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Quinoline-2-carbonitrile-fumaric acid (1/0.5).

ABSTRACT: The asymmetric unit of the title compound, C(10)H(6)N(2)·0.5C(4)H(4)O(4), consists of one quinoline-2-carbonitrile mol-ecule and a half-mol-ecule of fumaric acid, which lies on an inversion center. The quinoline-2-carbonitrile mol-ecule is almost planar, with an r.m.s. deviation of 0.008?(1)?Å. The acid and base are linked together via pairs of inter-molecular C-H?O and O-H?N hydrogen bonds, forming R(2) (2)(8) ring motifs. In the crystal, the carbonitrile mol-ecules are further linked by inter-molecular C-H?N hydrogen bonds, generating R(2) (2)(10) ring motifs, resulting in zigzag chains running along the c axis.

SUBMITTER: Loh WS

PROVIDER: S-EPMC3008075 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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Quinoline-2-carbonitrile-fumaric acid (1/0.5).

Loh Wan-Sin WS Quah Ching Kheng CK Hemamalini Madhukar M Fun Hoong-Kun HK

Acta crystallographica. Section E, Structure reports online 20100821 Pt 9

The asymmetric unit of the title compound, C(10)H(6)N(2)·0.5C(4)H(4)O(4), consists of one quinoline-2-carbonitrile mol-ecule and a half-mol-ecule of fumaric acid, which lies on an inversion center. The quinoline-2-carbonitrile mol-ecule is almost planar, with an r.m.s. deviation of 0.008 (1) Å. The acid and base are linked together via pairs of inter-molecular C-H⋯O and O-H⋯N hydrogen bonds, forming R(2) (2)(8) ring motifs. In the crystal, the carbonitrile mol-ecules are further linked by inter- ...[more]

PMID: 21588699

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Project description:To test the hypothesis that dimethyl fumarate (DMF, Tecfidera) elicits different biological changes from DMF combined with monoethyl fumarate (MEF) (Fumaderm, a psoriasis therapy), we investigated DMF and MEF in rodents and cynomolgus monkeys. Possible translatability of findings was explored with lymphocyte counts from a retrospective cohort of patients with MS. In rodents, we evaluated pharmacokinetic and pharmacodynamic effects induced by DMF and MEF monotherapies or in combination (DMF/MEF). Clinical implications were investigated in a retrospective, observational analysis of patients with MS treated with DMF/MEF (n = 36). In rodents and cynomolgus monkeys, monomethyl fumarate (MMF, the primary metabolite of DMF) exhibited higher brain penetration, whereas MEF was preferentially partitioned into the kidney. In mice, transcriptional profiling for DMF and MEF alone identified both common and distinct pharmacodynamic responses, with almost no overlap between DMF- and MEF-induced differentially expressed gene profiles in immune tissues. The nuclear factor (erythroid-derived 2)-like 2 (Nrf2)-mediated oxidative stress response pathway was exclusively regulated by DMF, whereas apoptosis pathways were activated by MEF. DMF/MEF treatment demonstrated that DMF and MEF functionally interact to modify DMF- and MEF-specific responses in unpredictable ways. In patients with MS, DMF/MEF treatment led to early and pronounced suppression of lymphocytes, predominantly CD8+ T cells. In a multivariate regression analysis, the absolute lymphocyte count (ALC) was associated with age at therapy start, baseline ALC, and DMF/MEF dosage but not with previous immunosuppressive medication and sex. Furthermore, the ALC increased in a small cohort of patients with MS (n = 6/7) after switching from DMF/MEF to DMF monotherapy. Fumaric acid esters exhibit different biodistribution and may elicit different biological responses; furthermore, pharmacodynamic effects of combinations differ unpredictably from monotherapy. The strong potential to induce lymphopenia in patients with MS may be a result of activation of apoptosis pathways by MEF compared with DMF.

Dataset Information

Quinoline-2-carbonitrile-fumaric acid (1/0.5).

Publications

Quinoline-2-carbonitrile-fumaric acid (1/0.5).

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