Purine analogues as antiparasitic agents

Expert Opinion on Therapeutic Patents

Volumn 15, Issue 8, 2005, Pages 987-994

  Lawton, Philippe ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Antiparasitic chemotherapy; Immucillin; MTAP; Nucleoside hydrolase; Purine analogue; Purine nucleoside phosphorylase (PNP); Purine salvage

Indexed keywords

5' METHYLTHIOADENOSINE PHOSPHORYLASE; 6 BENZYLTHIOINOSINE; ADENOSINE KINASE; ALLOPURINOL; ANTIPARASITIC AGENT; DIDANOSINE; FORMYCIN B; HYPOXANTHINE; ICN 10776; IMMUCILLIN A DERIVATIVE; INOSINE DERIVATIVE; NITROBENZYLTHIOINOSINE; NUCLEOSIDASE; NUCLEOSIDE TRANSPORTER; PURINE NUCLEOSIDE PHOSPHORYLASE; PURINE NUCLEOSIDE PHOSPHORYLASE INHIBITOR; TUBERCIDIN; UNCLASSIFIED DRUG;

CHAGAS DISEASE; DRUG RESEARCH; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME MECHANISM; GIARDIASIS; HELMINTHIASIS; HUMAN; LEISHMANIASIS; MALARIA; NONHUMAN; PATENT; POLYAMINE SYNTHESIS; REVIEW; TOXOPLASMOSIS;

EID: 23844545372     PISSN: 13543776     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543776.15.8.987     Document Type: Review

References (36)

1. EL KOUNI MH: Potential chemotherapeutic targets in the purine metabolism of parasites. Pharmacol. Ther. (2003) 99:283-309.
2. ABRAHAMSEN MS, TEMPLETON TJ, ENOMOTO S et al.: Complete genome sequence of the apicomplexan, Cryptosporidium parvum. Science (2004) 304:441-445.
3. CHAUDHARY K, DARLING JA, FOHL ML et al.: Purine salvage pathways in the Apicomplexan Toxoplasma gondii. J. Biol. Chem. (2004) 279:(30)31221-32227.
4. ULLMAN B, CARTER D: Molecular and biochemical studies on the hypoxanthine-guanine phosphoribosyltransferases of the pathogenic haemoflagellates. Int. J. Parasitol. (1999) 27:(2)203-213.
5. NAGUIB FN, ILTZSCH MH, EL KOUNI MM, PANZICA RP, EL KOUNI MH: Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyltransferase from Toxoplasma gondii. Biochem Pharmacol. (1995) 50:(10)1685-1693.
6. SOMMER JM, MA H, WANG CC: Cloning, expression and characterization of an unusual guanine phosphoribosyltransferase from Giardia lamblia. Mol. Biochem. Parasitol. (1999) 78:185-193.
7. SUCHAIL S, SARCIRON MES, PETAVY AF: Purine metabolism in Echinococcus multilocularis. Comp. Biochem. Physiol. (1998) 120B:633-637.
8. DOYLE PS, KANAANI J, WANG CC: Hypoxanthine, guanine, xanthine phosphoribosyltransferase activity in Cryptosporidium parvum. Exp. Parasitol. (1998)89:9-15.
9. MUNAGALA NR, WANG CC: Adenosine is the primary precursor of all purine nucleotides in Trichomonas vaginalis. Mol. Biochem. Parasitol. (2003) 127:143-149.
10. CRAIG SP III, EAKIN EA: Purine salvage enzymes of parasites as targets for structure-based inhibitor design. Parasitol. Today (1997) 13:(6)238-241.
11. STRIEPEN B, KISSINGER JC: Genomics meet transgenics in the elusive Cryptosporidium drug target. Trends Parasitol. (2004) 20:(8)355-358.
12. YADAV V, CHU CK, RAIS RH et al.: Synthesis, biological activity and molecular modelling of 6-benzylthioinosine analogues as subversive substrates of Toxoplasma gondii adenosine kinase. J. Med Chem. (2004) 47:(8)1987-1996.
13. BZOWSKA A, KULIKOWSKA E, SHUGAR D: Purine nucleoside phosphorylases: properties, functions and clinical aspects. Pharmacol. Ther. (2000) 88:349-425.
14. GHERARDI A, SARCIRON ME, PETAVY AF, PEYRON F: Purine pathway enzymes in a cyst forming strain of Toxoplasma gondii. Life Sci. (1999) 65:(17)1733-1738.
15. FREITAS DA SILVEIRA NJ, UCHOA HB, CANDURI F et al.: Structural bioinformatics study of PNP from Schistosoma mansoni. Biochem. Biophys. Res. Comm. (2004) 322:100-104.
16. FURNEAUX RH, SCHRAMM VL, TYLER PC: Transition state analogue inhibitors of protozoan nucleoside hydrolases. Bioorg. Med. Chem. (1999) 7:(11)2599-2606.
17. EVANS GB, FURNEAUX RH, GAINSFORD GJ et al.: 8-Aza-immucillins as transition-state analogue inhibitors of purine nucleoside phosphorylase and nucleoside hydrolases. J. Med. Chem. (2003) 46:155-160.
18. SUFFRIN JR, MESHNICK SR, SPIESS AJ, GAROFALO-HANNAN J, PAN XQ, BACCHI CJ: Methionine recycling pathways and antimalarial drug design. Antimicrob. Agents Chemother. (1995) 39:(11)2511-2515.
19. UMEJIEGO NN, LI C, RIERA T, HEDSTROM L, STRIEPEN B: Cryptosporidium parvum IMP dehydrogenase. Identification of functional, structural, and dynamic properties that can be exploited for drug design. J. Biol. Chem. (2004) 279:(39)40320-40327.
20. CASS CE, YOUNG JD, BALDWIN SA et al.: Nucleoside transporters of mammalian cells. Pharm. Biotechnol. (1999) 12:313-352.
21. CARTER NS, LANDFEAR SM, ULLMAN B: Nucleoside transporters of parasitic protozoa. Trends Parasitol. (2001) 17:142-145.
22. DE KONING HP, AL-SALABI MI, COHEN AM, COOMBS GH, WASTLING JM: Identification and characterisation of high affinity nucleoside and nucleobase transporters in Toxoplasma gondii. Int. J. Parasitol. (2003) 33:(8)821-831.
23. SARCIRON ME, LAWTON P, PETAVY AF, PEYRON F: Alterations of Toxoplasma gondii induced by 2′,3′-dideoxyinosine in vitro. J. Parasitol. (1998) 84:1055-1059.
24. SARCIRON ME, LAWTON P, SACCHARIN C, PETAVY AF, PEYRON F: Effects of 2′,5′-Dideoxyinosine on Toxoplasma gondii cysts in mice. Antimicrob. Agents Chemother. (1997) 41:1531-1536.
25. LAWTON P, HEJL C, MANCASSOLA R, NACIRI M, PETAVY AF: Effects of purine nucleosides on the in vitro growth of Cryptosporidium parvum. FEMS Microbiol. Lett. (2003) 226:39-43.
26. BALAÑA-FOUCE R, REGUERA RM, CUBRIA JC, ORDOÑEZ D: The pharmacology of leishmaniasis. Gen. Pharmacol. (1998) 30:(4)435-443.
27. LEE H, HANES J, JOHNSON KA: Toxicity of nucleoside analogues used to treat AIDS and the selectivity of the mitochondrial DNA polymerase. Biochemistry (2003) 42:(50)14711-14719.
28. BOTROS S, WILLIAM S, HAMMAM O, ZIDEK Z, HOLY A: Activity of 9-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]adenine against schistosomiasis mansoni in mice. Antimicrob. Agents Chemother. (2003) 47:(12)3853-3858.
29. DREW ME, MORRIS JC, WANG Z et al.: The adenosine analog tubercidin inhibits glycolysis in Trypanosoma brucei as revealed by an RNA interference library. J. Biol Chem. (2003) 278:(47)46596-46600.
30. PFEFFERKORN ER, BZIK DJ, HONSINGER CP: Toxoplasma gondii: mechanism of the parasitostatic action of 6-thioxanthine. Exp. Parasitol. (2001) 99:235-243.
31. SCHRAMM VL: Immucillins as antibiotics for T-cell proliferation and malaria. Nucleosides Nucleotides Nucleic acids (2004) 23:(8-9)1305-1311.
32. SCHRAMM VL: Enzymatic transition states: thermodynamics, dynamics and analogue design. Arch. Biochem. Biophys. (2005) 433:13-26.
33. LAWTON P, HEJL C, SARCIRON ME, MANCASSOLA R, NACIRI M, PETAVY AF: Use of a non-adherent cell culture system for testing the effect of 2′,3′-dideoxyinosine against Cryptosporidium parvum. FEMS Microbiol. Lett. (1999) 176:235-240.
34. KICSKA GA, TYLER PC, EVANS GB, FURNEAUX RH, SCHRAMM VL, KIM K: Purine-less death in Plasmodium falciparum induced by immucillin-H, a transition state analogue of purine nucleoside phosphorylase. J. Biol Chem. (2002) 277:(5)3226-3231.
35. TING LM, SHI W, LEWANDOWICZ A et al.: Targeting a novel Plasmodium falciparum purine recycling pathway with specific immucillins. J. Biol. Chem. (2005) 280:(10)9547-9554.
36. BORROTO-ESODA K, MYRICK F, FENG J, JEFFREY J, FURMAN P: In vitro combination of amdoxovir and the inosine monophosphate dehydrogenase inhibitors mycophenolic acid and ribavirin demonstrates potent activity against wild-type and drug-resistant variants of human immunodeficiency virus Type 1. Antimicrob. Agents Chemother. (2004) 48:(11)4387-4394.