The antimicrobial activity and toxicity od alkyltetrahydroisoquinolones

E. Terenteva, S. Sasmakov, S. Azimov, V. Vinogradova, D. Abdurakhmanov, Z. Khashimova, A. Saidov
Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent; Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent; Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent; Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences; Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences; Institute of the Bioorganic Chemistry, Uzbek Academy of Sciences,Tashkent; Samarkand State University, Samarkand

Abstract


The antibacterial and antifungal activity against gram-positive and gram-negative bacteria and Candida albicans fungal strain for alkyltetrahydroisoquinoline
derivatives were evaluated. It was established, that 1,11-bis(6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)undecan shows pronounced antibacterial properties against all the microorganism strains and strong antifungal activity against Candida albicans with greater inhibition area than the reference drug. IC50 value of the compound is 2,1±0,1 μg/ml, LD50 value is 324,9±18,2 mg/kg.


Keywords


alkyltetrahydroisoquinolines, IC50, LD50, the antimicrobial activity, toxicity.

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References


Chen C, Wu J, Zhu P, Xu C, Yao L. Investigating isoquinoline derivatives for inhibition of inhibitor of apoptosis proteins for ovarian cancer treatment. Drug Des Devel Ther. 2017;11: 2697-2707

Uesawa Y, Mohri K, Kawase M, Ishihara M, Sakagami H. Quantitative structure-activity relationship (QSAR) analysis of tumor-specificity of 1,2,3,4-tetrahydroisoquinoline derivatives. Anticancer Res. 2011;31(12): 4231-8.

Dembitsky VM, Gloriozova TA, Poroikov VV. Naturally occurring plant isoquinoline N-oxide alkaloids: Their pharmacological and SAR activities, Phytomedicine. 2015; 22 (1): 183-202.

Seo JW, Srisook E, Son HJ, Hwang O, Cha YN, et al. Synthesis of tetrahydroisoquinoline derivatives that inhibit NO production in activated BV-2 microglial cells.Eur. J. Med. Chem. 2008; 43:1160-70.

Mihoubi M, Micale N, Scala A, Jarraya RM, Bouaziz A, et al. Synthesis of C3/C1-Substituted Tetrahydroisoquinolines. Molecules, 2015; 20(8): 14902-14.

Zablotskaya A, Segal I, Geronikaki A, Eremkina T, Belyakov S, et al. Synthesis, physicochemical characterization, cytotoxicity, antimicrobial, anti-inflammatory and psychotropic activity of new N-[1,3-(benzo)thiazol-2-yl]-ω-[3,4-dihydroisoquinolin-2(1H)-yl]alkanamides. Eur. J. Med. Chem. 2013;70: 846-56.

Abe K, Saitoh T, Horiguchi Y, Utsunomiya I, Taguchi K. Synthesis and neurotoxicity of tetrahydroisoquinoline derivatives for studying Parkinson's disease. Biol. Pharm. Bull.2005; 28: 1355-62.

Bentley KW. β-Phenylethylamines and the isoquinoline alkaloids. Previous Review. Nat. Prod. Rep. 2006; 23: 444-63.

Турсунходжаева ФМ, Рахимов ШБ, Джахангиров ФН, Виноградова ВИ, Режепов Ж, Сагдуллаев ШШ. Патент Uz IAP 04590. 1-(4'-метоксифенил)-2β-гидроксиэтил-6,7-диметокси-1,2,3,4-терагидроихохинолин гидрохлорид (1), проявляющий местноанестезирующее и анальгетическое действие, 2012; IAP 2010 0136.

Журакулов ШН, Виноградова ВИ, Левкович МГ. Синтез 1-арилтетрагидроизохинолиновых алкалоидов и их аналогов. Химия природных соединений.2013; 65.

Саидов АШ, Левкович МГ, Виноградова ВИ. Синтез 1-алкилтетрагидроизохинолинов. Химия природных соединений. 2013; 771.

Саидов АШ, Алимова М, Левкович МГ, Виноградова ВИ. Синтез бис-тетрагидроизохинолинов на основе гомовератриламина и ряда двухосновных кислот. Химия природных соединений. 2013;257.

Wayne P. Clinical and Laboratory Standards Institute (CLSI) performance standards for antimicrobial disk diffusion susceptibility tests 19th ed. approved standard. CLSI document M100-S19 2009.

DIN, Deutsche Institution für Normung e.V., DIN Taschenbuch 222, Medizinische Mikrobiologie und Immunologie. Beuth-Verlag, Berlin.2004

Mosmann T. Rapid colorimetric assay for cellular growth and survival:Application to proliferation and cytotoxicity assays. J. Immunol. Methods. 1983;65:55–63.

Криштопенко СВ,Тихов МС.Токсикометрия эффективных доз, Изд-во НГУ, Н.Новгород.1997; 156.

Galán A, Moreno L, Párraga J, Serrano Á, Sanz MJ, Cortes D, Cabedo N. Novel isoquinoline derivatives as antimicrobial agents. Bioorg. Med. Chem.2013; 21(11): 3221-30.

Терентьева ЕО, Хашимова ЗС, Цеомашко НЕ, Тошева НА, Журакулов ШН, Саидов АШ, Виноградова ВИ, Азимова ШС. Изучение 1-замещенных тетрагидроизохинолинов на различных типах клеточных культур. Узбекский биологический журнал. 2016; 3: 3-6.




DOI: http://dx.doi.org/10.17721/1728_2748.2017.74.51-55

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