Synthesis of an Antimicrobial Thioanthraquinone Compound to Produce Biodegradable Electrospun Mats for Tissue Engineering Purposes

Yeşim Müge Şahin

doi:10.18596/jotcsa.422255

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Year 2018, Volume: 5 Issue: 3, 1119 - 1134, 01.09.2018

Yeşim Müge Şahin

https://doi.org/10.18596/jotcsa.422255

Cited By: 3

Abstract

References

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2. Rath G Ndonzao M, Hostettmann K. Antifungal anthraquinones from Morinda lucida. International journal of pharmacognosy. 1995; 33(2): 107-114.
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20. Gouda, M. A., Berghot, M. A., Shoeib, A. I., & Khalil, A. M. (2010). Synthesis and antimicrobial of new anthraquinone derivatives incorporating pyrazole moiety. European journal of medicinal chemistry, 45(5), 1843-1848.
21. Nor, S. M. M., Sukari, M. A. H. M., Azziz, S. S. S. A., Fah, W. C., Alimon, H., & Juhan, S. F. (2013). Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions. Molecules, 18(7), 8046-8062.
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Synthesis of an Antimicrobial Thioanthraquinone Compound to Produce Biodegradable Electrospun Mats for Tissue Engineering Purposes

Year 2018, Volume: 5 Issue: 3, 1119 - 1134, 01.09.2018

Yeşim Müge Şahin

https://doi.org/10.18596/jotcsa.422255

Cited By: 3

Abstract

In the present study
for the first time in the literature, novel S-substituted bioactive
anthraquinone compound were synthesized with a new, easy and less energetic
reaction method (Patent Number: TR2016/19610) from 1-chloro-9,10-dihydrodiagnosisxy-anthraquinone
and butyl-3-mercaptopropionate. The resultant structure present remarkable
biological properties It was purified by column chromatography. All obtained
structures were characterized with spectroscopic methods (NMR, MS, FT-IR, UV
etc). Antimicrobial properties of bioactive compound were determined as well.
The resultant thioanthraquinone compound has been synthesized for the first
time in the literature and its applications as a biomaterial were discussed in
the present study.

Subsequently, biodegradable electrospun mats were
produced via electrospinning method for their usage in treatment as a
biomaterial. Structural (FTIR), morphological (FEG-SEM) biological
(antimicrobial and in-vitro tests) and mechanical (tensile testing) characterizations
were conducted for these nanobiomaterials. Presenting an advantage of the novel
antimicrobial compound, the produced electrospun nanobiocomposites exhibited
remarkable biological, mechanical properties. With a purposeful compound
synthesis and a subsequent nanobiocomposite production, the obtained
electrospun mats are good canditates for biomaterials for tissue engineering
purposes and wound healing materials.

Keywords

Anthraquinone, synthesis, electrospun mat, biomaterial, biodegradable material, biomaterial

References

1. Ozkok F, Sahin Y M. Biyoaktif Antrakinon Analogları Ve Bunların Sentezine Yönelik Metot. TR. Patent No TR2016/19610.
2. Rath G Ndonzao M, Hostettmann K. Antifungal anthraquinones from Morinda lucida. International journal of pharmacognosy. 1995; 33(2): 107-114.
3. Cowan M M. Plant products as antimicrobial agents. Clinical microbiology reviews. 1999; 12(4): 564-582.
4. Nomura T, Fukai T. Phenolic constituents of licorice (Glycyrrhiza species). In: Fortschritte der Chemie organischer Naturstoffe/Progress in the Chemistry of Organic Natural Products. Springer Vienna, 1998; p 1-140.
5. Ali A M, Ismail N H, Mackeen M M, Yazan L S, Mohamed S M, Ho A S H, Lajis N H. Antiviral, cyototoxic and antimicrobial activities of anthraquinones isolated from the roots of Morinda elliptica. Pharmaceutical Biology. 2000; 38(4): 298-301.
6. Agarwal S K, Singh S S, Verma S, Kumar S. Antifungal activity of anthraquinone derivatives from Rheum emodi. Journal of ethnopharmacology. 2000; 72(1-2): 43-46.
7. Kupchan S M, Karim A. Tumor inhibitors. 114. Aloe emodin: antileukemic principle isolated from Rhamnus frangula L. Lloydia. 1976; 39(4): 223-224.
8. Velasquez W S, Lew D, Grogan TM, Spiridonidis C H, Balcerzak S P, Dakhil S R, Fisher R I. Combination of fludarabine and mitoxantrone in untreated stages III and IV low-grade lymphoma: S9501. Journal of clinical oncology. 2003; 21(10): 1996-2003.
9. Thomas X, Archimbaud E. Mitoxantrone in the treatment of acute myelogenous leukemia: a review. Hematology and cell therapy. 1997; 39(4): 163-174.
10. Shenkenberg T D, Von Hoff D D. Mitoxantrone: a new anticancer drug with significant clinical activity. Annals of internal medicine. 1986; 105(1): 67-81.
11. Neuhaus O, Kieseier B C, Hartung H P. Therapeutic role of mitoxantrone in multiple sclerosis. Pharmacology & therapeutics. 2006; 109(1-2): 198-209.
12. Berger T. Current therapeutic recommendations in multiple sclerosis. Journal of the neurological sciences. 2009; 287: S37-S45.
13. Li N, Ma Y, Yang C, Guo L, Yang X. Interaction of anticancer drug mitoxantrone with DNA analyzed by electrochemical and spectroscopic methods. Biophysical chemistry. 2005; 116 (3): 199-205.
14. Lown J W, Morgan A R, Yen S F, Wang Y H, Wilson W D. Characteristics of the binding of the anticancer agents mitoxantrone and ametantrone and related structures to deoxyribonucleic acids. Biochemistry. 1985; 24(15): 4028-4035.
15. Agarwal S, Jangir D P, Mehrotra R. Spectroscopic studies of the effects of anticancer drug mitoxantrone interaction with calf-thymus DNA. Journal of Photochemistry and Photobiology B: Biology. 2013; 120: 177-182.
16. Pommier Y, Leo E, Zhang H, Marchand C. DNA topoisomerases and their poisoning by anticancer and antibacterial drugs. Chemistry & biology. 2010; 17(5): 421-433.
17. Hande K R. Topoisomerase II inhibitors. Update on Cancer Therapeutics. 2008; 3(1): 13-26.
18. Montoya, S. N., Comini, L. R., & Cabrera, J. L. (2011). Antimicrobial activity of natural photosensitizing anthraquinones.
19. Ali, A. M., Ismail, N. H., Mackeen, M. M., Yazan, L. S., Mohamed, S. M., Ho, A. S. H., & Lajis, N. H. (2000). Antiviral, cyototoxic and antimicrobial activities of anthraquinones isolated from the roots of Morinda elliptica. Pharmaceutical Biology, 38(4), 298-301
20. Gouda, M. A., Berghot, M. A., Shoeib, A. I., & Khalil, A. M. (2010). Synthesis and antimicrobial of new anthraquinone derivatives incorporating pyrazole moiety. European journal of medicinal chemistry, 45(5), 1843-1848.
21. Nor, S. M. M., Sukari, M. A. H. M., Azziz, S. S. S. A., Fah, W. C., Alimon, H., & Juhan, S. F. (2013). Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions. Molecules, 18(7), 8046-8062.
22. Routier, S., Cotelle, N., Catteau, J. P., Bernier, J. L., Waring, M. J., Riou, J. F., & Bailly, C. (1996). Salen-anthraquinone conjugates. Synthesis, DNA-binding and cleaving properties, effects on topoisomerases and cytotoxicity. Bioorganic & medicinal chemistry, 4(8), 1185-1196:
23. Ishmael, D. R., & Adelsteinsson, O. (2014). 1, 4, 5, 8-Tetrakis-[(2-N, N-dimethylaminoethyl) amino] anthraquinone as a potential anticancer agent: its synthesis, characterization and anticancer properties.
24. Teng, C. H., Won, S. J., & Lin, C. N. (2005). Design, synthesis and cytotoxic effect of hydroxy-and 3-alkylaminopropoxy-9, 10-anthraquinone derivatives. Bioorganic & medicinal chemistry, 13(10), 3439-3445.
25. Gouda, M. A., Berghot, M. A., Shoeib, A. I., & Khalil, A. M. (2010). Synthesis and antimicrobial of certain new thiazolidinone, thiazoline, and thiophene derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, 185(7), 1455-1462.
26. Ibis, C., Tuyun, A. F., Bahar, H., Ayla, S. S., Stasevych, M. V., Musyanovych, R. Y., ... & Novikov, V. (2013). Synthesis of novel 1, 4-naphthoquinone derivatives: antibacterial and antifungal agents. Medicinal Chemistry Research, 22(6), 2879-2888.
27. Huang, H. S. (2005). U.S. Patent Application No. 10/615,695.
28. Huang, H. S., Chiou, J. F., Chiu, H. F., Hwang, J. M., Lin, P. Y., Tao, C. W., ... & Jeng, W. R. (2002). Synthesis of symmetrical 1, 5-bis-thio-substituted anthraquinones for cytotoxicity in cultured tumor cells and lipid peroxidation. Chemical and pharmaceutical bulletin, 50(11), 1491-1494.
29. Lord W M, Peters A T. Reactions in NN-dimethylformamide. Part II. Halogen replacement in the anthraquinone series. Journal of the Chemical Society C: Organic. 1968; 783-785.
30. Ruediger E H, Kaldas M L, Gandhi S S, Fedryna C, Gibson M S. Reactions of 1, 5- dichloroanthraquinone with nucleophiles. The Journal of Organic Chemistry. 1980; 45(10): 1974- 1978.
31. Zhang Y, Ouyang H, Lim C T, Ramakrishna S, Huang Z M. Electrospinning of gelatin fibers and gelatin/PCL composite fibrous scaffolds. Journal of Biomedical Materials Research Part B: Applied Biomaterials. 2005; 72(1): 156-165.
32. Kehoe S, Zhang, X F, Boyd D. FDA approved guidance conduits and wraps for peripheral nerve injury: a review of materials and efficacy. Injury. 2012; 43(5): 553-572.
33. Polat E. Polikaprolaktonun Elektrostatik Eğirmesi ve Rgd Yüzey Modifikasyonu ile Periferik Sinir İyileşme Kanalları Üretim ve Karakterizasyonu. Fen Bilimleri Enstitüsü, Yüksek Lisans Tezi, 2013 Ankara.
34. Sahin Y M, Su S, Ozbek B, Yucel S, Pinar O, Kazan D, Gunduz O. Production and characterization of electrospun fish sarcoplasmic protein based nanofibers. Journal of Food Engineering. 2018; 222: 54-62.
35. Aliakbarshirazi S, Talebian A. Electrospun gelatin nanofibrous scaffolds for cartilage tissue engineering. Materials Today: Proceedings. 2017; 4(7): 7059-7064.
36. Erdem R, Sancak E. Elektroçekim yöntemiyle elde edilen poliamid 6/kitosan bazlı nanoliflerin morfolojik özelliklerinin incelenmesi. İstanbul Ticaret Üniversitesi Fen Bilimleri Dergisi. 2013; 12.24: 53.
37. Burger C, Hsiao B S, Chu B. Nanofibrous materials and their applications. Annual Review of Materials Research. 2006; 36: 333-368.
38. Buluş E. Doğal izole edilmiş biyoseramiklerden elektrospinning yöntemi ile polimerik biyokompozit malzeme eldesi, Fırat Üniversitesi, Fen Bilimleri Enstitüsü, Yüksek lisans tezi, 2017 Elazığ.
39. Sill T J, Von Recum H A. Electrospinning: applications in drug delivery and tissue engineering. Biomaterials. 2008; 29(13): 1989-2006.
40. Jones R N, Sader H S, Mendes R E, Flamm R K. Update on antimicrobial susceptibility trends among Streptococcus pneumoniae in the United States: report of ceftaroline activity from the SENTRY Antimicrobial Surveillance Program (1998–2011). Diagnostic microbiology and infectious disease. 2013; 75(1): 107-109.
41. Cuenca-Estrella M, Gomez-Lopez A, Alastruey-Izquierdo A, Bernal-Martinez L, Cuesta I, Buitrago M J, Rodriguez-Tudela J L. Comparison of the Vitek 2 antifungal susceptibility system with the Clinical and Laboratory Standards Institute (CLSI) and European Committee on Antimicrobial Susceptibility Testing (EUCAST) broth microdilution reference methods and with the Sensititre YeastOne and Etest techniques for in vitro detection of antifungal resistance in yeast isolates. Journal of clinical microbiology. 2010; 48(5): 1782-1786.
42. Zhu G, Li T. Properties of polyurethane–polystyrene graft copolymer membranes used for separating water–ethanol mixtures. European polymer journal. 2005; 41(5): 1090-1096.
43. Jeevitha D, Amarnath K. Chitosan/PLA nanoparticles as a novel carrier for the delivery of anthraquinone: Synthesis, characterization and in vitro cytotoxicity evaluation. Colloids and Surfaces B: Biointerfaces. 2013; 101: 126-134.
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Details

Primary Language	English
Subjects	Chemical Engineering
Journal Section	Articles
Authors	Yeşim Müge Şahin 0000-0003-2119-1216
Publication Date	September 1, 2018
Submission Date	May 9, 2018
Acceptance Date	September 20, 2018
Published in Issue	Year 2018 Volume: 5 Issue: 3

Cite

Vancouver	Şahin YM. Synthesis of an Antimicrobial Thioanthraquinone Compound to Produce Biodegradable Electrospun Mats for Tissue Engineering Purposes. JOTCSA. 2018;5(3):1119-34.