Abstract
Abstract
The red-colored prodiginines, exemplified by prodigiosin 1, are secondary metabolites produced by a number of microorganisms, including the bacterium Serratia marcescens. These tripyrrole natural products and their synthetic analogs have received renewed attention over the past deacade, primarily because of their promising immunosuppressive and anticancer activities. One of the hallmarks of prodiginin chemistry is the ability of the monoprotonated ligand to bind anions, including the essential chloride and bicarbonate ions. The resulting lipophilic ion pair is then able to diffuse across the hydrophobic barrier presented by phospholipid bilayers. Thus, prodiginines have been found to be potent transmembrane anion transporters and HCl cotransporters. In this chapter, the author reviews what is known about the solid-state structure of prodiginins and their anion complexes, the solution conformation of prodiginines, and the biochemcal evidence for the ability to bind anions and to transport HCl across cell membranes. Recent progress in making synthetic models of prodiginines and recent results on the ability of prodigiosin to transport HCO 3 − across lipid membranes are discussed.
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Notes
- 1.
The same group later reported similar studies as described in [14].
References
Bizio B (1823) Biblioteca Italiana o sia Giornale di Letteratura, Scienze e Arti Tomo 30:275–295
Merlino CP (1924) J Bacteriol 9:527–543
Hubbard R, Rimington C (1950) Biochem J 46:200–225
Gaughran ER (1969) Trans NY Acad Sci 31:3–24
Bennett JW (2000) Adv Appl Microbiol 47:1–32
Fürstner A (2003) Angew Chem Int Ed 42:3582–3603
Wrede IF, Hettche O (1929) Ber Deut Chem Ges 62:2678–2687
Wasserman HH, McKeon JE, Smith L, Forgione P (1960) J Am Chem Soc 82:506–507
Rapoport H, Holden KG (1962) J Am Chem Soc 84:634–642
Manderville RA (2001) Curr Med Chem Anticancer Agents 1:195–218
Perez-Tomas R, Montaner B, Llagostera E, Soto-Cerrato V (2003) Biochem Pharm 66:1447–1452
Williamson NR, Fineran PC, Gristwood T, Chawrai SR, Leeper FJ, Salmond GPC (2007) Future Microbiol 2:605–618
Pandey R, Chander R, Sainis KB (2009) Curr Pharm Design 15:732–741
Yamamoto C, Takemoto H, Kuno K, Yamamoto D, Tsubaru A, Kamata K, Hirata H, Yamamoto A, Kano H, Seki T, Inoue K (1999) Hepatology 30:894–902
Nakashima T, Tamura T, Kurachi M, Yamaguchi K, Oda T (2005) Biol Pharm Bull 28:2289–2295
Melvin MS, Ferguson DC, Lindquist N, Manderville RA (1999) J Org Chem 64:6861–6869
Melvin MS, Tomlinson JT, Saluta GR, Kucera GL, Lindquist N, Manderville RA (2000) J Am Chem Soc 122:6333–6334
Sessler JL, Eller LR, Cho WS, Nicolaou S, Aguilar A, Lee JT, Lynch VM, Magda DJ (2005) Angew Chem Int Ed 44:5989–5992
Baldino CM, Parr J, Wilson CJ, Ng SC, Yohannes D, Wasserman HH (2006) Bioorg Med Chem Lett 16:701–704
Fürstner A, Radkowski K, Peters H, Seidel G, Wirtz C, Mynott R, Lehmann CW (2007) Chem Eur J 13:1929–1945
Diaz RIS, Bennett SM, Thompson A (2009) Chem Med Chem 4:742–745
Clift MD, Thomson RJ (2009) J Am Chem Soc 131:14579–14583
For more information on Aida Pharmaceuticals and their development of prodigiosin 1 as an anti-cancer agent, see the website: http://www.crunchbase.com/company/aida-pharmaceuticals
Dairi K, Yao Y, Faley M, Tripathy S, Rioux E, Billot X, Rabouin D, Gonzalez G, Lavallee JF, Attardo G (2007) Org Process Res Dev 11:1051–1054
O’Brien SM, Claxton DF, Crump M, Faderl S, Kipps T, Keating MJ, Viallet J, Cheson BD (2009) Blood 113:299–305
D’Alessio R, Bargiotti A, Carlini O, Colotta F, Ferrari M, Gnocchi P, Isetta A, Mongelli N, Motta P, Rossi A, Rossi M, Tibolla M, Vanotti E (2000) J Med Chem 43:2557–2565
Stepkowski SM, Erwin-Cohen RA, Behbod F, Wang ME, Qu X, Tejpal N, Nagy ZS, Kahan BD, Kirken RA (2002) Blood 99:680–689
Williamson NR, Fineran PC, Leeper FJ, Salmond GPC (2006) Nat Rev Microbiol 4:887–899
Chawrai SR, Williamson NR, Salmond GPC, Leeper FJ (2008) Chem Commun:1862–1864
Gerber NN (1975) Prodigiosin-like pigments. CRC Crit Rev Microbiol 3:469–485
Kim D, Kim J, Yim JH, Kwon SK, Lee CH, Lee HK (2008) J Microbiol Biotech 18:1621–1629
Rizzo V, Morelli A, Pinciroli V, Sciangula D, D’Alessio R (1999) J Pharm Sci 88:73–78
Sertan-de Guzman AA, Predicala RZ, Bernardo EB, Neilan BA, Elardo SP, Mangalindan GC, Tasdemir D, Ireland CM, Barraquio WL, Concepcion GP (2007) FEMS Microbiol Lett 277:188–196
Blake AJ, Hunter GA, McNab H (1990) Chem Commun:734–736
La JQH, Michaelides AA, Manderville RA (2007) J Phys Chem B 111:11803–11811
Fürstner A, Grabowski J, Lehmann CW (1999) J Org Chem 64:8275–8280
Melvin MS, Tomlinson JT, Park G, Day CS, Saluta GR, Kucera GL, Manderville RA (2002) Chem Res Toxicol 15:734–741
Jenkins S, Incarvito CD, Parr J, Wasserman HH (2009) CrystEngComm 11:242–245
Chen K, Rannulu NS, Cai Y, Lane P, Liebl AL, Rees BB, Corre C, Challis GL, Cole RB (2008) J Am Soc Mass Spectrom 19:1856–1866
Duarte HA, Duani H, De Almeida WB (2003) Chem Phys Lett 369:114–124
Skawinski WJ, Venanzi TJ, Venanzi CA (2004) A molecular orbital study of tambjamine E and analogues. J Phys Chem A108:4542–4550
Sessler JL, Weghorn SJ, Lynch V, Fransson K (1994) J Chem Soc Chem Commun:1289–1290
Sessler JL, Camiolo S, Gale PA (2003) Coord Chem Rev 240:17–55
Park G, Tomlinson JT, Melvin MS, Wright MW, Day CS, Manderville RA (2003) Org Lett 5:113–116
Nelson N, Perzov N, Cohen A, Hagai K, Padler V, Nelson H (2000) J Exp Biol 203:89–95
Sato T, Konno H, Tanaka Y, Kataoka T, Nagai K, Wasserman HH, Ohkuma S (1998) J Biol Chem 273:21455–21462
Ohkuma S, Sato T, Okamoto M, Matsuya H, Arai K, Katakoa T, Nagai K, Wasserman HH (1998) Biochem J 334:731–741
Konno H, Matsuya H, Okamoto M, Sato T, Tanaka Y, Yokoyama K, Katakoa T, Nagai K, Wasserman HH, Ohkuma S (1998) J Biochem 124:547–556
Matsuya H, Okamoto M, Ochi T, Nishikawa A, Shimizu S, Katakoa T, Nagai K, Wasserman HH, Ohkuma S (2000) Biochem Pharm 60:1855–1863
Lee MH, Kataoka T, Magae J, Nagai K (1995) Biosci Biotechnol Biochem 59:1417–1421
Kataoka T, Muroi M, Ohkuma S, Waritani T, Magae J, Takatsuki A, Kondo S, Yamasaki M, Nagai K (1995) FEBS Lett 359:53–59
Kawauchi K, Shibutani K, Yagisawa H, Nakatsuji S, Anzai H, Yokoyama Y, Ikegami Y, Moriyama Y, Hirata H (1997) Biochem Biophys Res Commun 237:543–547
Woo JT, Ohba Y, Tagami K, Sumitani K, Kataoka T, Nagai K (1997) Biosci Biotech Biochem 61:400–402
Tanigaki K, Sato T,Tanaka Y, Ochi T,Nishikawa A, Nagai K, Kawashima H, Ohkuma S(2002) FEBS Lett.524:37-42
Rea PA, Poole RJ (1993) Annu Rev Plant Physiol Plant Mol 44:157–180
Maeshima M, Nakayasu T, Kawauchi K, Hirata H, Shimmen T (1999) Plant Cell Physiol 40:439–442
Nakayasu T, Kawauchi K, Hirata H, Shimmen T (2000) Plant Cell Physiol 41:857–863
Lagadic-Gossmann D, Huc L, Lecureur V (2004) Cell Death Differ 11:953–961
Yamamoto C, Takemoto H, Kuno K, Yamamoto D, Nakai K, Baden T, Kamata K, Hirata H, Watanabe T, Inoue K (2001) Oncology 8:821–824
Francisco R, Pérez-Tomás R, Gimènez-Bonafé P, Soto-Cerrato V, Giménez-Xavier P, Ambrosio S (2007) Eur J Pharmcol 572:111–119
Kawauchi K, Tobiume K, Iwashita K, Inagaki H, Morikawa T, Shibukawa Y, Moriyama Y, Hirata H, Kamata H (2008) Biosci Biotechnol Biochem 72:1564–1570
Seganish JL, Davis JT (2005) Chem Commun:5781–5783
McNally BA, Koulov AV, Smith BD, Joos JB, Davis AP (2005) Chem Commun:1087–1089
Krasne S, Eisenman G, Szabo G (1971) Science 174:412–414
Kano K, Fendler JH (1978) Biochim Biophys Acta 509:289–299
Sáez DÃaz RI, Regourd J, Santacroce PV, Davis JT, Jakeman DL, Thompson A (2007) Chem Commun:2701–2703
Gale PA, Light ME, McNally B, Navakhun K, Sliwinski KE, Smith BD (2005) Chem Commun:3773–3775
Gale PA (2005) Chem Commun:3761–3772
Davis JT, Gale PA, Okunola OA, Prados P, Iglesias-Sánchez JC, Torroba T, Quesada R (2009) Nat Chem 1:138–144
Stefayne D (1960) J Org Chem 25:1261–1262
Davis AP, Sheppard DN, Smith BD (2007) Chem Soc Rev 36:348–357
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Davis, J.T. (2010). Anion Binding and Transport by Prodigiosin and Its Analogs. In: Gale, P., Dehaen, W. (eds) Anion Recognition in Supramolecular Chemistry. Topics in Heterocyclic Chemistry, vol 24. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2010_29
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