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Study on synthesis and bioactivity of biotinylated emodin

  • Biotechnological products and process engineering
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Abstract

A novel compound biotinylated emodin was synthesized by a two-step acyl chloride method which connects the biotin to emodin with esterification reaction. The product was characterized with ultraviolet–visible spectrophotometry, fourier transform infrared and high-performance liquid chromatography tandem mass spectrometry techniques. Its antibacterial activity against Staphylococcus aureus CMCC 26003 was investigated, and the emodin- and biotinylated emodin-caused antibacterial mechanism was proposed. It was shown that the product was isolated and activity of emodin was remained. These results indicated that our study provides a kind of chemosynthesis method under mild conditions and a strong molecular tool for investigating the emodin-binding protein.

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References

  • Belley A, Mckay GA, Arhin FF, Sarmiento I, Beaulieu S, Fadhil I, Parr TR, Moeck G (2010) Oritavancin disrupts membrane integrity of Staphylococcus aureus and vancomycin-resistant enterococci to effect rapid bacterial killing. Antimicrob Agents Ch 54(12):5369–5371. doi:10.1128/AAC.00760-10

    Article  CAS  Google Scholar 

  • Chen X, Xie S, Bhat S, Kumar N, Shapiro TA, Liu JO (2009) Fumagillin and fumarranol interact with P. falciparum methionine aminopeptidase 2 and inhibit malaria parasite growth in vitro and in vivo. Chem Biol 16(2):193–202. doi:10.1016/j.chembiol.2009.01.006

    Article  CAS  PubMed  Google Scholar 

  • Conrad PG, Givens RS, Weber JFW, Kandler K (2000) New Phototriggers: 1 extending the, p -Hydroxyphenacyl π−π* absorption range. Org Lett 2(11):1545–1547

    Article  CAS  PubMed  Google Scholar 

  • Cunha ARD, Duarte EL, Lamy MT, Coutinho K (2014) Protonation/deprotonation process of emodin in aqueous solution and pKa determination: UV/Visible spectrophotometric titration and quantum/molecular mechanics calculations. Chem Phys 440(28):69–79

    Article  Google Scholar 

  • Dan L, Liu S, Shen Y, Yang J, He Y (2015) Molecular spectroscopic studies on the interactions of rhein and emodin with thioglycolic acid-capped core/shell CdTe/CdS quantum dots and their analytical applications. Luminescence 30(1):60–66. doi:10.1002/bio.2690

    Article  Google Scholar 

  • Ghantous A, Saikali M, Rau T, Gali-Muhtasib H, Schneider-Stock R, Darwiche N (2012) Inhibition of tumor promotion by parthenolide: epigenetic modulation of p21. Cancer Prev Res 5(11):1298–1309. doi:10.1158/1940-6207

    Article  CAS  Google Scholar 

  • Gong J, Cui XJ, Chen YG, Xie ZW, Qu LY (2004) UV-Vis spectra of N, N′-bis (4′-aminophenyl)-1, 4-quinonenediimine doped with H4SiW12O40. Macromol Res 12(1):22–25

    Article  CAS  Google Scholar 

  • Khan I, Saeed A, Arshad MI, White JM (2016) Antimicrobial profile of some novel keto esters: synthesis, crystal structures and structure-activity relationship studies. Pak J Pharm Sci 29(1):39–49

    CAS  PubMed  Google Scholar 

  • Kim YS, Gu MB (2014) Advances in aptamer screening and small molecule aptasensors. Adv Biochem Eng biot 140:29–67. doi:10.1007/10_2013_225

    CAS  Google Scholar 

  • Lai MY, Hour MJ, Wingcheung LH, Yang WH, Lee HZ (2007) Chaperones are the target in aloe-emodin-induced human lung nonsmall carcinoma H460 cell apoptosis. Eur J Pharmacol 573(1–3):1–10

    Article  CAS  PubMed  Google Scholar 

  • Lee YS, Kang OH, Choi JG, Oh YC, Keum JH, Kim SB, Jeong GS, Kim YC, Shin DW, Kwon DY (2010) Synergistic effect of emodin in combination with ampicillin or oxacillin against methicillin-resistant Staphylococcus aureus. Pharm Biol 48(11):1285–1290. doi:10.3109/13880201003770150

    Article  CAS  PubMed  Google Scholar 

  • Lindenmeyer MT, Hrenn A, Kern C, Castro V, Murillo R, Müller S, Laufer S, Schulte-Mönting J, Siedle B, Merfort I (2006) Sesquiterpene lactones as inhibitors of IL-8 expression in HeLa cells. Bioorgan Med Chem 14(8):2487–2497. doi:10.1016/j.bmc.2005.11.027

    Article  CAS  Google Scholar 

  • Liu M, Peng W, Qin R, Yan Z, Cen Y, Zheng X, Pan X, Jiang W, Li B, Li X (2015) The direct anti-MRSA effect of emodin via damaging cell membrane. Appl Microbiol and Biot 99(18):7699–7709. doi:10.1007/s00253-015-6657-3

    Article  CAS  Google Scholar 

  • Long EC, Barton JK (1990) On demonstrating DNA intercalation. Accounts Chem Res 23(9):271–273. doi:10.1021/ar00177a001

    Article  CAS  Google Scholar 

  • Pan CJ, Jin W, Nan H (2010) Preparation, characterization and in vitro anticoagulation of emodin-eluting controlled biodegradable stent coatings. Colloid Surface B 77(2):155–160. doi:10.1016/j.colsurfb.2010.01.019

    Article  CAS  Google Scholar 

  • Park GD, Lee JH, Lee JK, Kang YC (2014) Effect of esterification reaction of citric acid and ethylene glycol on the formation of multi-shelled cobalt oxide powders with superior electrochemical properties. Nano Res 7(12):1738–1748

    Article  CAS  Google Scholar 

  • Ropartz L, Meeuwenoord NJ, Marel GAVD, Leeuwen PWNMV, Slawin AMZ, Kamer PCJ (2007) Phosphine containing oligonucleotides for the development of metallodeoxyribozymes. Chem Commun 38(15):1556–1558. doi:10.1039/b617871e

    Article  Google Scholar 

  • Saito ST, Silva G, Pungartnik C, Brendel M (2012) Study of DNA-emodin interaction by FTIR and UV-vis spectroscopy. J Photoch Photobio B 111(11):59–63. doi:10.1016/j.jphotobiol.2012.03.012

    Article  CAS  Google Scholar 

  • Schülke JP, McAllister LA, Geoghegan KF, Parikh V, Chappie TA, Verhoest PR, Schmidt CJ, Johnson DS, Brandon NJ (2014) Chemoproteomics demonstrates target engagement and exquisite selectivity of the clinical phosphodiesterase 10A inhibitor MP-10 in its native environment. ACS Chem Biol 9(12):2823–2832. doi:10.1021/cb500671j

    Article  PubMed  Google Scholar 

  • Shan B, Cai YZ, Johnd B, Harold C (2008) Antibacterial properties of Polygonum cuspidatum roots and their major bioactive constituents. Food Chem 109(3):530–537

    Article  CAS  Google Scholar 

  • Stroes-Gascoyne S, Schippers A, Schwyn B, Poulain S, Sergeant C, Simonoff M, Marrec CL, Altmann S, Nagaoka T, Mauclaire L (2007) Microbial community analysis of Opalinus clay drill core samples from the Mont Terri underground research laboratory, Switzerland. Geomicrobiol J 24(1):1–17

    Article  CAS  Google Scholar 

  • Su YT, Chang HL, Shyue SK, Hsu SL (2005) Emodin induces apoptosis in human lung adenocarcinoma cells through a reactive oxygen species-dependent mitochondrial signaling pathway. Biochem Pharmacol 70(2):229–241. doi:10.1016/j.bcp.2005.04.026

    Article  CAS  PubMed  Google Scholar 

  • Sui JQ, Xie KP, Zou W, Xie MJ (2014) Emodin inhibits breast cancer cell proliferation through the ERα-MAPK/Akt-cyclin D1/Bcl-2 signaling pathway. Asian Pac J Cancer P 15(15):6247–6251

    Article  Google Scholar 

  • Tenover FC (2006) Mechanisms of antimicrobial resistance in bacteria. Am J Infection Control 199(6):S3–S10. doi:10.1016/j.ajic.2006.05.219

  • Wang Z, Hsieh TC, Zhang Z, Ma Y, Wu JM (2004) Identification and purification of resveratrol targeting proteins using immobilized resveratrol affinity chromatography. Biochem Bioph Res Co 323(3):743–749. doi:10.1016/j.bbrc.2004.08.174

    Article  CAS  Google Scholar 

  • Wang H, Zou D, Xie K, Xie M (2014) Antibacterial mechanism of fraxetin against Staphylococcus aureus. Mol Med Rep 10(5):2341–2345. doi:10.3892/mmr.2014.2529

    CAS  PubMed  PubMed Central  Google Scholar 

  • Xu J, Feng S, Wang Q, Cao Y, Sun M, Zhang C (2014) Four new furostanol saponins from the rhizomes and roots of Smilax scobinicaulis and their cytotoxicity. Molecules 19(12):20975–20987. doi:10.3390/molecules191220975

    Article  PubMed  Google Scholar 

  • Zempleni J, Wijeratne SSK, Hassan YI (2009) Biotin. Biofactors 35(1):36–46

    Article  PubMed  PubMed Central  Google Scholar 

  • Zhang L, Wang XJ, Wang J, Grinberg N, Krishnamurthy DK, Senanayake CH (2009) An improved method of amide synthesis using acyl chlorides. Tetrahedron Lette 50(24):2964–2966

    Article  CAS  Google Scholar 

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Acknowledgment

This work was supported by scientific research projects of the Inner Mongolia higher educational system (NJZY095).

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Authors and Affiliations

  1. College of Chemical Engineering, Inner Mongolia University of Technology, Hohhot, 010051, China

    Xueli Hou, Yunyun Fan, Jianbin Zhang, Ning Zhu, Hailong Hong & Cuiyan Wang

  2. Tongwei Food and Drug Administration, Gansu, 743300, China

    Wenqiang Wei

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  1. Xueli Hou
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  2. Wenqiang Wei
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  3. Yunyun Fan
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  4. Jianbin Zhang
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  5. Ning Zhu
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Correspondence to Cuiyan Wang.

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The article does not contain any studies with human participants performed by any of the authors.

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Hou, X., Wei, W., Fan, Y. et al. Study on synthesis and bioactivity of biotinylated emodin. Appl Microbiol Biotechnol 101, 5259–5266 (2017). https://doi.org/10.1007/s00253-017-8243-3

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  • DOI: https://doi.org/10.1007/s00253-017-8243-3

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