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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE (Open Access)

Effects of Different Phases of Cigarette Smoke on Lipid Peroxidation and Membrane Structure in Liposomes

Nadezhda P. Palmina A , Elena L. Maltseva A , Tatyana E. Chasovskaya A , Valery V. Kasparov A , Nataliya G. Bogdanova A , Valery A. Menshov A and Aleksei V. Trofimov A B
+ Author Affiliations
- Author Affiliations

A Emanuel Institute of Biochemical Physics, RAS, Kosygin str. 4, 119334 Moscow, Russia.

B Corresponding author. Email: avt_2003@mail.ru

Australian Journal of Chemistry 67(6) 858-866 https://doi.org/10.1071/CH13663
Submitted: 30 November 2013  Accepted: 21 January 2014   Published: 24 February 2014

Abstract

This paper discloses for the first time the effects of the gas phase (GP) and the tar of cigarette smoke on lipid peroxidation (LPO) and on the structure of different lipid regions in liposomes. The LPO development was analysed in terms of the total unsaturation of lipids (double-bond, DB, content) and the formation of dienic conjugates (DC), ketodienes (KD), and malonic dialdehyde (MDA). As expected, the exposure of liposomes to either the GP or the tar led to a significant decrease in the DB content. However, the formation of oxidation products revealed different dynamics: MDA generation was inhibited, while the formation of DC and KD increased during the first few hours of the LPO development followed by its inhibition. The smoke constituents exhibited opposite effects on the structure of the lipid bilayer of liposomes: the GP markedly enhanced the microviscosity of liposomal membranes, whereas the tar caused a drastic lowering of microviscosity.


References

[1]  H. Sies, D. P. Jones, in Encyclopaedia of Stress (Ed. G. Fink) 2007, pp. 45–48 (Elsevier: San Diego, CA).

[2]  I. M. Fearon, S. P. Faux, J. Mol. Cell. Cardiol. 2009, 47, 372.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXptVegsbY%3D&md5=8580127d217ab3fafd2fbcfee3384250CAS | 19481547PubMed |

[3]  B. Epe, P. Mützel, W. Adam, Chem. Biol. Interact. 1988, 67, 149.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXitlCm&md5=6d52565463c7329a934c97571ea4ae6fCAS | 2844422PubMed |

[4]  W. Adam, G. H. Grimm, C. R. Saha-Möller, F. Dall’Acqua, G. Miolo, D. Vedaldi, Chem. Res. Toxicol. 1998, 11, 1089.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXltlyhsbo%3D&md5=e172a7557a04cb7d32e8e430fcbefb10CAS | 9760284PubMed |

[5]  H.-C. Mahler, I. Schulz, W. Adam, G. H. Grimm, C. R. Saha-Möller, B. Epe, Mutat. Res. 2001, 461, 289.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXosFCgsrc%3D&md5=92a4fe719b389d6fb7c8c1d7c030b904CAS | 11104905PubMed |

[6]  D. Thorne, J. Wilson, T. S. Kumaravel, E. D. Massey, M. McEwan, Mutat. Res. 2009, 673, 3.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtlSktLc%3D&md5=bf6fcc49253c018da2575ba242f91056CAS | 19100859PubMed |

[7]  E. Passowicz-Muszyńska, A. Gostkowska-Malec, R. Jankowska, P. Piesiak, Pneumonol. Alergol. Pol. 2010, 78, 28.
         | 20162516PubMed |

[8]  R. Goralczyk, Nutr. Cancer 2009, 61, 767.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjsVOgsw%3D%3D&md5=c6c365adcb8ba22df86cc7c0af518288CAS | 20155614PubMed |

[9]  I. Horváth, Z. Lázár, N. Gyulai, M. Kollai, G. Losonczy, Eur. Respir. J. 2009, 34, 261.
         | Crossref | GoogleScholarGoogle Scholar | 19567608PubMed |

[10]  G. Lee, T. C. Walser, S. M. Dubinett, Curr. Opin. Pulm. Med. 2009, 15, 303.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXmslyitL0%3D&md5=7b336db3cd1281b8729dade557f95b6aCAS | 19417670PubMed |

[11]  P. Balakumar, J. Kaur, Pharmacol. Res. 2009, 60, 361.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtFSnsrrO&md5=1ec080fa2d8bd7947a69e8cf4f874e2bCAS | 19559087PubMed |

[12]  A. N. Thorndike, N. A. Rigotti, Curr. Opin. Cardiol. 2009, 24, 447.
         | Crossref | GoogleScholarGoogle Scholar | 19550307PubMed |

[13]  S. S. Hecht, F. Kassie, D. K. Hatsukami, Nat. Rev. Cancer 2009, 9, 476.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXnsFyntb4%3D&md5=1acc4b7c552e0d56fb66937d0cd084afCAS | 19550424PubMed |

[14]  A. Catassi, D. Servent, L. Paleari, A. Cesario, P. Russo, Mutat. Res. 2008, 659, 221.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtVKiur7P&md5=e49de28b020cb1b7459db23818b58318CAS | 18495523PubMed |

[15]  S. P. Faux, T. Tai, D. Thorne, Y. Xu, D. Breheny, M. Gaça, Biomarkers 2009, 14, 90.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtFehsb7F&md5=e780637e03107a76855bd1ccfeed63e7CAS | 19604067PubMed |

[16]  W. A. Pryor, Environ. Health Perspect. 1997, 105, 875.
         | 1:CAS:528:DyaK2sXls1els78%3D&md5=fbe0151517e779a0391491ba7a802d57CAS | 9255574PubMed |

[17]  D. F. Church, W. A. Pryor, Environ. Health Perspect. 1985, 64, 111.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28Xht1ChtLg%3D&md5=18c1a156945f0cc5bb33b86f75b33788CAS | 3007083PubMed |

[18]  B. Halliwell, C. E. Cross, Environ. Health Perspect. 1994, 102, 5.
         | 1:CAS:528:DyaK2MXjsVaisLg%3D&md5=e60c57e2556bd9adf64d02a1679b1b3bCAS | 7705305PubMed |

[19]  P. Kovacic, R. Somanathan, Rev. Environ. Contam. Toxicol. 2009, 201, 41.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXos1yitb8%3D&md5=c1d89ad727d9fb009fcd255db992313eCAS | 19484588PubMed |

[20]  V. L. Kinnula, K. Vuorinen, H. Ilumets, P. Rytilä, M. Myllärniemi, Curr. Med. Chem. 2007, 14, 213.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXitlamsr4%3D&md5=f940bb316c07f1b9a41ef4d0a6158b09CAS | 17266580PubMed |

[21]  R. A. Floyd, J. E. Schneider, in Membrane Lipid Oxidation (Ed. C. Vigo-Pelfrey) 1991, Vol. 3, pp. 69–85 (CRC Press: Boca Raton, FL).

[22]  I. Rahman, Cell Biochem. Biophys. 2005, 43, 167.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXpsFCgtbc%3D&md5=b070e195227e87c9b2f7351401eaa13eCAS | 16043892PubMed |

[23]  H. van der Vaart, D. S. Postma, W. Timens, N. H. Ten Hacken, Thorax 2004, 59, 713.
         | Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DC%2BD2cznvFCltA%3D%3D&md5=74086ba5a6a07aacd40ac9f6f212e6b4CAS | 15282395PubMed |

[24]  D. Hoffmann, S. S. Hech, in Chemical Cagcinogenesis and Mutagenesis (Eds C. S. Cooper, P. L. Grover) 1989, pp. 64–102 (Springer: New York, NY).

[25]  S. Chouchane, J. B. Wooten, F. J. Tewes, A. Wittig, B. P. Muller, Chem. Res. Toxicol. 2006, 19, 1602.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtlCitbzK&md5=78e474ee43b15b6a5b28f329b08097b9CAS | 17173373PubMed |

[26]  W. A. Pryor, Science 1983, 220, 425.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3sXhvFehsro%3D&md5=fb87fb6ce841bafa2e9510c649471122CAS | 6301009PubMed |

[27]  M. Culcasi, A. Muller, A. Mercier, J.-L. Clement, O. Payet, A. Rockenbauer, V. Marchand, S. Pietri, Chem. Biol. Interact. 2006, 164, 215.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xht1Ciu7jK&md5=d0255346c16524b584c90cc106851fdaCAS | 17083924PubMed |

[28]  F. Yan, S. Williams, G. D. Griffin, R. Jagannathan, S. E. Plunkett, K. H. Shafer, T. Vo-Dinh, J. Environ. Monit. 2005, 7, 681.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXlsF2ht7c%3D&md5=c986eb45a3c507ece4648e3cbc76b48dCAS | 15986047PubMed |

[29]  V. A. Menshov, A. V. Trofimov, Mini Rev. Org. Chem. 2011, 8, 394.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtlyitLfI&md5=506be35b7662f720a36bed20f4c7f728CAS |

[30]  R. R. Baker, in Tobacco Production, Chemistry and Technology (Eds D. L. Davis, M. T. Nielsen) 1999, pp. 398–439 (Blackwell Science Ltd: Oxford).

[31]  V. B. O’Donnell, P. H. Chumley, N. Hogg, A. Bloodsworth, V. M. Darley-Usmar, B. A. Freeman, Biochemistry 1997, 36, 15216.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXntlCltbs%3D&md5=6718e3c5c56a8cadfa7e10bd1c7e54c3CAS | 9398249PubMed |

[32]  N. Hogg, B. Kalyanaraman, Biochim. Biophys. Acta 1999, 1411, 378.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXjsF2qt74%3D&md5=f16dcc539ea1412ee0afb0cd40757967CAS | 10320670PubMed |

[33]  G. Cighetti, P. Allevi, S. Debiasi, R. Paroni, Chem. Phys. Lipids 1997, 88, 97.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXlvVKmur4%3D&md5=c85bd96c98f599f688030ce7a3584319CAS | 9314187PubMed |

[34]  S. Shimakawa, Y. Yoshida, E. Niki, Lipids 2003, 38, 225.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXjvFOrtb8%3D&md5=a3ffb4a55ab5049e75c65d377c3193f5CAS | 12784862PubMed |

[35]  H. H. Seliger, W. H. Biggley, J. P. Hamman, Science 1974, 185, 253.
         | Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DyaE2c3lslyjtA%3D%3D&md5=fbb0645729c63c8db54ba71cfd8d7b84CAS | 4833826PubMed |

[36]  G. F. Fedorova, V. A. Menshov, A. V. Trofimov, Yu. B. Tsaplev, R. F. Vasil’ev, Luminescence 2010, 25, 130.

[37]  Chemical and Biological Generation of Excited States (Eds W. Adam, G. Cilento) 1982 (Academic Press: New York, NY).

[38]  G. Cilento, W. Adam, Free Radic. Biol. Med. 1995, 19, 103.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXlvVagtrg%3D&md5=62fcc2c6717d0c7d661b21001c5ad3afCAS | 7635351PubMed |

[39]  W. Adam, J. Hartung, H. Okamoto, C. R. Saha-Möller, K. Spehar, Photochem. Photobiol. 2000, 72, 619.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXosVKitbs%3D&md5=9aa3e9f726149e388c660675e9fba73aCAS | 11107846PubMed |

[40]  C. Bohne, K. Faulhaber, B. Giese, A. Häfner, A. Hofmann, H. Ihmels, S. Köhler, A.-K. Perä, F. Schneider, M. A. L. Sheepwash, J. Am. Chem. Soc. 2005, 127, 76.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVKrsrfN&md5=a428883bba25fff47b69020e493bfd8cCAS | 15631456PubMed |

[41]  E. B. Burlakova, N. P. Pal’mina, E. L. Mal’tseva, in Membrane Lipid Oxidation (Ed. C. Vigo-Pelfrey) 1991, Vol. 3, pp. 209–238 (CRC Press: Boca Raton, FL).

[42]  V. E. Kagan, Lipid Peroxidation in Biomembranes 1988 (CRC Press: Boca Raton, FL).

[43]  R. J. Schaur, H. Zollner, H. Esterbauer, in Membrane Lipid Oxidation (Ed. C. Vigo-Pelfrey) 1991, Vol. 3, pp. 141–164 (CRC Press: Boca Raton, FL).

[44]  J. Lykkesfeldt, Clin. Chim. Acta 2007, 380, 50.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXjslSks74%3D&md5=c512a1623b27bd560650f949f7363709CAS | 17336279PubMed |

[45]  M. Guichardant, M. Lagarde, Eur. J. Lipid Sci. Technol. 2009, 111, 75.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXitV2qsbY%3D&md5=f4f977bd1104b039fd69a2f7bd0da6c9CAS |

[46]  A. N. Cimato, L. L. Piehl, G. B. Facorro, H. B. Torti, A. A. Hager, Free Radic. Biol. Med. 2004, 37, 2042.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXpslyisr0%3D&md5=509e5a2cb22403809bb84acebf7a5424CAS | 15544922PubMed |

[47]  T. Ohyashiki, A. Kadova, K. Kushida, Chem. Pharm. Bull. (Tokyo) 2002, 50, 203.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xks12ktbc%3D&md5=6f564e650571a2144953b2717c975791CAS | 11848210PubMed |

[48]  R. Klein, Biochim. Biophys. Acta 1970, 210, 486.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3MXhtVaksg%3D%3D&md5=c14f41c8792a050f478425c6d9ddebf8CAS | 5528599PubMed |

[49]  N. L. Parinandi, B. K. Weis, W. Natarajan, H. H. Schmid, Arch. Biochem. Biophys. 1990, 280, 45.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXkt1Wlsbs%3D&md5=20923b04be97e872413a2d06af2140a8CAS | 2353824PubMed |

[50]  Methods in Enzymology (Eds S. Fleisher, L. Packer) 1978 (Academic Press: New York, NY).

[51]  D. M. Lisitsyn, S. D. Razumovskii, M. A. Tishenin, V. N. Titov, Bull. Exp. Biol. Med. 2004, 138, 457.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXitlOjsb0%3D&md5=cf58aa5bed559f90a3025ad0bea7d7d0CAS | 15723125PubMed |

[52]  Spin Labeling: Theory and Application (Ed. L. J. Berliner) 1979 (Academic Press: New York, NY).

[53]  M. Abe, Chem. Rev. 2013, 113, 7011.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtFKgurvP&md5=4c0d2ccecdaa3251315379dd66f5a921CAS | 23883325PubMed |

[54]  E. I. Pinzar, N. P. Palmina, Membr. Cell Biol. 1998, 12, 241.
         | 1:STN:280:DyaK1M%2FpsFKhsg%3D%3D&md5=d81a421b9547065be780ec56a8246b03CAS | 9879547PubMed |

[55]  L. Xu, T. A. Davis, N. A. Porter, J. Am. Chem. Soc. 2009, 131, 13037.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtVCgt7zI&md5=60fd0b61ea02419c49eda44ff8bf9e7dCAS | 19705847PubMed |

[56]  R. S. Sargis, P. V. Subbaiah, Biochemistry 2003, 42, 11533.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXnt1Klsrk%3D&md5=b696e47b8c69667e7debb63fa0c189cbCAS |

[57]  M. Araseki, K. Yamamoto, K. Miyashita, Biosci. Biotechnol. Biochem. 2002, 66, 2573.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXht1Gqsg%3D%3D&md5=26aa378f8e6f9b6f0bc2fa93543f773aCAS | 12596850PubMed |

[58]  C. Bailly, J. C. Beauvillain, J. L. Bernier, J. P. Henichart, Cancer Res. 1990, 50, 385.
         | 1:CAS:528:DyaK3cXmvFGksg%3D%3D&md5=4fbcd3d8ad8bf9142341eb1cf5fee946CAS | 1688511PubMed |

[59]  H. Watanabe, A. Kobayashi, T. Yamamoto, S. Suzuki, H. Hayashi, N. Yamazaki, Free Radic. Biol. Med. 1990, 8, 507.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXkvVOjsrw%3D&md5=a7b7350eecb0ded86c86af31befcb026CAS | 2163349PubMed |

[60]  P. Jost, L. J. Libertini, V. C. Hebert, O. H. Griffith, J. Mol. Biol. 1971, 59, 77.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3MXkvVChu74%3D&md5=d24b3e6676ebeed772ebceac10f9c871CAS | 4326898PubMed |

[61]  D. Man, M. Podolak, G. Engel, Cell. Mol. Biol. Lett. 2006, 11, 56.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xht1OisrzI&md5=f56f580c9b3bb75dccaff8def89ceef0CAS | 16847748PubMed |

[62]  G. Facorro, F. Aguirre, L. Florentin, M. Diaz, T. De Paoli, J. E. Ihlo, A. A. Hager, J. C. Sanchez Avalos, H. A. Farach, C. P. Poole Jr, Acta Physiol. Pharmacol. Ther. Latinoam. 1997, 47, 137.
         | 1:STN:280:DyaK2svotVGksA%3D%3D&md5=d51af432d81a835d8ad7e9811d534e28CAS | 9339243PubMed |

[63]  P. G. Shields, J. Natl. Cancer Inst. 2002, 94, 1435.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XosVans7s%3D&md5=69e0de2094ceb57c1d7efe2ddeb28956CAS | 12359853PubMed |

[64]  W. MacNee, Chest 2000, 117, 303S.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXjvFSgsr4%3D&md5=de1feeccafef24a2a5d95791c2c2df9bCAS | 10843965PubMed |

[65]  R. S. Bruno, M. G. Traber, Pathophysiology 2006, 13, 143.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XmslyqtLw%3D&md5=9979d677cc7cb318fd98c308111d6ce1CAS | 16814530PubMed |

[66]  M. Malerba, B. Ragnoli, M. Corradi, Monaldi Arch. Chest Dis. 2008, 69, 28.

[67]  N. Louhelainen, M. Nyllarniem, I. Rahman, V. L. Kinnula, Int. J. COPD 2008, 3, 585.
         | 1:CAS:528:DC%2BD1MXjt1ChtLg%3D&md5=74bad31987cf5dd20d27747f60a4e7f9CAS |

[68]  S. E. Hannan, J. O. Harris, N. P. Sheridan, J. M. Patel, Am. Rev. Respir. Dis. 1989, 140, 1668.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXnt1WhsA%3D%3D&md5=e64d49116d139301cb34015fea440a90CAS | 2604295PubMed |

[69]  D. L. Baker, E. S. Krol, N. Jacobsen, D. C. Lieble, Chem. Res. Toxicol. 1999, 12, 535.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXjtVyisLc%3D&md5=2052dc2cc7f174863bb710d3d06e8f4aCAS | 10368317PubMed |

[70]  W. A. Pryor, S. K. Nuggehalli, K. V. Scherer, D. F. Church, Chem. Res. Toxicol. 1990, 3, 2.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXptlaqsw%3D%3D&md5=56b689e87597c4481a429210d2c8e716CAS | 1966699PubMed |

[71]  M. B. Newman, G. W. Arendash, R. D. Shytle, P. C. Bickford, T. Tighe, P. R. Sanberg, Life Sci. 2002, 71, 2807.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xns1SitLk%3D&md5=dbf5e966ed588b6988a951a99f0ac962CAS | 12377264PubMed |

[72]  E. Florek, E. Ignatowicz, J. Wrzosek, W. Piekoszewski, Pharmacol. Rep. 2005, 57, 84.
         | 1:CAS:528:DC%2BD2MXnsl2qtr0%3D&md5=a7ecf84649dfa869766830d17b73e4d3CAS | 15849381PubMed |

[73]  E. Florek, E. Ignatowicz, W. Piekoszewski, Pharmacol. Rep. 2009, 61, 935.
         | 1:CAS:528:DC%2BC3cXitFKnu7k%3D&md5=fe0879237d5d9fccf3df6e8ede035280CAS | 19904019PubMed |

[74]  B. Zappacosta, S. Persichilli, B. Giardina, P. De Sole, Luminescence 2000, 15, 165.
         | Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DC%2BD3czos1SmtA%3D%3D&md5=35cf6287ef7cc5aa0d76740c34eb5ab5CAS | 10862145PubMed |