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Fraxinellone.

ABSTRACT: In the title compound, C(14)H(16)O(3) [systematic name: (3R*,3aR*)-3-(3-furan-yl)-3a,7-dimethyl-3a,4,5,6-tetra-hydro-2-benzofuran-1(3H)-one], the pendant methyl and furan groups attached to the stereogenic centres lie to the same side of the fused ring system. The dihedral angle between the five-membered rings is 74.8?(2)°; the fused five-membered ring adopts a twisted conformation. In the crystal, mol-ecules are linked by weak C-H?O inter-actions, which generate [100] chains.

SUBMITTER: Gu HM

PROVIDER: S-EPMC3120588 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Fraxinellone.

Gu Hong-Mei HM Xu Hao H Zhong Zhao-Zhao ZZ Zhu Hai-Liang HL Li Qing-Shan QS

Acta crystallographica. Section E, Structure reports online 20110520 Pt 6

In the title compound, C(14)H(16)O(3) [systematic name: (3R*,3aR*)-3-(3-furan-yl)-3a,7-dimethyl-3a,4,5,6-tetra-hydro-2-benzofuran-1(3H)-one], the pendant methyl and furan groups attached to the stereogenic centres lie to the same side of the fused ring system. The dihedral angle between the five-membered rings is 74.8 (2)°; the fused five-membered ring adopts a twisted conformation. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, which generate [100] chains. ...[more]

PMID: 21754842

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Project description:Rationale: Tumor-associated fibroblasts (TAFs) play a critical role in the suppressive immune tumor microenvironment (TME), compromising the efficacy of immunotherapy. To overcome this therapeutic hurdle, we developed a nanoemulsion (NE) formulation to deliver fraxinellone (Frax), an anti-fibrotic medicine, to TAFs, as an approach to reverse immunosuppressive TME of desmoplastic melanoma. Methods: Frax NE was prepared by an ultrasonic emulsification method. The tumor inhibition effect was evaluated by immunofluorescence staining, masson trichrome staining and western blot analysis. Immune cell populations in tumor and LNs were detected by flow cytometry. Results: This Frax NE, with a particle size of around 145 nm, can efficiently accumulate in the tumor site after systemic administration and was taken up by TAFs and tumor cells. A significant decrease in TAFs and stroma deposition was observed after intravenous administration of Frax NE, and Frax NE treatment also remolded the tumor immune microenvironment, as was reflected by an increase of natural-killer cells, cytotoxic T cells (CTLs) as well as a decrease of regulatory B cells, and myeloid-derived suppressor cells in the TME. In addition, after treatment by Frax NEs, T helper 1 (Th1) cytokines of interferon gamma (IFN-?), which effectively elicit anti-tumor immunity, were enhanced. Transforming growth factor-? (TGF-?), chemokine (C-C motif) ligand 2 (CCL2) and interleukin 6 (IL6), which inhibit the development of anti-tumor immunity, were reduced. Although Frax NE demonstrated an inhibitory effect on tumor growth, this mono-therapy could only achieve partial antitumor efficacy, and the tumor growth effect was not maintained long-term after dosing stopped. Therefore, a tumor-specific peptide vaccine was combined with Frax NEs. The combination led to enhanced tumor-specific T-cell infiltration, activated death receptors on the tumor cell surface, and induced increased apoptotic tumor cell death. Conclusion: Collectively, Frax NE combined with tumor-specific peptide vaccine might be an effective and safe strategy to remodel fibrotic TME, thereby enhancing immune response activation, resulting in a prolonged efficiency for advanced desmoplastic melanoma.

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Fraxinellone.

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Fraxinellone.

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