Fosfonamidowe oraz fosfinopeptydowe inhibitory metaloproteaz

• Autorzy: Mucha, A.

Warianty tytułu

EN

Phosphonamidate and phosphinate inhibitors of metalloproteases

• Języki publikacji: PL

Abstrakty

PL

Przedstawiono wyniki prac dotyczące syntezy i aktywności biologicznej pseudopeptydów zawierających ugrupowanie fosfonamidowe oraz fosfinowe, uważanych za analogi tetraedrycznego stanu przejściowego enzymatycznej hydrolizy wiązania amidowego. Opisano procedury zastosowane do syntezy ich bezpośrednich prekursorów, tj. monoestrów kwasów N-benzyloksykarbonylo-a-aminoalkanofosfonowych oraz H-fosfinowych. Szczególną uwagę poświęcono otrzymywaniu enancjomerycznie czystych substratów oraz kontroli ich czystości optycznej z użyciem odpowiednich dyskryminatorów chiralności, takich jak: cyklodekstryny lub alkaloidy chinolinowe oraz prostych metod spektroskopowych i chromatograficznych. Przestudiowano przebieg tworzenia wiązania fosfonamidowego w różnych typach reakcji wiodących przez odpowiednie fosfonochlorki. Skorelowano labilność hydrolityczną otrzymanych fosfonamidów z ich strukturą, a przede wszystkim z obecnością grup ochronnych w cząsteczce oraz z pH roztworu. Udowodniono wyjątkową nietrwałość wiązania P-N (pH < 12) w całkowicie odblokowanych analogach dipeptydów wykluczającą ich praktyczne zastosowania. Wykazano interesującą reaktywność O-fenylowych fosfonamidów, które ulegały transestryfikacji w zasadowych warunkach. W badaniach dotyczących syntezy fosfinopeptydów skoncentrowano się na rozwijaniu metod otrzymywania ich elektrofilowych prekursorów - alfa-podstawionych akrylanów. Opracowano także metodę umożliwiającą na wprowadzenie i wielokierunkową funkcjonalizację podstawnika P1' odpowiednich dipeptydów oraz przetestowano nowe metody wydłużania łańcucha pseudopeptydowego. Otrzymane związki posłużyły do badań nad regulacją aktywności takich metaloproteaz, jak: matryksyny oraz leucyloaminopeptydazy, a także protez cysteinowych, np. katepsyna C. Do opracowania efektywnych inhibitorów oraz optymalizacji ich struktury użyto metod chemii kombinatorycznej oraz racjonalnego projektowania ligandów wiążących się do odpowiednich receptorów.

EN

Synthesis and biological activity of pseudopeptides containing phosphonamidate or phosphinate moiety considered as to be the analogues of a transition state of the amide bond hydrolysis, have been investigated. The procedures applied to synthesize their direct precursors, namely N-benzyloxycarbonyl-?-aminoalkane-phosphonate and H-phosphinate monoesters have been described. Particular attention has been devoted to obtaining enantiomerically pure substrates as well as to the control of their optical activity with the use of the appropriate chiral selectors such as cyclodextrins or quinoline alkaloids, and simple chromatographic and spectroscopic methods. The formation of the phosphonamidate bond in various reactions via corresponding phosphonochloridates has been studied in some details. Hydrolytic lability of the phosphonamidates obtained has been correlated with their chemical structure and particularly with the presence of their functional groups, and with the solution pH. Exceptional instability of the P-N bond (at pH < 12) in unprotected dipeptide analogues has been proven, which makes their practical application impossible. An interesting reactivity in transesterification of O-phenyl phosphonamidates in basic medium has been shown. In the studies on phosphinic peptides, we have concentrated on new methods leading to their electrophilic precursors, i.e. ?-substituted acrylates. A convenient method allowing introduction and functionalisation of the P1' substitu-ents of phosphinic dipeptides has been also developed. Additionally, new methods of elongation of the pseudopeptide chain have been tested. The compounds obtained enabled the studies on controlling the activity of such metalloproteses as matrixins or leucine aminopeptidases, and cathepsin C, belonging to the family of cysteine proteases. Combinatorial chemistry and rational design of ligands capable of binding to the appropriate receptors has been used for development of the inhibitors and for the optimisation of their structure.

Słowa kluczowe

PL

pseudopeptydy fosfonamidowe; fosfinopeptydy; inhibitory enzymów proteolitycznych; metaloproteazy

EN

phosphonamidate inhibitor; phosphinate inhibitor; metalloproteases; pseudopeptides

• Czasopismo: Prace Naukowe Wydziału Chemicznego Politechniki Wrocławskiej. Monografie
• Rocznik: 2006
• Tom: Nr 1, nr 1
• Strony: 110-110
• Opis fizyczny: bibliogr. 319 poz.

Twórcy

autor

Mucha, A.

• Wydział Chemiczny Politechniki Wrocławskiej, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław

Bibliografia

• [1] PUENTE X.S., SANCHEZ L.M., OVERALL C.M., LOPEZ-OTIN C., Nat. Rev. Gen., 2003, 4, 544–558.
• [2] PUENTE X.S., SANCHEZ L.M., GUTIERREZ-FERNANDEZ A., VELASCO, G., LOPEZ-OTIN C., Biochem. Soc. Trans., 2005, 33, 331–334.
• [3] LEUNG D., ABBENANTE G., FAIRLIE D.P., J. Med. Chem., 2000, 43, 305–341.
• [4] LEBON F., LEDECQ M., Curr. Med. Chem., 2000, 7, 455–477.
• [5] WALKER B., LYNAS J.F., Cell. Mol. Life Sci., 2001, 58, 596–624.
• [6] STEIMETZER T., HAUPTMANN J., STÜRZEBECHER J., Exp. Opin. Invest. Drugs, 2001, 10, 845–864.
• [7] POWERS J.C., ASGIAN J.L., EKICI O D., JAMES K.E., Chem. Rev., 2002, 102, 4639–4750.
• [8] CONCHA N.O., ABDEL-MEGUID S.S., Curr. Med. Chem., 2002, 9, 713–726.
• [9] LEUNG-TOUNG R., LI W.R., TAM T.F., KARIMIAN K., Curr. Med. Chem., 2002, 9, 979–1002.
• [10] KIM W., KANG K., Exp. Opin. Ther. Patents, 2002, 12, 419–432.
• [11] DASH C., KULKARNI A., DUNN B., RAO M ., Crit. Rev. Biochem. Mol. Biol., 2003, 38, 89–119.
• [12] GOURLEY M., WILLIAMSON J.S., Curr. Pharm. Des., 2000, 6, 417–439.
• [13] BROWN P.D., Exp. Opin. Invest. Drugs, 2000, 9, 2167–2177.
• [14] SKILES J.W., GONNELLA N.C., JENG, A.Y., Curr. Med. Chem., 2001, 8, 425–474.
• [15] JEDINAK A., MALIAR T., Neoplasma, 2005, 53, 185–192.
• [16] TOMASSELLI A.G., HEINRIKSON R.L., Biochem. Biophys. Acta, 2000, 1477, 189–214.
• [17] DE CLERCQ E., Curr. Med. Chem., 2001, 8, 1543–1572.
• [18] ABDEL-RAHMAN H.M., AL-KARAMANY G.S., EL-KOUSSI N.A., YOUSSEF A.F., KISO Y., Curr. Med. Chem., 2002, 9, 1905–1922.
• [19] VIERLING P., GREINER J., Curr. Pharm. Des., 2003, 9, 1755–1770.
• [20] SELKOE D.J., Physiol. Rev., 2001, 81, 741–766.
• [21] LARNER A.J., Mini Rev. Med. Chem., 2002, 2, 1–9.
• [22] THOMPSON L.A., BRONSON J.J., ZUSI F.C., Curr. Pharm. Des., 2005, 11, 3383–3404.
• [23] HIGUCHI M., IWATA N., SAIDO, T.C., Bichem. Biophys. Acta., 2005, 1751, 60–67.
• [24] SUPURAN C.T., SCOZZAFAVA A., MASTROLORENZO A., Exp. Opin. Ther. Patents, 2001, 11, 221–259.
• [25] SUPURAN C.T., SCOZZAFAVA A., CLARE B.W., Med. Res. Rev., 2002, 22, 329–372.
• [26] LECAILLE F.,KALETA J., BRÖMME D., Chem. Rev., 2002, 102, 4459–4488.
• [27] CHUNG J.Y ., BAE Y.A ., NA B.K ., KONG Y ., Exp. Opin. Ther. Patents, 2005, 15, 995–1007.
• [28] MEROPS – The Peptidase Database (http://merops.sanger.ac.uk).
• [29] Handbook of Proteolytic Enzymes, Barrett A.J., Rawlings N.D., Woessner J.F., (Eds.), Academic Press, Amsterdam, 2002.
• [30] PAULING L., Am. Sci., 1948, 36, 51–58.
• [31] WOLFENDEN R., Nature, 1969, 223, 704–705.
• [32] SCHECHTER I., BERGER A., Biochem. Biophys. Res. Commun., 1967, 27, 157–162.
• [33] ENDO S., Hakko Kogaku Zashi,1962, 40, 346–367.
• [34] TITANI K., HERMODSON M.A., ERICSSON L.H., WALSH K.A., NEURATH H., Nat. New Biol., 1972, 238, 35–37.
• [35] MATTHEWS B.W., JANSONIUS J.N., COLMAN P.M., SCHOENBORN B.P., DUPOURQUE D., Nat. New Biol., 1972, 238, 37–41.
• [36] MATTHEWS B.W., COLMAN P.M., JANSONIUS J.N., TITANI K., WALSH K.A., NEURATH H., Nat. New Biol., 1972, 238, 41–43.
• [37] COLMAN P.M., JANSONIUS J.N., MATTHEWS B.W., J. Mol. Biol., 1972, 70, 701–724.
• [38] MATTHEWS B.W., WEAVER L.H., KESTER W.R., J. Biol. Chem., 1974, 249, 8030–8044.
• [39] HOLMES M.A., MATTHEWS B.W., J. Mol. Biol., 1982, 160, 623–639.
• [40] WEAVER L.H., KESTER W.R., MATTHEWS B.W., J. Mol. Biol., 1977, 114, 119–132.
• [41] HOLMES M.A., MATTHEWS B.W., Biochemistry, 1981, 20, 6912–6920.
• [42] HANGAUER D.G., MONZINGO A.F., MATTHEWS B.W., Biochemistry, 1984, 23, 5730–5741.
• [43] REES D.C., LEWIS M., LIPSCOMB W.N., J. Mol. Biol., 1983, 168, 367–387.
• [44] KESTER W.R., MATTHEWS B.W., J. Biol. Chem., 1977, 252, 7704–7710.
• [45] MATTHEWS B.W., Acc. Chem. Res., 1988, 21, 333–340.
• [46] KAM C.-M., NISHINO N., POWERS J.C., Biochemistry, 1979, 18, 3032–3038.
• [47] SUDA H., AOYAGI T., TAKEUCHI T., UMEZAWA H., J. Antibiot., 1973, 26, 621–623.
• [48] KOMIYAMA T., SUDA H., AOYAGI T., TAKEUCHI T., UMEZAWA H., FUJIMOTO K., UMEZAWA S., Arch. Biochem. Biophys., 1975, 171, 727–731.
• [49] BARTLETT P.A., MARLOWE C.K., Biochemistry, 1983, 22, 4618–4624.
• [50] BARTLETT P.A., MARLOWE C.K., Biochemistry,1987, 26, 8553–8561.
• [51] JACOBSEN N.E., BARTLETT P.A., J. Am. Chem. Soc., 1981, 103, 654–657.
• [52] YAMAUCHI K., OHTSUKI S., KINOSHITA M., Biochem. Biophys. Acta, 1985, 827, 275–282.
• [53] HANSON J.E., KAPLAN A.P., BARTLETT P.A., Biochemistry, 1989, 28, 6294–6305.
• [54] HOLDEN H.M., TRONRUD D.E., MONZINGO A.F., WEAVER L.H., MATTHEWS B.W., Bio-chemistry, 1987, 26, 8542–8553.
• [55] HOLLAND D.R., TRONRUD D.,E. PLEY H.W., FLAHERTY K.M., STARK W., JANSONIUS J.N., MCKAY D.B., MATTHEWS B.W., Biochemistry, 1992, 31, 11310–11316.
• [56] HOLLAND D.R., HAUSRATH A.C., JUERS D., MATTHEWS B.W., Protein Sci., 1995, 4, 1955–1965.
• [57] YIALLOUROS I., VASSILIOU S., YIOTAKIS A., ZWILLING R., STÖCKER W., DIVE V., Bio-chem. J., 1998, 331, 375–379.
• [58] COLLINSOVÁ M., JIRÁČEK J., Curr. Med. Chem., 2000, 7, 629–647.
• [59] SCHIØDT C.B., BUCHARDT J., TERP G.E., CHRISTENSEN U., BRINK M., LARSEN Y.B., MELDAL M., FOGED N.T., Curr. Med. Chem., 2001, 8, 967–976.
• [60] CHRISTIANSON D.W., LIPSCOMB W.N., J. Am. Chem. Soc., 1988, 110, 5560–5565.
• [61] KAPLAN A.P., BARTLETT P.A., Biochemistry, 1991, 30, 8165–8170.
• [62] TRONRUD D.E., HOLDEN H.M., MATTHEWS B.W., Science, 1987, 235, 571–574.
• [63] BARTLETT P.A., MARLOWE C.K., Science, 1987, 235, 569–571.
• [64] BASH P.A., CHANDRA SINGH U., BROWN F.K., LANGRIDGE R., KOLLMAN P.A., Science, 1987, 235, 574.
• [65] GROBELNY D., GOLI U.B., GALARDY R.E., Biochemistry, 1989, 28, 4948–4951.
• [66] MORGAN B.P., SCHOLTZ J.M., BALLINGER M.D., ZIPKIN I.D., BARTLETT P.A., J. Am. Chem. Soc., 1991, 113, 297–307.
• [67] GALARDY R.E., Biochemistry, 1982, 21, 5777–5781.
• [68] THORSETT E.D., HARRIS E.E., PETERSON E.R., GREENLEE W.J., PATCHETT A.A., ULM E.H., VASSIL T.C., Proc. Natl Acad. Sci. USA., 1982, 79, 2176–2180.
• [69] PETRILLO E.W., ONDETTI M.A., Med. Res. Rev., 1982, 2, 1–41.
• [70] GALARDY R.E., KONTOYIANNIDOU-OSTREM V., KORTYLEWICZ Z.P., Biochemistry, 1983, 22, 1990–1995.
• [35] MATTHEWS B.W., JANSONIUS J.N., COLMAN P.M., SCHOENBORN B.P., DUPOURQUE D., Nat. New Biol., 1972, 238, 37–41.
• [36] MATTHEWS B.W., COLMAN P.M., JANSONIUS J.N., TITANI K., WALSH K.A., NEURATH H., Nat. New Biol., 1972, 238, 41–43.
• [37] COLMAN P.M., JANSONIUS J.N., MATTHEWS B.W., J. Mol. Biol., 1972, 70, 701–724.
• [38] MATTHEWS B.W., WEAVER L.H., KESTER W.R., J. Biol. Chem., 1974, 249, 8030–8044.
• [39] HOLMES M.A., MATTHEWS B.W., J. Mol. Biol., 1982, 160, 623–639.
• [40] WEAVER L.H., KESTER W.R., MATTHEWS B.W., J. Mol. Biol., 1977, 114, 119–132.
• [41] HOLMES M.A., MATTHEWS B.W., Biochemistry, 1981, 20, 6912–6920.
• [42] HANGAUER D.G., MONZINGO A.F., MATTHEWS B.W., Biochemistry, 1984, 23, 5730–5741.
• [43] REES D.C., LEWIS M., LIPSCOMB W.N., J. Mol. Biol., 1983, 168, 367–387.
• [44] KESTER W.R., MATTHEWS B.W., J. Biol. Chem., 1977, 252, 7704–7710.
• [45] MATTHEWS B.W., Acc. Chem. Res., 1988, 21, 333–340.
• [46] KAM C.-M., NISHINO N., POWERS J.C., Biochemistry, 1979, 18, 3032–3038.
• [47] SUDA H., AOYAGI T., TAKEUCHI T., UMEZAWA H., J. Antibiot., 1973, 26, 621–623.
• [48] KOMIYAMA T., SUDA H., AOYAGI T., TAKEUCHI T., UMEZAWA H., FUJIMOTO K., UMEZAWA S., Arch. Biochem. Biophys., 1975, 171, 727–731.
• [49] BARTLETT P.A., MARLOWE C.K., Biochemistry, 1983, 22, 4618–4624.
• [50] BARTLETT P.A., MARLOWE C.K., Biochemistry,1987, 26, 8553–8561.
• [51] JACOBSEN N.E., BARTLETT P.A., J. Am. Chem. Soc., 1981, 103, 654–657.
• [52] YAMAUCHI K., OHTSUKI S., KINOSHITA M., Biochem. Biophys. Acta, 1985, 827, 275–282.
• [53] HANSON J.E., KAPLAN A.P., BARTLETT P.A., Biochemistry, 1989, 28, 6294–6305.
• [54] HOLDEN H.M., TRONRUD D.E., MONZINGO A.F., WEAVER L.H., MATTHEWS B.W., Bio-chemistry, 1987, 26, 8542–8553.
• [55] HOLLAND D.R., TRONRUD D.,E. PLEY H.W., FLAHERTY K.M., STARK W., JANSONIUS J.N., MCKAY D.B., MATTHEWS B.W., Biochemistry, 1992, 31, 11310–11316.
• [56] HOLLAND D.R., HAUSRATH A.C., JUERS D., MATTHEWS B.W., Protein Sci., 1995, 4, 1955–1965.
• [57] YIALLOUROS I., VASSILIOU S., YIOTAKIS A., ZWILLING R., STÖCKER W., DIVE V., Bio-chem. J., 1998, 331, 375–379.
• [58] COLLINSOVÁ M., JIRÁČEK J., Curr. Med. Chem., 2000, 7, 629–647.
• [59] SCHIØDT C.B., BUCHARDT J., TERP G.E., CHRISTENSEN U., BRINK M., LARSEN Y.B., MELDAL M., FOGED N.T., Curr. Med. Chem., 2001, 8, 967–976.
• [60] CHRISTIANSON D.W., LIPSCOMB W.N., J. Am. Chem. Soc., 1988, 110, 5560–5565.
• [61] KAPLAN A.P., BARTLETT P.A., Biochemistry, 1991, 30, 8165–8170.
• [62] TRONRUD D.E., HOLDEN H.M., MATTHEWS B.W., Science, 1987, 235, 571–574.
• [63] BARTLETT P.A., MARLOWE C.K., Science, 1987, 235, 569–571.
• [64] BASH P.A., CHANDRA SINGH U., BROWN F.K., LANGRIDGE R., KOLLMAN P.A., Science, 1987, 235, 574.
• [65] GROBELNY D., GOLI U.B., GALARDY R.E., Biochemistry, 1989, 28, 4948–4951.
• [66] MORGAN B.P., SCHOLTZ J.M., BALLINGER M.D., ZIPKIN I.D., BARTLETT P.A., J. Am. Chem. Soc., 1991, 113, 297–307.
• [67] GALARDY R.E., Biochemistry, 1982, 21, 5777–5781.
• [68] THORSETT E.D., HARRIS E.E., PETERSON E.R., GREENLEE W.J., PATCHETT A.A., ULM E.H., VASSIL T.C., Proc. Natl Acad. Sci. USA., 1982, 79, 2176–2180.
• [69] PETRILLO E.W., ONDETTI M.A., Med. Res. Rev., 1982, 2, 1–41.
• [70] GALARDY R.E., KONTOYIANNIDOU-OSTREM V., KORTYLEWICZ Z.P., Biochemistry, 1983, 22, 1990–1995.
• [71] PETRILLO E.W., CUSHMAN D.W., DUGGAN M.E., HEIKES J.E., KARANEWSKY D.S., ONDETTI M.A., O’REILLY B., ROVNYAK G.C., SCHWARTZ J., SPITZMILLER E.R., WANG N.-Y., In Proceedings of the Eight American Peptide Symposium – Peptides: Structure and Function, Hruby V.J., Rich D.H., (Eds.), Pierce Chemical Co., Rockford, 1983, 541–550.
• [72] KRAPCHO J., TURK C., CUSHMAN D.W., POWELL J.R., DEFORREST J.M., SPITZMILLER E.R., KARANEWSKY D.S., DUGGAN M.E., ROVNYAK G.C., SCHWARTZ J., NATARAJAN S., GODFREY J.D., RYONO D.E., NEUBECK R., ATWAL K.S., PETRILLO E.W., J. Med. Chem., 1988, 31, 1148–1160.
• [73] MURDOCH D., MCTAVISH D., Drugs, 1992, 43, 123–140.
• [74] WAGSTAFF A.J., DAVIS R., MCTAVISH D., Drugs, 1996, 51, 777–791.
• [75] DIVE V., COTTON J., YIOTAKIS A., MICHAUD A., VASSILIOU S., JIRÁČEK J., VAZEUX G., CHAUVET M.-T., CUNIASSE P., CORVOL P., Proc. Natl Acad. Sci. USA, 1999, 96, 4330–4335.
• [76] VAZEUX G., COTTON J., CUNIASSE P., DIVE V., Biochem. Pharmacol., 2001, 61, 835–841.
• [77] GEORGIADIS D., BEAU F., CZARNY B., COTTON J., YIOTAKIS A., DIVE V., Circ. Res., 2003, 93, 148–154.
• [78] ROUSSEAU A., MICHAUD A., CHAUVET M.-T., LENFANT M., CORVOL P., J. Biol. Chem., 1995, 270, 3656–3661.
• [79] YIOTAKIS A., VASSILIOU S., JIRÁČEK J., DIVE V., J. Org. Chem., 1996, 61, 6601–6605.
• [80] JIRÁČEK J., YIOTAKIS A., VINCENT B., LECOQ A., NICOLAU A., CHECLER F., DIVE V., J. Biol. Chem., 1995, 270, 21701–21706.
• [81] JIRÁČEK J., YIOTAKIS A., VINCENT B., CHECLER F., DIVE V., J. Biol. Chem., 1996, 271, 19606–19611.
• [82] YIOTAKIS A., GEORGIADIS D., MATZIARI M., MAKARITIS A., DIVE V., Curr. Org. Chem., 2004, 8, 1135–1158.
• [83] MAFFRE-LAFON D., ESCALE R., DUMY P., VIDAL J.-P., GIRARD J.-P., Tetrahedron Lett., 1994, 35, 4097–4098.
• [84] JUNOT C., GONZALES M.-F., EZAN E., COTTON J., VAZEUX G., MICHAUD A., AZIZI M., VASSILIOU S., YIOTAKIS A., CORVOL P., DIVE V., J. Pharmacol. Exp. Therapeut., 2001, 297, 606–611.
• [85] GRAMS F., DIVE V., YIOTAKIS A., YIALLOUROS I., VASSILIOU S., ZWILLING R., BODE W., STÖCKER W., Nat. Struct. Biol., 1996, 3, 671–675.
• [86] GALL A.L., RUFF M., KANNAN R., CUNIASSE P., YIOTAKIS A., DIVE V., RIO M.-C., BASSET P., MORAS. D., J. Mol. Biol., 2001, 307, 577–686.
• [87] SELKTI M., TOMAS A., GAUCHER J.-F., PRANGÉ T., FOURNIÉ-ZALUSKI M.-C., CHEN H., ROQUES B.-P., Acta Cryst. D, 2003, 59, 1200–1205.
• [88] COPIÉ V., KOLBERT A.C., DREWRY D.H., BARTLETT P.A., OAS T., GRIFFIN R.G., Biochemi-stry, 1990, 29, 9176–9184.
• [89] KAFARSKI P., LEJCZAK B., In Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity, Kukhar V.P., Hudson H.R., (Eds.), John Wiley & Sons, Chichester, 2000, 173–203, 407–442.
• [90] DIVE V., LUCET-LEVANNIER K., GEORGIADIS D., COTTON J., VASSILIOU S., CUNIASSE P., YIOTAKIS A., Biochem. Soc. Trans., 2000, 28, 455–460.
• [91] DIVE V., GEORGIADIS D., MATZIARI M., MAKARITIS A., BEAU F., CUNIASSE P., YIOTAKIS A., Cell. Mol. Life Sci., 2004, 61, 2010–2019.
• [92] CUNIASSE P., DEVEL L., MAKARITIS A., BEAU F., GEORGIADIS D., MATZIARI M., YIOTAKIS A., DIVE V., Bichemie, 2005, 87, 393–402.
• [93] Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity, Kukhar V.P., Hudson H.R., (Eds.), John Wiley & Sons, Chichester, 2000.
• [94] KAFARSKI P., MASTALERZ P., Beitr. Wirkstofforschung, 1984, 21, 1–110. [95] KAFARSKI P., LEJCZAK B., Phosphorus, Sulphur and Silikon, 1991, 63, 193–216.
• [96] MAIER L., DIEL P.J., Phosphorus, Sulphur and Silicon, 1994, 90, 259–279.
• [97] DHAWAN B., REDMORE D., Phosphorus, Sulfur and Silicon, 1987, 32, 119–144.
• [98] KAFARSKI P., LEJCZAK B., Curr. Med. Chem. – Anti-Cancer Agents, 2001, 1, 301–312.
• [99] HOFFMANN M., Pol. J. Chem., 1979, 53, 1153–1158.
• [100] HOFFMANN M., Phosphorus, Sulfur and Silicon, 1992, 73, 173–184.
• [101] ŽEMLIČKA J., CHLADEK S., Collect. Chech. Chem. Commun., 1969, 34, 1007–1014.
• [102] GILMORE W.F., MCBRIDE H.A., J. Pharm. Sci., 1974, 63, 965–966.
• [103] BARTLETT P.A., HANSON J.E., GIANNOUSIS P.P., J. Org. Chem., 1990, 55, 6268–6274.
• [104] GEORGIADIS D., MATZIARI M., VASSILIOU S., DIVE V., YIOTAKIS A., Tetrahedron, 1999, 55, 14635–14648.
• [105] BAYLIS E.K., CAMPBELL C.D., DINGWALL J.G., J. Chem. Soc. Perkin Trans. I, 1984, 2845–2853.
• [106] DUMY P., ESCALE R., GIRARD J.-P., PARELLO J., VIDAL J.-P., Synthesis, 1992, 1226–1228.
• [107] DORFF P.H., CHIU G., GOLDSTEIN S.W., MORGAN B.P., Tetrahedron Lett., 1998, 39, 3375–3378.
• [108] GEORGIADIS D., MATZIARI M., YIOTAKIS A., Tetrahedron, 2001, 57, 3471–3478.
• [109] WASIELEWSKI C., SOBCZAK A., SZEWCZYK J., Rocz. Chem., 1976, 50, 1795–1799.
• [110] HOFFMANN M., J. Prakt. Chimie, 1988, 330, 820–824.
• [111] CAMPBELL D.A., BERNAK J.C., J. Am. Chem. Soc., 1994, 114, 6039–6040.
• [112] GRAY M.D.M., SMITH D.J.H., Tetrahedron Lett., 1980, 21, 859–860.
• [113] SAADY M., LEBEAU L., MIOSKOWSKI C., J. Org. Chem., 1995, 60, 2946–2947.
• [114] GALÉOTTI N., COSTE J., BEDOS P., JOUIN P., Tetrahedron Lett., 1996, 37, 3997–3998.
• [115] HOFFMANN M., Synthesis, 1986, 557–559.
• [116] WASIELEWSKI C., HOFFMANN M., WITKOWSKA E., RACHOŃ J., Rocz. Chem., 1976, 50, 1613–1620.
• [117] HOFFMANN M., WASIELEWSKI C., Rocz. Chem., 1976, 50, 139–146.
• [118] KARANEWSKY D.S., BADIA M.C., Tetrahedron Lett., 1986, 27, 1751–1754.
• [119] BARTLETT P.A., GIANGIORDANO M.A., J. Org. Chem., 1996, 61, 3433–3438.
• [120] SAMPSON N.S., BARTLETT P.A., J. Org. Chem., 1988, 53, 4500–4503.
• [121] ALLEN M.C., FUHRER W., TUCK B., WADE R., WOOD J.M., J. Med. Chem., 1989, 32, 1652–1661.
• [122] GIANNOUSIS P.P., BARTLETT P.A., J. Med. Chem., 1987, 30, 1603–1609.
• [123] GILMORE W.F., MCBRIDE H.A., J. Pharm. Sci., 1974, 63, 1087–1090.
• [124] MUCHA A., KAFARSKI P., PLENAT F., CRISTAU H.-J., Phosphorus, Sulphur and Silicon, 1995, 105, 187–193.
• [125] MUCHA A., KAFARSKI P., PLENAT F., CRISTAU H.-J., Tetrahedron, 1994, 50, 12743–12754.
• [126] MUCHA A., KAFARSKI P., Tetrahedron, 2002, 58, 5855–5863.
• [127] VO-QUANG Y., GRAVEY A.M., SIMONNEAU R., VO–QUANG L., LACOSTE A.M., LE GOFFIC F., Tetrahedron Lett., 1987, 28, 6167–6170.
• [128] YANG K.W., BRANDT J.J., CHATWOOD L.L., CROWDER M.W., Bioorg. Med. Chem. Lett., 2000, 10, 1085–1087.
• [129] OLEKSYSZYN J., SUBOTKOWSKA L., MASTALERZ P., Synthesis, 1979, 985–986.
• [130] SZEWCZYK J., LEJCZAK B., KAFARSKI P., Synthesis, 1982, 409–412.
• [131] GREMBECKA J., MUCHA A., CIERPICKI T., KAFARSKI P., J. Med. Chem., 2003, 46, 2641–2655.
• [132] MUCHA A., GREMBECKA J., CIERPICKI T., KAFARSKI P., Eur. J. Org. Chem., 2003, 46 4797–4803.
• [133] STANO A., MUCHA A., KAFARSKI P., Synthetic Commun., 1999, 29, 4269–4277.
• [134] GALLAGHER M.J., HONEGGER H., Aust. J. Chem., 1980, 33, 287–294.
• [135] KUKHAR V.P., SOLOSHONOK V.A., SOLODENKO V.A., Phosphorus, Sulfur and Silicon, 1994, 92, 239–264.
• [136] KOLODIAZHNYI O.I., Tetrahedron: Asymmetry, 1998, 9, 1279–1332.
• [137] KUKHAR V.P., In Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity, Kukhar V.P., Hudson H.R., (Eds.), John Wiley & Sons, Chichester, 2000, 127–172.
• [138] MUCHA A., TYKA R., SAWKA-DOBROWOLSKA W., GŁOWIAK T., Phosphorus, Sulphur and Silicon, 1995, 104, 129–138.
• [139] LÄMMERHOFER M., LINDNER W., J. Chromatogr. A, 1996, 741, 33–48.
• [140] MAIER N.M., NICOLETTI L., LÄMMERHOFER M., LINDNER W., Chirality, 1999, 11, 522–528.
• [141] LÄMMERHOFER M., HEBENSTREIT D., GAVIOLI E., LINDNER W., MUCHA A., KAFARSKI P., WIECZOREK P., Tetrahedron: Asymmetry, 2003, 14, 2557–2565.
• [142] CZERWENKA C., LÄMMERHOFER M., MAIER N.M., RISSANEN K., LINDNER W., Anal. Chem., 2002, 74, 5658–5666.
• [143] MAIER N.M., SCHEFZICK S., LOMBARDO G.M., FELIZ M., RISSANEN K., LINDNER W., LIPKOWITZ K.B., J. Am. Chem. Soc., 2002, 124, 8611–8629.
• [144] ZARBL E., LÄMMERHOFER M., HAMMERSCHMIDT F., WUGGENIG F., HANBAUER M., MAIER N.M., SAJOVIC L., LINDNER W., Anal. Chim. Acta, 2000, 404, 169–177.
• [145] LÄMMERHOFER M., ZARBL E., LINDNER W., PERIC SIMOW B., HAMMERSCHMIDT F., Electrophoresis, 2001, 22, 1182–1187.
• [146] DŻYGIEL P., RUDZIŃSKA E., WIECZOREK P., KAFARSKI P., J. Chromatogr. A, 2000, 895, 301–307.
• [147] RUDZIŃSKA E., DŻYGIEL P., WIECZOREK P., KAFARSKI P., J. Chromatogr. A, 2002, 979, 115–122.
• [148] RUDZIŃSKA E., WIECZOREK P., KAFARSKI P., Electrophoresis, 2003, 15, 2693–2697.
• [149] BERLICKI Ł., RUDZIŃSKA E., KAFARSKI P., Tetrahedron: Asymmetry, 2003, 14, 1535–1539.
• [150] BERLICKI Ł., RUDZIŃSKA E., MUCHA A., KAFARSKI P., Tetrahedron: Asymmetry, 2004, 15, 1597–1602.
• [151] RUDZIŃSKA E., DRAPAŁA A., BERLICKI Ł., MUCHA A., DŻYGIEL P., WIECZOREK P., KAFARSKI P., praca złożona do J. Chromatogr. A.
• [152] BERLICKI L., RUDZIŃSKA E., MUCHA A., LÄMMERHOFER M., LINDNER W., KAFARSKI P., In 18th Polish Peptide Symposium, Wrocław 2005, 85.
• [153] BARTLETT P.A., MARLOWE C.K., GIANNOUSIS P.E., HANSON J.E., Cold Spring Harbor Symp. Quant. Biol., 1987, 52, 83–90.
• [154] YAMAUCHI K., KINOSHITA M., IMOTO M., Bull. Chem. Soc. Jpn., 1972, 45, 2528–2531.
• [155] YAMAUCHI K., KINOSHITA M., IMOTO M., Bull. Chem. Soc. Jpn., 1972, 45, 2531–2534.
• [156] YAMAUCHI K., MITSUDA Y., KINOSHITA M., Bull. Chem. Soc. Jpn., 1975, 48, 3285–3286.
• [157] HARIHARAN M., CHABEREK S., MARTELL A.E., Synth. Commun., 1973, 3, 375–379.
• [158] HARIHARAN M., MOTEKAITES R.J., MARTELL A.E., J. Org. Chem., 1975, 40, 470–473.
• [159] JACOBSEN N.E., BARTLETT P.A., J. Am. Chem. Soc., 1983, 105, 1613–1619.
• [160] JACOBSEN N.E., BARTLETT P.A., J. Am. Chem. Soc., 1983, 105, 1619–1626.
• [161] MALACHOWSKI W.P., COWARD J.K., J. Org. Chem., 1994, 59, 7616–7624.
• [162] MALACHOWSKI W.P., COWARD J.K., J. Org. Chem., 1994, 59, 7625–7634.
• [163] HIRSCHMANN R., YAGER K.M., TAYLOR C.M., MOORE W., SPRENGELER P.A., WITHERINGTON J., PHILLIPS B.W., SMITH A.B.III, J. Am. Chem. Soc., 1995, 117, 6370–6371.
• [164] HIRSCHMANN R., YAGER K.M., TAYLOR C.M., WITHERINGTON J., SPRENGELER P.A., PHILLIPS B.W., MOORE W., SMITH A.B.III, J. Am. Chem. Soc., 1997, 119, 8177–8190.
• [165] YAMAUCHI K., OHTSUKI S., KINOSHITA M., J. Org. Chem., 1984, 49, 1158–1163.
• [166] ELLIOTT R.L., MARKS N., BERG M.J., PORTOGHESE P.S., J. Med. Chem., 1985, 28, 1208–1216.
• [167] MOOKTHIAR K.A., MARLOWE C.K., BARTLETT P.A., VAN WART H.E., Biochemistry, 1987, 26, 1962–1965.
• [168] YIOTAKIS A., LECOQ A., NICOLAOU A., LABADIE J., DIVE V., Biochem. J., 1994, 303, 323–327.
• [169] BARTLETT P.A., LAMDEN L.A., Bioorg. Chem., 1986, 14, 356–377.
• [170] MCLEOD D.A., BRINKWORTH R.I., ASHLEY J.A., JANDA K.D., WIRSCHING P., Bioorg. Med. Chem. Lett., 1991, 1, 653–658.
• [171] YUAN C., WANG G., Phosphorus, Sulfur and Silicon, 1992, 71, 207–212.
• [172] CAMP N.P., HAWKINS P.C.D., HITCHCOCK P.B., GANI D., Bioorg. Med. Chem. Lett., 1992, 2, 1047–1052.
• [173] BATESON J.H., GASSON B.C., KHUSHI T., NEALE J.E., PAYNE D.J., TOLSON D.A., WALKER G., Bioorg. Med. Chem. Lett., 1994, 4, 1667–1672.
• [174] MUSIOL H.-J., GRAMS F., RUDOLPH-BÖHNER S., MORODER L., J. Org. Chem., 1994, 59, 6144–6146.
• [175] CAMP N.P., PERRY D.A., KINCHINGTON D., HAWKINS P.C.D., GANI D., Bioorg. Med. Chem., 1995, 3, 297–312.
• [176] ISSLEIB K., DÖPFER K.P., BALSZUWEIT A., Synth. React. Inorg. Met. Org. Chem., 1983, 13, 527–536.
• [177] NATCHEV I.A., Tetrahedron, 1991, 47, 1239–1248.
• [178] NATCHEV I.A., Bull. Chem. Soc. Jpn., 1988, 61, 3705–3711.
• [179] SIKORA D., NONAS T., GAJDA T., Tetrahedron, 2001, 57, 1619–1625.
• [180] ATHERTON F.R., OPENSHAW H.T., TODD A.R., J. Chem. Soc., 1945, 660–663.
• [181] ELHADDADI M., JACQUIER R., PETRUS C., PETRUS F., Phosphorus, Sulfur and Silicon, 1991, 63, 255–259.
• [182] CHEN R.Y., DAN S.C., Phosphorus, Sulfur and Silicon, 1991, 56, 39–48.
• [183] DUMY P., ESCALE R., VIDAL J.-P., GIRARD J.-P., PARELLO J., Compt. Rend. Acad. Sci. Paris, 1991, 312, 235–240.
• [184] CHRISTIANSON D.W., LIPSCOMB W.N., J. Am Chem. Soc., 1986, 108, 545–546.
• [185] YUAN W., MUNOZ B., WONG C.-H., HAEGGSTOEM J.Z., WETTERHOLM A., SAMUELSSON B., J. Med. Chem., 1993, 36, 211–220.
• [186] CULLIS P.M., HARGER M.J.P., Chem. Commun., 2002, 458–459.
• [187] OLEKSYSZYN J., POWERS J.C., Biochemistry, 1991, 30, 485–493.
• [188] POWERS J.C., ODAKE S., OLEKSYSZYN J., HORI H., UEDA T., BODUSZEK B., KAM C.M., In Proteases, Protease Inhibitors and Protease-Derived Peptides, Cheronis J.C., Repine J.E., (Eds.), Birkhäuser Ver-lag, Basel, 1993, 3–18.
• [189] OLEKSYSZYN J., In Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity, Kukhar V.P., Hudson H.R., (Eds.), John Wiley & Sons, Chichester, 2000, 537–558.
• [190] SAMPSON N.S., BARTLETT P.A., Biochemistry, 1991, 30, 2255–2263.
• [191] BONE R., SAMPSON N.S., BARTLETT P.A., AGARD D.A., Biochemistry, 1991, 30, 2263–2272.
• [192] CHEN R.Y., DAN S.C., Phosphorus, Sulfur and Silicon, 1990, 51/52, 481–484.
• [193] MUCHA A., KUNERT A., GREMBECKA J., PAWEŁCZAK M., KAFARSKI P., Eur. J. Med. Chem., 2006, w druku.
• [194] MATHIS F., Phosphorus, Sulfur and Silicon, 1976, 1, 109–128.
• [195] HARGER M.J.P., PATER C., Chem. Commun., 1999, 931–932.
• [196] THOTTATHIL J.K., RYONO D.E., PRZYBYLA C.A., MONIOT J.L., NEUBECK R., Tetrahedron Lett., 1984, 25, 4741–4744.
• [197] THOTTATHIL J.K., PRZYBYLA C.A., MONIOT J.L., Tetrahedron Lett., 1984, 25, 4737–4740.
• [198] BOYD E.A., REAGAN A.C., JAMES K., Tetrahedron Lett., 1992, 33, 813–816.
• [199] BOYD E.A., REAGAN A.C., JAMES K., Tetrahedron Lett., 1994, 35, 4223–4226.
• [200] BOYD E.A., BOYD M.E.K., LOH V.M.JR., Tetrahedron Lett., 1996, 37, 1651–1654.
• [201] LIU X., HU X.E., TIAN X., MAZUR A., EBETINO F.H., J. Organomet. Chem., 2002, 646, 212–222.
• [202] PARSONS W.H., PATCHETT A.A., BULL H.G., SCHOEN W.R., TAUB D., DAVIDSON J., COMBS P.L., SPRINGER J.P., GADEBUSCH H., WEISSBERGER B., VALIANT M.E., MELLIN T.N., BUSCH R.D., J. Med. Chem., 1998, 31, 1772–1778.
• [203] CRISTAU H.-J., COULOMBEAU A., GENEVOIS-BORELLA A., PIRAT J.-L., Tetrahedron Lett., 2001, 42, 4491–4494.
• [204] CRISTAU H.-J., COULOMBEAU A., GENEVOIS-BORELLA A., SANCHEZ F., PIRAT J.-L., J. Organomet. Chem., 2002, 643/644, 381–391.
• [205] MALY D.J., HUANG L., ELLMAN J.A., ChemBioChem, 2002, 3, 17–37.
• [206] BATRA S., SRINVASAN T., RASTOGI S.K., KUNDU B., Curr. Med. Chem., 2002, 9, 307–319.
• [207] CAMPAGNE J.-M., COSTE J., GUILLOU L., HEITZ A., JOUIN P., Tetrahedron Lett., 1993, 34, 4181–4184.
• [208] MATZIARI M., YIOTAKIS A., Org. Lett., 2005, 7, 4049–4052.
• [209] BUCHARDT J., FERRERAS M., KROG-JENSEN C., DELAISSÉ J.-M., FOGED N.T., MELDAL M., Chem. Eur. J., 1999, 5, 2877–2884.
• [210] VALIAEVA N., BARTLEY D., KONNO T., COWARD J.K., J. Org. Chem., 2001, 66, 5146–5154.
• [211] BARTLEY D.M., COWARD J.K., J. Org. Chem., 2005, 70, 6757–6774.
• [212] KENDE A.S., DONG H.-Q., LIU X., EBETINO F.H., Tetrahedron Lett., 2002, 43, 4973–4976.
• [213] MATZIARI M., GEORGIADIS D., DIVE V., YIOTAKIS A., Org. Lett., 2001, 3, 659–662.
• [214] MATZIARI M., BEAU F., CUNIASSE P., DIVE V., YIOTAKIS A., J. Med. Chem., 2004, 47, 325–336.
• [215] MAKARITIS A., GEORGIADIS D., DIVE V., YIOTAKIS A., Chem. Eur. J., 2003, 9, 2079–2094.
• [216] STETTER H., KUHLMANN H., Synthesis, 1979, 29–30.
• [217] CZUBAK M., KUNERT A., OLEJKO A., GREMBECKA J., MUCHA A., KAFARSKI P., In XLVII Zjazd PTChem i SITPChem, Materiały Zjazdowe, Tom 1, Wrocław 2004, 80.
• [218] VASSILIOU S., XEILARI M., MUCHA A., YIOTAKIS A., In 1st Hellenic Symposium of Organic Synthesis from Chemistry to Biology, Medicine and Material Science, Athens 2004, 114.
• [219] MUCHA A., PAWEŁCZAK M., HUREK J., KAFARSKI P., Bioorg. Med. Chem. Lett., 2004, 14, 3113–3116.
• [220] GAŁĘZOWSKA J., SOBEK S., DRĄG M., MUCHA A., KAFARSKI P., KOZŁOWSKI H., Pol. J. Chem., 2005, 79, 603–617.
• [221] BERLICKI Ł., MUCHA A., KAFARSKI P., w przygotowaniu.
• [222] GEORGIADIS D., DIVE V., YIOTAKIS A., J. Org. Chem., 2001, 66, 6604–6610.
• [223] REITER L.A., JONES B.P., J. Org. Chem., 1997, 62, 2808–2812.
• [224] CHEN H., NOBLE F., MOTHÉ A., MEUDAL H., CORIC P., DANASCIMENTO S., ROQUES B.P., GEORGE P., FOURNIÉ-ZALUSKI M.-C., J. Med. Chem., 2000, 43, 1398–1408.
• [225] RAGUIN O., FOURNIÉ-ZALUSKI M.-C., ROMIEU A., PÉLEGRIN A., CHATALET F., PÉLAPRAT D., BARBET J., ROQUES B.P., GRUAZ-GUYON A., Angew. Chem. Int. Ed., 2005, 44, 4058–4061.
• [226] FIRCZUK M., MUCHA A., BOCHTLER M., J. Mol. Biol., 2005, 354, 578–590.
• [227] BOCHTLER M., ODINTSOV S., MARCYJANIAK M., SABALA I., Protein Sci., 2004, 13, 854–861.
• [228] BERLICKI Ł., Projektowanie i synteza inhibitorów syntetazy glutaminy, Praca doktorska, Wrocław, 2004.
• [229] RADKIEWICZ J.L., MCALLISTER M.A., GOLDSTEIN E., HOUK K.N., J. Org. Chem., 1998, 63, 1419–1428.
• [230] PEYMAN A., In Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity, Kukhar V.P., Hudson H.R., (Eds.), John Wiley & Sons, Chichester, 2000, 559–577.
• [231] BARTLETT P.A., HANSON J.E., ACHER F., GIANNOUSIS P.P., In Biophosphates and Their Analogues – Synthesis, Structure, Metabolism and Activity, Bruzik K.S., Stec W.J., (Eds.), Elsevier, Amsterdam, 1986, 429–440.
• [232] GALARDY R.E., GROBELNY D., Biochemistry, 1983, 22, 4556–4561.
• [233] DIVE V., YIOTAKIS A., NICOLAOU A., TOMA F., Eur. J. Biochem., 1990, 191, 685–693.
• [234] BARELLI H., DIVE V., YIOTAKIS A., VINCENT J.-P., CHECLER F., Biochem. J., 1992, 287, 621–625.
• [235] VINCENT B., DIVE V., YIOTAKIS A., SMADJA C., MALDONADO R., VINCENT J.-P., CHECLER F., Brit. J. Pharmacol., 1995, 115, 1053–1063.
• [236] YIOTAKIS A., LECOQ A., VASSILIOU S., RAYNAL I., CUNIASSE P., DIVE V., J. Med. Chem., 1994, 37, 2713–2720.
• [237] CHACKALAMANNIL S., CHUNG S., STAMFORD A.W., MCKITTRICK B.A., WANG Y., TSAI H., CLEVEN R., FAWZI A., CZARNIECKI M., Bioorg. Med. Chem. Lett., 1996, 6, 1257–1260.
• [238] MCKITTRICK B.A., STAMFORD A.W., WENG X., MA K., CHACKALAMANNIL S., CZARNIECKI M., CLEVEN R.M., FAWZI A., Bioorg. Med. Chem. Lett., 1996, 6, 1629–1634.
• [239] LLOYD J., SCHMIDT J.B., HUNT J.T., BARRISH J.C., LITTLE D.K., TYMIAK A.A., Bioorg. Med. Chem. Lett., 1996, 6, 1323–1326.
• [240] GEORGIADIS D., VAZEUX G., LLORENS-CORTES C., YIOTAKIS A., DIVE V., Biochemistry, 2000, 39, 1152–1155.
• [241] CHEN H., NOBLE F., ROQUES B.P., FOURNIÉ-ZALUSKI M.-C., J. Med. Chem., 2001, 44, 3523–3530.
• [242] GURULINGAPPA H., BUCKHALTS P., KINZLER K.W., VOGELSTEIN B., KHAN S.R., Bioorg. Med. Chem. Lett., 2004, 14, 3531–3533.
• [243] BARTLETT P.A., KEZER W.B., J. Am. Chem. Soc., 1984, 106, 4282–4283.
• [244] FRASER M.E., STRYNADKA N.C.J., BARTLETT P.A., HANSON J.E., JAMES M.N.G., Biochemi-stry, 1992 , 31 , 5201–5214.
• [245] DREYER G.B., METCALF B.W., TOMASZEK T.A.JR., CARR T.J., CHANDLER A.C.I., HYLAND R., FAKHOURY S.A., MAGAARD V.W., MOORE M.L., STRICKLER J.E., DEBOUCK C., MEEK T.D., Proc. Natl Acad. Sci. USA, 1989, 86, 9752–9756.
• [246] GROBELNY D., WONDRAK E.M., GALARDY R.E., OROSZLAN S., Biochem. Biophys. Res. Commun., 1990, 169, 1111–1116.
• [247] ABDEL-MEGUID S.S., ZHAO B., MURTHY K.H.M., WINBORNE E., CHOI J.-K., DESJARLAIS R.L., MINNICH M.D., CULP J.S., DEBOUCK C., TOMASZEK T.A.JR., MEEK T.D., DREYER G.B., Biochemistry, 1993, 32, 7972–7980.
• [248] PEYMAN A., WAGNER K., BUDT K.-H., SPANIG J., RUPPERT D., MEICHSNER C., PAESSENS A., Bioorg. Med. Chem. Lett., 1994, 4, 1191–1194.
• [249] TOH H., ONO M., SAIGO K., MIYATA T., Nature, 1985, 315, 691.
• [250] PEARL L.H., TAYLOR W.R., Nature, 1987, 329, 351–354.
• [251] WALKER B., WHARRY S., HAMILTON R.J., MARTIN S.L., HEALY A., WALKER B.J., Biochem. Biophys. Res. Commun., 2000, 276, 1235–1239.
• [252] GREEN D.ST.C., SKORDALAKES E., SCULLY M.F., DEADMAN J.J., In Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity, Kukhar V.P., Hudson H.R., (Eds.), John Wiley & Sons, Chichester, 2000, 579–596.
• [253] PAYNE D.J., WENSHENG D., BATESON J.H., Exp. Opin. Invest. Drugs, 2000, 9, 247–261.
• [254] HIRATAKE J., J. Synth. Org. Chem., Jpn., 2002, 60, 1095–1103.
• [255] EL ZOEIBY A., SANSCHAGRIN F., LEVESQUE R.C., Mol. Microbiol., 2003, 47, 1–12.
• [256] SILVER L.L., Curr. Opin. Microbiol., 2003, 6, 431–438.
• [257] NAGASE H., WOESSNER J.F.JR., J. Biol. Chem., 1999, 274, 21491–21494.
• [258] VISSE R., NAGASE H., Circ. Res., 2003, 92, 827–839.
• [259] STERNLICHT M.D., WERB Z., Annu. Rev. Cell Dev. Biol., 2001, 17, 463–516.
• [260] STAMENKOVIC I., J. Pathol., 2003, 200, 448–464.
• [261] CURRAN S., MURRAY G. I., J. Pathol., 1999, 189, 300–308.
• [262] JOHANSSON N., AHONEN M., KÄHÄRI V.-M., Cell. Mol. Life. Sci., 2000, 57, 5–15.
• [263] VIHINEN P., KÄHÄRI V.-M., Int. J. Cancer, 2002, 99, 157–166.
• [264] HANDSLEY M.M., EDWARDS D.R., Int. J. Cancer, 2005, 115, 849–860.
• [265] MICHAELIDES M.R., CURTIN M.L., Curr. Pharm. Design, 1999, 5, 787–819.
• [266] WHITTAKER M., FLOYD C.D., BROWN P., GEARING A.J.H., Chem. Rev., 1999, 99, 2735–2776.
• [267] COUSSENS L.M., FINGLETON B., MATRISIAN L.M., Science, 2002, 295, 2387–2392.
• [268] BREUER E., FRANT J., REICH R., Exp. Opin. Ther. Patents, 2005, 15, 253–269.
• [269] CHEN E.X., SIU L.L., Curr. Pharm. Design, 2005, 11, 265–272.
• [270] RAO B.G., Curr. Pharm. Design, 2005, 11, 295–322.
• [271] GALARDY R.E., GROBELNY D., KORTYLEWICZ Z.P., PONCZ L., In Matrix Metalloproteinases Inhib., Proc. Matrix Metalloproteinase Conf. 1989, Birkedal-Hansen H., (Ed.), Fischer, Stuttgart, 1992, 259–262.
• [272] KORTYLEWICZ Z.P., GALARDY R.E., J. Med. Chem., 1990, 33, 263–273.
• [273] GOULET J.L., KINNEARY J.F., DURETTE P.L., STEIN R.L., HARRISON R.K., IZQUIERDO-MARTIN M., KUO D.W., LIN T.-Y., HAGMANN W.K., Bioorg. Med. Chem. Lett., 1994, 4, 1221–1224.
• [274] CALDWELL C.G., SAHOO S.P., POLO S.A., EVERSOLE R.R., LANZA T.J., MILLS S.G., NIEDZWIECKI L.M., IZQUIERDO-MARTIN M., CHANG B.C., HARRISON R.K., KUO D.W., LIN T.-Y., STEIN R.L., DURETTE P.L., HAGMANN W.K., Bioorg. Med. Chem. Lett., 1996, 6, 323–328.
• [275] VASSILIOU S., MUCHA A., CUNIASSE P., GEORGIADIS D., LUCET-LEVANNIER K., BEAU F., KANNAN R., MURPHY G., KNÄUPER V., RIO M.-C., BASSET P., YIOTAKIS A., DIVE V., J. Med. Chem., 1999, 42, 2610–2620.
• [276] BASSET P., BELLOCQ J.P., WOLF C., STOLL I., HUTIN P., LIMACHER J.M., PODHAJCER O.L., CHENARD M.-P., RIO M.-C., CHAMBON P., Nature, 1990, 348, 699–704.
• [277] MUCHA A., CUNIASSE P., BEAU F., DIVE V., In Peptydy ’99, XV Polskie Sympozjum Peptydowe, Waplewo k/Olsztyna 1999, K–21.
• [278] LOVEJOY B., CLEASBY A., HASSELL A.M., LONGLEY K., LUTHER M.A., WEIGL D., MCGEEHAN G., MCELROY A.B., DREWRY D., LAMBERT M.H., JORDAN S.R., Science, 1994, 263, 375–377.
• [279] MASKOS K., Biochemie, 2005, 87, 249–263.
• [280] MUCHA A., CUNIASSE P., KANNAN R., BEAU F., YIOTAKIS A., BASSET P., DIVE V., J. Biol. Chem., 1998, 273, 2763–2768.
• [281] REITER L.A., RIZZI J.P., PANDIT J., LASUT M.J., MCGAHEE S.M., PARIKH V.D., BLAKE J.F., DANLEY D.E., LAIRD E.R., LOPEZ-ANAYA A., LOPRESTI-MORROW L.L., MANSOUR M.N., MARTINELLI G.J., MITCHELL P.G., OWENS B.S., PAULY T.A., REEVES L.M., SCHULTE G.K., YOCUM S.A., Bioorg. Med. Chem. Lett., 1999, 9, 127–132.
• [282] REITER L.A., MITCHELL P.G., MARTINELLI G.J., LOPRESTI-MORROW L.L., YOCUM S.A., ESKRA J.D., Bioorg. Med. Chem. Lett., 2003, 13, 2331–2336.
• [283] BUCHARDT J., SCHIØDT C.B., KROG-JENSEN C., DELAISSÉ J.-M., FOGED N.T., MELDAL M., J. Comb. Chem., 2000, 2, 624–638.
• [284] CHRISTENSEN U., GROTH T., SCHIØDT C.B., FOGED N.T., MELDAL M., QSAR Comb. Sci., 2003, 22, 737–744.
• [285] TAYLOR A., Trends Biochem. Sci., 1993, 18, 167–171.
• [286] TAYLOR A., FASEB J., 1993, 7, 290–298.
• [287] KIM H., LIPSCOMB W.N., Adv. Enzymol. Relat. Areas Mol. Biol., 1994, 68, 153–213.
• [288] STRÄTER N., LIPSCOMB W.N., Biochemistry, 1995, 34, 14792–14800.
• [289] STRÄTER N., LIPSCOMB W.N., In Handbook of Proteolytic Enzymes, Barrett A.J., Rawlings N.D., Woessner J.F., (Eds.), Academic Press, Amsterdam, 2002, 1384–1389.
• [290] UMEZAWA H., Recent Results Cancer Res., 1980, 75, 115–125.
• [291] GUPTA S.K., AZIZ M., KHAN A.A., Indian J. Pathol. Microbiol., 1989, 32, 301–305.
• [292] TAYLOR A., DAIMS M., LEE J., SURGENOR T., Curr. Eye Res., 1982, 2, 47–56.
• [293] TAYLOR A., BROWN M.J., DAIMS M.A., COHEN J., Invest. Ophthalmol. Vis. Sci., 1983, 24, 1172–1180.
• [294] TAYLOR A., SURGENOR T., THOMSON D.K., GRAHAM R.J., OETTGEN H., Exp. Eye Res., 1984, 38, 217–229.
• [295] SCOTT C. S., DAVEY M., HAMILTON A., NORFOLK D.R., Blut, 1986, 52, 297–303.
• [296] PULIDO-CEJUDO G., CONWAY B., PROULX P., BROWN R., IZAGUIRRE C.A., Antiviral Res., 1997, 36, 167–177.
• [297] SUDA H., AOYAGI T., TAKEUCHI T., UMEZAWA H., Arch. Biochem. Biophys., 1976, 177, 196–200.
• [298] TAYLOR A., PELTIER C.Z., TORRE F.J., HAKAMIAN N., Biochemistry, 1993, 32, 784–790.
• [299] WILKES S.H., PRESCOTT J.M., J. Biol. Chem., 1985, 260, 13154–13162.
• [300] KIM H., LIPSCOMB W.N., Biochemistry, 1993, 32, 8465–8478.
• [301] KIM H., BURLEY S.K., LIPSCOMB W.N., J. Mol. Biol., 1993, 230, 722–724.
• [302] BURLEY S.K., DAVID P.R., SWEET R.M., TAYLOR A., LIPSCOMB W.N., J. Mol. Biol., 1992, 224, 113–140.
• [303] GREMBECKA J., KAFARSKI P., Mini Rev. Med. Chem., 2001, 1, 133–144.
• [304] LEJCZAK B., KAFARSKI P., ZYGMUNT J., Biochemistry, 1989, 28, 3549–3555.
• [305] BÖHM H.J., J. Comput. Aided Mol. Des., 1992, 6, 593–606.
• [306] BÖHM H.J., J. Mol. Recognit., 1993, 6, 131–137.
• [307] BÖHM H.J., J. Comput. Aided Mol. Des., 1994, 8, 623–632.
• [308] BÖHM H.J., J. Comput. Aided Mol. Des., 1996, 10, 265–272.
• [309] STRÄTER N., LIPSCOMB W.N., Biochemistry, 1995, 34, 9200–9210.
• [310] GREMBECKA J., SOKALSKI W.A., KAFARSKI P., J. Comput. Aided Mol. Des., 2000, 14, 531–544.
• [311] GREMBECKA J., SOKALSKI W.A., KAFARSKI P., Int. J. Quant. Chem., 2001, 84, 302–310.
• [312] KAFARSKI P., GREMBECKA J., MUCHA A., PAWEŁCZAK M., DRĄG M., BERLICKI Ł., OLECHNOWICZ D., Przemysł Chemiczny, 2003, 82, 1087–1089.
• [313] BERLICKI Ł., KAFARSKI P., Curr. Org. Chem., 2005, 9, 1829–1850.
• [314] BERLICKI Ł., OBOJSKA A., FORLANI G., KAFARSKI P., J. Med. Chem., 2005, 48, 6340–6349.
• [315] MUCHA A., GREMBECKA J., CIERPICKI T., KAFARSKI P., In Biologically Active Peptides, VIIth Conference, Collection Symposium Series, Slaninova J., (Ed.), Prague, 2001, 28–31.
• [316] GREMBECKA J., MUCHA A., CIERPICKI T., KAFARSKI P., Phosphorus, Sulfur and Silicon, 2002, 177, 1739–1743.
• [317] DRĄG M., GREMBECKA J., PAWEŁCZAK M., KAFARSKI P., Eur. J. Med. Chem., 2005, 40, 764–771.
• [318] ANDERSSON L., ISLEY T.C., WOLFENDEN R., Biochemistry, 1982, 21, 4177–4180.
• [319] MUCHA A., GREMBECKA J., VASSILIOU S., XEILARI M., YIOTAKIS A., PAWEŁCZAK M., KAFARSKI P., In 18th Polish Peptide Symposium, Wrocław 2005, 179.