Abstract:
:Thiazinogeldanamycin (2) was identified from Streptomyces hygroscopicus 17997 at the late stage of the fermentation. The pH was firstly proposed as an important factor in the biosynthesis of it. It was verified that 2 was produced by direct chemical reactions between geldanamycin (1, GDM) and cysteine or aminoethanethiol hydrochloride at pH > 7 in vitro. The proposed synthesis pathway for compound 2 was also discussed. Eleven new C-19-modified GDM derivatives, including five stable hydroquinone form derivatives, were synthesized, most of which exhibited desirable properties such as lower cytotoxicity, increased water solubility, and potent antitumor activity. Especially, compounds 5 and 8 showed antitumor activities against HepG2 cell with IC50 values of 2.97-6.61 μM, lower cytotoxicity and at least 15-fold higher water solubility compared with 1 in pH 7.0 phosphate buffer.
journal_name
J Asian Nat Prod Resjournal_title
Journal of Asian natural products researchauthors
Liu YF,Zhong JJ,Lin L,Liu JJ,Wang YG,He WQ,Yang ZYdoi
10.1080/10286020.2016.1160896subject
Has Abstractpub_date
2016-08-01 00:00:00pages
752-64issue
8eissn
1028-6020issn
1477-2213journal_volume
18pub_type
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