Hydroxypropyl-β-cyclodextrin-mediated alterations in cell permeability, lipid and protein profiles of steroid-transforming Arthrobacter simplex

Applied Microbiology and Biotechnology

Volumn 99, Issue 1, 2015, Pages 387-397

  Shen, Yanbing ^a   Liang, Jingting ^a   Li, Huanan ^a   Wang, Min ^a  

^a TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Arthrobacter simplex; Biotransformation; Cell envelope permeability; Hydroxypropyl cyclodextrin; Lipid; Protein

Indexed keywords

ATOMIC FORCE MICROSCOPY; BIOCONVERSION; CELLS; CYCLODEXTRINS; HIGH RESOLUTION TRANSMISSION ELECTRON MICROSCOPY; LIPIDS; PROTEINS; SURFACE STRUCTURE; UNSATURATED FATTY ACIDS;

ARTHROBACTER SIMPLEX; ATP-BINDING CASSETTE; BIOTRANSFORMATION; CELL ENVELOPES; DEHYDROGENASE ACTIVITY; LONG CHAIN FATTY ACID; MAJOR FACILITATOR SUPERFAMILY; SUBSTRATE SOLUBILITIES;

CYTOLOGY;

2 HYDROXYPROPYL BETA CYCLODEXTRIN; ADENOSINE TRIPHOSPHATE; AROMATIC AMINO ACID; CELL PROTEIN; FATTY ACID; LIPID; LONG CHAIN FATTY ACID; MEMBRANE PROTEIN; OXIDOREDUCTASE; PROTEIN; STEROID; TRYPSIN; UNSATURATED FATTY ACID; 2-HYDROXYPROPYL-BETA-CYCLODEXTRIN; BACTERIAL PROTEIN; BETA CYCLODEXTRIN DERIVATIVE; METHACRYLIC ACID METHYL ESTER; POLYSTYRENE DERIVATIVE; STYRENE-METHYLMETHACRYLATE COPOLYMER;

ANALYTIC METHOD; ARTICLE; ATOMIC FORCE MICROSCOPY; BIOTRANSFORMATION; CELL FUNCTION; CELL MEMBRANE PERMEABILITY; CELL ULTRASTRUCTURE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; HYDROPHOBICITY; LIPID COMPOSITION; LIPID SOLUBILITY; NONHUMAN; PIMELOBACTER SIMPLEX; PROTEIN ANALYSIS; PROTEIN CONTENT; STRUCTURE ANALYSIS; TRANSMISSION ELECTRON MICROSCOPY; ARTHROBACTER; CELL MEMBRANE; CHEMISTRY; CYTOSOL; DRUG EFFECTS; LIPID METABOLISM; METABOLISM; PERMEABILITY; ULTRASTRUCTURE;

ARTHROBACTER; BACTERIAL PROTEINS; BETA-CYCLODEXTRINS; CELL MEMBRANE; CYTOSOL; LIPID METABOLISM; LIPIDS; METHYLMETHACRYLATES; MICROSCOPY, ATOMIC FORCE; MICROSCOPY, ELECTRON, TRANSMISSION; PERMEABILITY; POLYSTYRENES; STEROIDS;

EID: 84925521874     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-014-6089-5     Document Type: Article

References (36)

1. Aachmann FL, Otzen DE, Larsen KL, Wimmer R (2008) Structural background of cyclodextrin-protein interactions. Protein Eng 16:905–912
2. Arun RA, Kumar ACK, Sravanthi VVNSS (2008) Cyclodextrins as drug carrier molecule: a review. Sci Pharm 76:567–598
3. Bagatolli LA, Ipsen JH, Simonsen AC, Mouritsen OG (2010) An outlook on organization of lipids in membranes: searching for a realistic connection with the organization of biological membranes. Prog Lipid Res 49:378–389
4. Dahan A, Miller JM, Hoffman A, Amidon GE, Amidon GL (2010) The solubility-permeability interplay in using cyclodextrins as pharmaceutical solubilizers: mechanistic modeling and application to progesterone. J Pharm Sci 99:2739–2749
5. Donova MV, Nikolayeva VM, Dovbnya DV, Gulevskaya SA, Suzina NE (2007) Methyl-β-cyclodextrin alters growth, activity and cell envelope features of sterol-transforming mycobacteria. Microbiology 153:1981–1992
6. Druzhinina AV, Andryushina VA, Stytsenko TS, Voishvillo NE (2008) Conversion of 17α-methyltestosterone to methandrostenolone by the bacterium Pimelobacter simplex VKPM Ac-1632 with the presence of cyclodextrins. Appl Biochem Microbiol 4:580–584
7. Fernandes P, Cruz A, Angelova B, Pinheiro HM, Cabral JMS (2003) Microbial conversion of steroid compounds: recent developments. Enzyme Microb Technol 32:688–705
8. Fuchs B, Süß R, Teuber K, Eibisch M, Schiller J (2011) Lipid analysis by thin-layer chromatography—a review of the current state. J Chromatogr A 1218:2754–2774
9. Getsin I, Nalbandian GH, Yee DC, Vastermark A, Paparoditis PC, Reddy V, Saier MH (2013) Comparative genomics of transport proteins in developmental bacteria: Myxococcus xanthus and Streptomyces coelicolor. BMC Microbiol 13:279
10. Hapiot F, Ponchel A, Tilloy S, Monflier E (2011) Cyclodextrins and their applications in aqueous-phase metal-catalyzed reactions. CR Chim 14:149–166
11. Jadoun J, Bar R (1993a) Microbial transformations in a cyclodextrin medium. Part 3. Cholesterol oxidation by Rhodococcus erythropolis. Appl Microbiol Biot 40(2–3):230–240
12. Jadoun J, Bar R (1993b) Microbial transformations in a cyclodextrin medium. Part 4. Enzyme vs microbial oxidation of cholesterol. Appl Microbiol Biot 40(4):477–482
13. Kilsdonk EPC, Yancey PG, Stoudt GW, Bangerter FW, Johnson WJ, Phillips MC, Rothblat GH (1995) Cellular cholesterol efflux mediated by cyclodextrins. J Biol Chem 270:17250–17256
14. Kolomytseva MP, Randazzo D, Baskunov BP, Scozzafava A, Briganti F, Golovleva LA (2009) Role of surfactants in optimizing fluorene assimilation and intermediate formation by Rhodococcus rhodochrous VKM B-2469. Bioresource Technol 100:839–844
15. Korycka-Machała M, Ziółkowski A, Rumijowska-Galewicz A, Lisowska K, Sedlaczek L (2001) Polycations increase the permeability of Mycobacterium vaccae cell envelopes to hydrophobic compounds. Microbiology 147:2769–2781
16. Larson SB, Greenwood A, Cascio D, Day J, McPherson A (1994) Refined molecular structure of pig pancreatic α-amylase at 2.1 Å resolution. J Mol Biol 235:1560–1584
17. Levitan I, Christian AE, Tulenko TN, Rothblat GH (2000) Membrane cholesterol content modulates activation of volume-regulated anion current in bovine endothelial cells. J Gen Physiol 115:405–416
18. Li G, Li F, Deng LS, Fang X, Zou H, Xu K, Li T, Tan GS (2013) Increased yield of biotransformation of exemestane with β-cyclodextrin complexation technique. Steroids 78:1148–1151
19. 1-dehydrogenation. J Steroid Biochem 117:146–151
20. Manosroi A, Saowakhon S, Manosroi J (2008) Enhancement of androstadienedione production from progesterone by biotransformation using the hydroxypropyl-β-cyclodextrin complexation technique. J Steroid Biochem 108:132–136
21. Mohamed SS, El-Refai AMH, Hashem AGM, Ali HA (2014) Approaches to improve the solubility and availability of progesterone biotransformation by Mucor racemosus. Biocatal Biotransfor 32:141–150
22. Nikaido H, Jarlier V (1991) Permeability of the mycobacterial cell wall. Res Microbiol 142:437–443
23. Nikaido H, Kim SH, Rosenberg EY (1993) Physical organization of lipids in the cell wall of Mycobacterium chelonae. Mol Microbiol 8:1025–1030
24. Piel G, Piette M, Barillaro V, Castagne D, Evrard B, Delattre L (2007) Study of the interaction between cyclodextrins and liposome membranes: effect on the permeability of liposomes. J Incl Phenom Macrocycl Chem 57:309–311
25. Puglisi G, Fresta M, Ventura CA (1996) Interaction of natural and modified β-cyclodextrins with a biological membrane model of dipalmitoylphosphatidylcholine. J Colloid Interf Sci 180:542–547
26. Qiu YZ, Huang ZH, Song FJ (2012) Enzymatic activity enhancement of non-covalent modified superoxide dismutase and molecular docking analysis. Molecules 17:3945–3956
27. Roglič U, Žnidaršič-Plazl P, Plazl I (2005) The influence of β-cyclodextrin on the kinetics of progesterone transformation by Rhizopus nigricans. Biocat Biotrans 23(5):299–305
28. Schmidt AK, Cottaz S, Driguez H, Schulz GE (1998) Structure of cyclodextrin glycosyltransferase complexed with a derivative of its main product β-cyclodextrin. Biochemistry-US 37:5909–5915
29. Shen YB, Wang M, Li HN, Wang YB, Luo JM (2012) Influence of hydroxypropyl-β-cyclodextrin on phytosterol biotransformation by different strains of Mycobacterium neoaurum. J Ind Microbiol Biot 39:1253–1259
30. Shen YB, Wang M, Zhang LT, Ma YH, Ma B, Zheng Y, Liu H, Luo JM (2011) Effects of hydroxypropyl-β-cyclodextrin on cell growth, activity, and integrity of steroid-transforming Arthrobacter simplex and Mycobacterium sp. Appl Microbiol Biot 90:1995–2003
31. Thurmond RL, Niemi AR, Lindblom G, Wieslander A, Rilfors L (1994) Membrane thickness and molecular ordering in Acholeplasma laidlawii strain A studied by 2H NMR spectroscopy. Biochemistry-US 33:13178–13188
32. Varona S, Martín Á, Cocero MJ (2011) Liposomal incorporation of lavandin essential oil by a thin-film hydration method and by particles from gas-saturated solutions. J Ind Eng Chem Res 50:2088–2097
33. Wieslander Å, Nordström S, Dahlqvist A, Rilfors L, Lindblom G (1995) Membrane lipid composition and cell size of Acholeplasma laidlawii strain A are strongly influenced by lipid acyl chain length. Eur J Biochem 227:734–744
34. Williamson MP, Le Gal-Coëffet MF, Sorimachi K, Furniss CS, Archer DB, Williamson G (1997) Function of conserved tryptophans in the Aspergillus niger glucoamylase 1 starch binding domain. Biochemistry-US 36:7535–7539
35. Xiong D, Gao Z, Fu B, Sun H, Tian S, Xiao Y, Qin Z (2013) Effect of pyrimorph on soil enzymatic activities and respiration. Eur J Soil Biol 56:44–48
36. Zidovetzki R, Levitan I (2007) Use of cyclodextrins to manipulate plasma membrane cholesterol content: evidence, misconceptions and control strategies. BBA-Biomembranes 1768:1311–1324