Pharmacokinetic Alteration of Paclitaxel by Ferulic Acid Derivative
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials
2.2. Synthesis of FA Derivatives
2.2.1. Methylation of Ferulic Acid
2.2.2. General Procedure for the Synthesis of Esters
2.2.3. General Procedure for Hydrolysis
2.2.4. General Synthesis Amides
Synthesis of (E)-3-(3-methoxy-4-propoxyphenyl)-1-(piperidin-1-yl)prop-2-en-1-one (Compound 5a)
Synthesis of (E)-3-(4-isobutoxy-3-methoxyphenyl)-1-(piperidin-1-yl)prop-2-en-1-one (Compound 5b)
Synthesis of (E)-3-(4-benzyloxy-3-methoxyphenyl)-1-(piperidin-1-yl)prop-2-en-1-one (Compound 5c) [17]
Synthesis of (E)-3-(3-methoxy-4-propoxyphenyl)-N,N-dimethylacrylamide (Compound 5d)
Synthesis of (E)-3-(4-isobutoxy-3-methoxyphenyl)-N,N-dimethylacrylamide (Compound 5e)
Synthesis of (E)-N-benzyl-3-(3-methoxy-4-propoxyphenyl)-N-methylacrylamide (Compound 5f)
Synthesis of (E)-3-(4-benzyloxy-3-methoxyphenyl)-N,N-dimethylacrylamide (Compound 5g)
Synthesis of (E)-1-(4-hydroxy-4-phenylpiperidin-1-yl)-3-(3-methoxy-4-propoxyphenyl) prop-2-en-1-one (Compound 5h)
2.3. Cytotoxicity Studies in P-gp Overexpressed Cells
2.4. [3H]-Daunomycin Accumulation and Efflux Studies
2.5. Human P-glycoprotein ATPase Activity Assay
2.6. Pharmacokinetic Study
2.7. Pharmacokinetic Analysis
2.8. Data Analysis
3. Results
3.1. Synthesis of Ferulic Amides, FA Derivatives
3.2. P-gp Inhibitory Effect of FA Derivatives in Vitro
3.3. BA Enhancing Effect of Compound 5c in Vivo
4. Discussion
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Category | Compounds | IC50 of DNM (μM) |
---|---|---|
Control | Negative Control | 31.7 |
VER | 3.1 | |
FA derivatives | 5a | 33.4 |
5b | 12.1 | |
5c | 2.2 | |
5d | 35.8 | |
5e | 19.1 | |
5f | 6.5 | |
5g | 7.2 | |
5h | 2.6 |
Concentration (μM) | Blank | VER | 5c | 5f | 5g | 5h |
---|---|---|---|---|---|---|
20 | 1.00 | 3.46 | 1.54 | 2.85 | 1.26 | 3.99 |
50 | 1.00 | 2.53 | 2.48 | 3.12 | 1.77 | 2.69 |
100 | 1.00 | 2.24 | 4.02 | 3.35 | 5.19 | 2.79 |
PK Parameters | PTX PO Control | Co- Administration of PTX with Compound 5c | ||
---|---|---|---|---|
0.5 mg/kg | 2 mg/kg | 5 mg/kg | ||
Cmax (ng/mL) | 187 ± 41 | 193 ± 97 | 249 ± 55 | 195 ± 25 |
Tmax (h) | 2.0 ± 0.0 | 2.0 ± 0.0 | 3.5 ± 1.0 | 2.2 ± 0.5 |
AUCinf (ng·h/mL) | 773 ± 169 | 909 ± 539 | 1880 ± 750 | 1456 ± 367 * |
t1/2 (h) | 2.8 ± 0.86 | 2.3 ± 0.5 | 6.5 ± 0.15 | 6.8± 1.3 ** |
Vz/F (L) | 35.14 ± 16.84 | 32.30± 19.10 | 34.80 ± 17.72 | 44.60 ± 12.27 |
Cl/F (L/h) | 8.22 ± 1.84 | 9.38± 4.81 | 4.10 ± 1.53 * | 4.53 ± 1.04 * |
RB (%) | 117.0 | 243.2 | 188.7 |
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Lee, J.; Chae, S.W.; Ma, L.; Lim, S.Y.; Alnajjar, S.; Park Choo, H.-Y.; Lee, H.J.; Rhie, S.J. Pharmacokinetic Alteration of Paclitaxel by Ferulic Acid Derivative. Pharmaceutics 2019, 11, 593. https://doi.org/10.3390/pharmaceutics11110593
Lee J, Chae SW, Ma L, Lim SY, Alnajjar S, Park Choo H-Y, Lee HJ, Rhie SJ. Pharmacokinetic Alteration of Paclitaxel by Ferulic Acid Derivative. Pharmaceutics. 2019; 11(11):593. https://doi.org/10.3390/pharmaceutics11110593
Chicago/Turabian StyleLee, Jaeok, Song Wha Chae, LianJi Ma, So Yeon Lim, Sarah Alnajjar, Hea-Young Park Choo, Hwa Jeong Lee, and Sandy Jeong Rhie. 2019. "Pharmacokinetic Alteration of Paclitaxel by Ferulic Acid Derivative" Pharmaceutics 11, no. 11: 593. https://doi.org/10.3390/pharmaceutics11110593