Helicid

CAS# 80154-34-3

Helicid

Catalog No. BCN1056----Order now to get a substantial discount!

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Quality Control of Helicid

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Chemical structure

Helicid

3D structure

Chemical Properties of Helicid

Cas No. 80154-34-3 SDF Download SDF
PubChem ID 12896796 Appearance White powder
Formula C13H16O7 M.Wt 284.26
Type of Compound Phenols Storage Desiccate at -20°C
Synonyms Helicide
Solubility Soluble in methanol and pyridine
Chemical Name 4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzaldehyde
SMILES C1=CC(=CC=C1C=O)OC2C(C(C(C(O2)CO)O)O)O
Standard InChIKey OLZAGZCCJJBKNZ-SYLRKERUSA-N
Standard InChI InChI=1S/C13H16O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-5,9-13,15-18H,6H2/t9-,10-,11-,12-,13-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Helicid

The roots of Helicia erratica Hook. f.

Biological Activity of Helicid

DescriptionHelicid analogues are mushroom tyrosinase inhibitors, some of them have more potent inhibitory activities than arbutin (IC50 =7.3 mM).Some helicid analogues exhibit potent cholinesterase (AChE) inhibitory activities.
TargetsAChR
In vitro

Bioavailability and pharmacokinetics profile of helicid in beagle dogs using gradient elution high performance liquid chromatography electrospray ionization mass spectrometry.[Pubmed: 25743699]

J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Apr 15;988:8-12.

A simple, sensitive and reliable gradient elution high performance liquid chromatography electrospray ionization mass spectrometry (HPLC-ESI-MS) method was developed for quantifying Helicid in dog plasma.
METHODS AND RESULTS:
The limit of detection (LOD) and the lower limit of quantitation (LLOQ) were 0.3 and 1 ng/mL, respectively. This method was validated for selectivity, linearity, accuracy and precision, extraction recoveries, matrix effects, carry-over, cross-talk, dilution integrity, stability and incurred sample reanalysis (ISR). Bioavailability and pharmacokinetic parameters of Helicid in beagle dogs were researched from a two period crossover design study. After intravenous administration (i.v.), Helicid had a mean (± SD) AUC0-∞ of 12062.06 ± 2482.69 ng/mL h and terminal half-life (t1/2 z) of 2.91 ± 1.37 h, while Cmax was 35613.23 ± 8157.18 ng/mL. Following intragastric gavage administration (i.g.), AUC0-∞ was 7589.16 ± 1797.20 ng/mL h along with a longer t1/2 z of 4.10 ± 4.35 h. Cmax was researched at 0.58 ± 0.20 h. The absolute bioavailability (F) of Helicid was 15.74 ± 1.87%.

Protocol of Helicid

Kinase Assay

Synthesis and biological evaluation of helicid analogues as novel acetylcholinesterase inhibitors.[Pubmed: 17574306 ]

Synthesis and biological evaluation of helicid analogues as mushroom tyrosinase inhibitors.[Pubmed: 18996693 ]

Bioorg Med Chem Lett. 2008 Dec 15;18(24):6490-3.


METHODS AND RESULTS:
A series of Helicid analogues were synthesized and evaluated as tyrosinase inhibitors. The results demonstrated that some compounds had more potent inhibitory activities than arbutin (IC(50) 7.3 mM). In particular, compound 1c bearing 4,6-O-benzylidene substituent on the sugar moiety was found to be the most potent inhibitor with IC(50) value of 0.052 mM. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that Helicid analogues were competitive inhibitors.
CONCLUSIONS:
The Circular dichroism spectra indicated that those compounds induced conformational changes of mushroom tyrosinase upon binding.

Eur J Med Chem. 2008 Jan;43(1):166-73.


METHODS AND RESULTS:
A series of Helicid analogues were prepared and evaluated in vitro for the cholinesterase (AChE and BuChE) inhibitory activities via UV spectroscopy. The results indicated that compounds 5, 6d and 8 exhibited potent AChE inhibitory activities with IC(50) values of 0.45+/-0.02microM, 0.49+/-0.02microM, and 0.20+/-0.01microM, respectively. High selectivity for AChE over BuChE was also observed.
CONCLUSIONS:
Kinetic study showed that the mechanism of AChE inhibition of compounds 5, 6d and 8 was all mixed-type.

Structure Identification
Spectrochim Acta A Mol Biomol Spectrosc. 2014 Apr 24;124:46-51.

Binding of helicid to human serum albumin: a hybrid spectroscopic approach and conformational study.[Pubmed: 24463239]


METHODS AND RESULTS:
The interaction between human serum albumin and Helicid was studied by steady-state fluorescence, ultraviolet-visible, circular dichroism, Fourier transform infrared techniques and molecular modeling. The binding site numbers, association constants, and corresponding thermodynamic parameters were used to investigate the quenching mechanism. The alternations of protein secondary structure in the presence of Helicid were demonstrated using synchronous fluorescence, Fourier transform infrared, circular dichroism and three-dimensional fluorescence spectra.
CONCLUSIONS:
The molecular modeling results revealed that Helicid could bind to hydrophobic pocket of HSA with hydrophobic and hydrogen bond force. The binding site of Helicid in HSA was ascertained. Moreover, an apparent distance of 3.33 nm between the Trp214 and Helicid was obtained via fluorescence resonance energy transfer method.

Helicid Dilution Calculator

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Helicid Molarity Calculator

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Preparing Stock Solutions of Helicid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.5179 mL 17.5895 mL 35.1791 mL 70.3581 mL 87.9477 mL
5 mM 0.7036 mL 3.5179 mL 7.0358 mL 14.0716 mL 17.5895 mL
10 mM 0.3518 mL 1.759 mL 3.5179 mL 7.0358 mL 8.7948 mL
50 mM 0.0704 mL 0.3518 mL 0.7036 mL 1.4072 mL 1.759 mL
100 mM 0.0352 mL 0.1759 mL 0.3518 mL 0.7036 mL 0.8795 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Helicid

Bioavailability and pharmacokinetics profile of helicid in beagle dogs using gradient elution high performance liquid chromatography electrospray ionization mass spectrometry.[Pubmed:25743699]

J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Apr 15;988:8-12.

A simple, sensitive and reliable gradient elution high performance liquid chromatography electrospray ionization mass spectrometry (HPLC-ESI-MS) method was developed for quantifying Helicid in dog plasma. The limit of detection (LOD) and the lower limit of quantitation (LLOQ) were 0.3 and 1 ng/mL, respectively. This method was validated for selectivity, linearity, accuracy and precision, extraction recoveries, matrix effects, carry-over, cross-talk, dilution integrity, stability and incurred sample reanalysis (ISR). Bioavailability and pharmacokinetic parameters of Helicid in beagle dogs were researched from a two period crossover design study. After intravenous administration (i.v.), Helicid had a mean (+/- SD) AUC0-infinity of 12062.06 +/- 2482.69 ng/mL h and terminal half-life (t1/2 z) of 2.91 +/- 1.37 h, while Cmax was 35613.23 +/- 8157.18 ng/mL. Following intragastric gavage administration (i.g.), AUC0-infinity was 7589.16 +/- 1797.20 ng/mL h along with a longer t1/2 z of 4.10 +/- 4.35 h. Cmax was researched at 0.58 +/- 0.20 h. The absolute bioavailability (F) of Helicid was 15.74 +/- 1.87%.

Synthesis and biological evaluation of helicid analogues as novel acetylcholinesterase inhibitors.[Pubmed:17574306]

Eur J Med Chem. 2008 Jan;43(1):166-73.

A series of Helicid analogues were prepared and evaluated in vitro for the cholinesterase (AChE and BuChE) inhibitory activities via UV spectroscopy. The results indicated that compounds 5, 6d and 8 exhibited potent AChE inhibitory activities with IC(50) values of 0.45+/-0.02microM, 0.49+/-0.02microM, and 0.20+/-0.01microM, respectively. High selectivity for AChE over BuChE was also observed. Kinetic study showed that the mechanism of AChE inhibition of compounds 5, 6d and 8 was all mixed-type.

Synthesis and biological evaluation of helicid analogues as mushroom tyrosinase inhibitors.[Pubmed:18996693]

Bioorg Med Chem Lett. 2008 Dec 15;18(24):6490-3.

A series of Helicid analogues were synthesized and evaluated as tyrosinase inhibitors. The results demonstrated that some compounds had more potent inhibitory activities than arbutin (IC(50) 7.3 mM). In particular, compound 1c bearing 4,6-O-benzylidene substituent on the sugar moiety was found to be the most potent inhibitor with IC(50) value of 0.052 mM. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that Helicid analogues were competitive inhibitors. The Circular dichroism spectra indicated that those compounds induced conformational changes of mushroom tyrosinase upon binding.

Binding of helicid to human serum albumin: a hybrid spectroscopic approach and conformational study.[Pubmed:24463239]

Spectrochim Acta A Mol Biomol Spectrosc. 2014 Apr 24;124:46-51.

The interaction between human serum albumin and Helicid was studied by steady-state fluorescence, ultraviolet-visible, circular dichroism, Fourier transform infrared techniques and molecular modeling. The binding site numbers, association constants, and corresponding thermodynamic parameters were used to investigate the quenching mechanism. The alternations of protein secondary structure in the presence of Helicid were demonstrated using synchronous fluorescence, Fourier transform infrared, circular dichroism and three-dimensional fluorescence spectra. The molecular modeling results revealed that Helicid could bind to hydrophobic pocket of HSA with hydrophobic and hydrogen bond force. The binding site of Helicid in HSA was ascertained. Moreover, an apparent distance of 3.33 nm between the Trp214 and Helicid was obtained via fluorescence resonance energy transfer method.

Description

Helicid (Helicide) is a major constituent of Helicia nilgirica Bedd. Helicid has been used to treat psychoneurosis for its sedative-hypnotic and analgesic properties.

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