Synthesis and biological evaluation of santacruzamate A analogues for anti-proliferative and immunomodulatory activity

Gromek, Samantha M.; deMayo, James A.; Maxwell, Andrew T.; West, Ashley M.; Pavlik, Christopher; Zhao, Ziyan; Jin, Li; Wiemer, Andrew J.; Zweifach, Adam; Balunas, Marcy J.

doi:10.1016/j.bmc.2016.08.040

Cited by 20 publications

(22 citation statements)

References 47 publications

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“…Analogs were categorized by their cap. It was found that the proliferation of MCF-7 breast cancer cells was inhibited in two group analogs and other analogs seemed to influence the degranulation of cytotoxic T-cells (121).…”

Section: N-(2-hydroxyphenyl)-2propylpentanamide N-(2-hydroxy-mentioning

confidence: 99%

Histone Deacetylase Inhibitors: An Attractive Therapeutic Strategy Against Breast Cancer

et al. 2017

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Abstract. With a lifetime risk estimated to be one in eight in industrialized countriesBreast cancer is the most frequently diagnosed cancer and the second leading cause of cancer-related death among women worldwide. According to the American Cancer Society about 12% U.S. women will develop breast cancer during their lifetime. Moreover, in 2015, about 2,300 men were diagnosed with breast cancer and 440 died from the disease (1, 2).In approximately 90% of breast cancer cases, estrogen receptor α (ERα), progesterone receptor (PR), or the human epidermal growth factor receptor2 (HER2/ERBB2) protooncogenic receptor are expressed. In many of these patients, treatment with anti-estrogens (e.g. aromatase inhibitors, tamoxifen, fulvestrant) and HER2-targeted agents has improved their survival significantly (3, 4). However, despite 35

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Section: N-(2-hydroxyphenyl)-2propylpentanamide N-(2-hydroxy-mentioning

confidence: 99%

Histone Deacetylase Inhibitors: An Attractive Therapeutic Strategy Against Breast Cancer

et al. 2017

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“…The general methods for the synthesis of O -thiocarbamates and dithiocarbamates traditionally rely on substitution reactions of the corresponding halogenated precursors, including thiophosgene [31–33], thiocarbamoyl chlorides [34–37], chlorothionoformates or chlorodithioformates [38–41] providing the appropriate thiocarbamate analogues in good yields (Scheme 1). However, these methods suffer from the formation of toxic, malodorous and/or extremely corrosive byproducts generated by the elimination of the halogen atoms.…”

Section: Introductionmentioning

confidence: 99%

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

Németh¹,

Keserü²,

Ábrányi‐Balogh³

2019

Beilstein J. Org. Chem.

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A new multicomponent reaction has been developed between isocyanides, sulfur and alcohols or thiols under mild reaction conditions to afford O-thiocarbamates and dithiocarbamates in moderate to good yields. The one-pot reaction cascade involves the formation of an isothiocyanate intermediate, thus a catalyst-free synthesis of isothiocyanates, as valuable building blocks from isocyanides and sulfur is proposed, as well. The synthetic procedure suits the demand of a modern organic chemist, as it tolerates a wide range of functional groups, it is atom economic and easily scalable.

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“…Santacruzamate A (CAY10683) is a potent selective HDAC inhibitor that has an IC50 of 119 pM for HDAC2 and a >3600-fold selectivity over other HDACs [ 10 ]. As a clinically approved HDAC inhibitor, CAY10683 has antiproliferative and immunomodulatory effects [ 11 ], thereby CAY10683 was used to treat cutaneous T-cell lymphoma [ 12 ] and breast cancer [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

The Protective Mechanism of CAY10683 on Intestinal Mucosal Barrier in Acute Liver Failure through LPS/TLR4/MyD88 Pathway

Wang

Chen

et al. 2018

Mediators of Inflammation

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The purpose of this study was to investigate the protective mechanism of HDAC2 inhibitor CAY10683 on intestinal mucosal barrier in acute liver failure (ALF). In order to establish ALF-induced intestinal epithelial barrier disruption models, D-galactosamine/LPS and LPS were, respectively, used with rats and NCM460 cell and then administrated with CAY10683. Transepithelial electrical resistance (TEER) was measured to detect the permeability of cells. Real-time PCR and Western blotting were employed to detect the key mRNA and protein levels. The intestinal epithelial tissue pathology was detected. After interfering with CAY10683, the mRNA and protein levels of TLR4, MyD88, TRIF, and TRAF6 were decreased compared with model group (P < 0.05), whereas the levels of ZO-1 and occluding were elevated (P < 0.05). The permeability was elevated in CAY10683-interfered groups, when compared with model group (P < 0.05). And the degree of intestinal epithelial tissue pathological damage in CAY10683 group was significantly reduced. Moreover, CAY10683 significantly decreased the TLR4 staining in animal tissue. The HDAC2 inhibitor CAY10683 could promote the damage of intestinal mucosal barrier in ALF through inhibiting LPS/TLR4/MyD88 pathway.

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Synthesis and biological evaluation of santacruzamate A analogues for anti-proliferative and immunomodulatory activity

Cited by 20 publications

References 47 publications

Histone Deacetylase Inhibitors: An Attractive Therapeutic Strategy Against Breast Cancer

Histone Deacetylase Inhibitors: An Attractive Therapeutic Strategy Against Breast Cancer

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

The Protective Mechanism of CAY10683 on Intestinal Mucosal Barrier in Acute Liver Failure through LPS/TLR4/MyD88 Pathway

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