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Qing Jia Laboratory Animal Centre, Wenzhou Medical University, Wenzhou, China

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Ziyue Wang Laboratory Animal Centre, Wenzhou Medical University, Wenzhou, China

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Shuqian Wang School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, China

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Shunjun Ma Laboratory Animal Centre, Wenzhou Medical University, Wenzhou, China

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Xueqi Qiao Laboratory Animal Centre, Wenzhou Medical University, Wenzhou, China

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Xueli Huang School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, China

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Xianqin Wang School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, China

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Congcong Wen Laboratory Animal Centre, Wenzhou Medical University, Wenzhou, China

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Xia-yin Zhu Department of Hematology, Taizhou Hospital of Zhejiang Province Affiliated to Wenzhou Medical University, Linhai, China

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Open access

Abstract

Objective

The levels of fraxetin, fraxin, and dimethylfraxetin in rat plasma to be measured using an ultra-performance liquid chromatography tandem mass-spectrometry (UPLC–MS/MS) technique and applied to their pharmacokinetics and bioavailability.

Methods

The protein precipitation technique was applied to the plasma preparation using acetonitrile and methanol (9:1, v/v). At a flow rate of 0.4 mL min−1, the elution time was 6 min. The mobile phase consisted of acetonitrile-water with 0.1% formic acid, and the chromatographic column was UPLC HSS T3 (50 mm × 2.1 mm, 1.8 μm). Quantitative analysis was conducted using multiple reaction monitoring (MRM) mode and detection was performed using electrospray ionization (ESI) positive ion mode. In each group, six rats were treated with fraxetin, fraxin, and dimethylfraxetin either orally (5 mg kg−1) or intravenously (1 mg kg−1).

Results

The calibration curves showed good linearity in the range of 2–4,000 ng mL−1, where r was greater than 0.99. The bioavailability of dimethylfraxetin, fraxin, and fraxetin was determinated to be 19.7, 1.4, and 6.0%.

Conclusion

The established UPLC-MS/MS method for determining the levels of these three compounds in rat plasma was successfully applied to the pharmacokinetics of dimethylfraxetin, fraxin, and fraxetin, and the bioavailability was calculated.

Abstract

Objective

The levels of fraxetin, fraxin, and dimethylfraxetin in rat plasma to be measured using an ultra-performance liquid chromatography tandem mass-spectrometry (UPLC–MS/MS) technique and applied to their pharmacokinetics and bioavailability.

Methods

The protein precipitation technique was applied to the plasma preparation using acetonitrile and methanol (9:1, v/v). At a flow rate of 0.4 mL min−1, the elution time was 6 min. The mobile phase consisted of acetonitrile-water with 0.1% formic acid, and the chromatographic column was UPLC HSS T3 (50 mm × 2.1 mm, 1.8 μm). Quantitative analysis was conducted using multiple reaction monitoring (MRM) mode and detection was performed using electrospray ionization (ESI) positive ion mode. In each group, six rats were treated with fraxetin, fraxin, and dimethylfraxetin either orally (5 mg kg−1) or intravenously (1 mg kg−1).

Results

The calibration curves showed good linearity in the range of 2–4,000 ng mL−1, where r was greater than 0.99. The bioavailability of dimethylfraxetin, fraxin, and fraxetin was determinated to be 19.7, 1.4, and 6.0%.

Conclusion

The established UPLC-MS/MS method for determining the levels of these three compounds in rat plasma was successfully applied to the pharmacokinetics of dimethylfraxetin, fraxin, and fraxetin, and the bioavailability was calculated.

Introduction

Cortex fraxini medicine contains a variety of chemical components [1, 2]. Modern pharmacological studies have shown that C. fraxini peel has antibacterial and antiviral, anti-inflammatory, analgesic and sedative, anti-tumor, antitussive, expectorant and asthma, promoting uric acid excretion and diuresis [3–5]. Studies have reported that C. fraxini contains coumarin, iridoids, lignin, phenols, sterols and triterpenoids, tannins, alkaloids, and other chemical components. Among them, coumarin is the main component of esculenta bark. For example, fraxetin, esculin, esculin B, fraxin, dimethylfraxetin, etc.

The HPLC method has a low detection sensitivity. In drug analysis, chemical composition, drug metabolism, and impurity identification, UPLC-MS/MS technology is extensively utilized because of its high sensitivity and minimal sample size requirements [6–10]. In vivo pharmacokinetic studies of fraxetin and fraxin have been reported [11, 12], but the simultaneous determination of fraxetin, fraxin and dimethylfraxetin has not been reported.

The purpose of this work is to determine the absolute bioavailability and the pharmacokinetics of fraxin, dimethylfraxetin, and fraxetin in rat plasma using a UPLC-MS/MS method, and provide experimental evidence for basic clinical pharmacy research.

Experiment

Reagents

The following products were acquired from Chengdu Manst Pharmaceutical Co.: fraxetin, fraxin, dimethylfraxetin, and tectorigenin (internal standard), all purity ≥98%, Fig. 1. LTD (Chengdu, China). Merck LTD provided us with HPLC pure acetonitrile and methanol (Darmstadt, Germany). The Milli-Q purification system produced ultra-pure water (resistance >18 MΩ) (Bedford, MA, USA).

Fig. 1.
Fig. 1.

Chemical structures of fraxetin, fraxin, dimethylfraxetin and tectorigenin

Citation: Acta Chromatographica 2024; 10.1556/1326.2024.01220

Instrument conditions

The compounds fraxetin, fraxin, and dimethylfraxetin were detected using a Waters XEVO TQ-S micro triple quadrupole tandem mass spectrometer and the ACQUITY H-Class UPLC.

With a temperature setting of 40 °C, the UPLC HSS T3 column (50 mm × 2.1 mm, 1.8 μm) was used. Elution took 6 min at a flow rate of 0.4 mL min−1 in acetonitrile-water with 0.1% formic acid as the mobile phase. The acetonitrile kept at 10% between 0 and 0.2 min, ranged from 10 to 75% between 0.2 and 2.4 min, from 75 to 90% between 2.4 and 5.0 min, and from 90 to 10% between 5.0 and 5.1 min. The acetonitrile percentage was maintained at 10% between 5.1 and 6 min.

Nitrogen was used as a desolvation gas (900 L h−1) and a conical gas (50 L h−1). The capillary voltage parameters were set to 2.5 kV, the ion source temperature to 150 °C, and the desolvation temperature to 450 °C. Quantitative analysis was conducted using MRM for ESI positive ion mode detection, fraxetin m/z 209.2→193.9 (cone voltage 40 v, collision voltage 20 v), fraxin m/z 371.3→ 209.0 (cone voltage 26 v, collision voltage 8 v), dimethylfraxetin m/z 237.2 → 176.0 (cone voltage 36 v, collision voltage 18 v) and internal standard m/z 301.1→ 168.0 (cone voltage 52 v, collision voltage 32 v), respectively.

Standard curve

Methanol was used to prepare stock solutions of fraxetin, fraxin, dimethylfraxetin, and tectorigenin (500 μg mL−1), in that order. Using methanol, dilute the stock solution to create standard working solutions with varying concentrations for fraxetin, fraxin and dimethylfraxetin (20, 100, 200, 400, 1,000, 2,000, 4,000, 10,000, 20,000, and 40,000 ng mL−1). To create a working solution containing 100 ng mL−1 of tectorigenin, the stock solution was diluted with acetonitrile-methanol (9:1, v/v). At 4 °C, both the working and stock solutions were kept.

Blank rat plasma was mixed with the appropriate volume of working solutions for fraxetin, fraxin and dimethylfraxetin. This resulted in rat plasma concentrations of 2, 10, 20, 40, 100, 200, 400, 1,000, 2,000, and 4,000 ng mL−1, which is the range of the standard curve. The same procedure was used to prepare quality control (QC) samples for four different plasma concentrations (2, 15, 300, and 3,000 ng mL−1).

Sample handling

After adding 50 μL of the plasma sample to a 1.5 mL eppendorf tube, mix in 150 μL of acetonitrile-methanol (9:1, v/v) with 100 ng mL−1 of tectorigenin, vortex mix for 1.0 min, and centrifuge (11,063 g, 4 °C, 10 min). Two microliters of the supernatant in injection bottle's lining tube were injected for UPLC-MS/MS analysis.

Pharmacokinetics

Male, 220–230 g Sprague-Dawley (SD) rats were purchased from the Wenzhou Medical University Animal Experimental Center (Wenzhou, China). The Animal Care Committee of Wenzhou Medical University (wydw2023-0450) approved all experimental procedures. There were six rats in each group, a total of thirty-six rats, to which fraxetin, fraxin and dimethylfraxetin, were given intravenously (iv) of 1 mg kg−1 and orally (po) of 5 mg kg−1, respectively. Heparinized tubes containing 0.3 mL of blood were collected from the tail vein at 0.083, 0.5, 1, 2, 3, 4, 6, 8, 12, and 24 h. The tubes were centrifuged for 10 min at 11,063 g. After that, 100 µL of the upper layer plasma was moved to a fresh 1.5 mL eppendorf tube and kept there until analysis. Software called DAS 2.0 was used to calculate the pharmacokinetic parameters (Wenzhou Medical University, Wenzhou, China).

Results

Selectivity

Figure 2 shows that the fraxetin, fraxin, dimethylfraxetin and internal standard, had retention time of 1.76 min, 1.61 min, 2.49 min, and 2.58 min, respectively. The fraxetin, fraxin, dimethylfraxetin and internal standard were successfully separated by the optimized gradient elution process. The method demonstrated good selectivity, and no endogenous component interference was found.

Fig. 2.
Fig. 2.

UPLC-MS/MS of fraxetin, fraxin, dimethylfraxetin and tectorigenin in rat plasma. A) blank rat plasma spiked with fraxetin, fraxin, dimethylfraxetin and tectorigenin, B) blank rat plasma

Citation: Acta Chromatographica 2024; 10.1556/1326.2024.01220

Standard curve

In the range of 2–4,000 ng mL−1, the typical regression equation for fraxetin in rat plasma was y1 = 0.0065x1-0.0723 (r = 0.9983), where x1 denotes the concentration of fraxetin in plasma and y1 denotes the ratio of fraxetin peak area to internal standard. Fraxin concentration in plasma is represented by x2, and the ratio of fraxin peak area to internal standard is represented by y2, in the typical regression equation of fraxin in rat plasma, which was y2 = 0.0130x2+0.0635 (r = 0.9980). In rat plasma, the typical regression equation for dimethylfraxetin was y3 = 0.0163x3-0.01497 (r = 0.9975), where x3 denotes the plasma concentration and y3 the ratio of the peak area of dimethylfraxetin to the internal standard. In rat plasma, fraxetin, fraxin, and dimethylfraxetin had a quantification lower limit of 2 ng mL−1 and a detection limit of 1 ng mL−1.

Precision, accuracy, recovery, and matrix effect

The results showed that the intra-day and inter-day precision of fraxetin was less than 14%, the intra-day and inter-day accuracy was 90–109%, the recovery was greater than 73%, and the matrix effect varied from 90 to 102%. Fraxin demonstrated intra-day and inter-day precision within 15%, intra-day and inter-day accuracy between 90 and 110%, recovery exceeding 69%, and matrix effect ranging from 86 to 93%. It shows that the intra-day and inter-day precision of the dimethylfraxetin was within 14%, intra-day and inter-day accuracy between 90 and 111%, the recovery was more than 83%, and matrix effects ranging from 86 to 102%, Table 1.

Table 1.

Accuracy, precision, matrix effect and recovery of fraxetin, fraxin and dimethylfraxetin in rat plasma

CompoundConcentration (ng mL−1)Accuracy (%)Precision (RSD%)Matrix effect (%)Recovery (%)
Intra-dayInter-dayIntra-dayInter-day
Fraxetin290.491.812.610.990.883.2
1591.395.37.813.9102.078.4
30093.5103.513.114.098.679.9
3,000108.695.39.58.795.873.7
Fraxin2109.390.79.510.386.376.9
1593.9108.112.88.289.273.9
30092.697.19.714.592.575.6
3,00098.190.88.811.989.669.5
Dimethylfraxetin296.2110.49.710.891.583.6
1590.595.611.513.5101.282.6
300100.9108.911.39.186.787.7
3,000108.697.410.413.2100.585.1

Stability

The plasma samples underwent three freeze-thaw cycles after being pretreated and left at room temperature for twenty-four hours. A 30-day test was conducted at −20 °C to determine stable. The results demonstrate the good stability of fraxetin, fraxin, and dimethylfraxetin, with an accuracy ranging from 86 to 112% and an RSD of less than 15%.

Pharmacokinetics

Figure 3 displays the concentration-time curves of fraxetin, fraxin, and dimethylfraxetin in rat plasma. Table 2 presents the primary parameters, indicating low oral bioavailability of 6.0, 1.4, and 19.7%, respectively.

Fig. 3.
Fig. 3.

The concentration-time curve of rats following oral (po) and intravenous (iv) administration of fraxetin, fraxin and dimethylfraxetin

Citation: Acta Chromatographica 2024; 10.1556/1326.2024.01220

Table 2.

Primary pharmacokinetic characteristics of fraxetin, fraxin, and dimethylfraxetin in rats following oral (5 mg kg−1) and intravenous (1 mg kg−1) administration

CompoundGroupAUC(0-t)AUC(0-∞)t1/2zCLz/FVz/FCmax
ng mL−1*hng mL−1*hhL h−1 kg−1L kg−1ng mL−1
Fraxetinpo117.9 ± 23.5118.8 ± 23.30.5 ± 0.143.5 ± 8.734.0 ± 8.9107.7 ± 19.1
iv390.0 ± 14.8393.3 ± 15.01.1 ± 0.22.5 ± 0.14.1 ± 0.9301.7 ± 43.0
Fraxinpo232.4 ± 33.7233.2 ± 34.11.2 ± 0.921.9 ± 3.436.8 ± 23.7173.4 ± 52.8
iv3365.0 ± 736.63365.8 ± 737.01.0 ± 0.50.3 ± 0.10.5 ± 0.22330.1 ± 437.6
Dimethylfraxetinpo2222.2 ± −204.22241.0 ± 208.33.7 ± 1.62.2 ± 0.212.0 ± 5.32964.2 ± 584.9
iv2250.4 ± 278.12254.1 ± 275.03.7 ± 2.20.5 ± 0.12.5 ± 1.93481.0 ± 236.9

Discussion

The optimal mass spectrometry conditions were achieved by monitoring fraxetin, fraxin, and dimethylfraxetin using both positive and negative ion modes. The positive ion mode was chosen for detection because fraxin, dimethylfraxetin, and fraxin all responded well in this mode, and the optimal mass spectrometry conditions produced higher signal strength and sensitivity. Ultimately, the standard sample was used to optimize and obtain the capillary voltage and collision energy.

The chromatographic behavior was significantly influenced by the chromatographic conditions during the pharmacokinetics of the components, which were investigated using UPLC-MS/MS [13, 14]. Several chromatographic columns, including BEH C18 and HSS T3, were tested in this experiment with various mobile phase compositions. The findings demonstrated that the HSS T3 (2.1 mm × 50 mm, 1.8 μm) and acetonitrile-0.1% formic acid mobile phase had good chromatographic peak and an appropriate peak time.

Protein precipitation (PPT), solid phase extraction (SPE), and liquid-liquid extraction (LLE) are the pretreatment techniques that are frequently used for biological samples. The cost of solid-phase extraction is increased by the intricate operation steps and expensive extraction columns. The protein precipitation method has the benefit of easier operation and better extraction recovery; liquid-liquid extraction requires specialized skills from its operators and is not appropriate for clinical determination. To prepare plasma samples, rats' blank plasma was mixed with fraxetin, fraxin, and dimethylfraxetin. Subsequently, the extraction efficiency of methanol and acetonitrile (1:1, v/v), methanol and acetonitrile (1:9, v/v), and methanol was examined. Methanol-acetonitrile (1:9, v/v) was chosen as the precipitant because the results demonstrated that it had a higher extraction efficiency.

In Traditional Chinese Medicine chemistry, fraxetin, fraxin, and dimethylfraxetin are coumarin compounds with C6–C3 structure. Tectorigenin is a flavonoid with the structural characteristics of C6–C3–C6. The structure and properties of tectorigenin were similar to those of the three tested compounds. According to Fig. 2, the chromatographic peak positions of tectorigenin were close to those of each analyte. In addition, tectorigenin was completely dissolved without chemical reaction with the tested compounds. Thus, tectorigenin was chosen as the internal standard.

In the pharmacokinetic study, the difference between AUC(0-∞) and AUC(0-t) values was almost negligible, indicating that the sampling time of each drug was reasonably designed. The oral t1/2z of fraxetin, fraxin and dimethylfraxetin were 0.5 ± 0.1 h, 1.2 ± 0.9 h and 3.7 ± 1.6 h, respectively, and the intravenous t1/2z were 1.1 ± 0.2 h, 1.0 ± 0.5 h and 3.7 ± 2.2 h, respectively. Combined with the CL of each compound, it was found that fraxetin had the fastest metabolism, and dimethylfraxetin had the slowest metabolism. However, the oral t1/2z of dimethylfraxetin is like that of intravenous t1/2z, and the bioavailability of dimethylfraxetin is 19.7%. The bioavailability of fraxin is low, and the amount of drug entering the blood circulation is small, but the area under the curve of intravenous injection is large, indicating that the low bioavailability of fraxin does not represent its poor efficacy, and the bioavailability can be increased by changing the dosage form.

Conclusion

In this work, the acetonitrile and methanol (9:1, v/v) precipitation method was used to treat plasma samples. Tectorigenin was used as the internal standard, and an UPLC-MS/MS analytical method was developed to determine the levels of fraxetin, fraxin, and dimethylfraxetin in rat plasma, applied to the pharmacokinetic study, and bioavailability was determinated to be 6.0, 1.4, and 19.7%. For the purpose of clinical medication regimens, drug efficacy prediction, and drug use rationalization, this pharmacokinetic study offers valuable information.

Conflict of interest

The authors declare no conflict of interest, financial or otherwise.

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    Wang, Y.; Hu, Y.; Wang, H.; Tong, M.; Gong, Y. J. Sep. Sci. 2020, 43, 34413448.

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Senior editors

Editor(s)-in-Chief: Kowalska, Teresa (1946-2023)

Editor(s)-in-Chief: Sajewicz, Mieczyslaw

Editors(s)

  • Danica Agbaba (University of Belgrade, Belgrade, Serbia)
  • Łukasz Komsta (Medical University of Lublin, Lublin, Poland)
  • Ivana Stanimirova-Daszykowska (University of Silesia, Katowice, Poland)
  • Monika Waksmundzka-Hajnos (Medical University of Lublin, Lublin, Poland)

Editorial Board

  • R. Bhushan (The Indian Institute of Technology, Roorkee, India)
  • J. Bojarski (Jagiellonian University, Kraków, Poland)
  • B. Chankvetadze (State University of Tbilisi, Tbilisi, Georgia)
  • M. Daszykowski (University of Silesia, Katowice, Poland)
  • T.H. Dzido (Medical University of Lublin, Lublin, Poland)
  • A. Felinger (University of Pécs, Pécs, Hungary)
  • K. Glowniak (Medical University of Lublin, Lublin, Poland)
  • B. Glód (Siedlce University of Natural Sciences and Humanities, Siedlce, Poland)
  • A. Gumieniczek (Medical University of Lublin, Lublin, Poland)
  • U. Hubicka (Jagiellonian University, Kraków, Poland)
  • K. Kaczmarski (Rzeszow University of Technology, Rzeszów, Poland)
  • H. Kalász (Semmelweis University, Budapest, Hungary)
  • K. Karljiković Rajić (University of Belgrade, Belgrade, Serbia)
  • I. Klebovich (Semmelweis University, Budapest, Hungary)
  • A. Koch (Private Pharmacy, Hamburg, Germany)
  • P. Kus (Univerity of Silesia, Katowice, Poland)
  • D. Mangelings (Free University of Brussels, Brussels, Belgium)
  • E. Mincsovics (Corvinus University of Budapest, Budapest, Hungary)
  • Á. M. Móricz (Centre for Agricultural Research, Budapest, Hungary)
  • G. Morlock (Giessen University, Giessen, Germany)
  • A. Petruczynik (Medical University of Lublin, Lublin, Poland)
  • R. Skibiński (Medical University of Lublin, Lublin, Poland)
  • B. Spangenberg (Offenburg University of Applied Sciences, Germany)
  • T. Tuzimski (Medical University of Lublin, Lublin, Poland)
  • Y. Vander Heyden (Free University of Brussels, Brussels, Belgium)
  • A. Voelkel (Poznań University of Technology, Poznań, Poland)
  • B. Walczak (University of Silesia, Katowice, Poland)
  • W. Wasiak (Adam Mickiewicz University, Poznań, Poland)
  • I.G. Zenkevich (St. Petersburg State University, St. Petersburg, Russian Federation)

 

KOWALSKA, TERESA (1946-2023)
E-mail: kowalska@us.edu.pl

SAJEWICZ, MIECZYSLAW
E-mail:msajewic@us.edu.pl

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Scimago  
Scimago
H-index
29
Scimago
Journal Rank
0,27
Scimago Quartile Score Chemistry (miscellaneous) (Q3)
Scopus  
Scopus
Cite Score
2,8
Scopus
CIte Score Rank
General Chemistry 210/409 (Q3)
Scopus
SNIP
0,586

2020
 
Total Cites
650
WoS
Journal
Impact Factor
1,639
Rank by
Chemistry, Analytical 71/83 (Q4)
Impact Factor
 
Impact Factor
1,412
without
Journal Self Cites
5 Year
1,301
Impact Factor
Journal
0,34
Citation Indicator
 
Rank by Journal
Chemistry, Analytical 75/93 (Q4)
Citation Indicator
 
Citable
45
Items
Total
43
Articles
Total
2
Reviews
Scimago
28
H-index
Scimago
0,316
Journal Rank
Scimago
Chemistry (miscellaneous) Q3
Quartile Score
 
Scopus
393/181=2,2
Scite Score
 
Scopus
General Chemistry 215/398 (Q3)
Scite Score Rank
 
Scopus
0,560
SNIP
 
Days from
58
submission
 
to acceptance
 
Days from
68
acceptance
 
to publication
 
Acceptance
51%
Rate

2019  
Total Cites
WoS
495
Impact Factor 1,418
Impact Factor
without
Journal Self Cites
1,374
5 Year
Impact Factor
0,936
Immediacy
Index
0,460
Citable
Items
50
Total
Articles
50
Total
Reviews
0
Cited
Half-Life
6,2
Citing
Half-Life
8,3
Eigenfactor
Score
0,00048
Article Influence
Score
0,164
% Articles
in
Citable Items
100,00
Normalized
Eigenfactor
0,05895
Average
IF
Percentile
20,349
Scimago
H-index
26
Scimago
Journal Rank
0,255
Scopus
Scite Score
226/167=1,4
Scopus
Scite Score Rank
Chemistry (miscellaneous) 240/398 (Q3)
Scopus
SNIP
0,494
Acceptance
Rate
41%

 

Acta Chromatographica
Publication Model Online only
Gold Open Access
Submission Fee none
Article Processing Charge 400 EUR/article
Regional discounts on country of the funding agency World Bank Lower-middle-income economies: 50%
World Bank Low-income economies: 100%
Further Discounts Editorial Board / Advisory Board members: 50%
Corresponding authors, affiliated to an EISZ member institution subscribing to the journal package of Akadémiai Kiadó: 100%
Subscription Information Gold Open Access
Purchase per Title  

Acta Chromatographica
Language English
Size A4
Year of
Foundation
1988
Volumes
per Year
1
Issues
per Year
4
Founder Institute of Chemistry, University of Silesia
Founder's
Address
PL-40-007 Katowice, Poland, Bankowa 12
Publisher Akadémiai Kiadó
Publisher's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
Responsible
Publisher
Chief Executive Officer, Akadémiai Kiadó
ISSN 2083-5736 (Online)

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