Skip to main content
Log in

Synthesis of new uracil-5-sulphonamide-p-phenyl derivatives and their effect onBiomphalaria alexandrina snail’s nucleoproteins

  • Research Articles
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

In continuation of the previous work (Fathalla, 1992) on the synthesis of some heterocycles containing uracil moiety, we report herein the incorporation of uracil moiety into cyanopyridine thione, thiosemecarbazone, semicarbazone, cyanopyridine, aminocyano pyridine, isoxazoline, pyrazoline, pyrimidine, triazolo pyrimidine, pyran, selena and thiazole derivatives which might modify their biological activities.

The biological studies revealed that the chemical compoundIII f showed high molluscicdal activity than other compounds. The profile of the nucleoprotein extracted from chemically (compoundIIIc, e, f andg) treated or UV-irradiatedB. alexandrina snails did not show appreciable differences when compared to non-treated (native) snails by using SDS-PAGE, where no animals with the nucleoprotein extracted from native, chemically (compoundIII f &g) treated or physically treatedB. alexandrina snails induced significant protection against challenge with normalS. mansoni cercariae, as compared to the non-immunized challenged control. As well as, a decrease in the number of granuloma formation and the size range of granuloma was also observed in immunized animals. It is concluded that, compoundsIII f andg have a potent molluscicidal activity. They also induced chemical modification comparable to that induced by physical treatment in the snail’s nucleoprotein, which could possibly be used in immunization againstS. mansoni infection.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Abbady, M. A., Ezbawy, S. R., Radwan Sh. M., Bayoumy, B. E. and Khalaf, A. A., Synthesis and biological activity of some New 4-(2-pyrzoline-3-yl)-,4-92-Isoxazlin-4-yl) and 4-(1,2,5,6-tetrahydro-2-thiopyrimidine-4-yl)-diaryl-sulphides and diaryl sulphones.Egypt. J. Pharm. Sci. 27, 43–56 (1986).

    CAS  Google Scholar 

  • Abdel-Hamid A. Z. and Fathalla O. A., Effect of Some uracil derivatives on mice bearing Ehlish Ascites Carcinoma.Egypt. J. Pharm. Sci., 34(1–3), 67–80 (1993).

    CAS  Google Scholar 

  • Abdel-hamid A. Z. and Rizk, M., High pressure Liquid Chomatographic Analysis of DNA from Different Snail Species, Target and Non-Target to Schitosoma Infection.Egypt. J. Bilh., 19, 59–73 (1997).

    Google Scholar 

  • Afifi, A., Contribution to the chemical carcinogenesis in xenopus. Ph. D. Thesis, UCL, Louvain ha Neuve, Belgium, 90–91, (1986).

    Google Scholar 

  • Al-Sherbiny, M., El-Ridi, R., Guirguis, N. and Dean, D. A., Identification and characterization of S.mansoni antigens recognized by T & B-lymphocyates of humans with early active intestinal and urinary Schistosomisis.Int. J. Parasitol., 25(1), 113–121 (1995).

    Article  PubMed  CAS  Google Scholar 

  • Bradford, M., A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the prenciples of protein dye binding.Annals of Biochem. 72, 248–254 (1976).

    Article  CAS  Google Scholar 

  • Dean, D. A., A review. Schistosoma and related genera: aquired resistance in mice.Exp. Parasitol., 55, 1–104 (1983).

    Article  PubMed  CAS  Google Scholar 

  • Dean, D. A., Murrel, K. D., Shoutals, X. U. and Mangold, B. L., Immunization of mice with ultra-violet irradiated S. mansoni cerriae: Are-evaulation.Am. J. Trop. Med. Hyg., 790–793 (1983).

  • Dissous, C., Jrzych, J. M. and Capron, A.,S. mansoni shares a protective oligosaccharid epitope with fresh water and marine snails.Nature, 323, 443–446 (1986).

    Article  PubMed  CAS  Google Scholar 

  • Dissous, C., Torpier, G., Duvaux-Miret, O. and Capron, A., Structural homology of tropomysin from human trematde S. mansoni and its intermediate host B. glabrata.Mol. Biochem. Parasitol., 43(2), 245–55 (1990).

    Article  PubMed  CAS  Google Scholar 

  • Dunne, D. W., Hagan, P. and Abath, F. G., Prospects for immunological control of Schistoniasis.Lancet, 345, 1488–1492 (1995).

    Article  PubMed  CAS  Google Scholar 

  • Duvall, R. H., and De Witt, W. B., An improved perfusion technique for recovering odult Schistosomomes from laboratory animals.Am. J. Trop. Med. Hyg. 16, 483–486 (1967).

    PubMed  CAS  Google Scholar 

  • Ebeid, M. Y., Kamel, M. M., Nofal, Z. M., Gadalla, K. Z. and Abdou, W. A. M., Synthesis of some new-p-cinnamoylamino)-pyrimidines and other related products of possible Antischistosomal activity.Egypt J. Pharm. Sci., vol. 32, No. 1-2, 381–387 (1991).

    CAS  Google Scholar 

  • El-Hamshary, A. S., El-Fakarany, A. F., EL-Tahawy, E. A., EL-Fouly, M. M., EL-Hawary, A. M., Immunological effects of NHN Vaccine, a chemically modified Biomphlalaria alexandrina snails antige.Egyp. J. Med. Sci., 17(2), 637–651 (1996).

    Google Scholar 

  • El-Hashash, M. A., El-Kady, M., Sayed, M. A. and El-Sawy, A. A., Some reactions of chalcone epoxides.Egypt. J. Chem., 27, 715 (1984).

    CAS  Google Scholar 

  • EL-Ridi, R., Lewis, S., Afifi, A. and Shoemak, C. B., Immunogenicity & protective capacity ofS. mansoni recombinant glyceraldehyde 3-phosphate dehydrogenase, condidate vaccine for human Schistosomisis.The SRP, International Conference on Schistosomiasis, March, 15–19 (1998).

  • Essawy, S. and Wasfy, A., Convenient Synthesis of Heterocyclic Compounds Bearing A Succinimido Moity.Egypt. J. Chem., 37, No. 3, 283–293 (1994).

    CAS  Google Scholar 

  • Fallon, P. G., Smith, P., Nicholls, T., Modha, J. and Doenhoff, M., Praziquantal induced exposure ofS. mansoni alkaline phosphatase: drug-antibody synergy which acts preferentially against female worms.J. Parasite. Imm. 16, 529–35 (1994).

    Article  CAS  Google Scholar 

  • Fathalla, O. A., Synthesis of some 1,3-dimethyluracil-5-sulphonamide-p-phenyl derivatives with expected biological activity.AL-Azhar Bull. Vol.3, No. 2, 713–726 (1992).

    CAS  Google Scholar 

  • Gammal-Eddin, F. M., Fayed, M. A., Iman, M. H., Bayoumy, A. M. S., EL-Kady, M. A. and Abdel-Raheem, M. A., The immunogenic effect of antigens ofB. alexandrina againstS. mansoni in experemental animals as measured by worm loadand viability ova.J. Egypt. Soc. Parasitol., 26(3), 609–617 (1996).

    Google Scholar 

  • Gazzinelli, R., Hakim, F., De-la-Cruz, V. F., Stover, C. K., James, S. L. and Pearce, E.: Immunization against parasites: bridging the gap between attenuated and non living vaccines.Inst. Mitt., 88, 244–248 (1991).

    Google Scholar 

  • Grzych, J. M., Dissous, C., Capron, M., Torres, S., Jampert, P. H. and Capron, A., Schistosoma mansoni. Shares with Keyhole limpet hemocyanine a protective carbohydrated epitope.J. Exp. Med., 165, 865–878 (1987).

    Article  PubMed  CAS  Google Scholar 

  • Hasaneen, H., Kamel, M. M., El-Zahar, M. L. and Eman, M., Synthesis ofp-Cinnamoyl anilino Lepidines and Other Related Products of Potential Antimicrobial Activity.Egypt. J. Chem. J. Chem., 38, No. 2, 241–248 (1995).

    CAS  Google Scholar 

  • Hussein, S., El-Kashef, B., El-Bayoumy and Talaat, I. A., Selenium Heterocycles I: Synthesis and Antibacterial Activity of Som New 1,2,3-Thia and 1,2,3-Selens-diazoles Containing Sulphonamides.Egypt. J. Pharm. Sci., 27, No. 1-4, 27–35 (1986).

    Google Scholar 

  • James, S. L. and De Blois, L. A., Induction of protective Immunity against Schistosoma mansoni by non vaccine. II Response of mouse strains with selective immune defects.J. Immunol., 130 (10), 3864–3871 (1986).

    Google Scholar 

  • Kamel, M. M., Gadalla, K. Z., Elhamouly, W. S. and Elwessimi, M. T., Synthesis of some new 4-cinnamoylanilinoquiolines of possible biological activity.Z. Naturforsch, 40b, 661–666 (1985).

    CAS  Google Scholar 

  • Lammli, U. K., Cleavage of structural proteins during assemply of the head bacteriphage T4.Nature, 177, 680 (1970).

    Article  Google Scholar 

  • Nabih, I., Immunological control of parasitic disease though chemically hosts for schistosomiasis IV. Gamma radiation as a physical mutation on deoxyribonucleic DNA in Biomphalaria alexandrina snails.Cell. Mol. Biol., 27, 270–282 (1981).

    Google Scholar 

  • Salama, M. A., Sayed, G. H., Abdou, W. A. M., Maghaby, A. S. and Flefil, E. M., Synthesis and Immunological studies of some new substituted tetrahydro-naphthaline on Biomphalaria alexandrina snails.Bull. Pharm. Cairo Univ. 35(1), 65–71 (1996).

    Google Scholar 

  • Schwick, H. G., Hungerer, K.D. and Zwisler, O., In New developments with human and verterinary vaccines, Ed. Mizrahi, A., Hertman, I., Klingberg, M. A. and Kohn, A., New York, 229 240 (1980).

  • Smythies, L. E., Penberton, R. M., Coulson, P. S., Mountford, A. R., T-cell derived cytokines associated with pulmonary immune mechanisms in mice vaccinated with irradiated cecariae of S. mansoni.J. Immunol., 148, 1512 (1992).

    PubMed  CAS  Google Scholar 

  • Tolba, M. R., Attalah, A., Nabih, I., Soliman, A. M. and EL-Sherbeny, M., Effects of irradiation and chemical treatment on Biomphalaria alexandrina antigens.J. Egypt. Ger. Soc. Zool., 18(A) Comp. Physiol., 352–376 (1995).

  • Vieira, L. Q. and Kusel, J. R.,Schistosoma mansoni andBiophalaria glabrata have some common epitopes. common epitopes are present on the surface of early stages ofS. mansoni.Comp. Biochem. Physiol., 100B(3), 507–516 (1991).

    CAS  Google Scholar 

  • WHO., Epideiology and control of schistosomiosis. World HealthOrg. Tech. Rep., ser 643 (1980).

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Fathalla O. A..

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fathalla, O.A., Gad, H.S.M. & Maghaby, A.S. Synthesis of new uracil-5-sulphonamide-p-phenyl derivatives and their effect onBiomphalaria alexandrina snail’s nucleoproteins. Arch Pharm Res 23, 128–138 (2000). https://doi.org/10.1007/BF02975501

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02975501

Key words

Navigation