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Chemical Compound Review:

ACCA (E)-2-cyano-3-(4- hydroxyphenyl)prop-2...

Synonyms: CHCA, alpha-CCA, alpha-CHCA, alpha-Cyano, CHEMBL76602, ...

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Disease relevance of alpha-cyano-4-hydroxycinnamic acid

Hypoxia produced an extracellular acidification that was strongly reduced in the presence of alpha-cyano-4-hydroxycinnamic acid and 4,4'-dibenzamidostilbene-2,2'-disulphonic acid [1].
Caudal fourth ventricular (CV4) infusion of the monocarboxylate transporter inhibitor, alpha-cyano-4-hydroxycinnamic acid (4CIN), causes hyperglycemia coincident with Fos expression in the hindbrain nucleus tractus solitarius, a rare central source of metabolic deficit signaling [2].
METHODS: We inhibited lactate transport in U87-MG gliomas with alpha-cyano-4-hydroxycinnamic acid (ACCA) [3].

High impact information on alpha-cyano-4-hydroxycinnamic acid

Using ionic alpha-cyano-4-hydroxycinnamic acid (Et3N-alpha-CHCA) as the matrix, matrix-free mass spectra in the m/z range of interest are acquired, and the B1, B2, G1, and G2 aflatoxins are readily detected with an LOD as low as 50 fmol [4].
In this method, the surfactant of cetrimonium bromide (CTAB) is added to the conventional matrix of alpha-cyano-4-hydroxycinnamic acid solution to prepare the MALDI samples [5].
A dried-droplet MALDI matrix consisting of 1:1 alpha-cyano-4-hydroxycinnamic acid/fructose proves to be an excellent matrix for photodissociation because [M + H]+ ions are formed with low internal energies, and the photofragment ion spectrum contains high abundances of sequence-informative ions [6].
Alpha-cyano-4-hydroxycinnamic acid affinity sample preparation. A protocol for MALDI-MS peptide analysis in proteomics [7].
In addition, spot-to-spot reproducibility, resolution, and mass accuracy for DNA oligonucleotides (< or = 12 mer) can be improved by the use of overlayer sample preparations with matrixes that have low aqueous solubilities, such as alpha-cyano-4-hydroxycinnamic acid, ferulic acid, and 2,4,6-trihydroxyacetophenone [8].

Chemical compound and disease context of alpha-cyano-4-hydroxycinnamic acid

The lactate transport inhibitor alpha-cyano-4-hydroxycinnamic acid (CHCA) was employed to distinguish the direct effects of hypoxia on adenosine output from the effects produced indirectly by a change in lactate concentration [9].
CONCLUSION: Inhibition of lactate efflux in malignant gliomas results in alterations of glycolytic metabolism, including decreased levels of the antioxidants taurine and glutathione and enhanced radiosensitivity of ACCA-treated cells [3].

Biological context of alpha-cyano-4-hydroxycinnamic acid

Inhibition of anaerobic glycolysis (iodoacetate, sodium fluoride) abolished DRSD during OD, whereas blockade of monocarboxylate utilization with alpha-cyano-4-hydroxycinnamic acid (4-CIN) provoked DRSD in normoxic medium [10].
Fatigue and recovery of mouse soleus and extensor digitorum longus muscles were investigated in standard saline and in saline containing the lactate + hydrogen ion transport blocker, alpha-cyano-4-hydroxycinnamic acid (cinnamate) [11].
However, beta-cell apical anion exchange was inhibited by alpha-cyano-4-hydroxycinnamic acid, with an IC50 of 2.4 mM [12].

Anatomical context of alpha-cyano-4-hydroxycinnamic acid

Induction of Fos immunoreactivity labeling in rat forebrain metabolic loci by caudal fourth ventricular infusion of the monocarboxylate transporter inhibitor, alpha-cyano-4-hydroxycinnamic acid [2].
This process was reduced by a protonophore, carbonylcyanide p-trifluoromethoxyphenylhydrazone, and a typical monocarboxylate transporter (MCT) inhibitor, alpha-cyano-4-hydroxycinnamic acid, suggesting that nicotinate uptake by rat astrocytes is mediated by H(+)-coupled monocarboxylate transport system [13].
Our results suggest that salicylate uptake across the basolateral membrane of D. melanogaster Malpighian tubules is mediated by a non-electrogenic, alpha-cyano-4-hydroxycinnamic acid-sensitive, Na(+):salicylate cotransport system [14].
The inhibitory effect of pyruvate required entry of pyruvate into mitochondria since it did not occur in the presence of alpha-cyano-4-hydroxycinnamic acid, an inhibitor of the mitochondrial pyruvate transporter [15].

Associations of alpha-cyano-4-hydroxycinnamic acid with other chemical compounds

The sensitivities of oligosaccharide derivatives in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOFMS) were compared using two matrixes, 2,5-dihydroxybenzoic acid (DHBA) and alpha-cyano-4-hydroxycinnamic acid (CHCA) [16].
Subsequently, the MALDI matrix alpha-cyano-4-hydroxycinnamic acid in methanol and 10% trifluoroacetic acid in water are added to the peptide-coated modified polymer surfaces [17].
Large signals from alpha-cyano-4-hydroxycinnamic acid (CHCA) matrix complexes with sodium and potassium ions were found to interfere with sensitive matrix-assisted laser desorption/ionization (MALDI) analysis of a hydrochloric acid digest of gelatine preparations [18].
The interaction was seen when 6-aza-2-thiothymine was used as a matrix (pH 5.4), but was disrupted with a more acidic matrix, alpha-cyano-4-hydroxycinnamic acid (pH 2.0) [19].
Very simple MALDI mass spectra are obtained by directly mixing spores with a matrix such as alpha-cyano-4-hydroxycinnamic acid or sinapinic acid [20].

Gene context of alpha-cyano-4-hydroxycinnamic acid

In addition, THAP offered improved sensitivity for detection of acidic glycopeptides over alpha-cyano-4-hydroxycinnamic acid [21].
Improved sensitivity for insulin in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry by premixing alpha-cyano-4-hydroxycinnamic acid matrix with transferrin [22].
Delayed extraction experiments using a repulsing potential before ion extraction: evidence of non-covalent clusters as ion precursor in UV matrix-assisted laser desorption/ionization. Part II--Dynamic effects with alpha-cyano-4-hydroxycinnamic acid matrix [23].
In addition to the M(1+) ion detected using sinapinic acid as a matrix, the M(2+) and M(3+) ions of transferrin were clearly detected using alpha-cyano-4-hydroxycinnamic acid as matrix and the molecular weight heterogeneity was identified more clearly in multivalent ions than that in the M(1+) ion [24].

Analytical, diagnostic and therapeutic context of alpha-cyano-4-hydroxycinnamic acid

The LC eluent was mixed with alpha-cyano-4-hydroxycinnamic acid matrix solution and deposited on a MALDI plate that had been precoated with nitrocellulose [25].
Matrix-embedded samples, dissolved in a large surplus of alpha-cyano-4-hydroxycinnamic acid, were prepared by nebulizer spray deposition, neat samples by the droplet technique [26].
Three organic matrices were tested for these assays, resulting in different crystallization behaviors and measurement reproducibilities. alpha-Cyano-4-hydroxycinnamic acid yielded the best results and was subsequently employed for the quantitative determination of all four analytes [27].
A systematic study was performed to identify the origin of surprisingly high analyte-to-matrix yield ratios recently observed in time-of-flight secondary ion mass spectrometry (TOF-SIMS) analysis of oligo- and polypeptides mixed in matrices of alpha-cyano-4-hydroxycinnamic acid (4HCCA) [28].

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