Copyright (c) 2015 AJC
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Synthesis of Naphthoquinone Dendrimer Based Materials as Potential Antimalarial Drugs
Corresponding Author(s) : C.M. Ndiaye
Asian Journal of Chemistry,
Vol. 27 No. 11 (2015): Vol 27 Issue 11
Abstract
The synthesis of two new PPI-G1 dendrimers containing lawsone (2-hydroxy-p-naphthoquinone) as pharmacophore is reported. The compounds were synthesized in course of Mannich reaction involving lawsone, the commercial PPI-G1 (polypropyleneimine-G1) dendrimer with functional amino groups on the exterior and acetaldehyde (1) or benzaldehyde (2) in 4:1:4 molar ratio. Their structures are authenticated via FT-IR, 1H and 13C{1H} NMR and mass spectra.
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- (a) WHO, World Malaria Report (2008); (b) WHO, World Malaria Report (2005).
- (a) I.J. Udeinya, J.A. Schmidt, M. Aikawa, L.H. Miller and I. Green, Science, 213, 555 (1981); doi:10.1126/science.7017935; (b) W.H. Wernsdorfer, in ed.: J.P. Kreier, The Importance of Malaria in the World; In: Malaria, Academic Press, New York, vol. 1, pp. 1-93 (1980).
- R.W. Snow, M. Craig, U. Deichmann and K. Marsh, Bull. World Health Organ., 77, 624 (1999).
- P.I. Trigg and A.V. Kondrachine, The Current Global Malaria Situation, In: Malaria: Parasite Biology, Pathogenesis, and Protection, ASM Press, Washington, pp. 11-22 (1998).
- B. Pradines, J. Dormoi, S. Briolant, H. Bogreau and C. Rogier, Revue Francoph. Labo, 51 (2010); doi:10.1016/S1773-035X(10)70510-4.
- (a) J.-F. Trape, G. Pison, M.-P. Preziosi, C. Enel, A.D. du Lou, V. Delaunay, B. Samb, E. Lagarde, J.-F. Molez and F. Simondon, C. R. Acad. Sci. III, 321, 689 (1998); doi:10.1016/S0764-4469(98)80009-7; (b) J.F. Trape, Am. J. Trop. Med. Hyg., 64, 12 (2001).
- P. Blolan, Drug Resistance in Malaria, WHO monograph, WHO/CDS/CSR/4 (2001).
- T.K. Mutabingwa, Acta Trop., 95, 305 (2005); doi:10.1016/j.actatropica.2005.06.009.
- WHO, World Malaria Report (2009).
- P.A. Kager, Trop. Med. Int. Health, 7, 1042 (2002); doi:10.1046/j.1365-3156.2002.00981.x.
- J. Delmont, Med. Trop., 62, 232 (2002).
- D. Camus, E. Dutoit, V. Masson, P. Inglebert and L. Delahaes, Méd. Trop., 62, 225 (2002).
- (a) J.P. Gil, F. Nogueira, J. Strömberg-Nörklit, J. Lindberg, M. Carrolo, C. Casimiro, D. Lopes, A.P. Arez, P.V. Cravo and V.E. Rosário, Mol. Cell. Probes, 17, 85 (2003); doi:10.1016/S0890-8508(03)00006-9; (b) E. Schwartz, S. Bujanover and K.C. Kain, Clin. Infect. Dis., 37, 450 (2003); doi:10.1086/375599.
- C. Biot and B. Pridines, Biofutur, 293, 38 (2008).
- (a) R. Duncan and L. Izzo, Adv. Drug Deliv. Rev., 57, 2215 (2005); doi:10.1016/j.addr.2005.09.019; (b) Y. Cheng, H. Qu, M. Ma, Z. Xu, P. Xu, Y. Fang and T. Xu, Eur. J. Med. Chem., 42, 1032 (2007); doi:10.1016/j.ejmech.2006.12.035; (c) D.G. Mullen, D.Q. McNerny, A. Desai, X. Cheng, S.C. DiMaggio, A. Kotlyar, Y. Zhong, S. Qin, C.V. Kelly, T.P. Thomas, I. Majoros, B.G. Orr Jr., J.R. Baker Jr. and M.M. Banaszak Holl, Bioconjug. Chem., 22, 679 (2011); doi:10.1021/bc100360v.
- S.-E. Stiriba, H. Frey and R. Haag, Angew. Chem. Int. Ed., 41, 1329 (2002); doi:10.1002/1521-3773(20020415)41:8<1329::AID-ANIE1329>3.0.CO;2-P.
- C. Kojima, K. Kono, K. Maruyama and T. Takagishi, Bioconjug. Chem., 11, 910 (2000); doi:10.1021/bc0000583.
- (a) M. Guillot-Nieckowski, S. Eisler and F. Diederich, New J. Chem., 31, 1111 (2007); doi:10.1039/B614877H; (b) J.P. Behr, Med. Sci., 12, 56 (1996).
- S. Langereis, Q.G. de Lussanet, M.H.P. van Genderen, E.W. Meijer, R.G.H. Beets-Tan, A.W. Griffioen, J.M.A. van Engelshoven and W.H. Backes, NMR Biomed., 19, 133 (2006); doi:10.1002/nbm.1015.
- (a) D.I. Bernstein, L.R. Stanberry, S. Sacks, N.K. Ayisi, Y.H. Gong, J. Ireland, R.J. Mumper, G. Holan, B. Matthews, T. McCarthy and N. Bourne, Antimicrob. Agents Chemother., 47, 3784 (2003); doi:10.1128/AAC.47.12.3784-3788.2003; (b) N. Bourne, L.R. Stanberry, E.R. Kern, G. Holan, B. Matthews and D.I. Bernstein, Antimicrob. Agents Chemother., 44, 2471 (2000); doi:10.1128/AAC.44.9.2471-2474.2000; (c) M. Tulu, N.M. Aghatabay, M. Senel, C. Dizman, T. Parali and B. Dulger, Eur. J. Med. Chem., 44, 1093 (2009); doi:10.1016/j.ejmech.2008.06.016.
- (a) M. Ma, Y. Cheng, Z. Xu, P. Xu, H. Qu, Y. Fang, T. Xu and L. Wen, Eur. J. Med. Chem., 42, 93 (2007); doi:10.1016/j.ejmech.2006.07.015; (b) M.K. Calabretta, A. Kumar, A.M. McDermott and C. Cai, Biomacromolecules, 8, 1807 (2007); doi:10.1021/bm0701088.
- D. Bhadra, S. Bhadra and N.K. Jain, Proceedings of the 2004 International Conference on MMEMS, NANO and Smart Systems (ICMENS’04).
- D. Bhadra, A.K. Yadav, S. Bhadra and N.K. Jain, Int. J. Pharm., 295, 221 (2005); doi:10.1016/j.ijpharm.2005.01.026.
- (a) D. Bhadra, S. Bhadra and N.K. Jain, J. Pharm. Pharm. Sci., 8, 467 (2005); (b) D. Bhadra, S. Bhadra and N.K. Jain, J. Drug Del. Sci. Tech., 15, 65 (2005); doi:10.1016/S1773-2247(05)50008-X.
- (a) A.T. Hudson, M. Dickin, C.D. Ginger, W.E. Gutteridge, T. Hodich, D.B. Hutchinson, M. Pudney, A.W. Randall and V.S. Latter, Drug Expt. Clin. Res., 17, 427 (1991); (b) A.T. Hudson, Parasitol. Today, 9, 66 (1993); doi:10.1016/0169-4758(93)90040-M; (c) L.F. Fieser and A.P. Richardson, J. Am. Chem. Soc., 70, 3156 (1948); doi:10.1021/ja01190a002.
- T. Hudson, in eds.: W. Peter and W.H.G. Richard, Lapinone, Menoctone, Hydroxyquinoline-quinones and Similar Structures, In: Antimalarial Drugs, Current Antimalarial and New Drug Developments, Springer-Verlag, Berlin, Heideburg, New York and Tokyo, p. 343 (1984).
- http://www.chem.tue.nl/smo.
- A. Baramee, A. Coppin, M. Mortuaire, L. Pelinski, S. Tomavo and J. Brocard, Bioorg. Med. Chem., 14, 1294 (2006); doi:10.1016/j.bmc.2005.09.054.
- A.P. Neves, C.C. Barbosa, S.J. Greco, M.D. Vargas, L.C. Visentin, C.B. Pinheiro, A.S. Mangrich, J.P. Barbosa and G.L. Costa, J. Braz. Chem. Soc., 20, 712 (2009); doi:10.1590/S0103-50532009000400015.
- S. Girault, P. Grellier, A. Berecibar, L. Maes, P. Lemiere, E. Mouray, E. Davioud-Charvet and C. Sergheraert, J. Med. Chem., 44, 1658 (2001); doi:10.1021/jm001096a.
- (a) N. Chavain, E. Davioud-Charvet, X. Trivelli, L. Mbeki, M. Rottmann, R. Brun and C. Biot, Bioorg. Med. Chem., 17, 8048 (2009); doi:10.1016/j.bmc.2009.10.008; (b) H. Bauer, K. Fritz-Wolf, A. Winzer, S. Kühner, S. Little, V. Yardley, H. Vezin, B. Palfey, R.H. Schirmer and E. Davioud-Charvet, J. Am. Chem. Soc., 128, 10784 (2006); doi:10.1021/ja061155v.
- (a) S.J. Wadher, N.A. Karande, D.S. Borkar and P.G. Yeole, Int. J. Chem. Tech. Res., 1, 1303 (2009); (b) T. Srivastava, A. Gaikwad, W. Haq, S. Sinha and S.B. Katti, ARKIVOC, 120 (2004); doi:10.3998/ark.5550190.0006.209.
- A. Dömling, B. Beck, E. Herdtweck, W. Antuch, C. Oeffner, N. Yehia, A. Gracia-Marques, ARKIVOC, 99 (2006); doi:10.3998/ark.5550190.0008.c08.
References
(a) WHO, World Malaria Report (2008); (b) WHO, World Malaria Report (2005).
(a) I.J. Udeinya, J.A. Schmidt, M. Aikawa, L.H. Miller and I. Green, Science, 213, 555 (1981); doi:10.1126/science.7017935; (b) W.H. Wernsdorfer, in ed.: J.P. Kreier, The Importance of Malaria in the World; In: Malaria, Academic Press, New York, vol. 1, pp. 1-93 (1980).
R.W. Snow, M. Craig, U. Deichmann and K. Marsh, Bull. World Health Organ., 77, 624 (1999).
P.I. Trigg and A.V. Kondrachine, The Current Global Malaria Situation, In: Malaria: Parasite Biology, Pathogenesis, and Protection, ASM Press, Washington, pp. 11-22 (1998).
B. Pradines, J. Dormoi, S. Briolant, H. Bogreau and C. Rogier, Revue Francoph. Labo, 51 (2010); doi:10.1016/S1773-035X(10)70510-4.
(a) J.-F. Trape, G. Pison, M.-P. Preziosi, C. Enel, A.D. du Lou, V. Delaunay, B. Samb, E. Lagarde, J.-F. Molez and F. Simondon, C. R. Acad. Sci. III, 321, 689 (1998); doi:10.1016/S0764-4469(98)80009-7; (b) J.F. Trape, Am. J. Trop. Med. Hyg., 64, 12 (2001).
P. Blolan, Drug Resistance in Malaria, WHO monograph, WHO/CDS/CSR/4 (2001).
T.K. Mutabingwa, Acta Trop., 95, 305 (2005); doi:10.1016/j.actatropica.2005.06.009.
WHO, World Malaria Report (2009).
P.A. Kager, Trop. Med. Int. Health, 7, 1042 (2002); doi:10.1046/j.1365-3156.2002.00981.x.
J. Delmont, Med. Trop., 62, 232 (2002).
D. Camus, E. Dutoit, V. Masson, P. Inglebert and L. Delahaes, Méd. Trop., 62, 225 (2002).
(a) J.P. Gil, F. Nogueira, J. Strömberg-Nörklit, J. Lindberg, M. Carrolo, C. Casimiro, D. Lopes, A.P. Arez, P.V. Cravo and V.E. Rosário, Mol. Cell. Probes, 17, 85 (2003); doi:10.1016/S0890-8508(03)00006-9; (b) E. Schwartz, S. Bujanover and K.C. Kain, Clin. Infect. Dis., 37, 450 (2003); doi:10.1086/375599.
C. Biot and B. Pridines, Biofutur, 293, 38 (2008).
(a) R. Duncan and L. Izzo, Adv. Drug Deliv. Rev., 57, 2215 (2005); doi:10.1016/j.addr.2005.09.019; (b) Y. Cheng, H. Qu, M. Ma, Z. Xu, P. Xu, Y. Fang and T. Xu, Eur. J. Med. Chem., 42, 1032 (2007); doi:10.1016/j.ejmech.2006.12.035; (c) D.G. Mullen, D.Q. McNerny, A. Desai, X. Cheng, S.C. DiMaggio, A. Kotlyar, Y. Zhong, S. Qin, C.V. Kelly, T.P. Thomas, I. Majoros, B.G. Orr Jr., J.R. Baker Jr. and M.M. Banaszak Holl, Bioconjug. Chem., 22, 679 (2011); doi:10.1021/bc100360v.
S.-E. Stiriba, H. Frey and R. Haag, Angew. Chem. Int. Ed., 41, 1329 (2002); doi:10.1002/1521-3773(20020415)41:8<1329::AID-ANIE1329>3.0.CO;2-P.
C. Kojima, K. Kono, K. Maruyama and T. Takagishi, Bioconjug. Chem., 11, 910 (2000); doi:10.1021/bc0000583.
(a) M. Guillot-Nieckowski, S. Eisler and F. Diederich, New J. Chem., 31, 1111 (2007); doi:10.1039/B614877H; (b) J.P. Behr, Med. Sci., 12, 56 (1996).
S. Langereis, Q.G. de Lussanet, M.H.P. van Genderen, E.W. Meijer, R.G.H. Beets-Tan, A.W. Griffioen, J.M.A. van Engelshoven and W.H. Backes, NMR Biomed., 19, 133 (2006); doi:10.1002/nbm.1015.
(a) D.I. Bernstein, L.R. Stanberry, S. Sacks, N.K. Ayisi, Y.H. Gong, J. Ireland, R.J. Mumper, G. Holan, B. Matthews, T. McCarthy and N. Bourne, Antimicrob. Agents Chemother., 47, 3784 (2003); doi:10.1128/AAC.47.12.3784-3788.2003; (b) N. Bourne, L.R. Stanberry, E.R. Kern, G. Holan, B. Matthews and D.I. Bernstein, Antimicrob. Agents Chemother., 44, 2471 (2000); doi:10.1128/AAC.44.9.2471-2474.2000; (c) M. Tulu, N.M. Aghatabay, M. Senel, C. Dizman, T. Parali and B. Dulger, Eur. J. Med. Chem., 44, 1093 (2009); doi:10.1016/j.ejmech.2008.06.016.
(a) M. Ma, Y. Cheng, Z. Xu, P. Xu, H. Qu, Y. Fang, T. Xu and L. Wen, Eur. J. Med. Chem., 42, 93 (2007); doi:10.1016/j.ejmech.2006.07.015; (b) M.K. Calabretta, A. Kumar, A.M. McDermott and C. Cai, Biomacromolecules, 8, 1807 (2007); doi:10.1021/bm0701088.
D. Bhadra, S. Bhadra and N.K. Jain, Proceedings of the 2004 International Conference on MMEMS, NANO and Smart Systems (ICMENS’04).
D. Bhadra, A.K. Yadav, S. Bhadra and N.K. Jain, Int. J. Pharm., 295, 221 (2005); doi:10.1016/j.ijpharm.2005.01.026.
(a) D. Bhadra, S. Bhadra and N.K. Jain, J. Pharm. Pharm. Sci., 8, 467 (2005); (b) D. Bhadra, S. Bhadra and N.K. Jain, J. Drug Del. Sci. Tech., 15, 65 (2005); doi:10.1016/S1773-2247(05)50008-X.
(a) A.T. Hudson, M. Dickin, C.D. Ginger, W.E. Gutteridge, T. Hodich, D.B. Hutchinson, M. Pudney, A.W. Randall and V.S. Latter, Drug Expt. Clin. Res., 17, 427 (1991); (b) A.T. Hudson, Parasitol. Today, 9, 66 (1993); doi:10.1016/0169-4758(93)90040-M; (c) L.F. Fieser and A.P. Richardson, J. Am. Chem. Soc., 70, 3156 (1948); doi:10.1021/ja01190a002.
T. Hudson, in eds.: W. Peter and W.H.G. Richard, Lapinone, Menoctone, Hydroxyquinoline-quinones and Similar Structures, In: Antimalarial Drugs, Current Antimalarial and New Drug Developments, Springer-Verlag, Berlin, Heideburg, New York and Tokyo, p. 343 (1984).
A. Baramee, A. Coppin, M. Mortuaire, L. Pelinski, S. Tomavo and J. Brocard, Bioorg. Med. Chem., 14, 1294 (2006); doi:10.1016/j.bmc.2005.09.054.
A.P. Neves, C.C. Barbosa, S.J. Greco, M.D. Vargas, L.C. Visentin, C.B. Pinheiro, A.S. Mangrich, J.P. Barbosa and G.L. Costa, J. Braz. Chem. Soc., 20, 712 (2009); doi:10.1590/S0103-50532009000400015.
S. Girault, P. Grellier, A. Berecibar, L. Maes, P. Lemiere, E. Mouray, E. Davioud-Charvet and C. Sergheraert, J. Med. Chem., 44, 1658 (2001); doi:10.1021/jm001096a.
(a) N. Chavain, E. Davioud-Charvet, X. Trivelli, L. Mbeki, M. Rottmann, R. Brun and C. Biot, Bioorg. Med. Chem., 17, 8048 (2009); doi:10.1016/j.bmc.2009.10.008; (b) H. Bauer, K. Fritz-Wolf, A. Winzer, S. Kühner, S. Little, V. Yardley, H. Vezin, B. Palfey, R.H. Schirmer and E. Davioud-Charvet, J. Am. Chem. Soc., 128, 10784 (2006); doi:10.1021/ja061155v.
(a) S.J. Wadher, N.A. Karande, D.S. Borkar and P.G. Yeole, Int. J. Chem. Tech. Res., 1, 1303 (2009); (b) T. Srivastava, A. Gaikwad, W. Haq, S. Sinha and S.B. Katti, ARKIVOC, 120 (2004); doi:10.3998/ark.5550190.0006.209.
A. Dömling, B. Beck, E. Herdtweck, W. Antuch, C. Oeffner, N. Yehia, A. Gracia-Marques, ARKIVOC, 99 (2006); doi:10.3998/ark.5550190.0008.c08.