Abstract
The biological activity and natural occurrence of the aminophosphonic acids were described half a century ago. Since then the chemistry and biology of this class of compounds have developed into the separate field of phosphorus chemistry. Today it is well acknowledged that these compounds possess a wide variety of promising, and in some cases commercially useful, physiological activities. Thus, they have found applications ranging from agrochemical (with the herbicides glyphosate and bialaphos being the most prominent examples) to medicinal (with the potent antihypertensive fosinopril and antiosteoporetic bisphosphonates being examples).
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References
Horiguchi M, Kandatsu M (1959) Nature 184:901
Mastalerz P (1959) Archiv Immun Ter Dosw 7(20):1. Chem Abst 53:18879b
Chavane V (1949) Gen Ann Chim 4:352. Chem Abst 45:7516g
Franz JE, Mao MK, Sikorski JA (1997) Glyphosate:a unique global herbicide. Monograph 189. American Chemical Society, Washington DC
Okuhara M, Kuroda Y, Goto T, Okamoto M, Terano H, Kohsaka M, Aoki H, Imanaka H (1980) J Antibiot 33:13
Allen JG, Atherton FR, Hall MJ, Hassall CH, Holmes SW, Lambert RW, Nisbet LJ, Ringrose PS (1978) Nature 272:56
Karanewsky DS, Badia MC, Cushman DW, De Forrest JM, Dejneka T, Loots MJ, Pern MG, Petrillo Jr RD, Powell RJ (1988) J Med Chem 31:204
Russell RGG (2006) Ann NY Acad Sci 1068:367–401
Kukhar VP, Hudson HR (eds) (2000) Aminophosphonic and aminophosphinic acids: chemistry and biological activity. Wiley, Chichester
Kafarski P, Lejczak B (1991) Phosphorus Sulfur Silicon 63:193
Collinsova M, Jiracek J (2000) Curr Med Chem 7:629
Kafarski P, Lejczak B (2001) Curr Med Chem – Anti-Cancer Agents 1:301
Berlicki L, Kafarski P (2005) Curr Org Chem 9:1829
Romanenko VD, Kukhar VP (2006) Chem Rev 106:3868
Wardle NJ, Bligh SWA, Hudson HR (2007) Curr Org Chem 11:1635
Hecker SJ, Erion MD (2008) J Med Chem 51:2328
Macciarulo A, Pellicciari R (2007) J Mol Graph Model 26:728
Dingledine R, Borges K, Bowie D, Traynelis SF (1999) Pharmacol Rev 51:7
Selvam C, Goudet C, Ouselatti N, Pin J-P, Acher FC (2007) J Med Chem 50:4656
Tikhonova IG, Baskin II, Palyulin VA, Zefirov NS, Bachurin SO (2002) J Med Chem 45:3836
Grazioso G, Moretti L, Scapozza L, de Amici M, de Micheli C (2005) J Med Chem 48:5489
Schoepp DD, Jane DE, Monn JA (1999) Neuropharmacology 38:1431
Baudy RB, Fletcher III H, Yardley JP, Zaleska MM, Bramlett RD, Tasse RP, Kowal DM (2001) J Med Chem 44:1516
Brandt MR, Cummons TA, Potestio L, Sukoff SJ, Rozenzweig-Lipson S (2005) J Pharm Exp Ther 313:1379
Feng B, Morley RM, Jane DE, Monaghan DT (2005) Neuropharm 48:354
Filosa R, Marinozzi M, Constantino G, Hermit MB, Thomsen C, Pellicciari R (2006) Bioorg Med Chem 14:3811
Amori L, Constantino G, Marinozzi M, Pellicciari R, Gasparini F, Flor PJ, Kuhn R, Vranesic I (2000) Bioorg Med Chem Lett 10:1447
Bettler B, Kaupman K, Mosbacher J, Gassman M (2004) Physiol Rev 84:835
Ong J, Kerr DIB (2005) CNS Drug Rev 11:317
Bon C, Galvan M (1996) Brit J Pharmacol 118:961–967
Alstermark C, Amin K, Dinn SR, Elbering T, Fjellström O, Fitzpatrick K, Geiss WB, Gottfries J, Guzzo PR, Harding JP, Holmén A, Kothare M, Lehmann A, Mattsson JP, Nilsson K, Sundén G, Swanson M, von Unge S, Woo AM, Wyle MJ, Zheng X (2008) J Med Chem 51:4315
Kerr DI, Ong J, Prager RH, Gynther BD, Curtis GR (1987) Brain Res 495:150
Bowery NG, Enna SJ (2000) J Pharmacol Exp Ther 292:2
Murata Y, Woodward RM, Miledi R, Overmann LE (1996) Bioorg Med Chem Lett 6:2073
Krehan D, Frolund B, Krogsgaard-Larsen P, Kehler J, Johnston GAR, Chebib M (2003) Neurochem Int 42:561
Orain D, Mattes H (2006) Tetrahedron Lett 47:1253
Hinton T Chebib M, Johnston GAR (2008) Bioorg Med Chem Lett 18:402
Bertaccini E, Trudel JR (2001) Int Rev Neurobiol 48:141
Bowery NG, Bettler B, Froestl W, Gallagher JP, Marshall F, Raiteri M, Bonner TI, Enna SJ (2003) 54:247
Li X, Cao J-H, Li Y, Ronard P, Zhang Y, Yi P, Liu J-F, Nan F-J (2008) J Med Chem 51:3057
Iron A, Monique R, Duboy J-P, Beranger M, Cassaigne A, Neuzil E (1981) Biochem Soc Trans 9:246
Lejczak B, Kafarski P, Makowiecka E (1987) Biochem J 242:81
Gasowska B, Wojtasek H, Jurek J, Drag M, Nowak K, Kafarski P (2002) Eur J Biochem 269:4098
Evsigneeva ZG, Solovieva NA, Sidelnikova LI (2003) Prikl Biokhim Mikrobiol 39:613
Berlicki L (2008) Mini Rev Med Chem 8:869
Logusch EW, Walker DM, McDonald JF, Franz JE (1989) Biochemistry 29:3034
Gill HS, Eisenberg D (2001) Biochemistry 40:1903
Krajewski WW, Jones AT, Mowbray SL (2005) Proc Natl Acad Sci USA 102:10499
Berlicki L, Obojska A, Forlani G, Kafarski P (2006) J Med Chem 48:6340
Forlani G, Obojska A, Berlicki L, Kafarski P (2006) J Agric Food Chem 54:796
Nordqvist A, Nilsson MT, Röttger S, Odeli LR, Krajewski WW, Andersson CE, Larhed M, Mowbray SL, Karlen A (2008) Bioorg Med Chem 16:5501
Zon J, Amrhein N (1992) Liebigs Ann Chem 625
Appert C, Zon J, Amrhein N (2003) Phytochemistry 62:415
Zon J, Szefczyk B, Sawka-Dobrowolska W, Gancarz R, Kucharska-Zon M, Latajka R, Amrhein N, Miziak P, Szczepanik W (2004) New J Chem 28:1048
Zon J. Miziak P, Amrhein N, Gancarz R (2005) Chem Biodiv 2:1187
Miziak P, Zon J, Amrhein N, Gancarz R (2007) Phytochemistry 68:407
Shie J-J, Fang J-M, Wang S-Y, Tsai K-C, Cheng Y-SE, Yang A-S, Hsiao S-C, Su C-Y, Wong C-H (2007) J Am Chem Soc 129:11892
Steere JA, Sampson PB, Honek JF (2002) Bioorg Med Chem Lett 12:457
Giannousis PP, Bartlett PA (1987) J Med Chem 30:1603
Lejczak B, Kafarski P, Zygmunt J (1989) Biochemistry 28:3549
Kim H, Lipscomb WN (1994) Adv Enzymol Relat Areas Mol Biol 68:153
Strater N, Lipscomb WN (1995) Biochemistry 34:9200
Grembecka J, Sokalski WA, Kafarski P (2000) J Comput-Aided Mol Design 14:531
Grembecka J, Sokalski WA, Kafarski P (2001) Int J Quant Chem 84:302
Grembecka J, Mucha A, Cierpicki T, Kafarski P (2003) J Med Chem 46:2641
Zhang Z-Y (2002) Ann Rev Pharmacol Toxicol 42:202
Tautz L, Pellechia M, Mustelin T (2006) Exp Opin Therapeut Agents 10:157
Burke Jr TR (2006) Curr Top Med Chem 6:1465
Oishi S, Karki RG, Shi Z-D, Worthy KM, Bindu L, Chertov O, Esposito D, Frank P, Gilette WK, Maderia M, Hatley J, Nicklaus MC, Barchi Jr JJ, Fisher RJ, Burke Jr TR (2005) Bioorg Med Chem 13:2431
Boutselis IG, Yu XS, Zhang Z-Y, Borch RF (2007) J Med Chem 50:856
Dourlat J, Valentin B, Liu W-Q, Garbay C (2007) Bioorg Med Che. Lett 17:3943
Shen K (2007) Methods 42:234
Johnson TO, Ermolieff J, Jarousek MR (2002) Nat Drug Discovery 1:696
Kumar S, Zhou B, Liang F, Wang W-Q, Huang Z, Zhang Z-Y (2004) Proc Natl Acad Sci USA 101:7943–7948
Walchi S, Espanel X, Harrenga A, Rossi M, Cesareni G, van Huijduijnen (2004) J Biol Chem 279:311–318
Santos WL, Heasly BH, Jarosz R, Carter KM, Lynch KR, Macdonald TL (2004) Bioorg Med Chem Lett 14:3473
Hale JJ, Doherty G, Toth L, Mills SG, Hajdu R, Keohane CA, Rosenbach M, Milligan J, Shei G-J, Chrebet G, Bergstrom J, Card D, Forrest M, Sun S-Y, West S, Xie H, Nomura N, Rosen H, Mandala S (2004) Bioorg Med Chem Lett 14:3501
Foss Jr FW, Snyder AH, Davis MD, Rouse M, Okusa MD, Lynch KR, Macdonald TL (2007) Bioorg Med Chem 15:663
Cui P, Tomsig JL, McCalmont WF, Lee S, Becker CJ, Lynch KR, Macdonald TL (2007) Bioorg Med Chem Lett 17:1634
Cui P, McCalmont WF, Tomsig JL, Lynch KR, Macdonald TL (2008) Bioorg Med Chem 16:2212
Hakogi T, Yamamoto T, Fujii S, Ikeda K, Katsumura S (2006) Tetrahedron Lett 47:2627
Cox RJ, Gibson JS, Hadfield AT (2005) Chem BioChem 2255
Balg C, Blais SP, Bernier S, Hout JL, Couture M, Lapointe J, Chênevert R (2007) Bioorg Med Chem 15:295
Notter RH, Wang Z, Wang Z, Davy AD, Schwan AL (2007) Bioorg Med Chem Lett 17:113
Wang Z, Chang Y, Schwan AL, Notter RH (2007) Am J Resp Cell Mol Biol 37:387
Cherenok S, Vovk A, Muravyova I, Shivanyuk A, Kukhar V, Lipokowksi J, Kalchenko V (2006) Org Lett 8:549
Drag M, Grembecka J, Pawelczak M, Kafarski P (2005) Eur J Med Chem 40:764
Mucha A, Kunert A, Grembecka J, Pawelczak M, Kafarski P (2006) Eur J Med Chem 41:768
Drag M, Grzywa R, Oleksyszyn J (2007) Bioorg Med Chem Lett 17:1516
Skinner-Adams TS, Lowther J, Teuscher F, Stack CM, Grembecka J, Mucha A, Kafarski P, Treholme TR, Dalton JP, Gardiner DL (2007) J Med Chem 50:602
Teuscher F, Lowther J, Skinner-Adams TS, Spielmann T, Dixon MWA, Stack CM, Donelly S, Mucha A, Kafarski P, Vassiliou S, Gardiner DL, Dalton JP, Trenholme KR (2007) J Biol Chem 282:30817
Vassiliou S, Xeilari M, Yiotakis A, Grembecka J, Pawelczak M, Kafarski P, Mucha A (2007) Bioorg Med Chem Lett 15:3187
Holz RC (2002) Coord Chem Rev 232:5
Berlicki L, Grembecka J, Dyguda-Kazimierowicz E, Kafarski P, Sokalski WA (2007) In: Sokalski WA Molecular materials with specific interactions – modeling and design. Challenges and advances in computational chemistry and physics, vol 4. Springer, Dordrecht, pp 365–398
Mucha A, Grembecka J, Cierpicki T, Kafarski P (2003) Eur J Org Chem 4797
Stack CM, Lowther J, Cunningham E, Donelly S, Gardiner DL, Treholme KR, Skinner-Adams TS, Teuscher F, Grembecka J, Mucha A, Kafarski P, Lua L, Bell A, Dalton JP (2007) J Biol Chem 282:2069
Reiter LA, Mitchell PG, Martinelli GJ, Lopresti-Morrow LL, Yocum SA, Eskra JD (2003) Bioorg Med Chem Lett 13:2331
Dive V, Georgiadis D, Matziari M, Makaritis A, Beau F, Cuniasse P, Yiotakis A (2004) Cell Mol Life Sci 61:2010
Matziari M, Beau F, Cuniasse P, Dive V, Yiotakis A (2004) J Med Chem 47:325
Agamemnone M, Campestre C, Preziuso S, Consalvi V, Crucianelli M, Mazza F, Politi V, Ragno R, Tortorella P, Gallina C (2005) Eur J Med Chem 40:271
Bianchi G, Aschi M, Cavicchio G, Crucianelli M, Prezusio S, Gallina C, Nastari A, Gavuzzo E, Mazza F (2005) Bioorg Med Chem 13:4740
Lauer-Fields J, Brew K, Whitehead JK, Li S, Hammer RP, Fields GB (2007) J Am Chem Soc 129:10408
Matziari M, Dive V, Yiotakis A (2007) Med Res Rev 27:528
Verma RP, Hansch C (2007) Bioorg Med Chem 15:2223
Gall A-L, Ruff M, Kannan R, Cuniasse P, Yiotakis A, Dive V, Rio M-C, Basset P, Moras D (2001) J Mol Biol 307:577
Makaritis A, Georgiadis D, Dive V, Yiotakis A (2003) Chem Eur J 9:2079
Manzenrieder F, Frank AO, Kessler H (2008) Angew Chem Int Ed 47:2608
Burchardt JU, Schiødt CB, Krog-Jensen C, Delaisse J-M, Foged NT, Meldal M (2000) J Comb Chem 2:624
Devel L, Rogakos V, David A, Makartis A, Beau F, Cuniasse P, Yiotakis A, Dive V (2006) J Biol Chem 281:11152
Aschi M, Besker N, Re N, Pochetti G, Coletti C, Mazza F (2007) J Med Chem 30:211
Mallari JP, Choy CJ, Hu Y, Martinez AR, Hosaka M, Toriyabe Y, Maung J, Blecha JE, Pavkovic SF, Berkman CE (2004) Bioorg Med Chem 12:6011
Adler M, Buckman B, Bryant J, Chang Z, Chu K, Emayan K, Hrvatin P, Islam I, Morser J, Sukovich D, West C, Yuan S, Whitlow M (2008) Acta Crystallogr D64:149
Grzywa R, Oleksyszyn J (2008) Bioorg Med Chem Lett 18:3734
Payne DJ, Du W, Bateson JH (2000) Exp Opin Invest Drugs 9:247
Gurulingappa H, Buckhalts P, Kinzler KW, Vogelstein B, Khan SR (2004) Bioorg Med Chem Lett 14:3531
Smith HK, Beckett RP, Clements JM, Doel S, East SP, Launchbury SB, Pratt LM, Spavold ZM, Thomas W, Todd RS, Whittaker M (2002) Bioorg Med Chem Lett 12:3595
Kruger RG, Barkallah S, Frankel BA, McCafferty DG (2004) Bioorg Med Chem 12:3723
Corradi HR, Chitapi I, Sewell BT, Georgiadis D, Dive V, Sturrock ED, Acharya KR (2007) Biochemistry 46:5473
Mores A, Matziari M, Beau F, Cuniasse P, Yiotakis A, Dive V (2008) J Med Chem 51:2216
Bartley DM, Coward JK (2005) J Org Chem 70:6757
Feng Y, Coward JK (2006) J Med Chem 49:770–788
Yang Y, Coward JK (2007) J Org Chem 72:5748
Vidossich P, Carloni P (2006) J Phys Chem B 110:1437
Manzenrieder F, Frank AO, Huber T, Dorner-Ciossek C, Kessler H (2007) Bioorg Med Chem 15:4136
Å trancar K, Blanot D, Gobec S (2006) Bioorg Med Chem Lett 16:343
Å trancar K, Boniface A, Blanot D, Gobec S (2007) Arch Pharm Chem Life Sci 340:127
Cressina E, Lloyd AJ, De Pascale G, Roper DI, Dowson CG Bugg TDH (2007) Bioorg Med Chem Lett 17:4654
Demange L, Dugave C (2001) Tetrahedron Lett 42:6295
Gobec S, Plantan I, Mravljak J, Wilson RA, Besra GS, Kikelj D (2004) Bioorg Med Chem Lett 14:3559
Gobec S, Plantan I, Mravljak J, Å vajger U, Wilson RA, Besra GS, Soares SL, Appelberg R, Kikelj D (2007) Eur J Med Chem 42:54
Han L, Hiratake J, Kamiyama A, Sakata K (2007) Biochemistry 46:1432
Mucha A, Pawelczak M, Hurek J, Kafarski P (2004) Bioorg Med Chem Lett 14:3113
Asojo O, Friedman J, Adir N, Belakhov V, Shoham Y, Baasov T (2001) Biochemistry 40:6326
Pan W, Ansiaux C, Vincent SP (2007) Tetrahedron Lett 48:4353
Suk D-H, Rejman D, Dykstra CC, Pohl R, Pankiewicz KW, Patterson SE (2007) Bioorg Med Chem Lett 17:2811
Zhou D, Staake M, Patterson S (2008) Org Lett 10:2179
Oleksyszyn J, Powers JC (1994) Amino acid and peptide phosphonate as specific inhibitors of serine peptidases. In: Barret AJ Methods in enzymology, vol 244. Academic, San Diego, pp 423–441
Skordalakes E, Dodson GG, St Clair Green D, Goodwin GA, Scully MF, Hudson HR, Kakkar VV, Deadman JJ (2001) J Mol Biol 311:549
Sienczyk M, Oleksyszyn J (2004) Tetrehedron Lett 45:7251
Joossens J, Van der Veken P, Surpateanu G, Lambeir A-M, El-Sayed I, Ali OM, Augustyns K, Haemers A (2006) J Med Chem 49:5785
Joossens J, Ali OM, El-Sayed I, Surpateanu G, Van der Veken P, Lambeir A-M, Setyono-Han B, Foeskens JA, Schneider A, Schmalix W, Haemers A, Augustyns K (2007) J Med Chem 50:6638
Gilmore BF, Lynas JF, Scott CJ, McGoohan C, Martin L, Walker B (2006) Biochem Biophys Res Commun 346:436
Augustyns K, Van der Veken P, Haemers A (2005) Curr Med Chem 12:971
Gilmore BF, Carson L, McShane LL, Quinn D, Coulter WA, Walker B (2006) Biochem Biophys Res Commun 347:373
Van der Veken P, Soroka A, Brandt I, Chen Y-S, Maes M-B, Lambeir A-M, Chen X, Haemers A, Scharpé S, Augustyns K, De Meester I (2007) J Med Chem 50:5568
Grzywa R, Dyguda-Kazimierowicz E, Sienczyk M, Feliks M, Sokalski WA, Oleksyszyn J (2007) J Mol Model 13:677
Zhou Y-X, Karle S, Tagiuchi H, Planque S, Nishiyama Y, Paul S (2002) J Immunol Meth 269:257–268
Taguchi H, Keck Z, Foung SKH, Paul S, Nishiyama Y (2004) Bioorg Med Chem Lett 14:4529
Marnett AB, Nomura AM, Shimba N, Ortiz de Montellano PR, Craik CS (2004) Proc Natl Acad Sci USA 101:6870
Planque S, Bangale Y, Song X-T, Karle S, Taguchi H, Poindexter B, Bick R, Edmundson A, Nishiyama Y, Paul S (2004) J Biol Chem 279:14024
Nishiyama Y, Mitsuda Y, Taguchi H, Planque S, Hara M, Karle S, Hanson CV, Uda T, Paul S (2005) J Mol Recogn 18:295
Nukaga M, Kumar S, Nukaga K, Pratt RF, Knox JR (2004) J Biol Chem 279:9344
Adediran SA, Nukaga M, Baurin S, Pratt RF (2005) Antimicrob Agents Chemother 49:4410
Han L, Hiratake J, Kamiyama A, Sakata K (2007) Biochemistry 46:1432
Fleisch H, Russel RGG, Staruman F (1966) Nature 212:901
Green JR (2004) Oncologist 9:4
Licata AA (2005) Ann Pharmacother 39:668
Russell RGG (2006) Ann NY Acad Sci 1068:367
Ogawa K, Mukai T, Ararno Y, Ono M, Hanaoka H, Ishino S, Hashimoto K, Nishimura H, Saji H (2005) Bioconjugate Chem 16:751
Mukherjee S, Song Y, Oldfield E (2008) J Am Chem Soc 130:1264
Shipman CM, Croucher PI, Russell RGG, Rogers MJ (1998) Cancer Res 58:5294
Ebetino FH, Roze CN, McKenna CE, Barnett CL, Dunfors JE, Russell RGG, Mielig GE, Rogers MJ (2005) J Organometal Chem 690:2679
Sanders JM, Song Y, Chan JMW, Zhang Y, Jennings S, Kosztowski T, Odeh S, Flessner R, Schwerdtfeger C, Kotsikorou E, Meints GA, Ortiz Gomaes A, Gonzales-Pacanowska D, Raker AM, Wang H, van Beek ER, Papapoulos SE, Morita CT, Oldfield E (2005) J Med Chem 48:2957
Dunford JE, Rogers MJ, Ebetino FH, Pipps RJ, Coxon FP (2006) J Bone Miner Res 21:684
Kavanagh KL, Guo K, Dunford JE, Wu X, Knapp S, Ebetino FH, Rogers MJ, Russell RGG, Oppermann U (2006) Proc Natl Acad Sci USA 103:7829
Leon A, Liu L, Yang Y, Hidock MP, Hall P, Yin F, Studer D, Puan K-J, Morita CT, Oldfield E (2006) J Med Chem 49:7331
Yin F, Cao R, Goddard A, Zhang Y, Oldfield E (2006) J Am Chem Soc 128:3524
Guo R-T, Cao R, Liang P-H, Ko T-P, Chang T-H, Hudock MP, Jeng W-J, Chen CK-M, Zhang Y, Song Y, Kuo C-J, Yin F, Oldfield E, Wang A H-J (2007) Proc Natl Acad Sci USA 104:10022
Wiemer AJ, Tong H, Swanson KM, Hohl RJ (2007) Biochem Biophys Res Commun 353:921
Dunford JE, Kwaasi AA, Rogers MJ, Barnett BL, Ebetino FH, Russell RGG, Opperman U, Kavanagh KL (2008) J Med Chem 51:2187
Hosfield DJ, Zhang Y, Dougan DR, Broun A, Tari LW, Swanson RV, Finn J (2004) J Biol Chem 279:8526
Mao J, Gao Y-G, Odeh S, Robinson H, Montavetti A, Docampo R, Oldfield E (2004) Acta Crystallogr D60:1863
Mao J, Mukherjee, Zhang Y, Cao R, Sanders JM, Song Y, Zhang Y, Meints GA, Mukkamala D, Hudock MP, Oldfield E (2006) J Am Chem Soc 128:14485
Rondeau JM, Bitsch F, Bourgier E, Geiser M, Hemming R, Kroemer M, Lehman S, Ramage P, Riffel S, Strauss A, Green JR, Jahnke W (2006) ChemMedChem 1:267
Martin MB, Arnold W, Heath III HT, Urbina JA, Oldfield E (1999) Biochem Biophys Res Commun 263:754
Berlicki L, Kafarski P (2002) Pestic Biochem Physiol 73:94
Dieterle F, Scglotterbeck G, Binder M, Ross A, Suter L, Senn H (2007) Chem Res Toxicol 20:1291
Gertz BJ, Holland SD, Kline WF, Matuszewski BK, Freeman A, Quan H, Lasseter KC, Mucklow JC, Porras AG (1995) Clin Pharmacol Therapeut 58:288
Hoffman A, Stepensky D, Ezra A, Van Gelder JM, Golomb G (2001) Int J Pharm 220:1
Vachal P, Hale JJ, Lu Z, Streckfuss EC, Mills SG, MacCoss M, Yin DH, Algayer K, Manser K, Kesisoglou F, Ghosh S, Alani LL (2006) J Med Chem 49:3060
Balas F, Manzano M, Horcjada P, Vallet-Regi M (2006) J Am Chem Soc 128:8116
Leite AF, Figueiredo PT, Melo NS, Acevedo AC, Paraiso Cavalcanti MG, Paula LM, Paula AP, Silva Guerra EN (2006) Oral Surg Oral Med Oral Pathol Oral Radiol Endod 102:14
Dannemann C, Grätz KW, Riener MO, Zwahlen RA (2007) Bone 40:828
Hess LM, Jeter JM, Benham-Hutchins M, Albers DS (2008) Am J Med 121:475
Subramaniam RM, Miller GM (2008) Eur J Radiol 66:e9
Uludag H (2002) Curr Pharm Des 8:99
Ogawa K, Mukai T, Ararno Y, Ono M, Hanaoka H, Ishino S, Hashimoto K, Nishimura H, Saji H (2005) Bioconj Chem 16:751
Ehrick RS, Capaccio M, Puelo DA, Bachas LG (2008) Bioconj Chem 19:315
Erez R, Ebner S, Attali B, Shabat D (2008) Bioorg Med Chem Lett 18:816
Urbina JA, Moreno B, Vierkotter S, Oldfield E, Payares G, Sanoja C, Bailey BN, Yan W, Scott DA, Moreno SNJ, Docampo R (1999) J Biol Chem 274:33609
Martin MB, Grimley JS, Lewis JC, Heath III HT, Bailey BN, Kendrick H, Yardley V, Caldera A, Lira R, Urbina JA, Moreno SNJ, Docampo R, Croft SL, Oldfield E (2001) J Med Chem 44:909
Martin MB, Sanders JM, Kendrick H, de Luca-Fradley K, Lewis JC, Grimley JS, van Brussel EM, Olsen JR, Meints GA, Burzynska A, Kafarski P, Croft SL, Oldfield E (2002) J Med Chem 45:2904
Szajnman SH, Bailey BN, Docampo R, Rodriguez JB (2001) Bioorg Med Chem Lett 11:789
Bouzahzah B, Jelicks LA, Morris SA, Weiss LM, Tarnowitz HB (2005) Parazitol Res 96:184
Rodriguez N, Bailey BN, Martin MB, Oldfield E, Urbina JA, Docampo R (2002) J Infect Dis 186:138
Yardley V, Khan AA, Martin MB, Slifer TR, Araujo FG, Moreno SN, Docampo R, Croft SL, Oldfield E (2002) Animicrob Agent Chemother 46:929
Garzoni LR, Waghabi MC, Baptista MM, de Castro SL, Meirelles MNL, Britto CC, Docampo R, Oldfield E, Urbina JA (2004) Int J Antimicrob Agents 23:286
Montalvetti A, Bailey BN, Martin MB, Severin GW, Oldfield E, Docampo R (2001) J Biol Chem 276:33930
Sanders JM, Gomes AO, Mao J, Meints GA, Van Brussel EM, Burzynska A, Kafarski P, Gonzales-Pacanowska D, Oldfield E (2003) J Med Chem 46:5171
Szajnman SH, Montalvetti A, Wang Y, Docampo R, Rodriguez JB (2003) Bioorg Med Chem Lett 13:3231
Szajnman SH, Ravaschino EL, Docampo R, Rodriguez JB (2005) Bioorg Med Chem Lett 15:4685
Hudock MP, Sanz-Rodriguez CE, Song Y, Chan JMW, Zhang Y, Odeh S, Kosztowski T, Leonrossell A, Cóncepcion JL, Yardely V, Croft SL, Urbina JA, Oldfield E (2006) J Med Chem 49:215
Kotsikorou E, Song Y, Chan JMW, Faelens S, Tovian Z, Broderick E, Bakalara N, Docampo R, Oldfield E (2005) J Med Chem 48:6128
Fernández D, Wenck MA, Craig III SP, Delfino JM (2004) Bioorg Med Chem Lett 14:4501
Wang L, Kamath A, Das H, Li L, Bukowski J (2001) J Clin Invest 108:1349
Verdijk R, Franke H, Vermes I (2003) Cancer Lett 246:308
Milner RJ, Farese J, Henry CJ, Selring K, Fan TM, de Lorimier L-P (2004) J Vet Intern Med 18:594
Fromigue O, Lagneaux L, Body JJ (2000) J Bone Miner Res 15:2211
Chuah C, Barnes DJ, Kwok M, Corbin A, Deininger MWN, Druker BJ, Melo JV (2005) Leukemia 19:1896
Segawa H, Kimura S, Kuroda J, Sato K, Nogawa M, Yuasa T, Yakota A, Hodohara K, Fujiyama Y, Maekawa T (2005) Leukemia Res 29:451
Roelofs AJ, Hulley PA, Meijer A, Ebetino FH, Russell RGG, Shipman CM (2006) Int J Cancer 119:1254
Horie N, Murata H, Kimura S, Takeshita H, Sakabe T, Matsui T, Kubo T, Fushiki S (2007) Brit J Cancer 96:255
Silva KL, Vasconcellos DV, Delfraro de Paula Castro E, da Cunha Vasconcelos F, Bigni R, Maia RC (2008) Cancer Chemo Pharmacol 62:165
Kunzmann V, Bauer E, Wilhelm N (1999) N Engl J Med 340:737
Wilhelm M, Kunzmann V, Eckstein S, Reimer P, Weissinger F, Ruedinger T, Tony H-P (2003) Blood 102:200
Sanders JM Ghosh S, Chan JMW, Meints GA, Wang H, Raker AM, Song Y, Colantino A, Burzynska A, Kafarski P, Morita CT, Oldfield E (2004) J Med Chem 47:375
Bukowski JF, Dascher CC, Das H (2005) Biochem Biophys Res Commun 328:746
Suzuki F, Fujikawa Y, Yamamoto S, Mizutani H, Ohya T, Ikai T, Oguchi T (1979) Ger Offen 2,831,578
Lejczak B, Boduszek B, Kafarski P, Forlani G, Wojtasek H, Wieczorek P (1996) J Plant Growth Regul 15:109
Forlani G, Kafarski P, Lejczak B, Wieczorek P (1997) J Plant Growth Regul 16:147
Kafarski P, Lejczak B, Forlani G, Gancarz R, Torreilles G, Grembecka J, Ryczek A, Wieczorek P (1997) J Plant Growth Regul 16:153
Oberhauser V, Gaudin J, Fonne-Pfister R, Schär H-P (1998) Pestic Biochem Physiol 60:111
Chuiko L, Lozinsky MO, Jasicka-Misiak I, Kafarski (1999) J Plant Growth Regul 18:171
Cromartie TH, Fisher KJ, Grossman JN (1999) Pestic Biochem Physiol 63:114
Kafarski P, Lejczak B, Forlani G (2000) Heteroatom Chem 11:449
Forlani G, Lejczak B, Kafarski P (2000) Aust J Plant Physiol 27:639
Obojska A, Berlicki L, Kafarski P, Lejczak B, Chicca M, Forlani G (2004) J Agric Food Chem 52:333
Forlani G, Lejczak B, Kafarski P (1999) J Plant Growth Regul 18:73
Gordon-Weeks R, Parmar S, Davies TGE, Leigh RA (1999) Biochem J 337:373
Szabo CM, Oldfield E (2001) Biochem Biophys Res Commun 287:468
Forlani G, Gilberti S, Berlicki L, Petrollino D, Kafarski P (2007) J Agric Food Chem 55:4340
Forlani G, Occhipinti A, Berlicjki L, Dziedziola G, Wieczorek A (2008) J Agric Food Chem 56:3193
Matczak-Jon E, Adrabinska-Videnowa V (2005) Coord Chem Rev 249:2458
Caravan P, Ellison JJ, McMurry TJ, Lauffer RB (1999) Chem Rev 99:2293
Volkert WA, Hoffman TJ (1999) Chem Rev 99:2269
Mondry A, Janicki R (2006) Dalton Trans, p 4702
Panwar P, Kumar N, Singh S, Rawat H, Mishra AK (2007) Bioorg Med Chem 15:1138
Vitha T, Kubicek V, Hermann P, Vander elst L, Muller RN, Kolar ZI, Wolterbeek HT, Breeman WAP, Lukes I, Peters JA (2008) J Med Chem 51:677
Djokic DD, Jankovic DL, Nikolic NS (2008) Bioorg Med Chem 16:4457
Goel A, Dispenzieri A, Witzig TE, Russell SJ (2006) Drug Discov Today Dis Mech 3:515
Arano Y, Mukai T, Uezono T, Wakisaka K, Motonari H, Akizawa H, Taoka Y, Yokoyama AQ (1994) J Nucl Med 35:890
Menda J, Bushnell DL, Williams RD, Miller SNR, Thomas MO (2000) Clin Nucl Med 25:698
Sapienza MT, Ono CR, Cury Guimarães MI, Watanabe T, Costa PA, Buchpiguel CA (2004) Rev Hop Clin FAc Med S Paulo 59:321
Tripathi M, Singhal T, Chandrasekhar N, Kumar P, Bal C, Jhulka PK, Bandopadhyaya G, Malhorta A (2006) Indian J Cancer 43:86
Adzamli IK, Gries H, Johnson D, Blau M (1989) J Med Chem 32:139
Alves FC, Donato P, Sherry AD, Zaheer AD, Zhand S, Lubag AJM, Merritt ME, Lenkinski RE, Frangioni JV, Neves M, Prata MIM, Santos AC, de Lima JJP, Geraldes CFGC (2003) Invest Radiol 38:750
Kubicek V, Rudowsky J, Kotek J, Herman P, Vander Elst L, Muller RN, Kolar ZI, wolterbeek HT, Peters JA, Lukes IA (2005) J Am Chem Soc 127:16477
Klenner T, Valenzuela P, Keppler BK, Scherf HR (1990) J Cancer Res Clin Oncol 116:453
Margiotta N, Ostuni R, Teoli D, Morpu rgo M, Realdon R, Palazzo B, Natali G (2007) Dalton Trans, p 3131
Wang L, Yang Z, Gao J, Xu K, Gu K, Zhang B, Zhang X, Xu B (2006) J Am Chem Soc 128:13358
Chaleix V, Lecouvey M (2007) Tetrahedron Lett 48:703
Poupot M, Griffe L, Marchand P, Maraval A, Rolland O, Martinet L, Turrin C-O, Caminade V, Fournie J-J, Majoral J-P, Poupot R (2006) FASEB J 20:2339
Griffe L, Poupot P, Marchand P, Marval O, Turrin C-O, Rolland O, Métivier P, Bacquet G, Fournié J-J, Caminade A-M, Poupot R, Majoral J-P (2007) Angew Chem Int Ed 46:2523
Rolland O, Griffe L, Poupot M, Maraval A, Ouali A, Coppel Y, Fournié J-J, Bacquet G, Turrin C-O, Caminadse A-M, MAjoral J-P, Poupot R (2008) Chem Eur J 14:4836
Kamiya T, Hemmi H, Takeno H, Hashimoto M (1980) Tetrahedron Lett 21:95
Hashimoto M, Hemmi K, Takeno H, Kamiya T (1980) Tetrahedron Lett 21:99
Kuzuyama T, Shimizu T, Takahashi S, Seto H (1998) Tetrahedron Lett 39:7913
Jomaa H, Wiesner J, Sanderbrand S, Altincicek B, Weidemeyer C, Hintz M, Turbachova I, Eberl M, Zeidler J, Lichtenthaler HK, Soldati D, Beck E (1999) Science 285:1573
Kuzuyama T, Takahashi S, Tagaki M, Seto H (2000) J Biol Chem 275:19928
Eisenreich W, Rohdich F, Bacher A (2001) Trends Plant Sci 6:78
Wiesner J, Seeber F (2005) Expert Opin Ther Targest 9:23
Missinou MA, Borrmann G, Schindler A, Issifou S, Adegnika AA, Matsiegui PB, Binder R, Lell B, Wiesner J, Baranek T, Jomaa H, Kremsner PG (2002) Lancet 360:1941
Lell B, Ruangweerayut R, Wiesner J, Missinou MA, Schindler A, Baranek T, Hintz M, Hutchinson D, Jomaa H, Kremsner PG (2003) Antimicrob Agents Chemother 47:735
Reichenberger A, Wiesner J, Weidemeyer C, Dreiseidler E, Sanderbrand S, Altincicek B, Beck E, Schlitzer M, Jomaa H (2001) Bioorg Med Chem Lett 11:833
Ortmann R, Wiesner J, Reichenberg A, Henschker D, Beck E, Jomaa H, Schilzer M (2005) Arch Pharm Life Sci 338:305
Kurz T, Schülter K, Kaula U, Bergmann B, Walter RD, Geffken D (2006) Bioorg Med Chem 14:5121
Schülter K, Walter RG Bergmann B, Kurz T (2006) Eur J Med Chem 41:1385
Haemers T, Wiesner J, Van Poecke S, Goeman J, Henschker D, Beck E, Jomaa H, Van Calenbergh S (2006) Bioorg Med Chem Lett 16:1888
Devreux V, Wiesner J, Jomaa H, Rozenski J, Van der Eycken J, Van Calenbergh S (2008) J Org Chem 72:3783
Courtois M, Mincheva Z, Andreu F, Rideau M, Viaud-Massuard MC (2004) J Enzyme Inhib Med Chem 19:559
Kuntz L, Trisch D, Grosdemange-Billiard C, Hemmerlin A, Willem A, Bach TJ, Rohmer M (2005) Biochem J 386:127
Haemers T, Wiesner J, Giesmann D, Verbrugghen T, Hillaert U, Ortmann R, Jomaa H, Link A, Schilzer M, Van Calenbergh S (2008) Bioorg Med Chem 16:3361
Mincheva Z, Courtois M, Andreu F, Rideau M, Viaud-Massuard M-C (2005) Phytochemistry 66:1797
Seto H, Kuzuyama T (1999) Nat Prod Rep 16:589
Yamato M, Koguchi T, Okachi R, Yamada K, Nakayama K, Kase H, Karasawa A, Shuto K (1986) J Antibiot 39:44
Ntai I, Bachmann B (2008) Bioorg Med Chem Lett 18:3068
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Lejczak, B., Kafarski, P. (2009). Biological Activity of Aminophosphonic Acids and Their Short Peptides. In: Bansal, R. (eds) Phosphorous Heterocycles I. Topics in Heterocyclic Chemistry, vol 20. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2008_14
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