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Mini Review on Tricyclic Compounds As an Inhibitor of Trypanothione Reductase Review Article Mini review on tricyclic compounds as an inhibitor of trypanothione reductase Suresh Kumar, Md. Rahmat Ali, Sandhya Bawa Department of ABSTRACT Pharmaceutical Chemistry, Trypanosomiasis and leishmaniasis are two most ruinous parasitic infectious diseases caused by Trypanosoma Faculty of Pharmacy, Jamia Hamdard, and Leishmania species. The disease affects millions of people all over the world and associated with high New Delhi, India morbidity and mortality rates. The review discuss briefly on current treatment of these parasitic diseases and trypanothione reductase (TryR) as potential targets for rational drug design. The enzyme trypanothione reductase Address for correspondence: (TryR) has been identified as unique among these parasites and has been proposed to be an effective target Dr. Sandhya Bawa, against for developing new drugs. The researchers have selected this enzyme as target is due to its substrate E-mail: sandhyabawa761@ specificity in contrast to human analogous glutathione reductase and its absence from the host cell which yahoo.com makes this enzyme an ideal target for drug discovery. In this review we have tried to present an overview of the different tricyclic compounds which are potent inhibitors of TryR with their inhibitory activities against the parasites are briefly discussed. Received : 21-10-13 Review completed : 06-11-13 Accepted : 15-11-13 KEY WORDS: Tricyclic, trypanosomiasis and leishmaniasis, trypanothione reductase he hemoflagellate protozoa of the family Trypanosomatidae resistance, low efficacy and poor safety. The development of new T are the causative agents of tropical diseases such chemotherapeutic agents for the treatment of these parasitic as human African sleeping sickness (Trypanosoma brucei diseases has been hindered due to lack of interest shown by gambiense, T. brucei rhodesiense), Chagas’ disease (South top innovator pharmaceutical companies, which might be due American trypanosomiasis, Trypanosoma cruzi) and the to low profitability in this domain as poor are more sufferer of visceral, cutaneous and mucocutaneous manifestations of these disease.[1-4] leishmaniasis (e.g., Leishmania donovani, Leishmania tropica, Leishmania braziliensis). According to world health organization The present review focuses on the major human diseases caused African trypanosomiasis was estimated to cause 48,000 deaths by trypanosomal and leishmanial infections and inhibitors and a disease burden of 1.5 million disability-adjusted life of tryanothione reductase as potential targets for designing years (DALYs) annually; Chagas’ disease, 14,000 deaths and a chemotherapeutic agents against these diseases. Table 1 disease burden of 0.7 million DALYs annually; leishmaniasis, gives an outline of the major human trypanosomiasis and 51,000 deaths and a disease burden of 2.1 million DALYs leishmaniasis with their global annual disease burdens in terms annually. Recently drug discovery program directed toward of DALY The chemical structures of various antitrypnosomal leishmaniasis, malaria, Chagas disease and sleeping sickness and antileishmanial agents are presented as Figure 1. has increased sharply and not only because they are major killing diseases, but also because disease control becomes There are several targets in these parasites through which more difficult due to a number of factors that limit the utility drug or an investigational molecules act and some of these of current drugs such as high cost, poor compliance, drug targets includes deoxyribonucleic acid (DNA) topoisomerases, Access this article online Ergosterol biosynthesis, Purine salvage pathway, trypanothione [5] Quick Response Code: reductase (TryR), microtubule assembly inhibitor etc. Among Website: all the targets known for trypanosomes and Leishmania, TryR www.jpbsonline.org has gained a lot of attention as a potential target for discovering a new antiparasitic drug for the treatment of human African DOI: sleeping sickness caused by T. brucei gambiense, T. brucei 10.4103/0975-7406.142943 rhodesiense, Chagas’ disease (South American trypanosomiasis, T. cruzi) and the visceral, cutaneous and mucocutaneous How to cite this article: Kumar S, Ali M, Bawa S. Mini review on tricyclic compounds as an inhibitor of trypanothione reductase. J Pharm Bioall Sci 2014;6:222-8. 222 Journal of Pharmacy and Bioallied Sciences October-December 2014 Vol 6 Issue 4 Kumar, et al.: Tricyclic compounds inhibitor of TryR manifestations of leishmaniasis (e.g., L. donovani, L. tropica, dinucleotide phosphate-oxidase-dependent flavoprotein L. braziliensis). oxidoreductase which maintains an intracellular reducing environment by the recycling of trypanothione disulfide As potential drug target in trypanosomes and Leishmania, T[S] 2 to its dithiol T[SH] 2 form. Trypanothione is oxidized TryR has been identified through the discovery of a back to T[S] 2 following reaction with potentially damaging fundamental difference between the redox defense system radicals and oxidants generated by aerobic metabolism and of the trypanosomal/leishmanial parasite and the infected by host macrophages. By maintaining a high intracellular ratio host. The mammalian redox defense system is based on of T[SH] 2 the TryR redox cycle is a primary line of defense glutathione (l-g-glutamyl-l-cysteinylglycine) and glutathione for these parasites against respiratory burst responses from disulfide reductase (glutathione reductase (GR); EC 1.6.4.2), the mammalian host. The trypanothione system is necessary this system is replaced in trypanosomatids by an analogous for protozoan survival because the dithiol trypanothione is system based on trypanothione (N, N-bis [glutathionyl] required for the synthesis of DNA precursors, the homeostasis spermidine) and trypanothione disulfide reductase (TryR; EC of ascorbate, the detoxification of hydroperoxides and the 1.6.4.8). The structures of the disulfide substrates for TryR and sequestration/export of thiol conjugates. Moreover, the GR are illustrated in Figure 2. TryR is a nicotinamide adenine majority of peroxidases that eliminate the reactive oxygen Table 1: The major trypanosomiasis and leishmaniasis and their causative agents current treatments Disease Causative agents Some widely used or recently introduced Disadvantages drugs or drug combinations (year first used) African T. brucei gambiense Suramine (1920), pentamidine (1939), Risk of severe adverse effects with all drugs. suramin and trypanosomiasis or and T. brucei melarsoprol (1949), eflornithine (1991) pentamidine not effective in late stage disease, eflornithine sleeping sickness rhodesiense expensive and only effective against T. brucei gambiense American T. cruzi Benznidazole (1974) nifurtimox (1970) Long treatment courses and adverse effects limit compliance; trypanosomiasis or not effective in late‑stage disease Chagas disease Visceral L. donovani Pentamidine (1939); pentavalent Efficacy loss/drug resistance to pentamidine and antimonials. leishmaniasis or antimonials (1950) liposomal amphotericin Cost high for liposomal amphotericin B. Adverse effects well kalazar B (1999) miltefosine (2002) described for other drugs. miltefosine is contraindicated in women of child‑bearing age T. brucei: Trypanosoma brucei, T. cruzi: Trypanosoma cruzi, L. donovani: Leishmania donovani + 62 2 + 1 + 1 1 1 + 1 2 26 1 1 6 $V &+ 2+ 2 1 6 1+ + 62 6XUDPLQH 0HODUVRSURO 2 1 &22+ &22+ 21 1 1 1+ +2 2+ 2 2 2 6 2 1 6E 6E +2 2 2 2 2+ 2 2 21 2+ 2+ 1LWULIXULPD[ %HQ]QLGD]ROH 3HQWRVWDP Figure 1: Structures of various drugs used for the treatment of trypanosomiasis and leishmaniasis a b Figure 2: (a) Structure of Trypanothione and glutathione and their reduced form. (b) Mechanism of redox recycling of T[S]2 to T[SH]2 and GSSG to GSH in parasite and host cell respectively Journal of Pharmacy and Bioallied Sciences October-December 2014 Vol 6 Issue 4 223 Kumar, et al.: Tricyclic compounds inhibitor of TryR species generated in the aerobic metabolism are trypanothione several tricyclic derivatives were identified as a potent inhibitor dependent. Disabling the function of TryR in Leishmania and TryR [Figure 3]. T. brucei has been shown to markedly increase the parasites’ sensitivity to oxidative stress. Recently, lunarine a spermidine-based macrocyclic alkaloid [Figure 4] has been identified as a competitive, T[S] 2 differs from glutathione disulfide (GSSG) by the time-dependent inhibitor of TryR. Lunarine is composed of a presence of a spermidine cross-link between the two glycyl spermidine chain with the terminal nitrogen atoms forming amide carboxyl groups [compare GSSG and T[S] 2 in Figure 2]. linkages with two α, β-unsaturated carboxylic acid functions Due to structural and charge differences between T[S] 2 and disposed upon an unusual 3-oxohexahydrodibenzofuranyl GSSG, TryR and GR are mutually exclusive with respect tricyclic scaffold.[11] to substrate specificity. Thus the essential requirement of TryR in trypanosomal/leishmanial parasite and its absence in A study done by Hamilton et al.[12] presented a possible host metabolism make it an attractive therapeutic target for mechanism for this time dependent inhibition, which involves designing specific inhibitor. In the preceding section we have the covalent modification of a redox-active cysteine residue tried to compile various tricyclic compounds, which have shown in the active site of TryR (C53) by conjugate addition to potent inhibiting activity against TryR.[6-8] one of these unsaturated amide moieties in the lunarine macrocycle [Figure
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