Effect of Benzothiazoline Ligand and Corresponding Organoantimony(V) Derivative on the Reproductive System of Male Rats

Shanker, D.; Rai, A. K.; Singh, Y. P.; Rehwani, H.; Khushalani, V.; Gupta, R. S.

doi:https://doi.org/10.1155/BCA/2006/20979

Bioinorganic Chemistry and Applications

On this page

Abstract References Copyright Related Articles

Open Access

Volume 2006 | Article ID 020979 | https://doi.org/10.1155/BCA/2006/20979

Effect of Benzothiazoline Ligand and Corresponding Organoantimony(V) Derivative on the Reproductive System of Male Rats

D. Shanker,¹A. K. Rai,¹Y. P. Singh,¹H. Rehwani,²V. Khushalani,²and R. S. Gupta²

Received24 Sept 2004

Revised05 Feb 2005

Accepted01 Mar 2005

Published04 Apr 2006

Abstract

Benzothiazoline HNC6H4SC︹(C6H5)CH:C(OH)COOCH3 1 prepared by the condensation reaction of aroyl pyruvate and 2-aminothiophenol has been treated with Ph3Sb(OPri)2 to yield Ph3Sb[SC6H4NC(C6H5)CH:CO︹COOCH3] 2. These compounds have been characterized by elemental analyses and molecular weight determinations. The probable structures of the ligand as well as antimony complex have been tentatively proposed on the basis of IR and NMR (H1 and C13) spectral evidences. Both compounds have been tested for their antifertility activity in male albino rats. The oral administration of compounds 1 and 2 at the dose level of 10 mg/rat/day significantly reduced the weights of testes, epididymides, ventral prostate, and seminal vesicles. The production of preleptotene spermatocytes was decreased by 36.57%; 57.23%, pachytene spermatocytes by 40.06%; 62.01%, and secondary spermatocytes by 52.45%; 63.22%, following the treatment of compounds 1 and 2, respectively. The marked reduction in sperm motility and density resulted in infertility by 100%. Significant (P<.01) alterations were found in biochemical parameters of reproductive organs in treated animals as compared to control group. It is concluded that all these effects may finally impair the fertility of male rats.

References

Fr Demande, Antibacterial Organometallic Penicillium Societe d' Etudes de Recherches et al. Applications Scientifiques et medicales ERASME 1970; 14; CA 1971; 74, 3727.
J D Curry, Phenylantimony bis (2-pyridinethiol-1-oxide), Procter and Gamble co, USA, 1975, 5; CA 1975, 82, 88069.
B M Gatehouse, “The crystal structure of $[{\text{Fe}}({\text{CO}})_3 ]_2 ({\text{AsCH}}_3 )_4$ ; a compound with a noncyclic tetramethyltetra-arsine ligand,” Journal of the Chemical Society D: Chemical Communications, no. 17, pp. 948–949, 1969.
View at: Google Scholar
C A McAuliffe, “Phosphorus, arsenic, antimony and bismuth ligands,” in Comprehensive Coordination Chemistry, G Wilkinson, R D Gillard, and J A McCleverty, Eds., vol. 2, pp. 293; 989–1066, Pergamon Press, London, UK, 1987.
View at: Google Scholar
J L Wardell, “Arsenic, antimony and bismuth,” in Comprehensive Organometallic Chemistry, E W Abel, F GA Stone, and G Wilkinson, Eds., vol. 2, pp. 681–707, Pergamon Press, London, UK, 1982.
View at: Google Scholar
J L Wardell, “Arsenic, antimony and bismuth,” in Comprehensive Organometallic Chemistry, A G Davis, E W Abel, F GA Stone, and G Wilkinson, Eds., vol. 2, pp. 321–349, Pergamon Press, London, UK, 1995.
View at: Google Scholar
H BF Dixon, “The biochemical action of arsonic acids especially as phosphate analogs,” Advances in Inorganic Chemistry, vol. 44, pp. 191–227, 1997.
View at: Google Scholar
A Bara, C Socaciu, C Silvestru, and I Haiduc, “Antitumor organometallics. I. Activity of some diphenyltin(IV) and diphenylantimony(III) derivatives on in vitro and in vivo Ehrlich ascites tumor,” Anticancer Research, vol. 11, no. 4, pp. 1651–1655, 1991.
View at: Google Scholar
T Miyato, K Takahama, T Irie, and K Uekama, in Bioactive Molecules, R R Gupta, Ed., vol. 4, Elsevier Press, 1988, Amsterdam, The Netherlands, chapter 2.
L Julou, R Ducrot, J Fournel et al., “Toxicology of metiazinic acid [(10-methyl-2-phenothiazinyl) scetic acid],” Arzneim-Forsch, vol. 19, no. 8, pp. 1207–1214, 1969.
View at: Google Scholar
R Degkwitz, C Heushgem, L E Hollister et al., “The neuroleptics. 4. Toxicity and side effect in man and in the laboratory animal,” Modern problems of pharmacopsychiatry , vol. 5, pp. 71–84, 1970.
View at: Google Scholar
J H Ravina, “Hazardous therapeutics in the pregnant woman,” La Presse Médicale, vol. 72, pp. 3057–3059, 1964.
View at: Google Scholar
F E Harrington, R G Eggert, R D Wilbur, and W H Linkenheimer, “Effect of coitus on chlorpromazine inhibition of ovulation in the rat,” Endocrinology, vol. 79, no. 6, pp. 1130–1134, 1966.
View at: Google Scholar
R K Sharma, M P Dobhal, Y P Singh et al., “Effects of organoantimony(III) compounds of sterically hindered bifunctional tetradentate ligands on the reproductive system of male rats,” Metal-Based Drugs, vol. 7, no. 5, pp. 271–274, 2000.
View at: Google Scholar
S Sharma, R K Sharma, R Sharma et al., “Synthesis and characterisation of some new aluminium derivatives of Schiff bases containing N, O and S donor atoms and the anti fertility activity of the derivative ${\text{AL}}[{\text{SC}}_6 {\text{H}}_4 {\text{N}}:{\text{C}}({\text{CH}}_3 ){\text{CH}}_2 {\text{COCH}}_3 ]_3$ ,” Bioinorganic Chemistry & Applications, vol. 1, no. 3-4, pp. 215–225, 2003.
View at: Google Scholar
D Shanker, R K Sharma, J Sharma, A K Rai, and Y P Singh, “Synthesis and Characterization of a New Class of Benzothiazolines,” Phosphorus, Sulfur, and Silicon, vol. 180, no. 1, pp. 141–148, 2005.
View at: Google Scholar
J. Schmitt, “Continuing condensation of ethyl1 oxalate with acetone; continuing condensation of ethyl1 oxalate with two different ketones,” Ann., vol. 569, pp. 17–28, 1950.
View at: Google Scholar
D C Bradley, F M Abd-El Halim, R C Mehrotra, and W Wardlaw, “Reactions of acetyl chloride with zirconium alkoxides,” Journal of the Chemical Society (Resumed), pp. 4609–4612, 1952.
View at: Google Scholar
A I Vogel, A Text Book of Quantitative Inorganic Analysis, Longmans, London, UK, 5th edition, 1989.
M RN Prasad, N J Chinoy, and K M Kadam, “Changes in succinic dehydrogenase levels in the rat epididymis under normal and altered physiologic conditions,” Fertility and Sterility, vol. 23, no. 3, pp. 186–190, 1972.
View at: Google Scholar
J M Lynch, S S Raphael, L D Mellor, P D Spare, and M JH Inwood, Medical Laboratory Technology and Clinical Pathology, W. B. Saunders, Philadelphia, Pa, 1969.
W H Crosby, J I Munn, and F W Furth, “Standardizing a method for clinical hemoglobinometry,” United States Armed Forces Medical Journal, vol. 5, no. 5, pp. 693–703, 1954.
View at: Google Scholar
M M Strumia, A B Sample, and E D Hart, “An improved micro hematocrit method,” American Journal of Clinical Pathology, vol. 24, no. 9, pp. 1016–1024, 1954.
View at: Google Scholar
A M Astoor and E J King, “Simplified colorimetric blood sugar method,” The Biochemical Journal, vol. 56, p. 44, 1954.
View at: Google Scholar
A Zlatkis, B Zak, and A J Boyle, “A new method for the direct determination of serum cholesterol,” The Journal of Laboratory and Clinical Medicine, vol. 41, no. 3, pp. 486–492, 1953.
View at: Google Scholar
D B Zilversmit and A K Davis, “Microdetermination of plasma phospholipids by trichloroacetic acid precipitation,” The Journal of Laboratory and Clinical Medicine, vol. 35, no. 1, pp. 155–160, 1950.
View at: Google Scholar
S P Gottfried and B Rosenberg, “Improved manual spectrophotometric procedure for determination of serum triglycerides,” Clinical Chemistry, vol. 19, no. 9, pp. 1077–1078, 1973.
View at: Google Scholar
M Burstein, H R Scholnick, and R Morfin, “Rapid method for the isolation of lipoproteins from human serum by precipitation with polyanions,” Journal of Lipid Research, vol. 11, no. 6, pp. 583–595, 1970.
View at: Google Scholar
O H Lowry, N J Rosebrough, A L Farr, and R J Randall, “Protein measurement with the Folin phenol reagent,” The Journal of Biological Chemistry, vol. 193, no. 1, pp. 265–275, 1951.
View at: Google Scholar
L Warren, “The thiobarbituric acid assay of sialic acids,” The Journal of Biological Chemistry, vol. 234, no. 8, pp. 1971–1975, 1959.
View at: Google Scholar
R Montgomery, “Determination of glycogen,” Archives of Biochemistry and Biophysics, vol. 67, no. 2, pp. 378–386, 1957.
View at: Google Scholar
T Mann, The Biochemistry of Semen and of the Male Reproductive Tract, Methuen, London, UK, 1964.
B L Oser, Hawk's Physiological Chemistry, McGraw-Hill, New York, NY, 14th edition, 1965.
M Abercrombie, “Estimation of nuclear population from microtome sections,” The Anatomical Record, vol. 94, pp. 239–247, 1946.
View at: Google Scholar
W E McEwen, G H Briles, and B E Giddings, “Attack of alkoxide ions on antimony in tetraarylstibonium salts,” Journal of the American Chemical Society, vol. 91, no. 25, pp. 7079–7084, 1969.
View at: Google Scholar
E Jr Maslowsky, “Vibrational spectra of the organic derivatives of the group VB elements,” Journal of Organometallic Chemistry, vol. 70, no. 2, pp. 153–227, 1974.
View at: Google Scholar
R G Goel, E Jr Maslowsky, and C V Senoff, “Organoantimony compounds. III. Far-infrared and Raman spectroscopic studies on triorganoantimony(V) derivatives, R3SbX2,” Inorganic Chemistry, vol. 10, no. 11, pp. 2572–2577, 1971.
View at: Google Scholar
G O Doak, G G Long, and L D Freedman, “The infrared spectra of some phenyl-substituted pentavalent antimony compounds,” Journal of Organometallic Chemistry, vol. 4, no. 1, pp. 82–91, 1965.
View at: Google Scholar
F Neumann, “The antiandrogen cyproterone acetate: discovery, chemistry, basic pharmacology, clinical use and tool in basic research,” Experimental and Clinical Endocrinology, vol. 102, no. 1, pp. 1–32, 1994.
View at: Google Scholar
A Palacios, R D McClure, A Campfield, and R S Swerdloff, “Effect of testosterone enanthate on testis size,” The Journal of Urology, vol. 126, no. 1, pp. 46–48, 1981.
View at: Google Scholar
N R Kalla and M Vasudev, “Studies on the male antifertility agent-gossypol acetic acid. II. Effect of gossypol acetic acid on the motility and ATPase activity of human spermatozoa,” Andrologia, vol. 13, no. 2, pp. 95–98, 1981.
View at: Google Scholar
E D Gol'dberg, T G Borovskaia, E A Timina, T I Fomina, and V E Gol'dberg, “Spermatogenesis in rats after administration of the antineoplastic agent vepesid,” Biulleten' Eksperimental'noi Biologii i Meditsiny, vol. 124, no. 12, pp. 645–648, 1997 (Russian).
View at: Google Scholar
B Robaire and L Hermo, “Efferent ducts, epididymis, and vas deferens: structure, functions, and their regulation,” in The Physiology of Reproduction, E Knobil and J D Neill, Eds., pp. 999–1080, Raven Press, New York, NY, 1988.
View at: Google Scholar
S S Riar, B S Setty, and A B Kar, “Studies on the physiology and biochemistry of mammalian epididymis: biochemical composition of epididymis. A comparative study,” Fertility and Sterility, vol. 24, no. 5, pp. 355–363, 1973.
View at: Google Scholar
H Levinsky, R Singer, M Barnet, M Sagiv, and D Allalouf, “Sialic acid content of human spermatozoa and seminal plasma in relation to sperm counts,” Archives of Andrology, vol. 10, no. 1, pp. 45–46, 1983.
View at: Google Scholar
K P Gunaga, M C Rao, A R Sheth, and S S Rao, “The role of glycogen during the development of the rat testis and prostate,” Journal of Reproduction and Fertility, vol. 29, no. 2, pp. 157–162, 1972.
View at: Google Scholar
M Sarkar, P Gangopadhyay, B Basak et al., “The reversible antifertility effect of Piper betle Linn. on Swiss albino male mice,” Contraception, vol. 62, no. 5, pp. 271–274, 2000.
View at: Google Scholar
A Purohit and H MM Daradka, “Effect of mild hyperlipidaemia on testicular cell population dynamics in albino rats,” Indian Journal of Experimental Biology, vol. 37, no. 4, pp. 396–398, 1999.
View at: Google Scholar
J Parizek, J C Boursnell, M F Hay, A Babicky, and D M Taylor, “Zinc in the maturing rat testis,” Journal of Reproduction and Fertility, vol. 12, no. 3, pp. 501–507, 1966.
View at: Google Scholar
M J Hoey, “The effects of metallic salts on the histology and functioning of the rat testis,” Journal of Reproduction and Fertility, vol. 12, no. 3, pp. 461–472, 1966.
View at: Google Scholar

Copyright

Copyright © 2006 D. Shanker 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.

PDF Download Citation Order printed copies

Views

254

Downloads

905

Citations