7
14
KUMAR ET AL.
ANTIMICROB. AGENTS CHEMOTHER.
activity in vivo against the MDR rodent malaria parasite P.
yoelii. In conclusion, this study has identified AASMP as a new
class of TRSMs with antiplasmodial activity both in vitro and in
vivo.
23. Gemma, S., G. Campiani, S. Butini, G. Kukreja, B. P. Joshi, M. Persico, B.
Catalanotti, E. Novellino, E. Fattorusso, V. Nacci, L. Savini, D. Taramelli, N.
Basilico, G. Morace, V. Yardley, and C. Fattorusso. 2007. Design and syn-
thesis of potent antimalarial agents based on clotrimazole scaffold: exploring
an innovative pharmacophore. J. Med. Chem. 50:595–598.
2
4. Goldman, I. F., S. H. Qari, J. Skinner, S. Oliveira, J. M. Nascimento, M. M.
Povoa, W. E. Collins, and A. A. Lal. 1992. Use of glass beads and CF 11
cellulose for removal of leukocytes from malaria-infected human blood in
field settings. Mem. Inst. Oswaldo Cruz 87:583–587.
ACKNOWLEDGMENTS
S.K., S.K.D., M.G., and V.C. gratefully acknowledge the Council of
Scientific and Industrial Research, New Delhi, India, for providing
Senior Research fellowships to carry out this work and providing funds
through SIP0007 project.
2
2
5. Greenwood, B., and T. Mutabingwa. 2002. Malaria in 2002. Nature 415:670–
6
72.
6. Guha, M., S. Kumar, V. Choubey, P. Maity, and U. Bandyopadhyay. 2006.
Apoptosis in liver during malaria: role of oxidative stress and implication of
mitochondrial pathway. FASEB J. 20:1224–1226.
REFERENCES
27. Jing, X. B., X. B. Cai, H. Hu, S. Z. Chen, B. M. Chen, and J. Y. Cai. 2007.
Reactive oxygen species and mitochondrial membrane potential are modu-
lated during CDDP-induced apoptosis in EC-109 cells. Biochem. Cell Biol.
1
2
3
4
5
. Al-Qawasmeh, R. A., Y. Lee, M. Y. Cao, X. Gu, A. Vassilakos, J. A. Wright,
and A. Young. 2004. Triaryl methane derivatives as antiproliferative agents.
Bioorg. Med. Chem. Lett. 14:347–350.
. Ancelin, M. L., H. J. Vial, and J. R. Philippot. 1985. Inhibitors of choline
transport into Plasmodium-infected erythrocytes are effective antiplasmodial
compounds in vitro. Biochem. Pharmacol. 34:4068–4071.
. Babbs, C. F., and M. G. Steiner. 1990. Detection and quantitation of hy-
droxyl radical using dimethyl sulfoxide as molecular probe. Methods Enzy-
mol. 186:137–147.
. Begriche, K., A. Igoudjil, D. Pessayre, and B. Fromenty. 2006. Mitochondrial
dysfunction in NASH: causes, consequences and possible means to prevent
it. Mitochondrion 6:1–28.
8
5:265–271.
2
8. Kannan, R., K. Kumar, D. Sahal, S. Kukreti, and V. S. Chauhan. 2005.
Reaction of artemisinin with haemoglobin: implications for antimalarial
activity. Biochem. J. 385:409–418.
9. Kumar, S., and U. Bandyopadhyay. 2005. Free heme toxicity and its detox-
ification systems in human. Toxicol. Lett. 157:175–188.
2
30. Kumar, S., M. Guha, V. Choubey, P. Maity, and U. Bandyopadhyay. 2007.
Antimalarial drugs inhibiting hemozoin (beta-hematin) formation: a mech-
anistic update. Life Sci. 80:813–828.
31. Lambros, C., and J. P. Vanderberg. 1979. Synchronization of Plasmodium
falciparum erythrocytic stages in culture. J. Parasitol. 65:418–420.
32. Lemberg, R., and J. Legge. 1949. Hematin compounds and bile pigments:
their constitution, metabolism, and function. Interscience Publishers, New
York, NY.
. Biswas, K., U. Bandyopadhyay, I. Chattopadhyay, A. Varadaraj, E. Ali, and
R. K. Banerjee. 2003. A novel antioxidant and antiapoptotic role of omep-
razole to block gastric ulcer through scavenging of hydroxyl radical. J. Biol.
Chem. 278:10993–11001.
6
7
. Bolshan, Y., C. Y. Chen, J. R. Chilenski, F. Gosselin, D. J. Mathre, P. D.
O’Shea, A. Roy, and R. D. Tillyer. 2004. Nucleophilic displacement at ben-
zhydryl centers: asymmetric synthesis of 1,1-diarylalkyl derivatives. Org. Lett.
33. Lowry, O. H., N. J. Rosebrough, A. L. Farr, and R. J. Randall. 1951. Protein
measurement with the Folin phenol reagent. J. Biol. Chem. 193:265–275.
34. Mather, M. W., E. Darrouzet, M. Valkova-Valchanova, J. W. Cooley, M. T.
McIntosh, F. Daldal, and A. B. Vaidya. 2005. Uncovering the molecular
mode of action of the antimalarial drug atovaquone using a bacterial system.
J. Biol. Chem. 280:27458–27465.
35. McNally, J., S. M. O’Donovan, and J. P. Dalton. 1992. Plasmodium berghei
and Plasmodium chabaudi chabaudi: development of simple in vitro eryth-
rocyte invasion assays. Parasitology 105(Pt. 3):355–362.
36. Motterlini, R., R. Foresti, K. Vandegriff, M. Intaglietta, and R. M. Winslow.
1995. Oxidative-stress response in vascular endothelial cells exposed to acel-
lular hemoglobin solutions. Am. J. Physiol. 269:H648–H655.
37. Munzel, T., I. B. Afanas’ev, A. L. Kleschyov, and D. G. Harrison. 2002.
Detection of superoxide in vascular tissue. Arterioscler. Thromb. Vasc. Biol.
22:1761–1768.
6
:111–114.
. Brown, S. B., M. Shillcock, and P. Jones. 1976. Equilibrium and kinetic
studies of the aggregation of porphyrins in aqueous solution. Biochem. J.
1
53:279–285.
8
. Buege, J. A., and S. D. Aust. 1978. Microsomal lipid peroxidation. Methods
Enzymol. 52:302–310.
9
. Chattopadhyay, I., U. Bandyopadhyay, K. Biswas, P. Maity, and R. K.
Banerjee. 2006. Indomethacin inactivates gastric peroxidase to induce reac-
tive-oxygen-mediated gastric mucosal injury and curcumin protects it by
preventing peroxidase inactivation and scavenging reactive oxygen. Free
Radic. Biol. Med. 40:1397–1408.
1
0. Choubey, V., P. Maity, M. Guha, S. Kumar, K. Srivastava, S. K. Puri, and U.
Bandyopadhyay. 2007. Inhibition of Plasmodium falciparum choline kinase
by hexadecyltrimethylammonium bromide: a possible antimalarial mecha-
nism. Antimicrob. Agents Chemother. 51:696–706.
38. Nair, V., S. Thomas, S. C. Mathew, and K. G. Abhilash. 2006. Recent
advances in the chemistry of triaryl- and triheteroarylmethanes. Tetrahedron
62:6731–6747.
1
1
1. Clark, I. A., and N. H. Hunt. 1983. Evidence for reactive oxygen intermedi-
ates causing hemolysis and parasite death in malaria. Infect. Immun. 39:1–6.
2. Coban, C., K. J. Ishii, D. J. Sullivan, and N. Kumar. 2002. Purified malaria
pigment (hemozoin) enhances dendritic cell maturation and modulates the
isotype of antibodies induced by a DNA vaccine. Infect. Immun. 70:3939–
39. Novelli, F., B. Tasso, and F. Sparatore. 1999. Synthesis and pharmacological
evaluation of some thiolupinine derivatives. Farmaco 54:354–358.
40. Orjih, A. U., H. S. Banyal, R. Chevli, and C. D. Fitch. 1981. Hemin lyses
malaria parasites. Science 214:667–669.
41. Pagola, S., P. W. Stephens, D. S. Bohle, A. D. Kosar, and S. K. Madsen. 2000.
The structure of malaria pigment beta-haematin. Nature 404:307–310.
42. Panda, G., J. K. Mishra, S. Sinha, A. K. Gaikwad, A. K. Srivastava, R.
Srivastava, and B. S. Srivastava. 2005. 4-[10-(Methoxybenzyl)-9-anthryl-
]phenol derivatives as new antitubercular agents. Arkivoc ii:29–45.
43. Panda, G., M. K. Parai, S. K. Das, Shagufta, M. Sinha, V. Chaturvedi, A. K.
Srivastava, Y. S. Manju, A. N. Gaikwad, and S. Sinha. 2007. Effect of
substituents on diarylmethanes for antitubercular activity. Eur. J. Med.
Chem. 42:410–419.
44. Panda, G., Shagufta, J. K. Mishra, V. Chaturvedi, A. K. Srivastava, R.
Srivastava, and B. S. Srivastava. 2004. Diaryloxy methano phenanthrenes: a
new class of antituberculosis agents. Bioorg Med. Chem. 12:5269–5276.
45. Panda, G., Shagufta, A. K. Srivastava, and S. Sinha. 2005. Synthesis and
antitubercular activity of 2-hydroxy-aminoalkyl derivatives of diaryloxy
methano phenanthrenes. Bioorg Med. Chem. Lett. 15:5222–5225.
46. Pandey, A. V., N. Singh, B. L. Tekwani, S. K. Puri, and V. S. Chauhan. 1999.
Assay of beta-hematin formation by malaria parasite. J. Pharm. Biomed
Anal. 20:203–207.
47. Piccoli, C., R. Scrima, G. Quarato, A. D’Aprile, M. Ripoli, L. Lecce, D.
Boffoli, D. Moradpour, and N. Capitanio. 2007. Hepatitis C virus protein
expression causes calcium-mediated mitochondrial bioenergetic dysfunction
and nitro-oxidative stress. Hepatology 46:58–65.
3
943.
3. Cossarizza, A., M. Baccarani-Contri, G. Kalashnikova, and C. Franceschi.
993. A new method for the cytofluorimetric analysis of mitochondrial mem-
1
1
brane potential using the J-aggregate forming lipophilic cation 5,5Ј,6,6Ј-
tetrachloro-1,1Ј,3,3Ј-tetraethylbenzimidazolcarbocyanine iodide (JC-1). Bio-
chem. Biophys. Res. Commun. 197:40–45.
1
1
4. Das, S. K., Shagufta, and G. Panda. 2005. An easy access to unsymmetric
trisubstituted methane derivatives (TRSMs). Tetrahedron Lett. 46:3097–
3
102.
5. Desjardins, R. E., C. J. Canfield, J. D. Haynes, and J. D. Chulay. 1979.
Quantitative assessment of antimalarial activity in vitro by a semiautomated
microdilution technique. Antimicrob. Agents Chemother. 16:710–718.
6. Egan, T. J. 2003. Haemozoin (malaria pigment): a unique crystalline drug
target. Targets 2:115–124.
1
1
1
1
2
7. Egan, T. J. 2004. Haemozoin formation as a target for the rational design of
new antimalarials. Drug Design Rev. 1:93–110.
8. Egan, T. J. 2002. Physico-chemical aspects of hemozoin (malaria pigment)
structure and formation. J. Inorg. Biochem. 91:19–26.
9. Egan, T. J. 2001. Structure-function relationships in chloroquine and related
4
-aminoquinoline antimalarials. Mini Rev. Med. Chem. 1:113–123.
0. Francis, S. E., D. J. Sullivan, Jr., and D. E. Goldberg. 1997. Hemoglobin
metabolism in the malaria parasite Plasmodium falciparum. Annu. Rev.
Microbiol. 51:97–123.
48. Portela, C., C. M. Afonso, M. M. Pinto, and M. J. Ramos. 2004. Definition
of an electronic profile of compounds with inhibitory activity against hematin
aggregation in malaria parasite. Bioorg Med. Chem. 12:3313–3321.
49. Rosenthal, P. J., and S. R. Meshnick. 1998. Hemoglobin processing and the
metabolism of amino acids, heme and iron, p. 145–158. In I. W. Sherman
(ed.), Malaria: parasite biology, pathogenesis and protection. ASM Press,
Washington, DC.
2
2
1. Friedman, M. J. 1979. Oxidant damage mediates variant red cell resistance
to malaria. Nature 280:245–247.
2. Galli, U., L. Lazzarato, M. Bertinaria, G. Sorba, A. Gasco, S. Parapini, and
D. Taramelli. 2005. Synthesis and antimalarial activities of some furoxan
sulfones and related furazans. Eur. J. Med. Chem. 40:1335–1340.