Curcumin analogues as possible anti-proliferative & anti-inflammatory agents

European Journal of Medicinal Chemistry

Volumn 46, Issue 7, 2011, Pages 2722-2735

  Katsori, A M ^a   Chatzopoulou, M ^a   Dimas, K ^b   Kontogiorgis, C ^c   Patsilinakos, A ^d   Trangas, T ^e   Hadjipavlou Litina, D ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b UNIVERSITY OF THESSALY   (Greece)

^c KING'S COLLEGE LONDON   (United Kingdom)

^d SAPIENZA UNIVERSITY OF ROME   (Italy)

^e UNIVERSITY OF IOANNINA   (Greece)

Author keywords

Aldose reductase; Anti inflammatory activity; Anti proliferative activity; Carrageenin; Curcumin analogues; Lipoxygenase

Indexed keywords

1 ACRYLOYL 3,5 BIS(NAPHTHALEN 1 YLMETHYLENE)PIPERIDIN 4 ONE; 3,5 BIS(NAPHTHALEN 1 YLMETHYLENE)PIPERIDIN 4 ONE; 3,5 BIS(THIOPHEN 2 YLMETHYLENE)PIPERIDIN 4 ONE; 3,5 BIS[(1H IMIDAZOL 2 YL)METHYLENE]PIPERIDIN 4 ONE; 3,5 BIS[(1H INDOL 3 YL)METHYLENE]PIPERIDIN 4 ONE; 3,5 BIS[(1H INDOL 5 YL)METHYLENE]PIPERIDIN 4 ONE; 3,5 BIS[(3 METHYLTHIOPHEN 2 YL)METHYLENE]PIPERIDIN 4 ONE; 3,5 BIS[(5 METHYLTHIOPHEN 2 YL)METHYLENE]PIPERIDIN 4 ONE; 3,5 BIS[4 (4 BROMOBENZYLOXY)BENZYLIDENE]PIPERIDIN 4 ONE; 3,5 DIBENZYLIDENEPIPERIDIN 4 ONE; ALDEHYDE REDUCTASE; ALDOSE REDUCTASE 2; ANTIINFLAMMATORY AGENT; CURCUMIN; INDOMETACIN; LIPOXYGENASE; UNCLASSIFIED DRUG; AKR1B1 PROTEIN, RAT; ANTINEOPLASTIC AGENT; PROTEIN BINDING; VEGETABLE PROTEIN;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CONTROLLED STUDY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; HUMAN; HUMAN CELL; LIPOPHILICITY; MOLECULAR DOCKING; NONHUMAN; PAW EDEMA; PHYSICAL CHEMISTRY; RAT; ALLOSTERISM; ANALOGS AND DERIVATIVES; ANIMAL; ANTAGONISTS AND INHIBITORS; BINDING SITE; CHEMICAL PHENOMENA; CHEMISTRY; ENZYMOLOGY; SOYBEAN; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ALDEHYDE REDUCTASE; ALLOSTERIC REGULATION; ANIMALS; ANTI-INFLAMMATORY AGENTS; ANTINEOPLASTIC AGENTS; BINDING SITES; CELL LINE, TUMOR; CURCUMIN; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INDOMETHACIN; LIPOXYGENASE; MOLECULAR DOCKING SIMULATION; PLANT PROTEINS; PROTEIN BINDING; RATS; SOYBEANS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79957443191     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.03.060     Document Type: Article

References (97)

1. L.M. Espinoza-Fonseca The benefits of the multi-target approach in drug design and discovery Bioorg. Med. Chem. 14 2006 896 897 (Pubitemid 43059780)
2. A. Petrelli, and S. Giordano From single- to multi-target drugs in cancer therapy: when aspecificity becomes an advantage Curr. Med. Chem. 15 2008 422 432 (Pubitemid 351472408)
3. O. Keskin, A. Gursoy, B. Ma, and R. Nussinov Towards drugs targeting multiple proteins in a systems biology approach Curr. Top. Med. Chem. 7 2007 943 951 (Pubitemid 47040521)
4. F. Sams-Dodd Target-based drug discovery: is something wrong? Drug Discov. Today 10 2005 139 147 (Pubitemid 40247812)
5. G.R. Zimmermann, J. Lehár, and C.T. Keith Multi-target therapeutics: when the whole is greater than the sum of the parts Drug Discov. Today 12 2007 34 42 (Pubitemid 46014485)
6. R. Morphy, and Z. Rankovic Designing multiple ligands - medicinal chemistry strategies and challenges Curr. Pharm. Des. 15 2009 587 600
7. F. Colotta, P. Allavena, A. Sica, C. Garlanda, and A. Mantovani Cancer-related inflammation, the seventh hallmark of cancer: links to genetic instability Carcinogenesis 30 2009 1073 1081
8. A. Mantovani, P. Allavena, A. Sica, and F. Balkwill Cancer-related inflammation Nature 454 2008 436 444
9. B.B. Aggarwal Inflammation, a silent killer in cancer is not so silent! Curr. Opin. Pharmacol. 9 2009 347 350
10. M. Cuendet, and J.M. Pezzuto The role of cyclooxygenase and lipoxygenase in cancer chemoprevention Drug Metabol. Drug Interact. 17 2000 109 157 (Pubitemid 32049022)
11. D.M. Klurfeld, and A.W. Bull Fatty acids and colon cancer in experimental models Am. J. Clin. Nutr. 66 1997 1530S 1538S (Pubitemid 27518220)
12. K. Kashfi, S.J. Enna, and W. Michael Anti-inflammatory agents as cancer therapeutics Advances in Pharmacology 2009 Academic Press 31-89
13. A.T. Chan, S. Ogino, and C.S. Fuchs Aspirin and the risk of colorectal cancer in relation to the expression of COX-2 N. Engl. J. Med. 356 2007 2131 2142 (Pubitemid 47010839)
14. G.A. Piazza, A.B. Keeton, H.N. Tinsley, J.D. Whitt, B.D. Gary, B. Mathew, R. Singh, W.E. Grizzle, and R.C. Reynolds NSAIDs: old drugs reveal new anticancer targets Pharmaceuticals 3 2010 1652 1667
15. W.T. Gunning, P.M. Kramer, V.E. Steele, and M.A. Pereira Chemoprevention by lipoxygenase and leukotriene pathway inhibitors of vinyl carbamate-induced lung tumors in mice Cancer Res. 62 2002 4199 4201 (Pubitemid 34827271)
16. J. Epstein, I.R. Sanderson, and T.T. MacDonald Curcumin as a therapeutic agent: the evidence from in vitro, animal and human studies Br. J. Nutr. 103 2010 1545 1557
17. P. Anand, C. Sundaram, S. Jhurani, A.B. Kunnumakkara, and B.B. Aggarwal Curcumin and cancer: an "old-age" disease with an "age-old" solution Cancer Lett. 267 2008 133 164
18. E. Sikora, G. Scapagnini, and M. Barbagallo Curcumin, inflammation, ageing and age-related diseases Immun. Ageing 7 2010 1
19. M.-H. Teiten, S. Eifes, M. Dicato, and M. Diederich Curcumin - The paradigm of a multi-target natural compound with applications in cancer prevention and treatment Toxins 2 2010 128 162
20. B.B. Aggarwal, Y.-J. Surh, and S. Shishodia The molecular targets and therapeutic uses of curcumin in health and disease Advances in Experimental Medicine and Biology 2007 Springer US, New York
21. A. Shehzad, F. Wahid, and Y.S. Lee Curcumin in cancer chemoprevention: molecular targets, pharmacokinetics, bioavailability, and clinical trials Arch. Pharm. (Weinheim) 343 2010 489 499
22. A. Shehzad, and Y.S. Lee Curcumin: multiple molecular targets mediate multiple pharmacological actions - a review Drugs Future 35 2010 113 119
23. B.B. Aggarwal, and B. Sung Pharmacological basis for the role of curcumin in chronic diseases: an age-old spice with modern targets Trends Pharmacol. Sci. 30 2009 85 94
24. W.P. Steward, and A.J. Gescher Curcumin in cancer management: recent results of analogue design and clinical studies and desirable future research Mol. Nutr. Food Res. 52 2008 1005 1009
25. H. Hatcher, R. Planalp, J. Cho, F. Torti, and S. Torti Curcumin: from ancient medicine to current clinical trials Cell. Mol. Life Sci. 65 2008 1631 1652
26. G. Bar-Sela, R. Epelbaum, and M. Schaffer Curcumin as an anti-cancer agent: review of the gap between basic and clinical applications Curr. Med. Chem. 17 2010 190 197
27. A. Goel, A.B. Kunnumakkara, and B.B. Aggarwal Curcumin as "Curecumin": from kitchen to clinic Biochem. Pharmacol. 75 2008 787 809
28. P. Anand, A.B. Kunnumakkara, R.A. Newman, and B.B. Aggarwal Bioavailability of curcumin: problems and promises Mol. Pharm. 4 2007 807 818
29. E. Burgos-Morón, J.M. Calderón-Montaño, J. Salvador, A. Robles, and M. López-Lázaro The dark side of curcumin Int. J. Cancer 126 2010 1771 1775
30. P. Anand, S.G. Thomas, A.B. Kunnumakkara, C. Sundaram, K.B. Harikumar, B. Sung, S.T. Tharakan, K. Misra, I.K. Priyadarsini, K.N. Rajasekharan, and B.B. Aggarwal Biological activities of curcumin and its analogues (congeners) made by man and Mother Nature Biochem. Pharmacol. 76 2008 1590 1611
31. D.K. Agrawal, and P.K. Mishra Curcumin and its analogues: potential anticancer agents Med. Res. Rev. 30 2010 818 860
32. M.J.C. Rosemond, L. St. John-Williams, T. Yamaguchi, T. Fujishita, and J.S. Walsh Enzymology of a carbonyl reduction clearance pathway for the HIV integrase inhibitor, S-1360: role of human liver cytosolic aldo-keto reductases Chem. Biol. Interact. 147 2004 129 139 (Pubitemid 38324542)
33. B. Yadav, S. Taurin, R.J. Rosengren, M. Schumacher, M. Diederich, T.J. Somers-Edgar, and L. Larsen Synthesis and cytotoxic potential of heterocyclic cyclohexanone analogues of curcumin Bioorg. Med. Chem. 18 2010 6701 6707
34. U. Das, R.K. Sharma, and J.R. Dimmock 1,5-diaryl-3-oxo-1,4-pentadienes: a case for antineoplastics with multiple targets Curr. Med. Chem. 16 2009 2001 2020
35. B.K. Adams, E.M. Ferstl, M.C. Davis, M. Herold, S. Kurtkaya, R.F. Camalier, M.G. Hollingshead, G. Kaur, E.A. Sausville, F.R. Rickles, J.P. Snyder, D.C. Liotta, and M. Shoji Synthesis and biological evaluation of novel curcumin analogues as anti-cancer and anti-angiogenesis agents Bioorg. Med. Chem. 12 2004 3871 3883 (Pubitemid 38798249)
36. P. Lagisetty, D.R. Powell, and V. Awasthi Synthesis and structural determination of 3,5-bis(2-fluorobenzylidene)-4-piperidone analogues of curcumin J. Mol. Struct. 936 2009 23 28
37. P. Lagisetty, P. Vilekar, K. Sahoo, S. Anant, and V. Awasthi CLEFMA-An anti-proliferative curcuminoid from structure-activity relationship studies on 3,5-bis(benzylidene)-4-piperidones Bioorg. Med. Chem. 18 2010 6109 6120
38. A. Jha, and K.M. Duffield 3,5-Bis(arylmethylene)-4-piperidone derivatives as novel anticancer agents Indian J. Chem. Sect. B. Org. Chem. Incl. Med. Chem. 45B 2006 2313 2320 (Pubitemid 44850900)
39. M.V. Makarov, E.S. Leonova, E.Y. Rybalkina, P. Tongwa, V.N. Khrustalev, T.V. Timofeeva, and I.L. Odinets Synthesis, characterization and structure-activity relationship of novel N-phosphorylated E, E-3,5-bis(thienylidene)piperid-4-ones Eur. J. Med. Chem. 45 2010 992 1000
40. U. Das, J. Alcorn, A. Shrivastav, R. Sharma, E. De Clercq, J. Balzarini, and J. Dimmock Design, synthesis and cytotoxic properties of novel 1-[4-(2-alkylaminoethoxy)phenylcarbonyl]-3,5-bis(arylidene)-4-piperidones and related compounds Eur. J. Med. Chem. 42 2007 71 80 (Pubitemid 46198985)
41. U. Das, M. Kawase, H. Sakagami, A. Ideo, J. Shimada, J. Molnar, Z. Barath, Z. Bata, and J. Dimmock 3-(3,4,5-Trimethoxyphenyl)-1-oxo-2-propene: a novel pharmacophore displaying potent multidrug resistance reversal and selective cytotoxicity Bioorg. Med. Chem. 15 2007 3373 3380 (Pubitemid 46529268)
42. A.L. Kasinski, Y. Du, S.L. Thomas, J. Zhao, S.Y. Sun, F.R. Khuri, C.Y. Wang, M. Shoji, A. Sun, J.P. Snyder, D. Liotta, and H. Fu Inhibition of IkappaB kinase-nuclear factor-kappaB signaling pathway by 3,5-bis(2-flurobenzylidene) piperidin-4-one (EF24), a novel monoketone analog of curcumin Mol. Pharmacol. 74 2008 654 661
43. U. Das, P. Selvakumar, R.K. Sharma, T.A. Haas, and J.R. Dimmock N-Acyl-3,5-bis(arylidene)-4-piperidones and related compounds which stimulate fyn kinase J. Enzyme Inhib. Med. Chem. 22 2007 451 455 (Pubitemid 47225708)
44. J.R. Dimmock, V.K. Arora, S.L. Wonko, N.W. Hamon, J.W. Quail, Z. Jia, R.C. Warrington, W.D. Fang, and J.S. Lee 3,5-Bisbenzylidene-4-piperidones and related compounds with high activity towards P388 leukemia cells Drug Des. Deliv. 6 1990 183 194 (Pubitemid 20302002)
45. G. Liang, L. Shao, Y. Wang, C. Zhao, Y. Chu, J. Xiao, Y. Zhao, X. Li, and S. Yang Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents Bioorg. Med. Chem. 17 2009 2623 2631
46. M.W. Amolins, L.B. Peterson, and B.S.J. Blagg Synthesis and evaluation of electron-rich curcumin analogues Bioorg. Med. Chem. 17 2009 360 367
47. J.R. Dimmock, M.P. Padmanilayam, R.N. Puthucode, A.J. Nazarali, N.L. Motaganahalli, G.A. Zello, J.W. Quail, E.O. Oloo, H.-B. Kraatz, J.S. Prisciak, T.M. Allen, C.L. Santos, J. Balzarini, E. De Clercq, and E.K. Manavathu A conformational and structure-activity relationship study of cytotoxic 3,5-bis(arylidene)-4-piperidones and related N-acryloyl analogues J. Med. Chem. 44 2001 586 593 (Pubitemid 32156100)
48. J.R. Dimmock, V.K. Arora, M. Chen, T.M. Allen, and G.Y. Kao Cytotoxic evaluation of some N-acyl and N-acyloxy analogs of 3,5-bis(arylidene)-4- piperidones Drug Des. Discov. 12 1994 19 28 (Pubitemid 24252315)
49. H.I. El-Subbagh, S.M. Abu-Zaid, M.A. Mahran, F.A. Badria, and A.M. Al-Obaid Synthesis and biological evaluation of certain alpha, beta-unsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents J. Med. Chem. 43 2000 2915 2921 (Pubitemid 30599649)
50. D.V. Jovanovic, J.C. Fernandes, J. Martel-Pelletier, F.C. Jolicoeur, P. Reboul, S. Laufer, S. Tries, and J.P. Pelletier In vivo dual inhibition of cyclooxygenase and lipoxygenase by ML-3000 reduces the progression of experimental osteoarthritis: suppression of collagenase 1 and interleukin-1beta synthesis Arthritis Rheum. 44 2001 2320 2330 (Pubitemid 32977499)
51. C. Menna, F. Olivieri, A. Catalano, and A. Procopio Lipoxygenase inhibitors for cancer prevention: promises and risks Curr. Pharm. Des. 16 2010 725 733
52. L.G. Melstrom, D.J. Bentrem, M.R. Salabat, T.J. Kennedy, X.Z. Ding, M. Strouch, S.M. Rao, R.C. Witt, C.A. Ternent, M.S. Talamonti, R.H. Bell, and T.A. Adrian Overexpression of 5-lipoxygenase in colon polyps and cancer and the effect of 5-LOX inhibitors in vitro and in a murine model Clin. Cancer Res. 14 2008 6525 6530
53. L.T. Soumaoro, S. Iida, H. Uetake, M. Ishiguro, Y. Takagi, T. Higuchi, M. Yasuno, M. Enomoto, and K. Sugihara Expression of 5-lipoxygenase in human colorectal cancer World J. Gastroenterol. 12 2006 6355 6360 (Pubitemid 44712419)
54. J. Clria, and M. Romano Pharmacological intervention of cyclooxygenase-2 and 5-lipoxygenase pathways. Impact on inflammation and cancer Curr. Pharm. Des. 11 2005 3431 3447 (Pubitemid 41300769)
55. X.Z. Ding, R. Hennig, and T.E. Adrian Lipoxygenase and cyclooxygenase metabolism: new insights in treatment and chemoprevention of pancreatic cancer Mol. Cancer 2 2003 10
56. E. Pontiki, D. Hadjipavlou-Litina, G. Geromichalos, and A. Papageorgiou Anticancer activity and quantitative-structure activity relationship (QSAR) studies of a series of antioxidant/anti-inflammatory aryl-acetic and hydroxamic acids Chem. Biol. Drug Des. 74 2009 266 275
57. C.V. Rao Regulation of COX and LOX by curcumin B.B. Aggarwal, Y.-J. Surh, S. Shishodia, The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease 2007 Springer US 213 226
58. E. Skrzypczak-Jankun, N.P. McCabe, S.H. Selman, and J. Jankun Curcumin inhibits lipoxygenase by binding to its central cavity: theoretical and X-ray evidence Int. J. Mol. Med. 6 2000 521 526
59. J. Hong, M. Bose, J. Ju, J.-H. Ryu, X. Chen, S. Sang, M.-J. Lee, and C.S. Yang Modulation of arachidonic acid metabolism by curcumin and related β-diketone derivatives: effects on cytosolic phospholipase A2, cyclooxygenases and 5-lipoxygenase Carcinogenesis 25 2004 1671 1679 (Pubitemid 39214309)
60. C. Pergola, and O. Werz 5-Lipoxygenase inhibitors: a review of recent developments and patents Expert Opin. Ther. Pat. 20 2010 355 375
61. I.B. Taraporewala, and J.M. Kauffman Synthesis and structure-activity relationships of anti-inflammatory 9,10-dihydro-9-oxo-2-acridine-alkanoic acids and 4-(2-carboxyphenyl)aminobenzenealkanoic acids J. Pharm. Sci. 79 1990 173 178 (Pubitemid 20148540)
62. E. Pontiki, and D. Hadjipavlou-Litina Antioxidant and anti-inflammatory activity of aryl-acetic and hydroxamic acids as novel lipoxygenase inhibitors Med. Chem. 2 2006 251 264 (Pubitemid 44083143)
63. E. Pontiki, and D. Hadjipavlou-Litina Lipoxygenase inhibitors: a comparative QSAR study review and evaluation of new QSARs Med. Res. Rev. 28 2008 39 117 (Pubitemid 350274961)
64. K. Muller 5-Lipoxygenase and 12-lipoxygenase: attractive targets for the development of novel antipsoriatic drugs Arch. Pharm. (Weinheim) 327 1994 3 19 (Pubitemid 24035620)
65. P. Alexiou, K. Pegklidou, M. Chatzopoulou, I. Nicolaou, and V.J. Demopoulos Aldose reductase enzyme and its implication to major health problems of the 21(st) century Curr. Med. Chem. 16 2009 734 752
66. K.V. Ramana, and S.K. Srivastava Aldose reductase: a novel therapeutic target for inflammatory pathologies Int. J. Biochem. Cell Biol. 42 2010 17 20
67. N. Halder, S. Joshi, and S.K. Gupta Lens aldose reductase inhibiting potential of some indigenous plants J. Ethnopharmacol. 86 2003 113 116 (Pubitemid 36398665)
68. P. Muthenna, P. Suryanarayana, K.G. Shravan, J.M. Petrash, and G.B. Reddy Inhibition of aldose reductase by dietary antioxidant curcumin: mechanism of inhibition, specificity and significance FEBS Lett. 583 2009 3637 3642
69. Z.-Y. Du, Y.-D. Bao, Z. Liu, W. Qiao, L. Ma, Z.-S. Huang, L.-Q. Gu, and A.S.C. Chan Curcumin analogs as potent aldose reductase inhibitors Arch. Pharm. (Weinheim) 339 2006 123 128
70. T. Gui, T. Tanimoto, Y. Kokai, and C. Nishimura Presence of a closely related subgroup in the aldo-ketoreductase family of the mouse Eur. J. Biochem. 227 1995 448 453
71. A. Del Corso, L. Costantino, G. Rastelli, F. Buono, and U. Mura Aldose reductase does catalyse the reduction of glyceraldehyde through a stoichiometric oxidation of NADPH Exp. Eye Res. 71 2000 515 521
72. K. Dimas, S. Hatziantoniou, S. Tseleni, H. Khan, A. Georgopoulos, K. Alevizopoulos, J. Wyche, P. Pantazis, and C. Demetzos Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice Apoptosis 12 2007 685 694 (Pubitemid 46411476)
73. BioByte Corporation, C-QSAR database 201 West 4th Str., Suite 204, Claremont, California 91711, USA.
74. C. Kontogiorgis, K. Litinas, A. Makri, D. Nicolaides, A. Vronteli, D. Hadjipavlou-Litina, E. Pontiki, and A. Siohou Synthesis and biological evaluation of novel angular fused pyrrolocoumarins J. Enzyme Inhib. Med. Chem. 23 2008 43 49 (Pubitemid 351260349)
75. P. Brooks, and R. Day Nonsteroidal antiinflammatory drugs-differences and similarities N. Engl. J. Med. 324 1991 1716 1725
76. V.R. Shanbhag, A.M. Crider, R. Gokhale, A. Harpalani, and R.M. Dick Ester and amide prodrugs of ibuprofen and naproxen: synthesis, anti-inflammatory activity, and gastrointestinal toxicity J. Pharm. Sci. 81 1992 149 154
77. E.I. Howard, R. Sanishvili, R.E. Cachau, A. Mitschler, B. Chevrier, P. Barth, V. Lamour, M. Van Zandt, E. Sibley, C. Bon, D. Moras, T.R. Schneider, A. Joachimiak, and A. Podjarny Ultrahigh resolution drug design I: details of interactions in human aldose reductase-inhibitor complex at 0.66 Proteins 55 2004 792 804 (Pubitemid 38702939)
78. O. Trott, and A.J. Olson AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading J. Comput. Chem. 31 2010 455 461
79. M. Chatzopoulou, E. Mamadou, M. Juskova, C. Koukoulitsa, I. Nicolaou, M. Stefek, and V.J. Demopoulos Structure activity relations on [1-(3,5-difluoro-4- hydroxyphenyl)-1H-pyrrol-3-yl]phenylmethanone. The effect of methoxy substitution on aldose reductase inhibitory activity and selectivity Bioorg. Med. Chem. 19 2011 1426 1433
80. K.M. Bohren, C.E. Grimshaw, C.J. Lai, D.H. Harrison, D. Ringe, G.A. Petsko, and K.H. Gabbay Tyrosine-48 is the proton donor and histidine-110 directs substrate stereochemical selectivity in the reduction reaction of human aldose reductase: enzyme kinetics and crystal structure of the Y48H mutant enzyme Biochemistry 33 1994 2021 2032 (Pubitemid 24099596)
81. C.E. Grimshaw, K.M. Bohren, C.-J. Lai, and K.H. Gabbay Human aldose reductase: pK of tyrosine 48 reveals the preferred ionization state for catalysis and inhibition Biochemistry 34 1995 14374 14384
82. A. Podjarny, R.E. Cachau, T. Schneider, M. Van Zandt, and A. Joachimiak Subatomic and atomic crystallographic studies of aldose reductase: implications for inhibitor binding Cell. Mol. Life Sci. 61 2004 763 773 (Pubitemid 38650997)
83. W. Minor, J. Steczko, B. Stec, Z. Otwinowski, J.T. Bolin, R. Walter, and B. Axelrod Crystal structure of soybean lipoxygenase L-1 at 1.4 resolution Biochemistry 35 1996 10687 10701 (Pubitemid 26279648)
84. E. Pontiki, D. Hadjipavlou-Litina, K. Litinas, O. Nicolotti, and A. Carotti Design, synthesis and pharmacobiological evaluation of novel acrylic acid derivatives acting as lipoxygenase and cyclooxygenase-1 inhibitors with antioxidant and anti-inflammatory activities Eur. J. Med. Chem. 46 2011 191 200
85. H. Berman, K. Henrick, and H. Nakamura Announcing the worldwide Protein Data Bank Nat. Struct. Mol. Biol. 10 2003 980 (Pubitemid 37500485)
86. J.R. Dimmock, and U. Das Antineoplastic Compounds, WO/2007/059613 2007
87. © v.12 1986-2009 http://www.cambridgesoft.com/software/ChemDraw/
88. © v.2.2.3 2006 http://sourceforge.net/projects/ openbabel/
89. RCSB Protein Data Bank, operated by the Research Collaboratory for Structural Bioinformatics. www.pdb.org/.
90. http://www.cgl.ucsf.edu/chimera
91. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin UCSF Chimera-A visualization system for exploratory research and analysis J. Comput. Chem. 25 2004 1605 1612
92. J. Wang, R.M. Wolf, J.W. Caldwell, P.A. Kollman, and D.A. Case Development and testing of a general amber force field J. Comput. Chem. 25 2004 1157 1174
93. J. Wang, W. Wang, P.A. Kollman, and D.A. Case Automatic atom type and bond type perception in molecular mechanical calculations J. Mol. Graph. Model. 25 2006 247 260 (Pubitemid 44363172)
94. B. Hess, C. Kutzner, D. van der Spoel, and E. Lindahl GROMACS 4: algorithms for highly efficient, load-balanced, and scalable molecular simulation J. Chem. Theory Comput. 4 2008 435 447
95. K. Lindorff-Larsen, S. Piana, K. Palmo, P. Maragakis, J.L. Klepeis, R.O. Dror, and D.E. Shaw Improved side-chain torsion potentials for the Amber ff99SB protein force field Proteins 78 2010 1950 1958
96. © 1989-2010, The Scripps Research Institute.
97. Sargis Pallakyan PyRx-Python Prescription, v.0.5 2008-2010 The Scripps Research Institute http://pyrx.scripps.edu/