Functional characterization of heat shock protein 90 targeted compounds

Cruz, Isa N.; Zhang, Yixi; Fuente, María de la; Schätzlein, Andreas G.; Yang, Min

doi:10.1016/j.ab.2013.03.026

Cited by 3 publications

(2 citation statements)

References 24 publications

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“…Previously we demonstrated that the single glycosylation the 4'hydroxyl group of novobiocin ( Fig. 1A) could increase its anticancer activity 20,21 via binding to the Hsp90CTD 22 . Although protein modelling data indicate the formation of strong hydrogen bonds with Hsp90CTD peptides, the exact binding details is not clear.…”

Section: Introductionmentioning

confidence: 90%

Synthesis and characterization of photoaffinity labelling reagents towards the Hsp90 C-terminal domain

Simon

Huang

et al. 2017

Org. Biomol. Chem.

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Glucosyl-novobiocin-based diazirine photoaffinity labelling reagents (PALs) were designed and synthesized to probe the Hsp90 C-terminal domain unknown binding pocket and the structure-activity relationship. Five PALs were successfully synthesized from novobiocin in six consecutive steps employing phase transfer catalytic glycosylation. Reactions were monitored and guided by analytical LC/MS which led to different strategies of adding either a PAL precursor or a sugar moiety first. The structures and bonding linkages of these compounds were characterised by various 2D-NMR spectroscopy and MS techniques. Synthetic techniques provide powerful probes for unknown protein binding pockets.

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Section: Introductionmentioning

confidence: 90%

Synthesis and characterization of photoaffinity labelling reagents towards the Hsp90 C-terminal domain

Simon

Huang

et al. 2017

Org. Biomol. Chem.

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“…[14] It also possess anticancer activity by binding to the HSP90 chaperone. [15,16] The clinical use of this class of antibiotics has been restricted due to their low water solubility, low activity against Gram-negative bacteria [17] and toxicity in vivo. [18] Modifications of aminocoumarins have been made to achieve better activity in the past decade.…”

Section: Introductionmentioning

confidence: 99%

Regioselective glycosylation of novobiocin alters activity

Sun

Resende

Stapleton

et al. 2017

Carbohydrate Research

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Glycosylation is a promising approach to overcome antimicrobial drug resistance. In this study, we investigated Koenigs-Knorr and phase transfer glycosylation on novobiocin. While the former only gave a 4'-OH product, the later produced mainly a kinetic controlled 5-OH product, but still achieved the 4'-OH modification and novoise-glycosylated products (with stronger base), as well as a diglycosylated compound. Investigation on the antibacterial activity indicate that the presence of galactose moiety helps to improve activity possibly via enhanced cellular uptake.

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Fungal diseases and antifungal drugs

Kumar

Jha

2023

Anticandidal Therapeutics

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Functional characterization of heat shock protein 90 targeted compounds

Cited by 3 publications

References 24 publications

Synthesis and characterization of photoaffinity labelling reagents towards the Hsp90 C-terminal domain

Synthesis and characterization of photoaffinity labelling reagents towards the Hsp90 C-terminal domain

Regioselective glycosylation of novobiocin alters activity

Fungal diseases and antifungal drugs

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