Koruyucu Yardımcı Maddeler Olarak Kullanılan Parabenin Yeni Türevlerinin Sentezi Ve Antimikrobiyal Etkilerinin İncelenmesi

Year 2020, , 406 - 417, 01.03.2020

Mehmet Fatih Hakimoğlu Meltem Tan

https://doi.org/10.21597/jist.600910

Abstract

Bu çalışmada paraben bileşiklerinin zararlı etkilerini en aza indirecek alternatif bileşiklerin sentezlenmesi amaçlanmıştır. Paraben bileşiklerinde yer alan grupların değiştirilmesi sonucu, yeni alternatif bileşiklerin sentezi gerçekleştirilerek yapı karakterizasyonları yapılmıştır. İlaçlarda koruyucu yardımcı maddeler olarak kullanılabilecek potansiyele sahip bu sentetik bileşiklerin antimikrobiyal özelliklerinin araştırılması gerçekleştirilmiştir. Bu amaçla çeşitli gram pozitif ve gram negatif bakterilerden Klebsiella pneumoniae ATCC 13883, Escherichia coli ATCC 36218, Bacillus megaterium DSM-32, Staphylococcus aureus ATCC 25923 ve ökaryotik maya olan Candida albicans ATCC10231 ve Yarrowia lipolytica mikroorganizmalarına karşı aktiviteleri incelenmiştir.

Keywords

paraben, sentetik bileşik, antimikrobiyal özellik

Supporting Institution

Van Yüzüncü Yıl Üniversitesi

Project Number

THD-2018-7077

Thanks

Bu çalışma Van Yüzüncü Yıl Üniversitesi BAP birimi (THD-2018-7077) tarafından kısmi olarak desteklenmiştir.

Synthesis and Antimicrobial Effects of New Derivatives of Paraben Used as Protective Excipients

Abstract

In this study, new alternative compounds were synthesized as a result of changing the groups in these compounds with the aim of minimizing the harmful effects of paraben compounds. Due to the investigation of the antimicrobial properties of these synthetic com pounds which can be used as protective excipients in pharmaceuticals, gram positive and gram negative bacteria Klebsiella pneumoniae ATCC 13883, Escherichia coli ATCC 36218, Bacillus megaterium DSM-32, Staphylococcus aureus ATCC 25923 and eukaryotic yeast Candida albicans ATCC 10231 and Yarrowia lipolytica were used.

Keywords

paraben, synthetic compound, antimicrobial property

Project Number

THD-2018-7077

References

• Barry J, Bram G, Decodts G, Loupy A, Orange C, Petit A, Sansoulet J, 1985. Solid-liquid phase-transfer catalysis without added solvent. A simple, efficient, and inexpensive synthesis of aromatic carboxylic esters by alkylation of otassium carboxylates. Synthesis, 1: 40-45.
• Cavill GWK, Gibson NA, 1947. The esters of 4‐hydroxybenzoic acid and related compounds. Part III. Ethers of 4-hydroxybenzoic acid and their n‐alkyl esters. Journal of the Society of Chemical Industry, 66(8): 274-274.
• Claesen M, Van Dijck P, Vanderhaeghe H, 1954. A note on the tuberculostatic activity of benzoylhydrazides. Journal of Pharmacy and Pharmacology, 6(1): 127-128.
• Cohn L, Loewenstein J, 1908. Eine Gesetzmäßigkeit beim Benzoylieren aromatischer Oxysäuren und ihrer Ester. Chemische Berichte, 41: 3363-3367.
• Derdau V, Fey T, Atzrodt J, 2010. Synthesis of isotopically labelled SGLT inhibitors and their metabolites. Tetrahedron, 66(7): 1472-1482.
• Gunnam A, Suresh K, Ganduri R, Nangia A, 2016. Crystal engineering of a zwitterionic drug to neutral cocrystals: a general solution for floxacins. Chemical Communications, 52(85): 12610-12613.
• Hou F, Wang XC, Quan ZJ, 2018. Efficient synthesis of esters through oxone-catalyzed dehydrogenation of carboxylic acids and alcohols. Organic & Biomolecular Chemistry, 16(48): 9472-9476.
• Jee JP, Kim HJ, 2015. Development of Hydrogel Lenses with Surface‐immobilized PEG Layers to Reduce Protein Adsorption. Bulletin of the Korean Chemical Society, 36(11): 2682-2687.
• Khan KM, Rahat S, Choudhary MI, Ghani U, Perveen S, Khatoon S, Dar A, Malik A, 2002. Synthesis and Biological Screening of 2‐Substituted 5, 6‐Dihydro‐5‐oxo‐4H‐1, 3, 4‐oxadiazine‐4-propanenitriles and of Their Intermediates. Helvetica Chimica Acta, 85(2): 559-570.
• Lundov MD, Moesby L, Zachariae C, Johansen JD, 2009. Contamination versus preservation of cosmetics: A review on legislation, usage, infections, and contact allergy, Contact Dermatitis, 60(2): p. 70-78.
• Node M, Nishide K, Sai M, Fuji K, Fujita E, 1981. Hard acid and soft nucleophile systems. 3.Dealkylation of esters with aluminum halide-thiol and aluminum halide-sulfide systems. The Journal of Organic Chemistry, 46(10): 1991-1993.
• Soni MG, Carabin IG, Burdock GA, 2005. Safety assessment of esters of p-hydroxybenzoic acid (parabens). Food and Chemical Toxicology, 43(7): 985-1015.
• Steinberg D, 2006. Preservatives for Cosmetics, 2. baskı, s .1-129, Allured Publishing Co., Illinois, USA.
• Tan AS, Tüysüz M, 2013. Kozmetik Ürünlerde Koruyucu Madde Kullanımı Ve Koruyucu Etkinlik Testleri. Antibiyotik ve Kemoterapi Derneği Dergisi, 27(2): 83-91.
• Wang L, Liao C, Liu F, Wu Q, Guo Y, Moon HB, Nakata H, Kannan K, 2012. Occurrence and human exposure of p hydroxybenzoic acid esters (parabens), bisphenol A diglycidyl ether (BADGE), and their hydrolysis products in indoor dust from the United States and three East Asian countries. Environmental Science & Technology, 46: 11584-11593.
• Williams A, Naylor RA, 1971. Hydrolysis of phosphinic esters: general-base catalysis by imidazole. Journal of the Chemical Society B: Physical Organic, 1967-1972.
• Yamamoto Y, 2010. The First General and Selective Palladium (II)‐Catalyzed Alkoxycarbonylation of Arylboronates: Interplay among Benzoquinone‐Ligated Palladium (0) Complex, Organoboron, and Alcohol Solvent. Advanced Synthesis & Catalysis, 352(2‐3): 478-492.
• Yıldırım Z, İlk Y, Yıldırım M. 2014. The Synergist Effect of P-Hydroxybenzoic Acid and Propyl-Paraben on The Antibacterial Activity of Enterocin KP. Turkish Journal of Agriculture- Food Science and Technology, 2(1): 1-5.
• Yu W, Yang S, Xiong F, Fan T, Feng Y, Huang Y, Fu J, Wang, T, 2018. Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters via C–N bond activation. Organic & Biomolecular Chemistry, 16(17): 3099-3103.
• Zhang X, Wu G, Gao W, Ding J, Huang X. Liu M, Wu H, 2018. Synergistic Photo-Copper-Catalyzed Hydroxylation of (Hetero) aryl Halides with Molecular Oxygen. Organic Letters, 20(3): 708-711.