Inhibitors of purine nucleoside phosphorylase

References

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• References 1 and 2 are review articles on PNP.
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• References 13 to 15 present detailed descriptions of the structure-based design of PNP inhibitors.
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• An early paper on selective toxicity of a PNP inhibitor for T-cells.
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• The synthesis and biologic activity of 8-amino-9-benzylguanine are described.
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• Synthesis of 8-amino-3-arylmethylguanines and their inhibition of PNP.
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• Immunosuppressive activity of 8-amino-9-benzylguanine is de-scribed.
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• The selective toxicity of 8-amino-9-(2-thienylmethyl)guanine to T-cells (MOLT-4) is accompanied by a forty-fold increase in dGTP and a two-fold reduction in GTP.
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• GILBERTSEN RB, DONG MK, KOSSAREK LM: Aspects ofthe purine nucleoside phosphorylase (PNP) defident state produced in normal rats following oral admini-stration of 8-amino-9-(2-thienylmethyl)guanine (PD 119,229), a novel inhibitor of PNP. Agents Actions (1987) 22:379–384.
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• Oral administration of 8-amino-(2-thienylmethyl)guanine to rats raised plasma inosine and guanosine levels.
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• STEIN JM, STOECKLER JD, LI S-Y, TOLMAN EL, MACCOSSM, CHEN A, KARICAS JD, ASHTON WT, PARKS JR RE: Inhibition of human purine nucleoside phosphorylase by acyclic nucleosides and nucleotides. Biochem. Phar-macol. (1987) 36:1237–1244.
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• BZOWSKA A, KULIKOWSKA E, SHUGAR D, BING-YI C, LINDBORG B, JOHANSSON NG: Acyclonucleoside ana- logue inhibitors of mammalian purine nucleoside phosphorylase. Biochem. Pharmacol. (1991) 41:1791–1803.
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• References 28 and 29 describe acyclic nucleotides as inhibitors of PNP.
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• TUTTLE JV, ICRENITSICY TA: Effects of acyclovir and itsmetabolhes on purine nucleoside phosphorylase. Biol. Chem. (1984) 259:4065–4069.
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• Acyclovir diphosphate was found to be a potent inhibitor of PNP but not the mono- and triphosphates.
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• ICRENITSKY TA, TUTTLE JV, MILLER WH, MOORMAN AR, ORR GF, BEAUCHAMP L: Nucleotide analogue inhibitors of purine nucleoside phosphorylase. J. Biol. Chem. (1990) 265:3066–3069.
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• NAKAMURA CE, CHU S-H, STOECKLER JD, PARKS JR RE:Inhibition of purine nucleoside phosphorylase by 9-(phosphonoalkyl)hypoxanthines. Biochem. Pharmacol. (1986) 35:133–136.
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• Analogues of acyclovir diphosphate are less potent as PNP inhibitors.
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• NAKAMURA CE, CHU S-H, STOECKLER JD, PARKS JR RE:Inhibition of purine nucleoside phosphorylase by phosphonoalkylpurines. Nucleosides Nucleotides (1989) 8:1039–1040.
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• GUIDA WC, ELLIOTT' RD, THOMAS HJ, SECRIST IIIJA, BABUYS, BUGG CE, ERION MD, EALICK SE, MONTGOMERY JA: Structure-based design of inhibitors of purine nucleo-side phosphorylase. 4. A study of phosphate mimics. J. Med. Chem. (1994) 37:1109–1114.
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• References 33, 34, and 37 describe acyclic phosphonates as PNP inhibitors.
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• HALAZY S, EHRHARD A, DANZIN C: 9-(Difluorophos-phonoalkyl)guanines as a new class of multisubstrate analogue inhibitors of purine nucleoside phosphory-lase. J. Am. Chem. Soc. (1991) 113:315–317.
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• This paper describes the greater potency of difluorophosphonoal-kylguanines as inhibitors of PNP relative to phosphonoalkylguani-nes.
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• MAMONT PS, WEIBEL M, DANZIN C, HALAZY S: Effects of 9-(difiuorophosphonoalkyl)guanines, a new class ofmultisubstrate analogue inhibitors of purine nucleo- side phosphorylase, in cultured human leukemic lym- phoblast Molt-4 cells. Intl Purine Pyrim. Res. (1991) 2:62. 9-(7,7-Difluoro-7-phosphonoheptylguanine and its 5,5-difluoro-5-phosphonopentyl analogue, at 100 p,M, reduced the IC50 of 2'-de-oxyguanosine from 16. 5 p.M to 5 and 3. 8 gM, respectively.
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• JORDAN F, WU A: Inactivation of purine nucleoside phosphorylase by modification of arginine residues. Archiv. Biochem. Biophys. (1978) 190:699–704.
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• SALAMONE SJ, JORDAN F: Synthesis of 9-(3,4-dioxopen-tyl)hypoxanthine, the first arginine-directed purine derivative: an irreversible inactivator for purine nu-cleoside phosphorylase. Biochemistry (1982) 21:6383–6388.
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• References 38 and 39 describe the inactivation of PNP by glyoxals.
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• The inactivation of PNP by 2-(chloromethyl)quinazoline-4,5,8(3H)-trione is described.
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• A review of structure-based drug design, including PNP inhibitors.
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• This report describes the superiority of 9-deaza-9-(3-thienyl-methyl)guanine over its 8-amino derivative in inhibiting the prolif-eration of MOLT-4 and CEM T-cells in vitro and in elevating plasma inosine and guanosine levels in the rat.
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• DONG MK, GILBERTSEN RB: PD 141955 and CI-972: 9-deazaguanine analog purine nucleoside phosphory-lase inhibitors. II. Effects on nucleoside catabolism in human and rat blood in vitro. Agents and Actions (1993) 39.
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• References 44 to 46 help to establish the superiority of 9-deaza-9-(3-thienylmethyl)-9-guanine over its 8-amino derivative.
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• References 48 and 49 describe the inhibition of PNP by phosphonate derivatives of 9-benzylguanine at ca. 1 nM concentrations.
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