142
M. Goyal et al. / Free Radical Biology and Medicine 53 (2012) 129–142
[27] Alam, A.; Goyal, M.; Iqbal, M.S.; Bindu, S.; Dey, S.; Pal, C.; Maity, P.;
Mascarenhas, N.M.; Ghoshal, N.; Bandyopadhyay, U. Cysteine-3 and
cysteine-4 are essential for thioredoxin-like oxidoreductase and antioxidant
activities of Plasmodium falciparum macrophage migration inhibitory factor.
Free Radic. Biol. Med.; 2011.
[28] Kumar, S.; Das, S. K.; Dey, S.; Maity, P.; Guha, M.; Choubey, V.; Panda, G.;
Bandyopadhyay, U. Antiplasmodial activity of [(aryl)arylsulfanylmethyl]pyr-
idine. Antimicrob. Agents Chemother. 52:705–715; 2008.
[29] Kumar, S.; Guha, M.; Choubey, V.; Maity, P.; Srivastava, K.; Puri, S. K.;
Bandyopadhyay, U. Bilirubin inhibits Plasmodium falciparum growth
through the generation of reactive oxygen species. Free Radic. Biol. Med.
44:602–613; 2008.
[30] Trivedi, V.; Chand, P.; Srivastava, K.; Puri, S. K.; Maulik, P. R.; Bandyopadhyay,
U. Clotrimazole inhibits hemoperoxidase of Plasmodium falciparum and
induces oxidative stress. Proposed antimalarial mechanism of clotrimazole.
J. Biol. Chem. 280:41129–41136; 2005.
[31] Gemma, S.; Campiani, G.; Butini, S.; Kukreja, G.; Coccone, S. S.; Joshi, B. P.;
Persico, M.; Nacci, V.; Fiorini, I.; Novellino, E.; Fattorusso, E.; Taglialatela-Scafati,
O.; Savini, L.; Taramelli, D.; Basilico, N.; Parapini, S.; Morace, G.; Yardley, V.;
Croft, S.; Coletta, M.; Marini, S.; Fattorusso, C. Clotrimazole scaffold as an
innovative pharmacophore towards potent antimalarial agents: design, synth-
esis, and biological and structure-activity relationship studies. J. Med. Chem.
51:1278–1294; 2008.
[32] Gemma, S.; Campiani, G.; Butini, S.; Kukreja, G.; Joshi, B. P.; Persico, M.;
Catalanotti, B.; Novellino, E.; Fattorusso, E.; Nacci, V.; Savini, L.; Taramelli, D.;
Basilico, N.; Morace, G.; Yardley, V.; Fattorusso, C. Design and synthesis of
potent antimalarial agents based on clotrimazole scaffold: exploring an
innovative pharmacophore. J. Med. Chem. 50:595–598; 2007.
[47] Desjardins, R. E.; Canfield, C. J.; Haynes, J. D.; Chulay, J. D. Quantitative
assessment of antimalarial activity in vitro by a semiautomated microdilu-
tion technique. Antimicrob. Agents Chemother. 16:710–718; 1979.
[48] Lambros, C.; Vanderberg, J. P. Synchronization of Plasmodium falciparum
erythrocytic stages in culture. J. Parasitol. 65:418–420; 1979.
[49] Reed, L. J.; Muench, H. A simple method of estimating fifty percent endpoints.
Am. J. Hygiene 27:493–497; 1938.
[50] Muller, S. Redox and antioxidant systems of the malaria parasite Plasmodium
falciparum. Mol. Microbiol 53:1291–1305; 2004.
[51] Frey, P. A. Radicals in enzymatic reactions. Curr. Opin. Chem. Biol. 1:347–356;
1997.
[52] Duraisingh, M. T.; Roper, C.; Walliker, D.; Warhurst, D. C. Increased sensitivity
to the antimalarials mefloquine and artemisinin is conferred by mutations in
the pfmdr1 gene of Plasmodium falciparum. Mol. Microbiol. 36:955–961;
2000.
[53] Rosenthal, P.; Miller, L. The need for new approaches to antimalarial
chemotherapy. In: Georgiev, V., editor. Antimalarial chemotherapy. Totowa,
NJ: Human Press; 2001. p. 3–13.
[54] Mugittu, K.; Genton, B.; Mshinda, H.; Beck, H. P. Molecular monitoring of
Plasmodium falciparum resistance to artemisinin in Tanzania. Malar J. 5:126;
2006.
[55] Shagufta; Srivastava, A. K.; Sharma, R.; Mishra, R.; Balapure, A. K.; Murthy, P. S.;
Panda, G. Substituted phenanthrenes with basic amino side chains: a new
series of anti-breast cancer agents. Bioorg. Med. Chem. 14:1497–1505; 2006.
[56] Das, S. K.; Panda, G.; Chaturvedi, V.; Manju, Y. S.; Gaikwad, A. K.; Sinha, S.
Design, synthesis and antitubercular activity of diarylmethylnaphthol deri-
vatives. Bioorg. Med. Chem. Lett. 17:5586–5589; 2007.
[57] Panda, G.; Mishra, J. K.; Sinha, S.; Gaikwad, A. K.; Srivastava, A. K.; Srivastava,
R.; Srivastava, B. S. 4-[10-(Methoxybenzyl)-9-anthryl]phenol derivatives as
new antitubercular agents. Arkivoc ii :29–45; 2005.
[58] Panda, G.; Parai, M. K.; Das, S. K.; Shagufta; Sinha, M.; Chaturvedi, V.;
Srivastava, A. K.; Manju, Y. S.; Gaikwad, A. N.; Sinha, S. Effect of substituents
on diarylmethanes for antitubercular activity. Eur. J. Med. Chem. 42:410–419;
2007.
[33] Choubey, V.; Guha, M.; Maity, P.; Kumar, S.; Raghunandan, R.; Maulik, P. R.;
Mitra, K.; Halder, U. C.; Bandyopadhyay, U. Molecular characterization and
localization of Plasmodium falciparum choline kinase. Biochim. Biophys. Acta
1760:1027–1038; 2006.
[34] Trager, W.; Jensen, J. B. Human malaria parasites in continuous culture.
Science 193:673–675; 1976.
[35] Choubey, V.; Maity, P.; Guha, M.; Kumar, S.; Srivastava, K.; Puri, S. K.;
Bandyopadhyay, U. Inhibition of Plasmodium falciparum choline kinase by
hexadecyltrimethylammonium bromide: a possible antimalarial mechanism.
Antimicrob. Agents Chemother. 51:696–706; 2007.
[36] Lowry, O. H.; Rosebrough, N. J.; Farr, A. L.; Randall, R. J. Protein measurement
with the Folin phenol reagent. J. Biol. Chem. 193:265–275; 1951.
[37] Schejter, A.; Lanir, A.; Epstein, N. Binding of hydrogen donors to horseradish
peroxidase: a spectroscopic study. Arch. Biochem. Biophys. 174:36–44; 1976.
[38] Pandey, A. V.; Singh, N.; Tekwani, B. L.; Puri, S. K.; Chauhan, V. S. Assay of
beta-hematin formation by malaria parasite. J. Pharm. Biomed. Anal.
20:203–207; 1999.
[39] Sullivan Jr D. J.; Gluzman, I. Y.; Goldberg, D. E. Plasmodium hemozoin
formation mediated by histidine-rich proteins. Science 271:219–222; 1996.
[40] Trivedi, V.; Chand, P.; Maulik, P. R.; Bandyopadhyay, U. Mechanism of
horseradish peroxidase-catalyzed heme oxidation and polymerization
(beta-hematin formation). Biochim. Biophys. Acta 1723:221–228; 2005.
[41] Kalyanaraman, B.; Darley-Usmar, V.; Davies, K. J.; Dennery, P. A.; Forman, H.
J.; Grisham, M. B.; Mann, G. E.; Moore, K.; Roberts 2nd L. J.; Ischiropoulos, H.
Measuring reactive oxygen and nitrogen species with fluorescent probes:
challenges and limitations. Free Radic. Biol. Med. 52:1–6; 2012.
[42] Munzel, T.; Afanas’ev, I. B.; Kleschyov, A. L.; Harrison, D. G. Detection of
superoxide in vascular tissue. Arterioscler. Thromb. Vasc. Biol. 22:1761–1768;
2002.
[43] Babbs, C. F.; Steiner, M. G. Detection and quantitation of hydroxyl radical
using dimethyl sulfoxide as molecular probe. Methods Enzymol. 186:
137–147; 1990.
[44] Biswas, K.; Bandyopadhyay, U.; Chattopadhyay, I.; Varadaraj, A.; Ali, E.;
Banerjee, R. K. A novel antioxidant and antiapoptotic role of omeprazole to
block gastric ulcer through scavenging of hydroxyl radical. J. Biol. Chem.
278:10993–11001; 2003.
[59] Panda, G.; Shagufta; Mishra, J. K.; Chaturvedi, V.; Srivastava, A. K.; Srivastava,
R.; Srivastava, B. S. Diaryloxy methano phenanthrenes:
a new class of
antituberculosis agents. Bioorg. Med. Chem. 12:5269–5276; 2004.
[60] Panda, G.; Shagufta; Srivastava, A. K.; Sinha, S. Synthesis and antitubercular
activity of 2-hydroxy-aminoalkyl derivatives of diaryloxy methano phenan-
threnes. Bioorg. Med. Chem. Lett. 15:5222–5225; 2005.
[61] Parai, M. K.; Panda, G.; Chaturvedi, V.; Manju, Y. K.; Sinha, S. Thiophene
containing triarylmethanes as antitubercular agents. Bioorg. Med. Chem. Lett.
18:289–292; 2008.
[62] Al-Qawasmeh, R. A.; Lee, Y.; Cao, M. Y.; Gu, X.; Vassilakos, A.; Wright, J. A.;
Young, A. Triaryl methane derivatives as antiproliferative agents. Bioorg. Med.
Chem. Lett. 14:347–350; 2004.
[63] Ginsburg, H.; Famin, O.; Zhang, J.; Krugliak, M. Inhibition of glutathione-
dependent degradation of heme by chloroquine and amodiaquine as
a
possible basis for their antimalarial mode of action. Biochem. Pharmacol.
56:1305–1313; 1998.
[64] Golenser, J.; Marva, E.; Har-El, R.; Chevion, M. Induction of oxidant stress by
iron available in advanced forms of Plasmodium falciparum. Free Radic. Res.
Commun. 12-13(2):639–643; 1991.
[65] Agarwal, J.; Singh, S. P.; Chanda, D.; Bawankule, D. U.; Bhakuni, R. S.; Pal, A.
Antiplasmodial activity of artecyclopentyl mether a new artemisinin deriva-
tive and its effect on pathogenesis in Plasmodium yoelii nigeriensis infected
mice. Parasitol. Res. 109:1003–1008; 2011.
[66] Benoit-Vical, F.; Lelievre, J.; Berry, A.; Deymier, C.; Dechy-Cabaret, O.;
Cazelles, J.; Loup, C.; Robert, A.; Magnaval, J. F.; Meunier, B. Trioxaquines
are new antimalarial agents active on all erythrocytic forms, including
gametocytes. Antimicrob. Agents Chemother. 51:1463–1472; 2007.
[67] Dutta, G. P.; Bajpai, R.; Vishwakarma, R. A. Antimalarial efficacy of arteether
against multiple drug resistant strain of Plasmodium yoelii nigeriensis.
Pharmacol. Res. 21:415–419; 1989.
[45] Buege, J. A.; Aust, S. D. Microsomal lipid peroxidation. Methods Enzymol.
52:302–310; 1978.
[68] Soh, P. N.; Witkowski, B.; Olagnier, D.; Nicolau, M. L.; Garcia-Alvarez, M. C.;
Berry, A.; Benoit-Vical, F. In vitro and in vivo properties of ellagic acid in
malaria treatment. Antimicrob. Agents Chemother. 53:1100–1106; 2009.
[46] Levine, R. L.; Garland, D.; Oliver, C. N.; Amici, A.; Climent, I.; Lenz, A. G.; Ahn,
B. W.; Shaltiel, S.; Stadtman, E. R. Determination of carbonyl content in
oxidatively modified proteins. Methods Enzymol. 186:464–478; 1990.