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Can soybean lipoxygenases be real models for mammalian lipoxygenases? A bioinformatics approach

Yıl 2021, Cilt: 8 Sayı: 1, 79 - 102, 28.02.2021
https://doi.org/10.18596/jotcsa.785109

Öz

Soybean lipoxygenases (soybean lipoxygenase-1) has been a well-studied enzyme because it is considered as a model enzyme for mammalian lipoxygenases. In general, the soybean lipoxygenase-1 is used in the test of inhibitory activities of various compounds. The present study provides a bioinformatics approach for comparison of various lipoxygenases in the databases. Their various physical and chemical parameters such as molecular weight, theoretical pI, amino acid composition, aliphatic index and grand average of hydropathicity and the multiple sequence alignments of the lipoxygenases were computed by using several bioinformatics tools. In order to see phylogenetic relation among lipoxygenases, a phylogenetic tree was constructed. The first three most abundant amino acids in soybean lipoxygenase-1 and 15-lipoxygenase (human) are L (10.3 %), S (7.4 %), A (6.7 %) and L (13.3 %), G (7.4 %), V (7.1 %), respectively. According to the phylogenetic tree, the soybean lipoxygenases are within separate clade compared to the mammalian lipoxygenases. In conclusion, soybean lipoxygenase-1 may not fully characterise the human lipoxygenase-15 since there are remarkable sequence-based differences, which are obtained by using bioinformatics tools between soybean lipoxygenase-1 and lipoxygenases from other sources especially from human. In this context, the researchers aware of the problems described above and having similar concerns have begun to use recombinant DNA technology to produce recombinant h-15-LOX enzyme in Escherichia coli.

Teşekkür

We thank Prof. Dr. Theodore Holman from Chemistry and Biochemistry Department of UC Santa Cruz for sharing his valuable comments about LOXs.

Kaynakça

  • 1. Jacquot C, McGinley CM, Plata E, Holman TR, van der Donk WA. Synthesis of 11-thialinoleic acid and 14-thialinoleic acid, inhibitors of soybean and human lipoxygenases. Organic and Biomolecular Chemistry. 2008 Dec;6(22):4242-52.
  • 2. Newcomer ME, Brash AR. The structural basis for specificity in lipoxygenase catalysis. Protein Science. 2015 Mar;24(3):298-309.
  • 3. Skrzypczak-Jankun E, McCabe NP, Selman SH, Jankun J. Curcumin inhibits lipoxygenase by binding to its central cavity: theoretical and X-ray evidence. International Journal of Molecular Medicine. 2000 Nov;6(5):521-6.
  • 4. Simona V, Chedea VS, Dulf F, Socaciu C. The influence of quercetin concentration on its intermolecular interaction with soybean lipoxygenase-1. Bulletin USAMV-CN. 2006;62:376-80.
  • 5. Shrivastava SK, Srivastava P, Bandresh R, Tripathi PN, Tripathi A. Design, synthesis, and biological evaluation of some novel indolizine derivatives as dual cyclooxygenase and lipoxygenase inhibitor for anti-inflammatory activity. Bioorganic and Medicinal Chemistry. June 2017;25(16):4424-32.
  • 6. Yashaswini PS, Appu Rao AG, Singh SA. Inhibition of lipoxygenase by sesamol corroborates its potential anti-inflammatory activity. International Journal of Biological Macromolecules 2017 Jan;94(Pt B):781-7.
  • 7. ElBordiny HS, El-Miligy MM, Kassab SE, Daabees H, Mohamed Ali WA, El-Hawash SAM. Design, synthesis, biological evaluation and docking studies of new 3-(4,5-dihydro-1H-pyrazol/isoxazol-5-yl)-2-phenyl-1H-indole derivatives as potent antioxidants and 15-lipoxygenase inhibitors. European Journal of Medicinal Chemistry. 2018 Feb;145:594-605.
  • 8. Boyington JC, Gaffney BJ, Amzel LM. The three-dimensional structure of an arachidonic acid 15-lipoxygenase. Science. 1993 Jun;260(5113):1482-6.
  • 9. Ivanov I, Heydeck D, Hofheinz K, Roffeis J, O’Donnell VB, Kuhn H, Walther M. Molecular enzymology of lipoxygenases. Archives of Biochemistry and Biophysics. 2010 Nov;503(2):161-74.
  • 10. Segraves EN, Holman TR. Kinetic Investigations of the Rate-Limiting Step in Human 12- and 15-Lipoxygenase. Biochemistry. 2003 May;42(18):5236-43.
  • 11. Neidig ML, Wecksler AT, Schenk G, Holman TR, Solomon EI. Kinetic and Spectroscopic Studies of N694C Lipoxygenase: A Probe of the Substrate Activation Mechanism of a Nonheme Ferric Enzyme. Journal of the American Chemical Society. 2007 Jun;129(24):7531-7.
  • 12. Gardner HW. Recent investigations into the lipoxygenase pathway of plants. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism. 1991 Jul;1084(3):221-39.
  • 13. Yamamoto S. Mammalian lipoxygenases: molecular structures and functions. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism. 1992 Oct;1128(2-3):117-31.
  • 14. Maiga A, Malterud KE, Diallo D, Paulsen BS. Antioxidant and 15-lipoxygenase inhibitory activities of the Malian medicinal plants Diospyros abyssinica (Hiern) F. White (Ebenaceae), Lannea velutina A. Rich (Anacardiaceae) and Crossopteryx febrifuga (Afzel) Benth. (Rubiaceae). Journal of Ethnopharmacology. 2006 Mar;104(1-2):132-7.
  • 15. Kuhn H, Walther M, Kuban RJ. Mammalian arachidonate 15-lipoxygenases structure, function, and biological implications. Prostaglandins and Other Lipid Mediators. 2002 Aug;68-69:263-90.
  • 16. Mahesha HG, Singh SA, Appu Rao AG. Inhibition of lipoxygenase by soy isoflavones: Evidence of isoflavones as redox inhibitors. Archives of Biochemistry and Biophysics. 2007 May;461(2):176-85.
  • 17. Russell WR, Scobbie L, Duthie GG, Chesson A. Inhibition of 15-lipoxygenase-catalysed oxygenation of arachidonic acid by substituted benzoic acids. Bioorganic and Medicinal Chemistry. 2008 Apr;16(8):4589-93.
  • 18. Nguyen MD, Nguyen DH, Yoo JM, Myung PK, Kim MR, Sok DE. Effect of endocannabinoids on soybean lipoxygenase-1 activity. Bioorganic Chemistry. 2013 Aug;49:24-32.
  • 19. Oso BJ, Karigidi KO. Inhibitory action of dried leaf of Cassia alata (Linn.) Roxb against lipoxygenase activity and nitric oxide generation. Scientia Agropecuaria. 2019 Mar;10(2):185-90.
  • 20. Jonsson T, Glickman MH, Sun S, Klinman JP. Experimental Evidence for Extensive Tunneling of Hydrogen in the Lipoxygenase Reaction:  Implications for Enzyme Catalysis. Journal of the American Chemical Society. 1996 Oct;118(42):10319-20.
  • 21. Gousiadou C, Kouskoumvekaki I. LOX1 inhibition with small molecules. Journal of Molecular Graphics and Modelling. 2016 Jan;63:99-109.
  • 22. Sigal E, Craik CS, Highland E, Grunberger D, Costello LL, Dixon RA, Nadel JA. Molecular cloning and primary structure of human 15-lipoxygenase. Biochemical and Biophysical Research Communications. 1988 Dec;157(2):457-64.
  • 23. Holman TR, Zhou J, Solomon EI. Spectroscopic and Functional Characterization of a Ligand Coordination Mutant of Soybean Lipoxygenase-1: First Coordination Sphere Analogue of Human 15-Lipoxygenase. Journal of the American Chemical Society. 1998 Nov;120(48):12564-72.
  • 24. Minor W, Steczko J, Stec B, Otwinowski Z, Bolin JT, Walter R, Axelrod B. Crystal structure of soybean lipoxygenase L-1 at 1.4 A resolution. Biochemistry. 1996 Aug;35(33):10687-701.
  • 25. van Leyen K, Duvoisin RM, Engelhardt H, Wiedmann M. A function for lipoxygenase in programmed organelle degradation. Nature. 1998 Sep;395(6700):392-5.
  • 26. Kuhn H, Thiele BJ. The diversity of the lipoxygenase family. Many sequence data but little information on biological significance. FEBS Letters. 1999 Apr;449(1):7-11.
  • 27. Honn KV, Tang DG, Gao X, Butovich IA, Liu B, Timar J, Hagmann W. 12-lipoxygenases and 12(S)-HETE: role in cancer metastasis. Cancer and Metastasis Reviews. 1994 Dec;13(3-4):365-96.
  • 28. Werz O. Inhibition of 5-lipoxygenase product synthesis by natural compounds of plant origin. Planta Medica. 2007 Oct;73(13):1331-57.
  • 29. Mhater M. The role of the 5-lipoxygenase pathway in Alzheimer's disease. Drugs of the Future. 2006 Jan;31(1):83-9.
  • 30. Praticò D, Zhukareva V, Yao Y, Uryu K, Funk CD, Lawson JA, Trojanowski JQ, Lee VMY. 12/15-Lipoxygenase is increased in Alzheimer's disease - Possible involvement in brain oxidative stress. American Journal Of Pathology. 2004 May;164(5):1655-62.
  • 31. Schenk G, Neidig ML, Zhou J, Holman TR, Solomon EI. Spectroscopic Characterization of Soybean Lipoxygenase-1 Mutants: the Role of Second Coordination Sphere Residues in the Regulation of Enzyme Activity. Biochemistry. 2003 Jun;42(24):7294-302.
  • 32. Cengiz S, Cavas L, Yurdakoc K, Pohnert G. The sesquiterpene caulerpenyne from Caulerpa spp. is a lipoxygenase inhibitor. Marine Biotechnology. 2011 Apr;13(2):321-6.
  • 33. Richter P, Schubert G, Schaible AM, Cavas L, Werz O, Pohnert G. Caulerpenyne and Related Bis-enol Esters Are Novel-Type Inhibitors of Human 5-Lipoxygenase. ChemMedChem. 2014 Aug;9(8):1655-9.
  • 34. Omar YM, Abdu-Allah HHM, Abdel-Moty SG. Synthesis, biological evaluation and docking study of 1,3,4-thiadiazolethiazolidinone hybrids as anti-inflammatory agents with dual inhibition of COX-2 and 15-LOX. Bioorganic Chemistry. 2018 Oct;80:461-71.
  • 35. van der Vlag R, Guo H, Hapko U, Eleftheriadis N, Monjas L, Dekker FJ, Hirsch AKH. A combinatorial approach for the discovery of drug-like inhibitors of 15-lipoxygenase-1. European Journal of Medicinal Chemistry. 2019 Jul;174:45-55.
  • 36. Bouriche H, Miles EA, Selloum L, Calder PC. Effect of Cleome arabica leaf extract, rutin and quercetin on soybean lipoxygenase activity and on generation of inflammatory eicosanoids by human neutrophils. Prostaglandins Leukotrienes and Essential Fatty Acids. 2005 Mar;72(3):195-201.
  • 37. Zhang YY, Thakur K, Wei CK, Wang H, Zhang JG, Wei ZJ. Evaluation of inhibitory activity of natural plant polyphenols on Soybean lipoxygenase by UFLC-mass spectrometry. South African Journal of Botany. 2019 Jan;120:179-85.
  • 38. Sievers F, Wilm A, Dineen DG, Gibson TJ, Karplus K, Li W, Lopez R, McWilliam H, Remmert M, Söding J, Thompson JD, Higgins DG. Fast, scalable generation of high-quality protein multiple sequence alignments using Clustal Omega. Molecular Systems Biology. 2011 Oct;7:539.
  • 39. Madeira F, Park YM, Lee J, Buso N, Gur T, Madhusoodanan N, Basutkar P, Tivey ARN, Potter SC, Finn RD, Lopez R. The EMBL-EBI search and sequence analysis tools APIs in 2019. Nucleic Acids Research. 2019 Jul;47(W1):W636-W641.
  • 40. Gasteiger E, Hoogland C, Gattiker A, Duvaud S, Wilkins MR, Appel RD, Bairoch A. Protein Identification and Analysis Tools on the ExPASy Server. In: Walker JM (eds) The Proteomics Protocols Handbook. Humana Press, 2005;pp 571-607.
  • 41. Gasteiger E, Gattiker A, Hoogland C, Ivanyi I, Appel RD, Bairoch A. ExPASy: the proteomics server for in-depth protein knowledge and analysis. Nucleic Acids Research. 2003 Jul;31(13):3784-8.
  • 42. Jones DT. Protein secondary structure prediction based on position-specific scoring matrices. Journal of Molecular Biology. 1999 Sep;292(2):195-202.
  • 43. Kyte J, Doolittle RF. A simple method for displaying the hydropathic character of a protein. Journal of Molecular Biology. 1982 May;157(1):105-32.
  • 44. Mogul R, Holman TR. Inhibition Studies of Soybean and Human 15-Lipoxygenases with Long-Chain Alkenyl Sulfate Substrates. Biochemistry. 2001 Apr;40(14):4391-7.
  • 45. Galliard T, Chan HWS. Lipoxygenases. In: Stumpf PK, Conn EE (eds) The Biochemistry of Plants. Academic Press, New York, 1980;pp 4:131-61.
  • 46. Vidal-Mas J, Busquets M, Manresa A. Cloning and expression of a lipoxygenase from Pseudomonas aeruginosa 42A2. Antonie Van Leeuwenhoek. 2005 Apr;87(3):245-51.
  • 47. Sadeghian H, Jabbari A. 15-Lipoxygenase inhibitors: a patent review. Expert Opinion on Therapeutic Patents. 2016;26(1):65-88.
  • 48. Amagata T, Whitman S, Johnson TA, Stessman CC, Loo CP, Lobkovsky E, Clardy J, Crews P, Holman TR. Exploring Sponge-Derived Terpenoids for Their Potency and Selectivity against 12-Human, 15-Human, and 15-Soybean Lipoxygenases. Journal of Natural Products. 2003 Feb;66(2):230-5.
  • 49. Prigge ST, Boyington JC, Gaffney BJ, Amzel LM. Structure Conservation in Lipoxygenases: Structural Analysis of Soybean Lipoxygenase-1 and Modeling of Human Lipoxygenases. Proteins Structure Function and Bioinformatics. 1996 Mar;24(3):275-91.
  • 50. Gillmor SA, Villasenor A, Fletterick R, Sigal E, Browner MF. The structure of mammalian 15-lipoxygenase reveals similarity to the lipases and the determinants of substrate specificity. Nature Structural Biology. 1997 Dec;4(12):1003-9.
  • 51. Choi J, Chon JK, Kim S, Shin W. Conformational flexibility in mammalian 15S- lipoxygenase: Reinterpretation of the crystallographic data. Proteins. 2008 Feb;70(3):1023-32.
  • 52. Serpen A, Gökmen V. Effects of β-carotene on soybean lipoxygenase activity: kinetic studies. European Food Research and Technology. 2007 Apr;224(6):743-8.
  • 53. Eleftheriadis N, Thee S, te Biesebeek J, van der Wouden P, Baas BJ, Dekker FJ. Identification of 6-benzyloxysalicylates as a novel class of inhibitors of 15-lipoxygenase-1. European Journal of Medicinal Chemistry. 2015 Apr;94:265-75.
  • 54. Guo H, Verhoek IC, Prins GGH, van der Vlag R, van der Wouden PE, van Merkerk R, Quax WJ, Olinga P, Hirsch AKH, Dekker FJ. Novel 15-Lipoxygenase‑1 Inhibitor Protects Macrophages from Lipopolysaccharide-Induced Cytotoxicity. Journal of Medicinal Chemistry. 2019 May;62(9):4624-37.
Yıl 2021, Cilt: 8 Sayı: 1, 79 - 102, 28.02.2021
https://doi.org/10.18596/jotcsa.785109

Öz

Kaynakça

  • 1. Jacquot C, McGinley CM, Plata E, Holman TR, van der Donk WA. Synthesis of 11-thialinoleic acid and 14-thialinoleic acid, inhibitors of soybean and human lipoxygenases. Organic and Biomolecular Chemistry. 2008 Dec;6(22):4242-52.
  • 2. Newcomer ME, Brash AR. The structural basis for specificity in lipoxygenase catalysis. Protein Science. 2015 Mar;24(3):298-309.
  • 3. Skrzypczak-Jankun E, McCabe NP, Selman SH, Jankun J. Curcumin inhibits lipoxygenase by binding to its central cavity: theoretical and X-ray evidence. International Journal of Molecular Medicine. 2000 Nov;6(5):521-6.
  • 4. Simona V, Chedea VS, Dulf F, Socaciu C. The influence of quercetin concentration on its intermolecular interaction with soybean lipoxygenase-1. Bulletin USAMV-CN. 2006;62:376-80.
  • 5. Shrivastava SK, Srivastava P, Bandresh R, Tripathi PN, Tripathi A. Design, synthesis, and biological evaluation of some novel indolizine derivatives as dual cyclooxygenase and lipoxygenase inhibitor for anti-inflammatory activity. Bioorganic and Medicinal Chemistry. June 2017;25(16):4424-32.
  • 6. Yashaswini PS, Appu Rao AG, Singh SA. Inhibition of lipoxygenase by sesamol corroborates its potential anti-inflammatory activity. International Journal of Biological Macromolecules 2017 Jan;94(Pt B):781-7.
  • 7. ElBordiny HS, El-Miligy MM, Kassab SE, Daabees H, Mohamed Ali WA, El-Hawash SAM. Design, synthesis, biological evaluation and docking studies of new 3-(4,5-dihydro-1H-pyrazol/isoxazol-5-yl)-2-phenyl-1H-indole derivatives as potent antioxidants and 15-lipoxygenase inhibitors. European Journal of Medicinal Chemistry. 2018 Feb;145:594-605.
  • 8. Boyington JC, Gaffney BJ, Amzel LM. The three-dimensional structure of an arachidonic acid 15-lipoxygenase. Science. 1993 Jun;260(5113):1482-6.
  • 9. Ivanov I, Heydeck D, Hofheinz K, Roffeis J, O’Donnell VB, Kuhn H, Walther M. Molecular enzymology of lipoxygenases. Archives of Biochemistry and Biophysics. 2010 Nov;503(2):161-74.
  • 10. Segraves EN, Holman TR. Kinetic Investigations of the Rate-Limiting Step in Human 12- and 15-Lipoxygenase. Biochemistry. 2003 May;42(18):5236-43.
  • 11. Neidig ML, Wecksler AT, Schenk G, Holman TR, Solomon EI. Kinetic and Spectroscopic Studies of N694C Lipoxygenase: A Probe of the Substrate Activation Mechanism of a Nonheme Ferric Enzyme. Journal of the American Chemical Society. 2007 Jun;129(24):7531-7.
  • 12. Gardner HW. Recent investigations into the lipoxygenase pathway of plants. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism. 1991 Jul;1084(3):221-39.
  • 13. Yamamoto S. Mammalian lipoxygenases: molecular structures and functions. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism. 1992 Oct;1128(2-3):117-31.
  • 14. Maiga A, Malterud KE, Diallo D, Paulsen BS. Antioxidant and 15-lipoxygenase inhibitory activities of the Malian medicinal plants Diospyros abyssinica (Hiern) F. White (Ebenaceae), Lannea velutina A. Rich (Anacardiaceae) and Crossopteryx febrifuga (Afzel) Benth. (Rubiaceae). Journal of Ethnopharmacology. 2006 Mar;104(1-2):132-7.
  • 15. Kuhn H, Walther M, Kuban RJ. Mammalian arachidonate 15-lipoxygenases structure, function, and biological implications. Prostaglandins and Other Lipid Mediators. 2002 Aug;68-69:263-90.
  • 16. Mahesha HG, Singh SA, Appu Rao AG. Inhibition of lipoxygenase by soy isoflavones: Evidence of isoflavones as redox inhibitors. Archives of Biochemistry and Biophysics. 2007 May;461(2):176-85.
  • 17. Russell WR, Scobbie L, Duthie GG, Chesson A. Inhibition of 15-lipoxygenase-catalysed oxygenation of arachidonic acid by substituted benzoic acids. Bioorganic and Medicinal Chemistry. 2008 Apr;16(8):4589-93.
  • 18. Nguyen MD, Nguyen DH, Yoo JM, Myung PK, Kim MR, Sok DE. Effect of endocannabinoids on soybean lipoxygenase-1 activity. Bioorganic Chemistry. 2013 Aug;49:24-32.
  • 19. Oso BJ, Karigidi KO. Inhibitory action of dried leaf of Cassia alata (Linn.) Roxb against lipoxygenase activity and nitric oxide generation. Scientia Agropecuaria. 2019 Mar;10(2):185-90.
  • 20. Jonsson T, Glickman MH, Sun S, Klinman JP. Experimental Evidence for Extensive Tunneling of Hydrogen in the Lipoxygenase Reaction:  Implications for Enzyme Catalysis. Journal of the American Chemical Society. 1996 Oct;118(42):10319-20.
  • 21. Gousiadou C, Kouskoumvekaki I. LOX1 inhibition with small molecules. Journal of Molecular Graphics and Modelling. 2016 Jan;63:99-109.
  • 22. Sigal E, Craik CS, Highland E, Grunberger D, Costello LL, Dixon RA, Nadel JA. Molecular cloning and primary structure of human 15-lipoxygenase. Biochemical and Biophysical Research Communications. 1988 Dec;157(2):457-64.
  • 23. Holman TR, Zhou J, Solomon EI. Spectroscopic and Functional Characterization of a Ligand Coordination Mutant of Soybean Lipoxygenase-1: First Coordination Sphere Analogue of Human 15-Lipoxygenase. Journal of the American Chemical Society. 1998 Nov;120(48):12564-72.
  • 24. Minor W, Steczko J, Stec B, Otwinowski Z, Bolin JT, Walter R, Axelrod B. Crystal structure of soybean lipoxygenase L-1 at 1.4 A resolution. Biochemistry. 1996 Aug;35(33):10687-701.
  • 25. van Leyen K, Duvoisin RM, Engelhardt H, Wiedmann M. A function for lipoxygenase in programmed organelle degradation. Nature. 1998 Sep;395(6700):392-5.
  • 26. Kuhn H, Thiele BJ. The diversity of the lipoxygenase family. Many sequence data but little information on biological significance. FEBS Letters. 1999 Apr;449(1):7-11.
  • 27. Honn KV, Tang DG, Gao X, Butovich IA, Liu B, Timar J, Hagmann W. 12-lipoxygenases and 12(S)-HETE: role in cancer metastasis. Cancer and Metastasis Reviews. 1994 Dec;13(3-4):365-96.
  • 28. Werz O. Inhibition of 5-lipoxygenase product synthesis by natural compounds of plant origin. Planta Medica. 2007 Oct;73(13):1331-57.
  • 29. Mhater M. The role of the 5-lipoxygenase pathway in Alzheimer's disease. Drugs of the Future. 2006 Jan;31(1):83-9.
  • 30. Praticò D, Zhukareva V, Yao Y, Uryu K, Funk CD, Lawson JA, Trojanowski JQ, Lee VMY. 12/15-Lipoxygenase is increased in Alzheimer's disease - Possible involvement in brain oxidative stress. American Journal Of Pathology. 2004 May;164(5):1655-62.
  • 31. Schenk G, Neidig ML, Zhou J, Holman TR, Solomon EI. Spectroscopic Characterization of Soybean Lipoxygenase-1 Mutants: the Role of Second Coordination Sphere Residues in the Regulation of Enzyme Activity. Biochemistry. 2003 Jun;42(24):7294-302.
  • 32. Cengiz S, Cavas L, Yurdakoc K, Pohnert G. The sesquiterpene caulerpenyne from Caulerpa spp. is a lipoxygenase inhibitor. Marine Biotechnology. 2011 Apr;13(2):321-6.
  • 33. Richter P, Schubert G, Schaible AM, Cavas L, Werz O, Pohnert G. Caulerpenyne and Related Bis-enol Esters Are Novel-Type Inhibitors of Human 5-Lipoxygenase. ChemMedChem. 2014 Aug;9(8):1655-9.
  • 34. Omar YM, Abdu-Allah HHM, Abdel-Moty SG. Synthesis, biological evaluation and docking study of 1,3,4-thiadiazolethiazolidinone hybrids as anti-inflammatory agents with dual inhibition of COX-2 and 15-LOX. Bioorganic Chemistry. 2018 Oct;80:461-71.
  • 35. van der Vlag R, Guo H, Hapko U, Eleftheriadis N, Monjas L, Dekker FJ, Hirsch AKH. A combinatorial approach for the discovery of drug-like inhibitors of 15-lipoxygenase-1. European Journal of Medicinal Chemistry. 2019 Jul;174:45-55.
  • 36. Bouriche H, Miles EA, Selloum L, Calder PC. Effect of Cleome arabica leaf extract, rutin and quercetin on soybean lipoxygenase activity and on generation of inflammatory eicosanoids by human neutrophils. Prostaglandins Leukotrienes and Essential Fatty Acids. 2005 Mar;72(3):195-201.
  • 37. Zhang YY, Thakur K, Wei CK, Wang H, Zhang JG, Wei ZJ. Evaluation of inhibitory activity of natural plant polyphenols on Soybean lipoxygenase by UFLC-mass spectrometry. South African Journal of Botany. 2019 Jan;120:179-85.
  • 38. Sievers F, Wilm A, Dineen DG, Gibson TJ, Karplus K, Li W, Lopez R, McWilliam H, Remmert M, Söding J, Thompson JD, Higgins DG. Fast, scalable generation of high-quality protein multiple sequence alignments using Clustal Omega. Molecular Systems Biology. 2011 Oct;7:539.
  • 39. Madeira F, Park YM, Lee J, Buso N, Gur T, Madhusoodanan N, Basutkar P, Tivey ARN, Potter SC, Finn RD, Lopez R. The EMBL-EBI search and sequence analysis tools APIs in 2019. Nucleic Acids Research. 2019 Jul;47(W1):W636-W641.
  • 40. Gasteiger E, Hoogland C, Gattiker A, Duvaud S, Wilkins MR, Appel RD, Bairoch A. Protein Identification and Analysis Tools on the ExPASy Server. In: Walker JM (eds) The Proteomics Protocols Handbook. Humana Press, 2005;pp 571-607.
  • 41. Gasteiger E, Gattiker A, Hoogland C, Ivanyi I, Appel RD, Bairoch A. ExPASy: the proteomics server for in-depth protein knowledge and analysis. Nucleic Acids Research. 2003 Jul;31(13):3784-8.
  • 42. Jones DT. Protein secondary structure prediction based on position-specific scoring matrices. Journal of Molecular Biology. 1999 Sep;292(2):195-202.
  • 43. Kyte J, Doolittle RF. A simple method for displaying the hydropathic character of a protein. Journal of Molecular Biology. 1982 May;157(1):105-32.
  • 44. Mogul R, Holman TR. Inhibition Studies of Soybean and Human 15-Lipoxygenases with Long-Chain Alkenyl Sulfate Substrates. Biochemistry. 2001 Apr;40(14):4391-7.
  • 45. Galliard T, Chan HWS. Lipoxygenases. In: Stumpf PK, Conn EE (eds) The Biochemistry of Plants. Academic Press, New York, 1980;pp 4:131-61.
  • 46. Vidal-Mas J, Busquets M, Manresa A. Cloning and expression of a lipoxygenase from Pseudomonas aeruginosa 42A2. Antonie Van Leeuwenhoek. 2005 Apr;87(3):245-51.
  • 47. Sadeghian H, Jabbari A. 15-Lipoxygenase inhibitors: a patent review. Expert Opinion on Therapeutic Patents. 2016;26(1):65-88.
  • 48. Amagata T, Whitman S, Johnson TA, Stessman CC, Loo CP, Lobkovsky E, Clardy J, Crews P, Holman TR. Exploring Sponge-Derived Terpenoids for Their Potency and Selectivity against 12-Human, 15-Human, and 15-Soybean Lipoxygenases. Journal of Natural Products. 2003 Feb;66(2):230-5.
  • 49. Prigge ST, Boyington JC, Gaffney BJ, Amzel LM. Structure Conservation in Lipoxygenases: Structural Analysis of Soybean Lipoxygenase-1 and Modeling of Human Lipoxygenases. Proteins Structure Function and Bioinformatics. 1996 Mar;24(3):275-91.
  • 50. Gillmor SA, Villasenor A, Fletterick R, Sigal E, Browner MF. The structure of mammalian 15-lipoxygenase reveals similarity to the lipases and the determinants of substrate specificity. Nature Structural Biology. 1997 Dec;4(12):1003-9.
  • 51. Choi J, Chon JK, Kim S, Shin W. Conformational flexibility in mammalian 15S- lipoxygenase: Reinterpretation of the crystallographic data. Proteins. 2008 Feb;70(3):1023-32.
  • 52. Serpen A, Gökmen V. Effects of β-carotene on soybean lipoxygenase activity: kinetic studies. European Food Research and Technology. 2007 Apr;224(6):743-8.
  • 53. Eleftheriadis N, Thee S, te Biesebeek J, van der Wouden P, Baas BJ, Dekker FJ. Identification of 6-benzyloxysalicylates as a novel class of inhibitors of 15-lipoxygenase-1. European Journal of Medicinal Chemistry. 2015 Apr;94:265-75.
  • 54. Guo H, Verhoek IC, Prins GGH, van der Vlag R, van der Wouden PE, van Merkerk R, Quax WJ, Olinga P, Hirsch AKH, Dekker FJ. Novel 15-Lipoxygenase‑1 Inhibitor Protects Macrophages from Lipopolysaccharide-Induced Cytotoxicity. Journal of Medicinal Chemistry. 2019 May;62(9):4624-37.
Toplam 54 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Makaleler
Yazarlar

Sevilay Cengiz 0000-0003-3361-4319

Levent Cavas 0000-0003-2136-6928

Yayımlanma Tarihi 28 Şubat 2021
Gönderilme Tarihi 25 Ağustos 2020
Kabul Tarihi 18 Kasım 2020
Yayımlandığı Sayı Yıl 2021 Cilt: 8 Sayı: 1

Kaynak Göster

Vancouver Cengiz S, Cavas L. Can soybean lipoxygenases be real models for mammalian lipoxygenases? A bioinformatics approach. JOTCSA. 2021;8(1):79-102.