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Xenobiotica
the fate of foreign compounds in biological systems
Volume 53, 2023 - Issue 1
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General Xenobiochemistry

Species differences in plasma protein binding of the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) main protease inhibitor nirmatrelvir

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Pages 12-24 | Received 04 Jan 2023, Accepted 17 Feb 2023, Published online: 27 Feb 2023

References

  • Banker MJ, Clark TH, Williams JA. 2003. Development and validation of a 96-well equilibrium dialysis apparatus for measuring plasma protein binding. J Pharm Sci. 92(5):967–974.
  • Bohnert T, Gan L-S. 2013. Plasma protein binding: from discovery to development. J Pharm Sci. 102(9):2953–2994.
  • Brown AM. 2005. HERG block, QT liability and sudden cardiac death. Novartis Found Symp. 266:118–131.
  • Bteich M. 2019. An overview of albumin and alpha-1-acid glycoprotein main characteristics: highlighting the roles of amino acids in binding kinetics and molecular interactions. Heliyon. 5(11):e02879.
  • Ceciliani F, Pocacqua V. 2007. The acute phase protein alpha1-acid glycoprotein: a model for altered glycosylation during diseases. CPPS. 8(1):91–108.
  • Chamouard J, Barre J, Urien S, Houin G, Tillement JP. 1985. Diclofenac binding to albumin and lipoproteins in human serum. Biochem Pharmacol. 34(10):1695–1700.
  • Colclough N, Ruston L, Wood JM, Macfaul PA. 2014. Species differences in drug plasma protein binding. Med Chem Commun. 5(7):963–967.
  • Dale O, Nilsen OG. 1984. Differences in the serum protein binding of prazosin in man and rat. Biochem Pharmacol. 33(11):1719–1724.
  • Denissen JF, Grabowski BA, Johnson MK, Buko AM, Kempf DJ, Thomas SB, Surber BW. 1997. Metabolism and disposition of the HIV-1 protease inhibitor ritonavir (ABT-538) in rats, dogs, and humans. Drug Metab Dispos. 25(4):489–501.
  • Dente L, Ciliberto G, Cortese R. 1985. Structure of the human alpha-1-acid glycoprotein gene: sequence homology with other human acute phase protein genes. Nucl Acids Res. 13(11):3941–3952.
  • Di L. 2021. An update on the importance of plasma protein binding in drug discovery and development. Expert Opin Drug Discov. 16(12):1453–1465.
  • Eng H, Dantonio AL, Kadar EP, Obach RS, Di L, Lin J, Patel NC, Boras B, Walker GS, Novak JJ, et al. 2022. Disposition of PF-07321332 (Nirmatrelvir), an orally bioavailable inhibitor of SARS-CoV-2 3CL protease, across animals and humans. Drug Metab Dispos. 50(5):576–590.
  • Fournier T, Medjoubi NN, Porquet D. 2000. Alpha-1-acid glycoprotein. Biochim Biophys Acta. 1482(1-2):157–171.
  • Ghuman J, Zunszain PA, Petitpas I, Bhattacharya AA, Otagiri M, Curry S. 2005. Structural basis of the drug-binding specificity of human serum albumin. J Mol Biol. 353(1):38–52.
  • Hammond J, Leister-Tebbe H, Gardner A, Abreu P, Bao W, Wisemandle W, Baniecki M, Hendrick VM, Damle B, Simón-Campos A, et al. 2022. Oral nirmatrelvir for high-risk, nonhospitalized adults with covid-19. N Engl J Med. 386(15):1397–1408.
  • Hassan M, Azzazy E, Christenson RH. 1997. All about albumin: biochemistry, genetics, and medical applications. Clin Chem. 43(10):2014a–2015.
  • Huang RYC, Hudgens JW. 2013. Effects of desialylation on human α1-acid glycoprotein–ligand interactions. Biochemistry. 52(40):7127–7136.
  • Kimhofer T, Lodge S, Whiley L, Gray N, Loo RL, Lawler NG, Nitschke P, Bong S-H, Morrison DL, Begum S, et al. 2020. Integrative modeling of quantitative plasma lipoprotein, metabolic, and amino acid data reveals a multiorgan pathological signature of SARS-CoV-2 infection. J. Proteome Res. 19(11):4442–4454.
  • Kumar GN, Jayanti VK, Johnson MK, Uchic J, Thomas S, Lee RD, Grabowski BA, Sham HL, Kempf DJ, Denissen JF, et al. 2004. Metabolism and disposition of the HIV-1 protease inhibitor lopinavir (ABT-378) given in combination with ritonavir in rats, dogs, and humans. Pharm Res. 21(9):1622–1630.
  • Kuribayashi T, Shimizu M, Shimada T, Honjyo T, Yamamoto Y, Kuba K, Yamamoto S. 2003. Alpha 1-Acid Glycoprotein (AAG) levels in healthy and pregrant beagle dogs. Exp. Anim. 52(5):377–381.
  • Matsuzawa T, Nomura M, Unno T. 1993. Clinical pathology reference ranges of laboratory animals. J Vet Med Sci. 55(3):351–362.
  • Melillo A. 2007. Rabbit clinical pathology. J Exot Pet Med. 16(3):135–145.
  • Nishi K, Ono T, Nakamura T, Fukunaga N, Izumi M, Watanabe H, Suenaga A, Maruyama T, Yamagata Y, Curry S, et al. 2011. Structural insights into differences in drug-binding selectivity between two forms of human alpha1-acid glycoprotein genetic variants, the A and F1*S forms. J Biol Chem. 286(16):14427–14434.
  • Owen DR, Allerton CMN, Anderson AS, Aschenbrenner L, Avery M, Berritt S, Boras B, Cardin RD, Carlo A, Coffman KJ, et al. 2021. An oral SARS-CoV-2 M pro inhibitor clinical candidate for the treatment of COVID-19. Science. 374(6575):1586–1593.
  • Primozic S, McNamara PJ. 1985. Effect of the Sialylation State of Alpha-1 Acid Glycoprotein on Propanolol Binding. J Pharm Sci. 74(4):473–475.
  • Ray BK, Ray A. 1991. Molecular cloning and nucleotide sequence of complementary DNA encoding rabbit alpha 1-acid glycoprotein. Biochem Biophys Res Commun. 178(2):507–513.
  • Reddy MB, Morcos PN, Le Pogam S, Ou Y, Frank K, Lave T, Smith P. 2012. Pharmacokinetic/Pharmacodynamic predictors of clinical potency for hepatitis C virus nonnucleoside polymerase and protease inhibitors. Antimicrob Agents Chemother. 56(6):3144–3156.
  • Sathish JG, Bhatt S, DaSilva JK, Flynn D, Jenkinson S, Kalgutkar AS, Liu M, Manickam B, Pinkstaff J, Reagan WJ, et al. 2022. Comprehensive Nonclinical safety assessment of nirmatrelvir supporting timely development of the SARS-COV-2 antiviral therapeutic, Paxlovid™. Int J Toxicol. 0(0):1–15.
  • Schön A, del Mar Ingaramo M, Freire E. 2003. The binding of HIV-1 protease inhibitors to human serum proteins. Biophys Chem. 105(2-3):221–230.
  • Schönfeld DL, Ravelli RBG, Mueller U, Skerra A. 2008. The 1.8-A crystal sturcture of alpha1-acid glycoprotein (Orosomucoid) solved by UV RIP reveals the broad drug-binding activity of this human plasma lipocalin. J Mol Biol. 384(2):393–405.
  • Shtyrya YA, Mochalova LV, Bovin NV. 2009. Influenza virus neuraminidase: structure and function. Acta Naturae. 1(2):26–32.
  • Singh RSP, Toussi SS, Hackman F, Chan PL, Rao R, Allen R, Van Eyck L, Pawlak S, Kadar EP, Clark F, et al. 2022. Innovative randomized phase 1 study and dosing regimen selection to accelerate and inform pivotal COVID-19 trial of. Clin Pharma and Therapeutics. 112(1):101–111.
  • Smith SA, Waters NJ. 2019. Pharmacokinetic and pharmacodynamic considerations for drugs binding to alpha-1-acid glycoprotein. Pharm Res. 36(2):30.
  • Stanke‐Labesque F, Concordet D, Djerada Z, Bouchet S, Solas C, Mériglier E, Bonnet F, Mourvillier B, Ruiz S, Martin‐Blondel G, et al. 2021. Neglecting plasma protein binding in COVID‐19 patients leads to a wrong interpretation of lopinavir overexposure. Clin. Pharmacol. Ther. 109(4):1030–1033.
  • Vella-Brincat JWA, Begg EJ, Kirkpatrick CMJ, Zhang M, Chambers ST, Gallagher K. 2007. Protein binding of cefazolin is saturable in vivo both between and within patients. Br J Clin Pharmacol. 63(6):753–757.
  • Verkhivker GM, Bouzida D, Gehlhaar DK, Rejto PA, Arthurs S, Colson AB, Freer ST, Larson V, Luty BA, Marrone T, et al. 2000. Deciphering common failures in molecular docking of ligand-protein complexes. J Comput Aided Mol Des. 14(8):731–751.
  • Wang Z-m, Ho JX, Ruble JR, Rose J, Rüker F, Ellenburg M, Murphy R, Click J, Soistman E, Wilkerson L, et al. 2013. Structural studies of several clinically important oncology drugs in complex with human serum albumin. Biochim Biophys Acta. 1830(12):5356–5374.
  • Wang J, Li-Chan XX, Atherton J, Deng L, Espina R, Yu L, Horwatt P, Ross S, Lockhead S, Ahmad S, et al. 2010. Characterization of HKI-272 Covalent Binding to Human Serum Albumin. Drug Metab Dispos. 38(7):1083–1093.
  • Wong A, Hsia J. 1983. In vitro binding of propanolol and progesterone to native and desialylated human orosomucoid. Can J Biochem Cell Biol. 61(10):1114–1116.
  • Yamada K, Yokomaku K, Kureishi M, Akiyama M, Kihira K, Komatsu T. 2016. Artificial Blood for Dogs. Sci Rep. 6(1):36782.
  • Zhu M, Zhang D, Zhang H, Shyu WC. 2009. Integrated strategies for assessment of metabolite exposure in humans during drug development: analytical challenges and clinical development considerations. Biopharm. Drug Dispos. 30(4):163–184.
  • Zielinski K, Sekula B, Anna B, Szymczak I. 2020. Structural investigations of stereoselective profen binding by equine and leporine serum albumins. Chirality. 32(3):334–344.
  • Zini R, Morin D, Jouenne P, Tillement JP. 1988. Cicletanine binding to human plasma proteins and erythrocytes, a particular HSA-drug interaction. Life Sci. 43(25):2103–2115.

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