lippard, “Theoretical study of cisplatin binding to purine bases: why does cisplatin prefer guanine over adenine?”
*Journal of the American Chemical Society*, vol. 125, no. 46, pp. 14082–14092, 2003. View at Publisher · View at Google Scholar - F E Anderson, C J Duca, and J V Scudi, “Some heterocyclic thiosemicarbazones,”
*Journal of the American Chemical Society*, vol. 73, no. 10, pp. 4967–4968, 1951. View at Publisher · View at Google Scholar - B F Spielvogel, A Sood, B R Shaw, and I H Hall, “From boron analogues of amino acids to boronated DNA: potential new pharmaceuticals and neutron capture agents,”
*Pure and Applied Chemistry*, vol. 63, no. 3, pp. 415–418, 1991. View at Google Scholar - M K Biyala, N Fahmi, and R V Singh, “Reactivity and structural study of boron complexes with biochemical aspects,”
*Indian Journal of Chemistry*, vol. 43A, no. 8, pp. 1662–1666, 2004. View at Google Scholar - A H Soloway, A KM Anisuzzaman, F Alam, R F Barth, and L Liu, “The development of carboranyl nucleic acid precursors for use in neutron capture therapy of tumors,”
*Pure and Applied Chemistry*, vol. 63, no. 3, pp. 411–413, 1991. View at Google Scholar - R Barbieri and G J Alonzo, “The configuration and lattice dynamics of complexes of dialkyltin (IV) with adinosine ${5}^{\prime}$-monophosphate and phenyl phosphate,”
*Journal of the Chemical Society, Dalton Transactions*, pp. 789–794, 1987. View at Publisher · View at Google Scholar - A Jancsó, L Nagy, E Moldrheim, and E Sletten, “Potentiometric and spectroscopic evidence for co-ordination of dimethyltin(IV) to phosphate groups of DNA fragments and related ligands,”
*Journal of the Chemical Society, Dalton Transactions*, no. 10, pp. 1587–1594, 1999. View at Google Scholar - R Barbieri, A Silvestri, A M Giuliani, V Piro, F D Simone, and G Madonia, “Organotin compounds and deoxyribonucleic acid,”
*Journal of the Chemical Society, Dalton Transactions*, no. 4, pp. 585–590, 1992. View at Publisher · View at Google Scholar - N Höti, J Ma, S Tabassum, Y Wang, and M Wu, “Triphenyl tin benzimidazolethiol, a novel antitumor agent, induces mitochondrial-mediated apoptosis in human cervical cancer cells via suppression of HPV-18 encoded E6,”
*The Journal of Biochemistry*, vol. 134, no. 4, pp. 521–528, 2003. View at Google Scholar - F Huber and R Barbceri,
*Tin as a Vital Nutrient*, CRC Press, Boca Raton, Fla, 1986. - L Ghys, M Biesemans, M Gielen et al., “Multinuclear 1D and 2D NMR investigations on the interaction between the pyrimidic nucleotides ${5}^{\text{'}}$-CMP, ${5}^{\text{'}}$-dCMP, and ${5}^{\text{'}}$-UMP and diethyltin dichloride in aqueous medium,”
*European Journal of Inorganic Chemistry*, vol. 2000, no. 3, pp. 513–522, 2000. View at Publisher · View at Google Scholar - M Pellei, C Pettinari, C Santini, B W Skelton, N Somers, and A H White, “Synthesis, spectroscopic characterization, and structural systematics of new triorganophosphinecopper(I) poly(pyrazol-1-yl)borate complexes,”
*Journal of the Chemical Society, Dalton Transactions*, no. 19, pp. 3416–3424, 2000. View at Publisher · View at Google Scholar - J Bould, J D Kennedy, G Ferguson, F T Deeney, G M O'Riordan, and T R Spalding, “Metallaheteroborane chemistry: part 16. Contrasting metal to heteroborane bonding modes in isoelectronic $\left\{{\text{MC}}_{2}{\text{B}}_{9}\right\}$ and $\left\{{\text{MAs}}_{2}{\text{B}}_{9}\right\}$ clusters. Synthesis and characterisation of $[9-\{\text{Fe}{(\text{CO})}_{2}(\eta 5-{\text{C}}_{5}{\text{H}}_{5})\}-nido-7,8-{\text{C}}_{2}{\text{B}}_{9}{\text{H}}_{12}],\text{}[7-\{\text{Fe}{(\text{CO})}_{2}(\eta 5-{\text{C}}_{5}{\text{H}}_{5})\}-nido-7,8-{\text{As}}_{2}{\text{B}}_{9}{\text{H}}_{10}]$ and $[7-\{\text{M}{(\text{CO})}_{2}(\eta 7-{\text{C}}_{7}{\text{H}}_{7})\}-nido-7,8-{\text{As}}_{2}{\text{B}}_{9}{\text{H}}_{10}]$, where M is Mo or W,”
*Dalton Transactions*, no. 23, pp. 4557–4564, 2003. View at Publisher · View at Google Scholar - A Pasini, F Demartin, O Piovesana, B Chiari, A Cinti, and O Crispu, “Novel copper(II) complexes of “short” salen homologues. Structure and magnetic properties of the tetranuclear complex [${\text{Cu}}_{2}{({\text{L}}^{2})}_{2}{]}_{2}$ [${\text{H}}_{2}{\text{L}}^{2}$ = phenyl-
*N*,*N*${}^{\prime}$-bis(salicylidene)methanediamine],”*Journal of the Chemical Society, Dalton Transactions*, no. 19, pp. 3467–3472, 2000. View at Publisher · View at Google Scholar - S Sevagapandian, G Rajagopal, K Nehru, and P Athappan, “Copper(II), nickel(II), cobalt(II) and oxovanadium(IV) complexes of substituted $\beta $-hydroxyiminoanilides,”
*Transition Metal Chemistry*, vol. 25, no. 4, pp. 388–393, 2000. View at Publisher · View at Google Scholar - A Kumer, G Singh, R N Handa, S N Dubey, and P J Squattrito, “Synthesis and characterization of complexes of cobalt(II), Nickel(II), Copper(II) and Zinc(II) with Schiff Bases Derived from Cinnamaldehyde and 4-Amino-3-ethyl-5-mercapto-s-triazole and 4-Amino-5-mercapto-3-N-propyl-s-triazole,”
*Indian Journal of Chemistry*, vol. 38A, p. 613, 1999. View at Google Scholar - S M Tripathi and J P Tandon, “Acetoxyboron derivatives of N-substituted salicylaldimines,”
*Journal of Inorganic and Nuclear Chemistry*, vol. 40, no. 6, pp. 983–985, 1978. View at Publisher · View at Google Scholar - T Pandey and R V Singh, “Synthesis structure elucidation and biological screening of unsymmetrical borate complexes of fluoroimines,”
*Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry*, vol. 30, pp. 855–866, 2000. View at Google Scholar - L J Bellamy,
*The Infrared Spectra of Complex Molecules*, Chapman & Hall, London, UK, 3rd edition, 1975. - K Nakamoto,
*Infrared and Raman Spectra of Inorganic and Coordination Compounds*, John Wiley & Sons, New York, NY, 1978. - S Chandra, G Singh, V P Tyagi, and S Raizada, “Synthesis, esr, magnetic, and electronic spectral studies on manganese(II) complexes of semicarbazone and thiosemicarbazone,”
*Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry*, vol. 31, no. 10, pp. 1759–1769, 2001. View at Publisher · View at Google Scholar - W Jiazhu, H Jingshuo, H Liyiao, S Dashuang, and H Shengzhi, “Antitumor activity of organotin compounds. Reaction, synthesis and structure of ${\text{Et}}_{2}{\text{SnCl}}_{2}$(phen) with 5-fluorouracil,”
*Inorganica Chimica Acta*, vol. 152, no. 1, pp. 67–69, 1988. View at Publisher · View at Google Scholar - E-Q Gao, W-M Bu, G-M Yang et al., “Crystal structure, redox and spectral properties of copper(II) complexes with macrocyclic ligands incorporating both oxamido and imine groups,”
*Journal of the Chemical Society, Dalton Transactions*, no. 9, pp. 1431–1436, 2000. View at Publisher · View at Google Scholar - N Raman, A Kulandaisamy, and K Jeyasubramanian, “Synthesis, spectral, redox and biological studies of some Schiff base copper(II),nickel(II), cobalt(II), manganese(II), zinc(II) and oxovanadium(II) complexes derived from 1-phenyl-2,3-dimethyl-4
(4-iminopentan-2-one) pyrazol-5-one and 2-aminophenol/
2-aminothiophenol,”
*Indian Journal of Chemistry*, vol. 41A, pp. 942–949, 2002. View at Google Scholar - M C Jain, A K Srivastava, and P C Jain, “Some tetragonally distorted copper(II) complexes of 4-benzylamidothiosemicarbazide and its thiosemicarbazone,”
*Inorganica Chimica Acta*, vol. 23, pp. 199–203, 1977. View at Publisher · View at Google Scholar - B J Hathaway and D E Billing, “The electronic properties and stereochemistry of mono-nuclear complexes of the copper(II) ion,”
*Coordination Chemistry Reviews*, vol. 5, no. 2, pp. 143–207, 1970. View at Publisher · View at Google Scholar - B J Hathaway,
*Essays in Chemistry*, edited by JN Bradley and RD Gillard, Academic Press, New York, NY, 1971. - O L Hoyos, M R Bermejo, M Fondo et al., “Mn(III) complexes with asymmetrical ${\text{N}}_{2}{\text{O}}_{3}$ Schiff bases. The unusual crystal structure of [Mn(phenglydisal-3-Br,5-Cl)(dmso)] (${\text{H}}_{3}$phenglydisal = 3-aza-
*N*-$\{$2-[1-aza-2-(2-hydroxyphenyl)vinyl]phenyl$\}$-4-(2-hydroxyphenyl)but-3-enamide), a mononuclear single-stranded helical manganese(III) complex,”*Journal of the Chemical Society, Dalton Transactions*, no. 18, pp. 3122–3127, 2000. View at Publisher · View at Google Scholar - A Caballero, F Gómez-de la Torre, F A Jalón et al., “Synthesis and characterisation of a series of ruthenium scorpionate complexes with B—H$?$M agostic interactions. Crystal structure of [RuH(${?}^{2}$-
*N*,*BH*T${\text{p}}^{\text{Tn}}$)(${\text{PMe}}_{3}$)(cod)] (T${\text{p}}^{\text{Tn}}$ = hydrotris[3-(2-thienyl)pyrazol-1-yl]borate),”*Journal of the Chemical Society, Dalton Transactions*, no. 4, pp. 427–433, 2001. View at Publisher · View at Google Scholar - M Palaniandavar, T Pandiyan, M Lakshminarayanan, and H Manohar, “Facial co-ordination in bis[bis(benzimidazol-2-ylmethyl)-amine]copper(II) perchlorate dihydrate. Synthesis, structure, spectra and redox behaviour,”
*Journal of the Chemical Society, Dalton Transactions*, no. 3, pp. 455–461, 1995. View at Publisher · View at Google Scholar - R Mathur and P Mathur, “Monomeric Cu (II) complexes with tetradentate bis (benzimidazole) ligand ; synthesis, EPR, spectral and electrochemical studies,”
*Polyhedron*, vol. 17, no. 16, pp. 2607–2615, 1998. View at Publisher · View at Google Scholar - B J Hathaway and A AG Tomlinson, “Copper(II) ammonia complexes,”
*Coordination Chemistry Reviews*, vol. 5, no. 1, pp. 1–43, 1970. View at Publisher · View at Google Scholar - S Mahadevan and M Palaniandavar, “Chiral discrimination in the binding of tris(phenanthroline)ruthenium(II) to calf thymus DNA: an electrochemical study,”
*Bioconjugate Chemistry*, vol. 7, no. 1, pp. 138–143, 1996. View at Publisher · View at Google Scholar - X Lu, K Zhu, M Zhang, H Liu, and J Kang, “Voltammetric studies of the interaction of transition-metal complexes with DNA,”
*Journal of Biochemical and Biophysical Methods*, vol. 52, no. 3, pp. 189–200, 2002. View at Publisher · View at Google Scholar - J Liu, T Zhang, T Lu et al., “DNA-binding and cleavage studies of macrocyclic copper(II) complexes,”
*Journal of Inorganic Biochemistry*, vol. 91, no. 1, pp. 269–276, 2002. View at Publisher · View at Google Scholar - M Baldini, M Belicchi-Ferrari, F Bisceglie, G Pelosi, S Pinelli, and P Tarasconi, “Cu(II) complexes with heterocyclic substituted thiosemicarbazones: the case of 5-formyluracil. Synthesis, characterization, x-ray structures, DNA interaction studies, and biological activity,”
*Inorganic Chemistry*, vol. 42, no. 6, pp. 2049–2055, 2003. View at Publisher · View at Google Scholar - Å Sykfont, A Ericson, and S KC Elmroth, “Non-uniform rate for platination of guanine-N7 located in short DNA oligomers,”
*Chemical Communications*, no. 13, pp. 1190–1191, 2001. View at Publisher · View at Google Scholar - M-H Baik, R A Friesner, and S J Lippard, “
*cis*-[Pt${({\text{NH}}_{3})}_{2}$(L)${]}^{2+/+}$ (L = Cl, ${\text{H}}_{2}$O, N${\text{H}}_{3}$) binding to purines and CO: does $\pi $-back-donation play a role?”*Inorganic Chemistry*, vol. 42, no. 26, pp. 8615–8617, 2003. View at Publisher · View at Google Scholar - M-H Baik, R A Friesner, and S J Lippard, “Theoretical study of cisplatin binding to purine bases: why does cisplatin prefer guanine over adenine?”
*Journal of the American Chemical Society*, vol. 125, no. 46, pp. 14082–14092, 2003. View at Publisher · View at Google Scholar - A M Thomas, A D Naik, M Nethaji, and A R Chakravarty, “Photo-induced DNA cleavage activity of ternary
(N-salicylidene-L-methioninato)copper(II) complexes of phenanthroline bases,”
*Indian Journal of Chemistry*, vol. 43A, no. 4, pp. 691–700, 2004. View at Google Scholar