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Original Research

The Anti-Inflammation and Anti-Nociception Effect of Ketoprofen in Rats Could Be Strengthened Through Co-Delivery of a H2S Donor, S-Propargyl-Cysteine

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Pages 5863-5875 | Published online: 09 Nov 2021

References

  • Kokki H. Ketoprofen pharmacokinetics, efficacy, and tolerability in pediatric patients. Pediatr Drugs. 2010;12(5):313–329. doi:10.2165/11534910-000000000-00000
  • Mazìeres B. Topical ketoprofen patch. Drugs R D. 2005;6(6):337–344. doi:10.2165/00126839-200506060-00003
  • Cantisani C, Grieco T, Faina V, et al. Ketoprofen allergic reactions. Recent Pat Inflamm Allergy Drug Discov. 2010;4(1):58–64. doi:10.2174/187221310789895595
  • Boppana R, Kulkarni RV, Mohan GK, Mutalik S, Aminabhavi TM. In vitro and in vivo assessment of novel PH-sensitive interpenetrating polymer networks of a graft copolymer for gastro-protective delivery of ketoprofen. RSC Adv. 2016;6(69):64344–64356. doi:10.1039/C6RA04218J
  • Zeng Y, Lin X, Li F, et al. Ozonation of ketoprofen with nitrate in aquatic environments: kinetics, pathways, and toxicity. RSC Adv. 2018;8(19):10541–10548. doi:10.1039/C7RA12894K
  • Kuczyńska J, Nieradko-Iwanicka B. Future prospects of ketoprofen in improving the safety of the gastric mucosa. Biomed Pharmacother. 2021;139:111608.
  • Gaskell H, Derry S, Wiffen PJ, Moore RA. Single dose oral ketoprofen or dexketoprofen for acute postoperative pain in adults. Cochrane Database Syst Rev. 2017;2017:CD007355.
  • Nie W, Xu P, Hao C, Chen Y, Yin Y, Wang L. Efficacy and safety of over-the-counter analgesics for primary dysmenorrhea a network meta-analysis. Medicine. 2020;99:e19881.
  • Derry S, Conaghan P, Da Silva JAP, Wiffen PJ, Moore RA. Topical NSAIDs for chronic musculoskeletal pain in adults. Cochrane Database Syst Rev. 2016;2016:CD007400.
  • Latosinski GS, Amzalak MJ, Pantoja JCF. Efficacy of ketoprofen for treatment of spontaneous, culture-negative, mild cases of clinical mastitis: a randomized, controlled superiority trial. J Dairy Sci. 2020;103(3):2624–2635. doi:10.3168/jds.2019-17504
  • Sintes GF, Bruckmaier RM, Wellnitz O. Nonsteroidal anti-inflammatory drugs affect the mammary epithelial barrier during inflammation. J Dairy Sci. 2020;103(11):10742–10753. doi:10.3168/jds.2020-18818
  • Espinosa-Cano E, Aguilar MR, Portilla Y, Barber DF, Román JS. Anti-inflammatory polymeric nanoparticles based on ketoprofen and dexamethasone. Pharmaceutics. 2020;12(8):1–18. doi:10.3390/pharmaceutics12080723
  • Greig SL, Garnock-Jones KP. Loxoprofen: a review in pain and inflammation. Clin Drug Investig. 2016;36(9):771–781. doi:10.1007/s40261-016-0440-9
  • Mercadante S, Voza A, Serra S, et al. Analgesic efficacy, practicality and safety of inhaled methoxyflurane versus standard analgesic treatment for acute trauma Pain in the emergency setting: a randomised, open-label, active-controlled, multicentre trial in Italy (MEDITA). Adv Ther. 2019;36(11):3030–3046. doi:10.1007/s12325-019-01055-9
  • Ong CKS, Seymour RA, Lirk P, Merry AF. Combining paracetamol (Acetaminophen) with nonsteroidal antiinflammatory drugs: a qualitative systematic review of analgesic efficacy for acute postoperative pain. Anesth Analg. 2010;110(4):1170–1179. doi:10.1213/ANE.0b013e3181cf9281
  • Halen PK, Chagti KK, Giridhar R, Yadav MR. Combining anticholinergic and anti-inflammatory activities into a single moiety: a novel approach to reduce gastrointestinal toxicity of ibuprofen and ketoprofen. Chem Biol Drug Des. 2007;70(5):450–455. doi:10.1111/j.1747-0285.2007.00574.x
  • Cryer B, Feldman M. Cyclooxygenase-1 and cyclooxygenase-2 selectivity of widely used nonsteroidal anti-inflammatory drugs. Am J Med. 1998;104(5):413–421. doi:10.1016/S0002-9343(98)00091-6
  • Wu D, Wang H, Teng T, Duan S, Ji A, Li Y. Hydrogen sulfide and autophagy: a double edged sword. Pharmacol Res. 2018;131:120–127. doi:10.1016/j.phrs.2018.03.002
  • Olas B. Hydrogen sulfide in signaling pathways. Clin Chim Acta. 2015;439:212–218. doi:10.1016/j.cca.2014.10.037
  • Kumar M, Sandhir R. Hydrogen sulfide in physiological and pathological mechanisms in brain. CNS Neurol Disord Drug Targets. 2018;17(9):654–670. doi:10.2174/1871527317666180605072018
  • Wen YD, Wang H, Zhu YZ. The drug developments of hydrogen sulfide on cardiovascular disease. Oxid Med Cell Longev. 2018;2018:4010395.
  • Chen Z, Zhang M, Zhao Y. Hydrogen sulfide contributes to uterine quiescence through inhibition of NLRP3 inflammasome activation by suppressing the TLR4/NF-ΚB signalling pathway. J Inflamm Res. 2021;14:2753–2768. doi:10.2147/JIR.S308558
  • Sidhapuriwala JN, Hegde A, Ang AD, Zhu YZ, Bhatia M. Effects of S-propargyl-cysteine (SPRC) in caerulein-induced acute pancreatitis in mice. PLoS One. 2012;7(3):e32574. doi:10.1371/journal.pone.0032574
  • Wang Q, Wang XL, Liu HR, Rose P, Zhu YZ. Protective effects of cysteine analogues on acute myocardial ischemia: novel modulators of endogenous H2S production. Antioxid Redox Signal. 2010;12(10):1155–1165. doi:10.1089/ars.2009.2947
  • Li W, Ma F, Zhang L, et al. S-propargyl-cysteine exerts a novel protective effect on methionine and choline deficient diet-induced fatty liver via Akt/Nrf2/HO-1 pathway. Oxid Med Cell Longev. 2016;2016:4690857.
  • Costa SKPF, Muscara MN, Allain T, et al. Enhanced analgesic effects and gastrointestinal safety of a novel, hydrogen sulfide-releasing anti-inflammatory drug (Atb-352): a role for endogenous cannabinoids. Antioxid Redox Signal. 2020;33(14):1003–1009. doi:10.1089/ars.2019.7884
  • Głowacka U, Magierowska K, Wójcik D, et al. Microbiome profile and molecular pathways alterations in gastrointestinal tract by hydrogen sulfide-releasing nonsteroidal anti-inflammatory drug (ATB-352): insight into possible safer polypharmacy. Antioxid Redox Signal. 2021. doi:10.1089/ars.2020.8240
  • Gugliandolo E, Fusco R, D’Amico R. Anti-inflammatory effect of ATB-352, a H2S -releasing ketoprofen derivative, on lipopolysaccharide-induced periodontitis in rats. Pharmacol Res. 2018;132:220–231. doi:10.1016/j.phrs.2017.12.022
  • Chen L, Qian M, Zhang L, et al. Co-delivery of doxorubicin and ShRNA of beclin1 by folate receptor targeted pullulan-based multifunctional nanomicelles for combinational cancer therapy. RSC Adv. 2018;8(32):17710–17722. doi:10.1039/C8RA01679H
  • Suraphan N, Fan L, Liu B, Wu D. Co-delivery of chlorantraniliprole and avermectin with a polylactide microcapsule formulation. RSC Adv. 2020;10(43):25418–25425. doi:10.1039/D0RA03825C
  • Xu C, Tian H, Sun H, Jiao Z, Zhang Y, Chen X. A PH sensitive co-delivery system of SiRNA and doxorubicin for pulmonary administration to B16F10 metastatic lung cancer. RSC Adv. 2015;5(125):103380–103385. doi:10.1039/C5RA21934E
  • Wang GH, Yang HK, Zhao Y, Zhang DW, Zhang LM, Lin JT. Codelivery of doxorubicin and P53 by biodegradable micellar carriers based on chitosan derivatives. RSC Adv. 2015;5(128):105901–105907. doi:10.1039/C5RA19050A
  • Godsey ME, Suryaprakash S, Leong KW. Materials innovation for co-delivery of diverse therapeutic cargos. RSC Adv. 2013;3(47):24794–24811. doi:10.1039/c3ra43094d
  • Chen AM, Zhang M, Wei D, et al. Co-delivery of doxorubicin and Bcl-2 SiRNA by mesoporous silica nanoparticles enhances the efficacy of chemotherapy in multidrug-resistant cancer cells. Small. 2009;5(23):2673–2677. doi:10.1002/smll.200900621
  • Liu S, Guo Y, Huang R, et al. Gene and doxorubicin co-delivery system for targeting therapy of glioma. Biomaterials. 2012;33(19):4907–4916. doi:10.1016/j.biomaterials.2012.03.031
  • Creixell M, Peppas NA. Co-delivery of SiRNA and therapeutic agents using nanocarriers to overcome cancer resistance. Nano Today. 2012;7(4):367–379. doi:10.1016/j.nantod.2012.06.013
  • Wang H, Zhao Y, Wu Y, et al. Enhanced anti-tumor efficacy by co-delivery of doxorubicin and paclitaxel with amphiphilic methoxy PEG-PLGA copolymer nanoparticles. Biomaterials. 2011;32(32):8281–8290. doi:10.1016/j.biomaterials.2011.07.032
  • Liu W, Xi G, Yang X, et al. Poly(lactide-co-glycolide) grafted hyaluronic acid-based electrospun fibrous hemostatic fragments as a sustainable anti-infection and immunoregulation material. J Mater Chem B. 2019;7(32):4997–5010. doi:10.1039/C9TB00659A
  • Sherwani MA, Tufail S, Khan AA, Owais M. Dendrimer-PLGA based multifunctional immuno-nanocomposite mediated synchronous and tumor selective delivery of SiRNA and cisplatin: potential in treatment of hepatocellular carcinoma. RSC Adv. 2015;5(49):39512–39531. doi:10.1039/C5RA03651H
  • Thi Hiep N, Lee B-T. Electro-spinning of PLGA/PCL blends for tissue engineering and their biocompatibility. J Mater Sci. 2010;21(6):1969–1978.
  • Ji W, Yang F, Seyednejad H, et al. Biocompatibility and degradation characteristics of PLGA-based electrospun nanofibrous scaffolds with nanoapatite incorporation. Biomaterials. 2012;33(28):6604–6614. doi:10.1016/j.biomaterials.2012.06.018
  • Anderson JM, Shive MS. Biodegradation and biocompatibility of PLA and PLGA microspheres. Adv Drug Deliv Rev. 2012;64:72–82. doi:10.1016/j.addr.2012.09.004
  • Kapoor DN, Bhatia A, Kaur R, Sharma R, Kaur G, Dhawan S. PLGA: a unique polymer for drug delivery. Ther Deliv. 2015;6(1):41–58. doi:10.4155/tde.14.91
  • Arranz-Romera A, Davis BM, Bravo-Osuna I, et al. Simultaneous co-delivery of neuroprotective drugs from multi-loaded PLGA microspheres for the treatment of glaucoma. J Control Release. 2019;297:26–38. doi:10.1016/j.jconrel.2019.01.012
  • Wu WJ, Jia WW, Liu XH, et al. S-propargyl-cysteine attenuates inflammatory response in rheumatoid arthritis by modulating the Nrf2-ARE signaling pathway. Redox Biol. 2016;10:157–167. doi:10.1016/j.redox.2016.08.011
  • Liu C, Gu X, Zhu YZ. Synthesis and biological evaluation of novel leonurine-SPRC conjugate as cardioprotective agents. Bioorganic Med Chem Lett. 2010;20(23):6942–6946. doi:10.1016/j.bmcl.2010.09.135
  • Yu C, Zhang X, Sun X, et al. Ketoprofen and microRNA-124 co-loaded poly (Lactic-Co-Glycolic Acid) microspheres inhibit progression of adjuvant-induced arthritis in rats. Int J Pharm. 2018;552(1–2):148–153. doi:10.1016/j.ijpharm.2018.09.063
  • Tran BH, Yu Y, Chang L, et al. A novel liposomal S-propargyl-cysteine: a sustained release of hydrogen sulfide reducing myocardial fibrosis via TGF-Β1/Smad pathway. Int J Nanomed. 2019;14:10061–10077. doi:10.2147/IJN.S216667
  • Ma G, Zhang L, Zhang P, et al. Physicochemical characteristics and gastrointestinal absorption behaviors of s-propargyl-cysteine, a potential new drug candidate for cardiovascular protection and antitumor treatment. Xenobiotica. 2015;45:322–334.
  • Dvořák J, Hájková R, Matysová L, Nováková L, Koupparis MA, Solich P. Simultaneous HPLC determination of ketoprofen and its degradation products in the presence of preservatives in pharmaceuticals. J Pharm Biomed Anal. 2004;36(3):625–629. doi:10.1016/j.jpba.2004.07.018
  • Rhee YS, Choi JG, Park ES, Chi SC. Transdermal delivery of ketoprofen using microemulsions. Int J Pharm. 2001;228(1–2):161–170. doi:10.1016/S0378-5173(01)00827-4
  • Zakeri-Milani P, Barzegar-Jalali M, Tajerzadeh H, Azarmi Y, Valizadeh H. Simultaneous determination of naproxen, ketoprofen and phenol red in samples from rat intestinal permeability studies: HPLC method development and validation. J Pharm Biomed Anal. 2005;39(3–4):624–630. doi:10.1016/j.jpba.2005.04.008
  • Juhász Á, Ungor D, Berta K, Seres L, Csapó E. Spreadsheet-based nonlinear analysis of in vitro release properties of a model drug from colloidal carriers. J Mol Liq. 2021;328:115405. doi:10.1016/j.molliq.2021.115405
  • Zhu YZ, Zhong JW, Ho P, et al. Hydrogen sulfide and its possible roles in myocardial ischemia in experimental rats. J Appl Physiol. 2007;102(1):261–268. doi:10.1152/japplphysiol.00096.2006
  • Yu Y, Wang Z, Ding Q, et al. The preparation of a novel poly(Lactic Acid)-based sustained H2S releasing microsphere for rheumatoid arthritis alleviation. Pharmaceutics. 2021;13(5):742. doi:10.3390/pharmaceutics13050742
  • Chuang CH, Cheng YC, Lin SC, et al. Atractylodin suppresses dendritic cell maturation and ameliorates collagen-induced arthritis in a mouse model. J Agric Food Chem. 2019;67(24):6773–6784. doi:10.1021/acs.jafc.9b01163
  • Deuis JR, Dvorakova LS, Vetter I. Methods used to evaluate pain behaviors in rodents. Front Mol Neurosci. 2017;10:284. doi:10.3389/fnmol.2017.00284
  • Yu Y, Wang Z, Yang Q, et al. A novel dendritic mesoporous silica based sustained hydrogen sulfide donor for the alleviation of adjuvant-induced inflammation in rats. Drug Deliv. 2021;28(1):1031–1042. doi:10.1080/10717544.2021.1921075
  • Zheng YT, Zhu JH, Ma G, et al. Preclinical assessment of the distribution, metabolism, and excretion of S-propargyl-cysteine, a novel H 2S donor, in Sprague-Dawley rats. Acta Pharmacol Sin. 2012;33(6):839–844. doi:10.1038/aps.2012.15
  • Saeedi A, Najibi A, Mohammadi-Bardbori A. Effects of long-term exposure to hydrogen sulfide on human red blood cells. Int J Occup Environ Med. 2015;6(1):20–25. doi:10.15171/ijoem.2015.482
  • Kantor TG. Ketoprofen: a review of its pharmacologic and clinical properties. Pharmacother J Hum Pharmacol Drug Ther. 1986;6(3):93–102. doi:10.1002/j.1875-9114.1986.tb03459.x
  • Na M, Yiyun C, Tongwen X, et al. Dendrimers as potential drug carriers. part ii. prolonged delivery of ketoprofen by in vitro and in vivo studies. Eur J Med Chem. 2006;41(5):670–674. doi:10.1016/j.ejmech.2006.01.001
  • Lazzaroni M, Bianchi Porro G. Gastrointestinal side-effects of traditional non-steroidal anti-inflammatory drugs and new formulations. In: Proceedings of the Alimentary Pharmacology and Therapeutics. Blackwell Publishing Ltd. Vol. 20; 2004:48–58.
  • Lü J-M, Wang X, Marin-Muller C, et al. Current advances in research and clinical applications of PLGA-based nanotechnology. Expert Rev Mol Diagn. 2009;9(4):325. doi:10.1586/erm.09.15
  • Ma G. Microencapsulation of protein drugs for drug delivery: strategy, preparation, and applications. J Control Release. 2014;193:324–340. doi:10.1016/j.jconrel.2014.09.003
  • Park K, Otte A, Sharifi F, et al. Formulation composition, manufacturing process, and characterization of poly(Lactide-Co-Glycolide) microparticles. J Control Release. 2021;329:1150–1161. doi:10.1016/j.jconrel.2020.10.044
  • Andhariya JV, Choi S, Wang Y, Zou Y, Burgess DJ, Shen J. Accelerated in vitro release testing method for naltrexone loaded PLGA microspheres. Int J Pharm. 2017;520(1–2):79–85. doi:10.1016/j.ijpharm.2017.01.050
  • Hua Y, Wang Z, Wang D, et al. Key factor study for generic long-acting PLGA microspheres based on a reverse engineering of vivitrol ®. Molecules. 2021;26:1247.
  • Yu Y, Wang Z, Ding Q, et al. The preparation of a novel poly(Lactic Acid)-based sustained H 2 S releasing microsphere for rheumatoid arthritis alleviation. Pharmaceutics. 2021;13:742.
  • Wang JF, Xu HJ, He ZL, Yin Q, Cheng W, Yi M. Crocin alleviates pain hyperalgesia in AIA rats by inhibiting the spinal Wnt5a/ β -catenin signaling pathway and glial activation. Neural Plast. 2020;2020. doi:10.1155/2020/4297483
  • Kang M, Jung I, Hur J, et al. The analgesic and anti-inflammatory effect of WIN-34B, a new herbal formula for osteoarthritis composed of Lonicera Japonica Thunb and Anemarrhena Asphodeloides BUNGE in vivo. J Ethnopharmacol. 2010;131(2):485–496. doi:10.1016/j.jep.2010.07.025
  • A therapeutic dose of ketoprofen causes acute gastrointestinal Bl. Ingenta Connect. Available from: https://www.ingentaconnect.com/content/aalas/jaalas/2012/00000051/00000006/art00012;jsessionid=15oxmg6eue6rf.x-ic-live-01. Accessed September 19, 2021.
  • Perret-Gentil MI. Recommended surgical analgesic protocols for mice and rats; 2017.