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Xiaojun Cai School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, China

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Xiangyi Dai School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, China

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Zhou Li Wenzhou Customs Comprehensive Technical Service Center, Wenzhou, China

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Junying Chen 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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Meiling Zhang School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, China

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Abstract

A simple, rapid, and sensitive method based on UPLC-MS/MS was developed to determine spiraeoside in mouse blood, and was applied to the pharmacokinetics and bioavailability of spiraeoside after mice after intravenous (a dose of 5 mg kg−1) and oral (a dose of 20 mg kg−1) administration. On HSS T3 column set at 40 °C, chromatographic separation was obtained with the mobile phase of acetonitrile and 0.1% formic acid using the gradient elution. Spiraeoside and internal standard (IS) were quantitatively analyzed using multiple reaction monitoring (MRM) mode in electrospray (ESI) positive interface. The MRM mode was monitoring the fragmentation of m/z 465.4→303.1 and m/z 451.3→ 289.2 for spironoside and IS, respectively. The results showed a good linear relationship was in the concentration range of 1–200 ng mL−1 (r > 0.998) and the lower limit of quantification (LLOQ) was 1.0 ng mL−1. The intra- and the inter-day precision (RSD%) of the method was within 14.0%, and the accuracy ranged from 90.0% to 115.0%. The extraction recovery of spriaeoside was better than 63.0%, and the matrix effects were in the range of 86%–98%. It also showed the half-life was short, and the absolute bioavailability was 4.0% in mice. Therefore, the established UPLC-MS/MS method was suitable for the pharmacokinetic and bioavailability study of spiraeoside in mice.

Abstract

A simple, rapid, and sensitive method based on UPLC-MS/MS was developed to determine spiraeoside in mouse blood, and was applied to the pharmacokinetics and bioavailability of spiraeoside after mice after intravenous (a dose of 5 mg kg−1) and oral (a dose of 20 mg kg−1) administration. On HSS T3 column set at 40 °C, chromatographic separation was obtained with the mobile phase of acetonitrile and 0.1% formic acid using the gradient elution. Spiraeoside and internal standard (IS) were quantitatively analyzed using multiple reaction monitoring (MRM) mode in electrospray (ESI) positive interface. The MRM mode was monitoring the fragmentation of m/z 465.4→303.1 and m/z 451.3→ 289.2 for spironoside and IS, respectively. The results showed a good linear relationship was in the concentration range of 1–200 ng mL−1 (r > 0.998) and the lower limit of quantification (LLOQ) was 1.0 ng mL−1. The intra- and the inter-day precision (RSD%) of the method was within 14.0%, and the accuracy ranged from 90.0% to 115.0%. The extraction recovery of spriaeoside was better than 63.0%, and the matrix effects were in the range of 86%–98%. It also showed the half-life was short, and the absolute bioavailability was 4.0% in mice. Therefore, the established UPLC-MS/MS method was suitable for the pharmacokinetic and bioavailability study of spiraeoside in mice.

Introduction

Ulmus pumila is a common folk medicinal material of Kazak nationality in Xinjiang, which is recorded in the annals of Kazakh medicine [1]. U. pumila leaf mainly contains salicylates, phenolic glycosides, phenolic acids, flavonoids, tannins [2], and has the functions of anti-inflammatory, hemostasis, anti-ulcer, anticoagulation, anti-tumor, wound treatment, liver protection, anti-diabetes and brain strengthening [3–5]. As a kind of flavonoids, spiraeoside is one of the main active and specific components extracted from U. pumila leaf, which plays the role of antipyretic, analgesic, and anti-inflammatory [6–8]. At present, the pharmacodynamics and toxicology of spiraeoside are still in the experimental stage in vitro, and there is no literature about the determination of spiraeoside in biological samples by UPLC-MS/MS. In order to explore the therapeutic potential of spiraeoside in vivo, it is necessary to establish a rapid and simple bioanalytical method for its quantification in blood and clarify its pharmacokinetic behavior in biological matrix. High performance liquid chromatography-electrospray tandem mass spectrometry (HPLC-MS/MS) has the advantages of high sensitivity and accuracy [9, 10]. It has been recognized as an effective method for modern pharmacokinetic study [11]. In this study, based on UPLC-MS/MS, a simple and rapid analytical method was developed for the determination of spiraeoside in mouse blood and then applied to study the pharmacokinetics of spiraeoside after intravenous and oral administration to mice. This study will provide useful data and information for the clinical application and development of spiraeoside.

Materials and methods

Chemicals and animals

Spiraeoside (MUST-21042912, Fig. 1a) and flavanomarein (IS, MUST-20062815, Fig. 1b) with a purity of 98.0%, were purchased from Chengdu Manster Pharmaceutical Co., Ltd (Chengdu, China). HPLC grade methanol and acetonitrile were purchased from Merck Co., Ltd (Darmstadt, Germany). Ultra-pure water was provided by a Millipore purification system (Bedford, MA, USA). Institute of Cancer Research (ICR) mice, weight ranging from 20 to 22 g, male, were provided by animal experiment center of Wenzhou Medical University (Wenzhou, China).

Fig. 1.
Fig. 1.

Chemical structures of spiraeoside (a) and IS (b)

Citation: Acta Chromatographica 2022; 10.1556/1326.2022.01061

Chromatographic and mass spectrometric conditions

Acquity H-class UPLC and Xevo TQ-S micro triple quadrupole mass spectrometer (Waters Corp, Milford, MA, USA).

The chromatographic separation was performed on a UPLC HSS T3 column (2.1 × 100 mm, 1.7 μm) at 40 °C. The mobile phase composition was acetonitrile and water with 0.1% formic acid via the following gradient elution: 0–0.2 min, acetonitrile 10%; 0.2–1.2 min, acetonitrile 10%–95%; 1.2–2.0 min, acetonitrile 95%; 2.0–2.2 min, acetonitrile 95%–10%; 2.2–4.0 min, acetonitrile 10%. The flow rate was 0.4 mL min−1 and the elution time of blood sample was 4 min.

Nitrogen was used as desolvation gas (900 L h−1). The capillary voltage was set at 2.1 kV and the desolvation temperature was set at 450 °C. MRM in ESI positive interface was used for quantitative analysis. The mass spectrometric conditions (Fig. 2) were m/z 465.4→m/z 303.1 for spironoside (cone voltage 35 V, collision voltage 16 V) and m/z 451.3→m/z 289.2 for IS (cone voltage 52 V, collision voltage 18 V), respectively.

Fig. 2.
Fig. 2.

Mass spectrum of spiraeoside (a) and IS (b)

Citation: Acta Chromatographica 2022; 10.1556/1326.2022.01061

Standard solution and quality control (QC) samples

The stock solutions of spiraeoside (1.0 mg mL−1) and IS (0.1 mg mL−1) were prepared with methanol and water (50:50, v/v). In order to prepare a series of working solutions, the stock solution of spiraeoside was diluted with methanol. The stock solution of IS was also diluted with acetonitrile and methanol (90:10, v/v) to prepare the working solution containing 50 ng mL−1 for IS.

The working solution of spiraeoside and IS solution were accuratedly absorbed and added into the blank blood samples to prepare calibration standard solutions at concentrations of 1, 2, 5, 10, 20, 50, 100 and 200 ng mL−1 for spiraeoside with 50 ng mL−1 for IS, and a series of concentrations of standard curve were 1–200 ng mL−1. And then all the solutions were stored at 4 °C. The three levels of quality control (QC) samples were prepared in the same way as the calibration standard solutions. The concentrations of QC samples were low (3 ng mL−1), medium (18 ng mL−1), and high (180 ng mL−1) for spiraeoside by spiking blank blood samples.

Sample preparation

A simple protein precipitation method was used for treatment of mouse blood. 20 µL blood sample was transferred to 1.5-mL microcentrifuge tube, and 100 µL IS solution (50 ng mL−1) in acetonitrile and methanol (90:10, v/v) was added and mixed. After vortex mixing for 1.0 min, the mixture was centrifuged with 13000 rpm for 10 min at 4 °C. 80 µL supernatant was taken to the injection bottle, and 2-µL injection volume was injected into the UPLC-MS/MS system for analysis.

Method validation

The selectivity was evaluated by analyzing a blank mouse blood, a blank mouse blood spiked with spiraeoside and IS solution, and a mouse blood sample after oral administration of spiraeoside spiked with IS solution.

A series of standard solutions of spiraeoside (1–200 ng mL−1) with 50 ng mL−1 for IS were assayed under the same conditions as the blood sample. The peak-area ratios of spiraeoside to IS were detected, and the standard curve was developed by least squares linear fitting of the peak-area ratios to evaluate linearity.

The accuracy and precision were evaluated by determining six QC samples at the three levels of 3, 18 and 180 ng mL−1. The precision was expressed as relative standard deviation (RSD). The intra-day and inter-day precision of QC samples were calculated by measuring QC samples for three consecutive days. The accuracy of the intra-day and inter-day was then determined by the average value and the true value of QC samples.

The recovery was calculated by comparing the measured peak area of QC samples with that of the corresponding standard solution. The matrix effect was determined by comparing the measured peak area of the standard solution containing blank mouse blood after extraction with that of the corresponding standard solution.

Stability of spiraeoside in blood was investigated by analysis of QC samples at room temperature for 2 h, the frozen condition at −20 °C for 30 days and freeze/thaw cycles, respectively.

Pharmacokinetics

All experimental procedures and protocols were approved by the Animal Care Committee of Wenzhou Medical University (Wydw 2019-0982). Twelve mice were randomly divided into two groups (six mice per group). One group of mice was given intravenously of spiraeoside at a dose of 5 mg kg−1, and the other group of mice was given orally of spiraeoside at a dose of 20 mg kg−1. And blood samples (20 µL) were collected from the tail vein of mice at times 0.0833, 0.5, 1, 2, 3, 4, 6, 8 and 12 h after administration of spiraeoside, which were all stored at −20 °C until analysis. The main pharmacokinetic parameters were fitted using non-compartmental model by drug and statistics (DAS) software (version 2.0, China Pharmaceutical University).

Results

Selectivity

Figure 3 showed the chromatograms of blank blood, blank blood spiked with spiraoside and IS and a mouse blood sample after administration of spiraoside, which indicated there was no obvious impurities and endogenous substances interference at the retention time of spiraeside and IS. The retention time of spiraeoside and IS were 1.92 and 1.80 min, respectively. The method had good selectivity.

Fig. 3.
Fig. 3.

UPLC-MS/MS chromatography of spiraeoside and IS in mouse blood, (a) blank mouse blood, (b) blank mouse blood spiked with spiraeoside of LLOQ and IS, (c) a sample after administration of spiraeoside

Citation: Acta Chromatographica 2022; 10.1556/1326.2022.01061

Linearity

The standard curve equation of spiraeoside in mouse blood was Y = 0.0074X-0.0067 (r = 0.9987), where y was the peak-area ratios of spiraeoside to IS, and x was the concentration of spiraeoside. The result indicated that there was a good correlation between the ratio of peak area and concentration of spiraeoside in the experimental range. The LLOQ of the method for spiraeoside in mouse blood was 1.0 ng mL−1, which indicated that the method was sensitive for the quantitative determination of spiraeoside.

Precision, accuracy, recovery, and matrix effect

The intra-and inter-day precision of the method for spiraeoside in mouse blood was both less than 14%, and the accuracy ranged from 90.0% to 115.0%. The extraction recovery was better than 63%, and the matrix effect was in the range of 86%–98%, which met the requirements of pharmacokinetic study of spiraeoside (Table 1). It showed that the developed method was acceptable for the quantitative determination of spiraeoside in mouse blood.

Table 1.

Accuracy, precision, matrix effect and recovery of spiraeoside in mouse blood

Concentration (ng mL−1) Accuracy (%) Precision (RSD%) Matrix effect (%) Recovery (%)
Intra-day Inter-day Intra-day Inter-day
1 114.9 113.7 13.0 13.2 86.0 73.6
3 106 107.3 9.4 13.7 90.5 76.4
18 90.7 106 5.7 7.2 97.3 69.0
180 97.4 93.9 8.5 8.5 87.6 63.5

Stability

The variation of spiraeoside in mouse blood was within ±9.0%, with RSD less than 14.0%. The result indicated spiraeoside was stable in mouse blood samples (Table 2).

Table 2.

Stability of spiraeoside in mouse blood (%)

Concentration (ng mL−1) Autosampler (4 °C, 12 h) Ambient (2 h) –20 °C (30 d) Freeze-thaw
Accuracy RSD Accuracy RSD Accuracy RSD Accuracy RSD
3 98.6 8.0 107.0 7.5 92.9 12.7 92.6 5.6
18 96.4 6.0 98.8 1.7 101.7 9.4 101.2 13.4
180 103.2 2.7 99.4 6.5 102.6 6.8 96.4 9.5

Pharmacokinetics

Figure 4 showed the drug concentration-time curve. Table 3 showed the main pharmacokinetic parameters fitted by non-compartmental model. The half-life of spiraeoside in mice was relatively short, which indicated that the metabolism of spiraeoside was fast. The bioavailability of spiraeoside in mice was 4.0%, which indicated that the oral bioavailability was relatively low.

Fig. 4.
Fig. 4.

Time-curve of spiraeoside in mice after IV (5 mg kg−1) and PO (20 mg kg−1)

Citation: Acta Chromatographica 2022; 10.1556/1326.2022.01061

Table 3.

Main pharmacokinetic parameters after intravenous (IV) and oral (PO) administration of spiraeoside in mice

Group AUC(0t) ng mL−1*h AUC(0∞) ng mL−1 *h t 1/2z h CLz/F Lh−1kg V z/F L kg−1 C max ng mL−1
IV(5 mg kg−1) 23.7 ± 3.8 24.8 ± 4.0 2.9 ± 1.0 206.5 ± 37.2 857.8 ± 263.4 27.5 ± 8.1
PO(20 mg kg−1) 3.8 ± 1.0 4.3 ± 1.0 2.1 ± 0.9 4925.8 ± 1678.2 14425.2 ± 5376.1 2.8 ± 1.5

Discussion

The selection of positive and negative electrodes of ESI is usually used in methodological research [12, 13]. Compared with negative mode, ESI positive electrode was suitable for the detection for its higher sensitivity.

In this study, different column (C18 column and HSS T3 column) and mobile phase composition (methanol-water and acetonitrile-water) were also investigated. HSS T3 (2.1 mm × 100 mm, 1.8 µm) column with acetonitrile and 0.1% formic acid as mobile phase showed more sensitive than C18 column in the determination of spiraeoside and IS. It exhibited that the retention time of spiraeoside and IS was appropriate, the chromatographic peak shape was good, and the mass spectrum response was high, which could meet the bioanalytical method requirements.

Protein precipitation (PPT), liquid-liquid extraction (LLE) and solid phase extraction (SPE) are usually used to prepare biological samples [14, 15]. PPT is one of the most commonly sample treatment procedures because of its simplicity, economy, and practicality [16, 17]. In this study, PPT procedure was selected for blood sample pretreatment. Several protein precipitation solutions, including methanol, acetonitrile, methanol, and acetonitrile (1:1, v/v), methanol and acetonitrile (1:9, v/v), and 5% trichloroacetic acid and methanol were investigated and compared. The result indicated that the matrix effect of methanol and acetonitrile (1:9, v/v) used as protein precipitation solution was in the range of 86.0%–97.3%, and the extraction recovery was higher. Compared with traditional HPLC or gas chromatography analysis, UPLC-MS/MS method was used to quantitatively determine spiraeoside in mouse blood with the characteristics of higher sensitivity (the LLOQ was 1.0 ng mL−1) and rapidity. It only took 4 min to complete the analysis of a mouse blood sample.

Conclusion

A rapid, simple, and sensitive method for the determination of spiraeoside based on UPLC-MS/MS was established, optimized, and validated for the first time. The short run time of 4 min each sample and the simple protein precipitation procedure for blood sample pretreatment showed the efficiency and simplicity for analyzing blood samples. The developed method was successfully applied to the pharmacokinetics and oral bioavailability of spiraeoside in mice for the first time. The pharmacokinetic parameters were fitted and the bioavailability was calculated by non-compartmental mode. The results indicated that spiraeoside was metabolized rapidly in mice and its oral bioavailability was very low.

Acknowledgments

This study was supported by grants from the Wenzhou Science and Technology Bureau (Y2020069).

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    Huang, Z. H. ; Wang, Z. L. ; Shi, B. L. ; Wei, D. ; Chen, J. X. ; Wang, S. L. ; Gao, B. J. Int. J. Anal. Chem. 2015, 2015, 698630.

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    Ghosh, C. ; Chung, H. Y. ; Nandre, R. M. ; Lee, J. H. ; Jeon, T. I. ; KimI. S. ; Yang, S. H. ; Hwang, S. G. Food Chem. Toxicol. 2012, 50, 200915.

    • Search Google Scholar
    • Export Citation
  • 4.

    Ma, Q. ; Wei, R. ; Shang, D. ; Sang, Z. ; Liu, W. ; Cao, Z. Pak J. Pharm. Sci. 2019, 32, 20592064.

  • 5.

    Lee, J. H. ; Lee, Y. K. ; Choi, Y. R. ; Park, J. ; Jung, S. K. ; Chang, Y. H. Int. J. Biol. Macromol 2018, 111, 311318.

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    • Search Google Scholar
    • Export Citation
  • 8.

    Nile, A. ; Nile, S. H. ; Cespedes-Acuna, C. L. ; Oh, J. W. Food Chem. Toxicol. 2021, 154, 112327.

  • 9.

    Reddy, G. N. ; Laltanpuii, C. ; Sonti, R. Bioanalysis 2021, 13, 16971722.

  • 10.

    Famiglini, G. ; Palma, P. ; Termopoli, V. ; Cappiello, A. Anal. Chim. Acta 2021, 1167, 338350.

  • 11.

    Wang, Y. ; Zhang, L. ; Gu, S. ; Yin, Z. ; Shi, Z. ; Wang, P. ; Xu, C. Curr. Drug Metab. 2020, 21, 969978.

  • 12.

    Tong, S. ; Zeng, Y. ; Ma, J. ; Wen, C. Acta Chromatographica 2021, 33, 333337.

  • 13.

    Yu, X. ; Liu, H. ; Xu, X. ; Hu, Y. ; Wang, X. ; Wen, C. J. Chromatogr. B Analyt Technol. Biomed. Life Sci. 2021, 1179, 122840.

  • 14.

    Ma, J. ; Wang, X. J. Pharm. Biomed. Anal. 2021, 195, 113894.

  • 15.

    Sun, W. ; Jiang, X. ; Wang, X. ; Bao, X. Curr. Pharm. Anal. 2021, 17, 547553.

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    Chen, L. ; Ma, J. ; Wang, X. ; Zhang, M. Biomed. Res. Int. 2020, 2020, 1030269.

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    Shen, X. W. ; Ma, J. S. ; Wang, X. Q. ; Wen, C. C. ; Zhang, M. L. Biomed. Res. Int. 2020, 2020, 8247270.

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Editor(s)-in-Chief: Kowalska, Teresa

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

Editors(s)

  • Danica Agbaba (University of Belgrade, Belgrade, Serbia)
  • 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)
  • Ł. Komsta (Medical University of Lublin, Lublin, Poland)
  • 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
E-mail: kowalska@us.edu.pl

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

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2021  
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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
1992
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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