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References

  1. Cheng H, Cao X, Xian M, Fang L, Cai TB, Ji JJ, et al. 2005. Synthesis and enzyme-specific activation of carbohydrategeldanamycin conjugates with potent anticancer activity. J. Med. Chem. 48: 645-652.
    Pubmed CrossRef
  2. DeBoer C, Meulman PA, Wnuk RJ, Peterson DH. 1970. Geldanamycin, a new antibiotic. J. Antibiot. (Tokyo) 23: 442-447.
    CrossRef
  3. Dhakal D, Le TT, Pandey RP, Jha AK, Gurung R, Parajuli P, et al. 2015. Enhanced production of nargenicin A1 and generation of novel glycoslated derivatives. Appl. Biochem. Biotechnol. 175: 2934-2949.
    Pubmed CrossRef
  4. Elshahawi SI, Shaaban KA, Kharel MK, Thorson JS. 2015. A comprehensive review of glycosylated bacterial natural products. Chem. Soc. Rev. DOI: 10.1039/c4cs00426d.
    CrossRef
  5. Fukuyo Y, Hunt CR, Horikoshi N. 2009. Geldanamycin and its anti-cancer activities. Cancer Lett. 290: 24-35.
    Pubmed CrossRef
  6. Hong YS, Lee D, Kim W, Jeong JK, Kim CG, Sohng JK, et al. 2004. Inactivation of the carbamoyltransferase gene refines post-polyketide synthase modification steps in the biosynthesis of the antitumor agent geldanamycin. J. Am. Chem. Soc. 126:11142-11143.
    Pubmed CrossRef
  7. Kim W, Lee D, Hong SS, Na Z, Shin JC, Roh SH, et al. 2009. Rational biosynthetic engineering for optimization of geldanamycin analogues. ChemBioChem 10: 1243-1251.
    Pubmed CrossRef
  8. Kim W, Lee JS, Lee D, Cai XF, Shin JC, Lee K, et al. 2007. Mutasynthesis of geldanamycin by the disruption of gene producing starter unit: generation of structural diversity at the benzoquinone ring. ChemBioChem 8: 1491-1494.
    Pubmed CrossRef
  9. Lee D, Lee K, Cai XF, Dat NT, Boovanahalli SK, Lee M, et al. 2006. Biosynthesis of the heat-shock protein 90 inhibitor geldanamycin: new insight into the formation of the benzoquinone moiety. ChemBioChem 7: 246-248.
    Pubmed CrossRef
  10. Lee K, Ryu JS, Jin Y, Kim W, Kaur N, Chung SJ, et al. 2008. Synthesis and anticancer activity of geldanamycin derivatives derived from biosynthetically generated mebabolites. Org. Biomol. Chem. 6: 340-348.
    Pubmed CrossRef
  11. Pandey RP, Gurung RB, Parajuli PP, Koirala N, Tuoi LT, Sohng JK. 2014. Assessing acceptor substrate promiscuity of YjiC-mediated glycosylation toward flavonoids. Carbohydr. Res. 393: 26-31.
    Pubmed CrossRef
  12. Pandey RP, Parajuli P, Shin JY, Lee J, Lee S, Hong YS, et al. 2014. Enzymatic biosynthesis of novel resveratrol glucoside and glycoside derivatives. Appl. Environ. Microbiol. 80: 72357243.
    Pubmed PMC CrossRef
  13. Schulte TW, Neckers LM. 1998. The benzoquinone ansamycin 17-allylamino-17-demethoxy geldanamycin binds to HSP90 and shares important biologic activities with geldanamycin. Cancer Chemother. Pharmacol. 42: 273-279.
    Pubmed CrossRef
  14. Singh S, Phillips GJ, Thorson JS. 2012. The structural biology of enzymes involved in natural product glycosylation. Nat. Prod. Rep. 29: 1201-1237.
    Pubmed PMC CrossRef
  15. Solárová Z, Mojžiš J, Solár P. 2015. Hsp90 inhibitor as a sensitizer of cancer cells to different therapies. Int. J. Oncol. 46: 907-926.
    Pubmed
  16. Supko JG, Hickman RL, Grever MR, Malspeis L. 1995. Preclinical pharmacologic evaluation of geldanamycin as an antitumor agent. Cancer Chemother. Pharmacol. 36: 305-315.
    Pubmed CrossRef
  17. Whitesell L, Mimnaugh EG, Costa BD, Myers CE, Neckers LM. 1994. Inhibition of heat shock protein HSP90-pp60v-src heteroprotein complex formation by benzoquinone ansamycins:essential role for stress proteins in oncogenic transformation. Proc. Natl. Acad. Sci. USA 91: 8324-8328.
    Pubmed PMC CrossRef
  18. Wu CZ, Jang JH, Woo MH, Ahn JS, Kim JS, Hong YS. 2012. Enzymatic glycosylation of non benzoquinone geldanamycin analogs via Bacillus UDP-glycosyltransferase. Appl. Environ. Microbiol. 78: 7680-7686.
    Pubmed PMC CrossRef
  19. Yang L, Wang Z, Lei H, Chen R, Wang X, Peng Y, Dai J. 2014. Neuroprotective glucosides of magnolol and honokiol from microbial-specific glycosylation. Tetrahedron 70: 8244-8251.
    CrossRef

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Article

Note

J. Microbiol. Biotechnol. 2016; 26(1): 56-60

Published online January 28, 2016 https://doi.org/10.4014/jmb.1508.08069

Copyright © The Korean Society for Microbiology and Biotechnology.

Biosynthesis of Novel Glucosides Geldanamycin Analogs by Enzymatic Synthesis

Qiang Huo 1, Hong-Mei Li 1, Jae Kyoung Lee 2, Jing Li 1, Tao Ma 1, Xinyu Zhang 1, Yiqun Dai 1, Young-Soo Hong 2 and Cheng-Zhu Wu 1*

1Faculty of Pharmacy, Bengbu Medical College, Bengbu, Anhui 233030, P.R. China, 2Chemical Biology Research Center, KRIBB, Cheongju 28116, Republic of Korea

Received: August 24, 2015; Accepted: October 9, 2015

Abstract

Two new glucosides (1 and 2) of geldanamycin (GA) analogs were obtained from in vitro
glycosylation by UDP-glycosyltransferase (YjiC). Based on spectroscopic (HR-ESI-MS, 1D, and
2D-NMR) analyses, the glucosides were elucidated as 4,5-dihydro-7-O-descarbamoyl-7-
hydroxyl GA-7-O-β-D-glucoside (1) and ACDL3172-18-O-β-D-glucoside (2). Furthermore, the
water solubility of compounds 1 and 2 was about 215.2 and 90.7 times higher respectively,
than that of the substrates. Among compounds 1-4, only 3 showed weak antiproliferative
activity against four human tumor cell lines: MDA-MB-231, SMMC7721, HepG2, and SW480
(IC50: 13.6, 15.1, 31.8, and 22.7 μM, respectively).

Keywords: Geldanamycin analogs, glycosyltransferase, water-solubility, cytotoxicity

References

  1. Cheng H, Cao X, Xian M, Fang L, Cai TB, Ji JJ, et al. 2005. Synthesis and enzyme-specific activation of carbohydrategeldanamycin conjugates with potent anticancer activity. J. Med. Chem. 48: 645-652.
    Pubmed CrossRef
  2. DeBoer C, Meulman PA, Wnuk RJ, Peterson DH. 1970. Geldanamycin, a new antibiotic. J. Antibiot. (Tokyo) 23: 442-447.
    CrossRef
  3. Dhakal D, Le TT, Pandey RP, Jha AK, Gurung R, Parajuli P, et al. 2015. Enhanced production of nargenicin A1 and generation of novel glycoslated derivatives. Appl. Biochem. Biotechnol. 175: 2934-2949.
    Pubmed CrossRef
  4. Elshahawi SI, Shaaban KA, Kharel MK, Thorson JS. 2015. A comprehensive review of glycosylated bacterial natural products. Chem. Soc. Rev. DOI: 10.1039/c4cs00426d.
    CrossRef
  5. Fukuyo Y, Hunt CR, Horikoshi N. 2009. Geldanamycin and its anti-cancer activities. Cancer Lett. 290: 24-35.
    Pubmed CrossRef
  6. Hong YS, Lee D, Kim W, Jeong JK, Kim CG, Sohng JK, et al. 2004. Inactivation of the carbamoyltransferase gene refines post-polyketide synthase modification steps in the biosynthesis of the antitumor agent geldanamycin. J. Am. Chem. Soc. 126:11142-11143.
    Pubmed CrossRef
  7. Kim W, Lee D, Hong SS, Na Z, Shin JC, Roh SH, et al. 2009. Rational biosynthetic engineering for optimization of geldanamycin analogues. ChemBioChem 10: 1243-1251.
    Pubmed CrossRef
  8. Kim W, Lee JS, Lee D, Cai XF, Shin JC, Lee K, et al. 2007. Mutasynthesis of geldanamycin by the disruption of gene producing starter unit: generation of structural diversity at the benzoquinone ring. ChemBioChem 8: 1491-1494.
    Pubmed CrossRef
  9. Lee D, Lee K, Cai XF, Dat NT, Boovanahalli SK, Lee M, et al. 2006. Biosynthesis of the heat-shock protein 90 inhibitor geldanamycin: new insight into the formation of the benzoquinone moiety. ChemBioChem 7: 246-248.
    Pubmed CrossRef
  10. Lee K, Ryu JS, Jin Y, Kim W, Kaur N, Chung SJ, et al. 2008. Synthesis and anticancer activity of geldanamycin derivatives derived from biosynthetically generated mebabolites. Org. Biomol. Chem. 6: 340-348.
    Pubmed CrossRef
  11. Pandey RP, Gurung RB, Parajuli PP, Koirala N, Tuoi LT, Sohng JK. 2014. Assessing acceptor substrate promiscuity of YjiC-mediated glycosylation toward flavonoids. Carbohydr. Res. 393: 26-31.
    Pubmed CrossRef
  12. Pandey RP, Parajuli P, Shin JY, Lee J, Lee S, Hong YS, et al. 2014. Enzymatic biosynthesis of novel resveratrol glucoside and glycoside derivatives. Appl. Environ. Microbiol. 80: 72357243.
    Pubmed KoreaMed CrossRef
  13. Schulte TW, Neckers LM. 1998. The benzoquinone ansamycin 17-allylamino-17-demethoxy geldanamycin binds to HSP90 and shares important biologic activities with geldanamycin. Cancer Chemother. Pharmacol. 42: 273-279.
    Pubmed CrossRef
  14. Singh S, Phillips GJ, Thorson JS. 2012. The structural biology of enzymes involved in natural product glycosylation. Nat. Prod. Rep. 29: 1201-1237.
    Pubmed KoreaMed CrossRef
  15. Solárová Z, Mojžiš J, Solár P. 2015. Hsp90 inhibitor as a sensitizer of cancer cells to different therapies. Int. J. Oncol. 46: 907-926.
    Pubmed
  16. Supko JG, Hickman RL, Grever MR, Malspeis L. 1995. Preclinical pharmacologic evaluation of geldanamycin as an antitumor agent. Cancer Chemother. Pharmacol. 36: 305-315.
    Pubmed CrossRef
  17. Whitesell L, Mimnaugh EG, Costa BD, Myers CE, Neckers LM. 1994. Inhibition of heat shock protein HSP90-pp60v-src heteroprotein complex formation by benzoquinone ansamycins:essential role for stress proteins in oncogenic transformation. Proc. Natl. Acad. Sci. USA 91: 8324-8328.
    Pubmed KoreaMed CrossRef
  18. Wu CZ, Jang JH, Woo MH, Ahn JS, Kim JS, Hong YS. 2012. Enzymatic glycosylation of non benzoquinone geldanamycin analogs via Bacillus UDP-glycosyltransferase. Appl. Environ. Microbiol. 78: 7680-7686.
    Pubmed KoreaMed CrossRef
  19. Yang L, Wang Z, Lei H, Chen R, Wang X, Peng Y, Dai J. 2014. Neuroprotective glucosides of magnolol and honokiol from microbial-specific glycosylation. Tetrahedron 70: 8244-8251.
    CrossRef