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Synthesis and biological evaluation of novel cYY analogues targeting Mycobacterium tuberculosis CYP121A1.

Kishk SM, McLean KJ, Sood S, Helal MA, Gomaa MS, Salama I, Mostafa SM, de Carvalho LPS, Munro AW, Simons C.

Bioorg Med Chem. 2019 Apr 15;27(8):1546-1561. doi: 10.1016/j.bmc.2019.02.051. Epub 2019 Feb 27.


Novel insights into P450 BM3 interactions with FDA-approved antifungal azole drugs.

Jeffreys LN, Poddar H, Golovanova M, Levy CW, Girvan HM, McLean KJ, Voice MW, Leys D, Munro AW.

Sci Rep. 2019 Feb 7;9(1):1577. doi: 10.1038/s41598-018-37330-y.


Cytochrome P450 1A1 opens up to new substrates.

Munro AW.

J Biol Chem. 2018 Dec 14;293(50):19211-19212. doi: 10.1074/jbc.H118.006715. Epub 2018 Dec 14.


Characterization of Cytochrome P450 Enzymes and Their Applications in Synthetic Biology.

Jeffreys LN, Girvan HM, McLean KJ, Munro AW.

Methods Enzymol. 2018;608:189-261. doi: 10.1016/bs.mie.2018.06.013. Epub 2018 Aug 20.


Structural and catalytic properties of the peroxygenase P450 enzyme CYP152K6 from Bacillus methanolicus.

Girvan HM, Poddar H, McLean KJ, Nelson DR, Hollywood KA, Levy CW, Leys D, Munro AW.

J Inorg Biochem. 2018 Nov;188:18-28. doi: 10.1016/j.jinorgbio.2018.08.002. Epub 2018 Aug 3.


Expression, Purification, and Biochemical Characterization of the Flavocytochrome P450 CYP505A30 from Myceliophthora thermophila.

Baker GJ, Girvan HM, Matthews S, McLean KJ, Golovanova M, Waltham TN, Rigby SEJ, Nelson DR, Blankley RT, Munro AW.

ACS Omega. 2017 Aug 31;2(8):4705-4724. doi: 10.1021/acsomega.7b00450. Epub 2017 Aug 18.


Structure and function of the cytochrome P450 peroxygenase enzymes.

Munro AW, McLean KJ, Grant JL, Makris TM.

Biochem Soc Trans. 2018 Feb 19;46(1):183-196. doi: 10.1042/BST20170218. Epub 2018 Feb 6. Review.


Novel Aryl Substituted Pyrazoles as Small Molecule Inhibitors of Cytochrome P450 CYP121A1: Synthesis and Antimycobacterial Evaluation.

Taban IM, Elshihawy HEAE, Torun B, Zucchini B, Williamson CJ, Altuwairigi D, Ngu AST, McLean KJ, Levy CW, Sood S, Marino LB, Munro AW, de Carvalho LPS, Simons C.

J Med Chem. 2017 Dec 28;60(24):10257-10267. doi: 10.1021/acs.jmedchem.7b01562. Epub 2017 Dec 7.


Design, synthesis and evaluation against Mycobacterium tuberculosis of azole piperazine derivatives as dicyclotyrosine (cYY) mimics.

El-Wahab HAAA, Accietto M, Marino LB, McLean KJ, Levy CW, Abdel-Rahman HM, El-Gendy MA, Munro AW, Aboraia AS, Simons C.

Bioorg Med Chem. 2018 Jan 1;26(1):161-176. doi: 10.1016/j.bmc.2017.11.030. Epub 2017 Nov 21.


Effect of DMSO on Protein Structure and Interactions Assessed by Collision-Induced Dissociation and Unfolding.

Chan DS, Kavanagh ME, McLean KJ, Munro AW, Matak-Vinković D, Coyne AG, Abell C.

Anal Chem. 2017 Sep 19;89(18):9976-9983. doi: 10.1021/acs.analchem.7b02329. Epub 2017 Aug 25.


Fragment Profiling Approach to Inhibitors of the Orphan M. tuberculosis P450 CYP144A1.

Kavanagh ME, Chenge J, Zoufir A, McLean KJ, Coyne AG, Bender A, Munro AW, Abell C.

Biochemistry. 2017 Mar 21;56(11):1559-1572. doi: 10.1021/acs.biochem.6b00954. Epub 2017 Mar 6.


Production of alkenes and novel secondary products by P450 OleTJE using novel H2 O2 -generating fusion protein systems.

Matthews S, Tee KL, Rattray NJ, McLean KJ, Leys D, Parker DA, Blankley RT, Munro AW.

FEBS Lett. 2017 Mar;591(5):737-750. doi: 10.1002/1873-3468.12581. Epub 2017 Feb 21.


Corrigendum: Substrate Fragmentation for the Design of M. tuberculosis CYP121 Inhibitors.

Kavanagh ME, Gray JL, Gilbert SH, Coyne AG, McLean KJ, Davis HJ, Munro AW, Abell C.

ChemMedChem. 2017 Jan 20;12(2):194-195. doi: 10.1002/cmdc.201600619. Epub 2016 Dec 19. No abstract available.


Catalytic Determinants of Alkene Production by the Cytochrome P450 Peroxygenase OleTJE.

Matthews S, Belcher JD, Tee KL, Girvan HM, McLean KJ, Rigby SE, Levy CW, Leys D, Parker DA, Blankley RT, Munro AW.

J Biol Chem. 2017 Mar 24;292(12):5128-5143. doi: 10.1074/jbc.M116.762336. Epub 2017 Jan 4.


Structural Characterization and Ligand/Inhibitor Identification Provide Functional Insights into the Mycobacterium tuberculosis Cytochrome P450 CYP126A1.

Chenge JT, Duyet LV, Swami S, McLean KJ, Kavanagh ME, Coyne AG, Rigby SE, Cheesman MR, Girvan HM, Levy CW, Rupp B, von Kries JP, Abell C, Leys D, Munro AW.

J Biol Chem. 2017 Jan 27;292(4):1310-1329. doi: 10.1074/jbc.M116.748822. Epub 2016 Dec 8.


Drug targeting of heme proteins in Mycobacterium tuberculosis.

McLean KJ, Munro AW.

Drug Discov Today. 2017 Mar;22(3):566-575. doi: 10.1016/j.drudis.2016.11.004. Epub 2016 Nov 14. Review.


An oxidative N-demethylase reveals PAS transition from ubiquitous sensor to enzyme.

Ortmayer M, Lafite P, Menon BR, Tralau T, Fisher K, Denkhaus L, Scrutton NS, Rigby SE, Munro AW, Hay S, Leys D.

Nature. 2016 Nov 24;539(7630):593-597. doi: 10.1038/nature20159. Epub 2016 Nov 16.


Analysis of Heme Iron Coordination in DGCR8: The Heme-Binding Component of the Microprocessor Complex.

Girvan HM, Bradley JM, Cheesman MR, Kincaid JR, Liu Y, Czarnecki K, Fisher K, Leys D, Rigby SE, Munro AW.

Biochemistry. 2016 Sep 13;55(36):5073-83. doi: 10.1021/acs.biochem.6b00204. Epub 2016 Sep 1.


Substrate Fragmentation for the Design of M. tuberculosis CYP121 Inhibitors.

Kavanagh ME, Gray JL, Gilbert SH, Coyne AG, McLean KJ, Davis HJ, Munro AW, Abell C.

ChemMedChem. 2016 Sep 6;11(17):1924-35. doi: 10.1002/cmdc.201600248. Epub 2016 Jul 19. Erratum in: ChemMedChem. 2017 Jan 20;12 (2):194-195.


Structural characterization of CYP144A1 - a cytochrome P450 enzyme expressed from alternative transcripts in Mycobacterium tuberculosis.

Chenge J, Kavanagh ME, Driscoll MD, McLean KJ, Young DB, Cortes T, Matak-Vinkovic D, Levy CW, Rigby SE, Leys D, Abell C, Munro AW.

Sci Rep. 2016 May 26;6:26628. doi: 10.1038/srep26628.


Applications of microbial cytochrome P450 enzymes in biotechnology and synthetic biology.

Girvan HM, Munro AW.

Curr Opin Chem Biol. 2016 Apr;31:136-45. doi: 10.1016/j.cbpa.2016.02.018. Epub 2016 Mar 22. Review.


Fragment-Based Approaches to the Development of Mycobacterium tuberculosis CYP121 Inhibitors.

Kavanagh ME, Coyne AG, McLean KJ, James GG, Levy CW, Marino LB, de Carvalho LP, Chan DS, Hudson SA, Surade S, Leys D, Munro AW, Abell C.

J Med Chem. 2016 Apr 14;59(7):3272-302. doi: 10.1021/acs.jmedchem.6b00007. Epub 2016 Mar 22.


Biological diversity of cytochrome P450 redox partner systems.

McLean KJ, Luciakova D, Belcher J, Tee KL, Munro AW.

Adv Exp Med Biol. 2015;851:299-317. doi: 10.1007/978-3-319-16009-2_11. Review.


Single-step fermentative production of the cholesterol-lowering drug pravastatin via reprogramming of Penicillium chrysogenum.

McLean KJ, Hans M, Meijrink B, van Scheppingen WB, Vollebregt A, Tee KL, van der Laan JM, Leys D, Munro AW, van den Berg MA.

Proc Natl Acad Sci U S A. 2015 Mar 3;112(9):2847-52. doi: 10.1073/pnas.1419028112. Epub 2015 Feb 17.


The structure, function and properties of sirohaem decarboxylase--an enzyme with structural homology to a transcription factor family that is part of the alternative haem biosynthesis pathway.

Palmer DJ, Schroeder S, Lawrence AD, Deery E, Lobo SA, Saraiva LM, McLean KJ, Munro AW, Ferguson SJ, Pickersgill RW, Brown DG, Warren MJ.

Mol Microbiol. 2014 Jul;93(2):247-61. doi: 10.1111/mmi.12656. Epub 2014 Jun 18.


Human P450-like oxidation of diverse proton pump inhibitor drugs by 'gatekeeper' mutants of flavocytochrome P450 BM3.

Butler CF, Peet C, McLean KJ, Baynham MT, Blankley RT, Fisher K, Rigby SE, Leys D, Voice MW, Munro AW.

Biochem J. 2014 Jun 1;460(2):247-59. doi: 10.1042/BJ20140030.


Strength of axial water ligation in substrate-free cytochrome P450s is isoform dependent.

Conner KP, Schimpf AM, Cruce AA, McLean KJ, Munro AW, Frank DJ, Krzyaniak MD, Ortiz de Montellano P, Bowman MK, Atkins WM.

Biochemistry. 2014 Mar 11;53(9):1428-34. doi: 10.1021/bi401547j. Epub 2014 Feb 27.


Structure and biochemical properties of the alkene producing cytochrome P450 OleTJE (CYP152L1) from the Jeotgalicoccus sp. 8456 bacterium.

Belcher J, McLean KJ, Matthews S, Woodward LS, Fisher K, Rigby SE, Nelson DR, Potts D, Baynham MT, Parker DA, Leys D, Munro AW.

J Biol Chem. 2014 Mar 7;289(10):6535-50. doi: 10.1074/jbc.M113.527325. Epub 2014 Jan 18.


Overview on theoretical studies discriminating the two-oxidant versus two-state-reactivity models for substrate monoxygenation by cytochrome P450 enzymes.

de Visser SP, Porro CS, Quesne MG, Sainna MA, Munro AW.

Curr Top Med Chem. 2013;13(18):2218-32. Review.


Key mutations alter the cytochrome P450 BM3 conformational landscape and remove inherent substrate bias.

Butler CF, Peet C, Mason AE, Voice MW, Leys D, Munro AW.

J Biol Chem. 2013 Aug 30;288(35):25387-99. doi: 10.1074/jbc.M113.479717. Epub 2013 Jul 3.


Overcoming the limitations of fragment merging: rescuing a strained merged fragment series targeting Mycobacterium tuberculosis CYP121.

Hudson SA, Surade S, Coyne AG, McLean KJ, Leys D, Munro AW, Abell C.

ChemMedChem. 2013 Sep;8(9):1451-6. doi: 10.1002/cmdc.201300219. Epub 2013 Jun 20. No abstract available.


Nanoelectrospray ionization mass spectrometric study of Mycobacterium tuberculosis CYP121-ligand interactions.

Duffell KM, Hudson SA, McLean KJ, Munro AW, Abell C, Matak-Vinković D.

Anal Chem. 2013 Jun 18;85(12):5707-14. doi: 10.1021/ac400236z. Epub 2013 May 29.


Unusual cytochrome p450 enzymes and reactions.

Guengerich FP, Munro AW.

J Biol Chem. 2013 Jun 14;288(24):17065-73. doi: 10.1074/jbc.R113.462275. Epub 2013 Apr 30. Review.


Heme sensor proteins.

Girvan HM, Munro AW.

J Biol Chem. 2013 May 10;288(19):13194-203. doi: 10.1074/jbc.R112.422642. Epub 2013 Mar 28. Review.


Bacillus megaterium has both a functional BluB protein required for DMB synthesis and a related flavoprotein that forms a stable radical species.

Collins HF, Biedendieck R, Leech HK, Gray M, Escalante-Semerena JC, McLean KJ, Munro AW, Rigby SE, Warren MJ, Lawrence AD.

PLoS One. 2013;8(2):e55708. doi: 10.1371/journal.pone.0055708. Epub 2013 Feb 14.


What makes a P450 tick?

Munro AW, Girvan HM, Mason AE, Dunford AJ, McLean KJ.

Trends Biochem Sci. 2013 Mar;38(3):140-50. doi: 10.1016/j.tibs.2012.11.006. Epub 2013 Jan 26. Review.


Application of fragment screening and merging to the discovery of inhibitors of the Mycobacterium tuberculosis cytochrome P450 CYP121.

Hudson SA, McLean KJ, Surade S, Yang YQ, Leys D, Ciulli A, Munro AW, Abell C.

Angew Chem Int Ed Engl. 2012 Sep 10;51(37):9311-6. doi: 10.1002/anie.201202544. Epub 2012 Aug 13. No abstract available.


Cholesterol, an essential molecule: diverse roles involving cytochrome P450 enzymes.

McLean KJ, Hans M, Munro AW.

Biochem Soc Trans. 2012 Jun 1;40(3):587-93. doi: 10.1042/BST20120077. Review.


Mycobacterium tuberculosis cytochrome P450 enzymes: a cohort of novel TB drug targets.

Hudson SA, McLean KJ, Munro AW, Abell C.

Biochem Soc Trans. 2012 Jun 1;40(3):573-9. doi: 10.1042/BST20120062. Review.


Unusual spectroscopic and ligand binding properties of the cytochrome P450-flavodoxin fusion enzyme XplA.

Bui SH, McLean KJ, Cheesman MR, Bradley JM, Rigby SE, Levy CW, Leys D, Munro AW.

J Biol Chem. 2012 Jun 1;287(23):19699-714. doi: 10.1074/jbc.M111.319202. Epub 2012 Apr 12.


Special issue: Cytochrome P450 structure and function: introduction.

Munro AW, Leys D.

FEBS J. 2012 May;279(9):1515. doi: 10.1111/j.1742-4658.2012.08578.x. Epub 2012 Apr 5.


The crystal structure of the FAD/NADPH-binding domain of flavocytochrome P450 BM3.

Joyce MG, Ekanem IS, Roitel O, Dunford AJ, Neeli R, Girvan HM, Baker GJ, Curtis RA, Munro AW, Leys D.

FEBS J. 2012 May;279(9):1694-706. doi: 10.1111/j.1742-4658.2012.08544.x. Epub 2012 Mar 16.


Characterization of Cupriavidus metallidurans CYP116B1--a thiocarbamate herbicide oxygenating P450-phthalate dioxygenase reductase fusion protein.

Warman AJ, Robinson JW, Luciakova D, Lawrence AD, Marshall KR, Warren MJ, Cheesman MR, Rigby SE, Munro AW, McLean KJ.

FEBS J. 2012 May;279(9):1675-93. doi: 10.1111/j.1742-4658.2012.08543.x. Epub 2012 Mar 21.


Analysis of the oxidation of short chain alkynes by flavocytochrome P450 BM3.

Waltham TN, Girvan HM, Butler CF, Rigby SR, Dunford AJ, Holt RA, Munro AW.

Metallomics. 2011 Apr;3(4):369-78. doi: 10.1039/c1mt00004g. Epub 2011 Mar 23.


The Mycobacterium tuberculosis cytochromes P450: physiology, biochemistry & molecular intervention.

McLean KJ, Belcher J, Driscoll MD, Fernandez CC, Le Van D, Bui S, Golovanova M, Munro AW.

Future Med Chem. 2010 Aug;2(8):1339-53. doi: 10.4155/fmc.10.216. Review.


A novel intermediate in the reaction of seleno CYP119 with m-chloroperbenzoic acid.

Sivaramakrishnan S, Ouellet H, Du J, McLean KJ, Medzihradszky KF, Dawson JH, Munro AW, Ortiz de Montellano PR.

Biochemistry. 2011 Apr 12;50(14):3014-24. doi: 10.1021/bi101728y. Epub 2011 Mar 22.


Identification of N-terminal regions of wheat leaf ferredoxin NADP+ oxidoreductase important for interactions with ferredoxin.

Bowsher CG, Eyres LM, Gummadova JO, Hothi P, McLean KJ, Munro AW, Scrutton NS, Hanke GT, Sakakibara Y, Hase T.

Biochemistry. 2011 Mar 22;50(11):1778-87. doi: 10.1021/bi1014562. Epub 2011 Feb 23.


Characterisation of PduS, the pdu metabolosome corrin reductase, and evidence of substructural organisation within the bacterial microcompartment.

Parsons JB, Lawrence AD, McLean KJ, Munro AW, Rigby SE, Warren MJ.

PLoS One. 2010 Nov 16;5(11):e14009. doi: 10.1371/journal.pone.0014009.


FdC1, a novel ferredoxin protein capable of alternative electron partitioning, increases in conditions of acceptor limitation at photosystem I.

Voss I, Goss T, Murozuka E, Altmann B, McLean KJ, Rigby SE, Munro AW, Scheibe R, Hase T, Hanke GT.

J Biol Chem. 2011 Jan 7;286(1):50-9. doi: 10.1074/jbc.M110.161562. Epub 2010 Oct 21.

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