Trietanolamin Esaslı Tuzların In Vitro Antiproliferatif, Antibakteriyel ve Anti-Anjiyojenik Çalışmaları

Yıl 2024, Cilt: 14 Sayı: 3, 1192 – 1203, 15.09.2024

Hüseyin Akbaş , Seçil Erden Tayhan , Sema Bilgin

https://doi.org/10.31466/kfbd.1446890

Öz

Siklopropankarboksilat, merkaptoasetat, trikloroasetat ve 4-dodesilbenzensülfonat anyonları ile trietanolamonyum (TEA) katyonu TEA esaslı tuzların oluşumuna yol açtı. TEA tuzlarının antibakteriyel aktivitesi bazı bakterilere karşı incelendi ve elde edilen sonuçlar minimum inhibitör konsantrasyon (MİK) değerlerinin hesaplanmasında kullanıldı. Ek olarak, TEA tuzlarının antiproliferatif aktiviteleri meme kanseri hücre hattı üzerinde in vitro olarak incelendi. Ayrıca, bu tuzların anti-anjiyogenik etkisini değerlendirmek için HUVEC’ler (insan vasküler endotelyal hücre hattı) tarafından in vitro çizik analizi yapılmıştır. Bu bileşikler, kanser hücrelerinin hücre canlılığını kayda değer düzeyde değiştirmdi. Öte yandan TEA tuzlarının insan endotel hücre göçünü bir miktar engellediği gösterildi. Dolayısıyla, bu bileşiklerin anjiyogenezi engelleme konusunda sınırlı yeteneğe sahip olduğu belirlendi.

Anahtar Kelimeler

Anti-anjiyojenik etki, Antiproliferatif etki, Antibakteriyel etki, Trietanolamonyum tuzları

Kaynakça

• Adamovich, S.N., and Mirskova, A.N., (2018). Synthesis of immunoactive tris(2-hydroxyethyl)ammonium 1-R-indol-3-ylsulfanyl(sulfonyl)acetates. Russian Journal of Applied Chemistry, 91, 469-472.
• Adamovich, S.N., Mirskov, R.G., Mirskova, A.N., and Voronkov, M.G., (2012). Biologically active protic (2-hydroxyethyl) ammonium ionic liquids. Liquid aspirin. Russian Chemical Bulletin, 61, 1260-1261.
• Adamovich, S.N., Oborina, E.N., and Mirskova A.N., (2018). Synthesis and pharmacological activity of tris(2-hydroxyethyl)ammonium 4-chlorophenylsulfonylacetate. Russian Journal of Applied Chemistry, 91, 701-705.
• Akbaş, H., Yıldırım, A., Menevşe, Ş., and Gökşen, N., (2020). Antiproliferative and antimicrobial effects of tris(2-hydroxyethyl)ammonium-based protic ionic liquids with some fatty acids. Journal of the Institute of Science and Technology, 10, 2021-2027.
• Akbaş, H., Erden Tayhan S., and Bilgin, S., (2023). A novel approach to determine anti-proliferative, anti-migratory and anti-microbial properties of 2-phenylethylammonium carboxylate molecular salts. Indian Journal of Chemistry, 62, 207-216.
• Akyoshi, O., Takao, K., Shinichi, K., and Yasuhide, Y., (1994). Shampoos and hair rinses containing thioglycolic acid. Espacenet, Patent Number: JPH06116124A.
• Antuganov, D., Timofeev, V., Timofeeva, K., Antuganova, Y., and Kondratenko, Y.A., (2019). Evaluation of protic ionic liquids based on triethanolammonium and tris(hydroxymethyl)methylammonium salts as buffers for 68Ga-radiolabelling of PSMA-HBED-CC. Chemistry Select, 4, 12524-12527.
• Brusina, M.A., Nikolaev, D.N., Fundamenskii, V.S., Gurzhii, V.V., Zolotarev, A.A., Selitrenikov, A.V., Zevatskii, Y.E., Potapkin, A.M., Ramsh, S.M., and Piotrovskii, LB., (2018). Water-soluble form of 1-alkyl(aryl)ımidazole-4,5-dicarboxylic acids. structure and anticonvulsant activity of the triethanolammonium salt of 1-propylimidazole-4,5-dicarboxylic acid. Pharmaceutical Chemistry Journal, 52, 299-303.
• Elmas, G., Okumuş, A., Kılıç, Z., Özbeden, P., Açık, L., Çağdaş Tunalı, B., Türk, M., Çerçi, N.A., and Hökelek, T., (2020). Phosphorus-nitrogen compounds. Part 48. Syntheses of the phosphazenium salts containing 2-pyridyl pendant arm: Structural characterizations, thermal analysis, antimicrobial and cytotoxic activity studies. Indian Journal of Chemistry -Section A, 59, 533-550.
• Environmental Protection Agency, (2014). Amine salts of alkyl (C8-C24) benzenesulfonic acid (olmithylaminopropylamine, isoprodvlamine, mono-, di-, and teiethanolamine); exemption from the requirement of a tolerance. Federal Register, 79, 28444-28447.
• Erden Tayhan, S., Bilgin, S., and Elmastaş, M., (2018). Evaluation of the wound healing potential of teucrioside. International Journal of Chemistry and Technology, 2, 16-19.
• Ferraz, R. , Teixeira, V., Rodrigues, D., Fernandes, R., Prudencio, C., Noronha, J.P., Petrovski, Z., and Branco, L.C., (2014). Antibacterial activity of Ionic Liquids based on ampicillin against resistant bacteria. RSC Advances, 4, 4301-4307.
• Gruzdev, M.S., Shmukler, L.E., Kudryakova, N.O., Kolker, A.M., and Safonova, L.P., (2018). Synthesis and properties of triethanolamine-based salts with mineral and organic acids as protic ionic liquids. Journal of Molecular Liquids, 249, 825-830.
• Ha, A.W., Hong, K.H., Kim, H.S., and Kim, W.K., (2013). Inorganic sulfur reduces cell proliferation by inhibiting of ErbB2 and ErbB3 protein and mRNA expression in MDA-MB-231 human breast cancer cells. Nutrition Research and Practice, 7, 89-95.
• İnan, A., Sünbül, A.B., İkiz, M., Erden Tayhan, S., Bilgin, S., Elmastaş, M., Sayın, K., Ceyhan, G., Köse, M., and İspir, E., (2018). Half-sandwich Ruthenium(II) arene complexes bearing the azo-azomethine ligands: Electrochemical, computational, antiproliferative and antioxidant properties. Journal of Organometallic Chemistry, 870, 76-89.
• İspir, E., İkiz, M., Inan, A., Sünbül, A.B., Erden Tayhan, S., Bilgin, S., Köse, M., Elmastaş, M., (2019). Synthesis, structural characterization, electrochemical, photoluminescence, antiproliferative and antioxidant properties of Co(II), Cu(II) and Zn(II) complexes bearing the azo-azomethine ligands. Journal of Molecular Structure, 1182, 63-71.
• Kondratenko, Y., Kochina, T., Fundamensky, V., Ignatyev, I., Panikorovskii, T., and Nyanikova G., (2016). Triethanolammonium salicylate-protic alkanolammonium ionic liquid. Journal of Molecular Liquids, 221, 1218-1124.
• Kondratenko, Y.A., and Kochina, T.A., (2021). Contribution of the scientific school of academician m.g. Voronkov to the development of the chemistry of biologically active atranes (protatranes and hydrometallatranes) (a review). Russian Journal of General Chemistry, 91, 2331-2351.
• Kondratenko, Y.A., Gurzhii, V.V., Panova, G.G., Anikina, L.M., Udalova, O.R., Krutikov, V.I., Ugolkov, V.L., and Kochina, T.A., (2020). Biological activity of protic ionic liquids based on tris(2-hydroxyethyl)ammonium salts and the crystal structure of tris(2-hydroxyethyl)ammonium malate. Russian Journal of Inorganic Chemistry, 65, 1407-1415.
• Kondratenko, Y.A., Nyanikova, G.G., Molchanova, K.V., and Kochina, TA., (2017). Characteristics of protic ionic liquids based on triethanolammonium salts of biologically active carboxylic acids and their impact on the growth properties of the Rhizopus oryzae fungus. Glass Physics and Chemistry, 43, 445-451.
• Kumer, A., and Khan, M.W., (2021). Synthesis, characterization, antimicrobial activity and computational exploration of ortho toludinium carboxylate ionic liquids. Journal of Molecular Structure, 1245, 131087.
• Lavorgna, M., Iacovino, R., Russo, C., Donato, C.D., Piscitelli, C., and Isidori, M., (2019). A new approach for improving the antibacterial and tumor cytotoxic activities of pipemidic acid by including it in trimethyl-β-cyclodextrin. International Journal of Molecular Sciences, 20, 416.
• Lukyanova, S.V., Gefan, N.G., Adamovich, S.N., Oborina, E.N., Khaptanova, N.V., Kuznetsov, V.I., Ostyak, A.S., Kosilko, V.S., and Balakhonov S.V., (2020). Study of the effect of a biologically active compound tris(2-hydroxyethyl)ammonium 4-chlorophenylsulfanylacetate on the growth of listeria monocytogenes and staphylococcus aureus. Acta Biomedica Scientifica, 5, 47-53.
• Miranda, J.A., Garnero, C., Chattah, A.K., Oliveria, Y.S., Ayala, A.P., and Longhi, M.R., (2019). Furosemide: triethanolamine salt as a strategy to improve the biopharmaceutical properties and photostability of the drug. Crystal Growth & Design, 19, 2060-2068.
• Mirskova, A.N., Adamovich, S.N., Mirskov, R.G., and Voronkov, M.G., (2010). Tris-(2-hydroxyethyl)ammonium 2-methyl- and 2-methyl-4-chlorophenoxyacetate serve as effective inhibitors of thrombocyte aggregation and antioxidants. Doklady Biological Sciences, 433, 244-246.
• Mirskova, A.N., Levkovskaya, G.G., Mirskov, R.G., and Voronkov, M.G., (2008). Hydroxyalkylammonium salts of organylsulfanyl(sulfonyl)acetic acids-New stimulators of biological processes. Russian Journal of Organic Chemistry, 44, 1478-1485.
• Mirskova, A.N., Levkovskaya, G.G., Stupina, A.G., Chkhenkeli, V.A., and Voronkov, M.G., (2003). The effect of tris-(2-hydroxyethyl)ammonium aroxy-, arylthio-, and arylsulfonylacetates on the vital activity of bifidobacteria. Doklady Biological Sciences, 390, 239-241.
• Odinokov, S.E., Glazunov, V.P., and Nabiullin, A.A., (1984). Infrared spectroscopic studies of hydrogen bonding in triethylammonium salts. Part 3.-Strong hydrogen bonding. Journal of the Chemical Society, Faraday Transactions 2: Molecular and Chemical Physics, 80, 899-908.
• Privalova, E.A., Tiguntseva, N.P., Adamovich, S.N., Mirskov, R.G., and Mirskova, A.N., (2017). Tris(2-hydroxyethyl)ammonium arylchalcogenylacetates, growth stimulants of alcohol yeast Saccharomyces cerevisiae, Russian Chemical Bulletin, 66, 1320-1324.
• Toshimitsu, K., (1994). Water-base ink composition for ball-point pen. Espacenet, Patent Number: JPH06100826A.
• Trapp, S., Franco, A., and Mackay, D., (2010). Activity-based concept for transport and partitioning of ıonizing organics. Environmental Science and Technology, 44, 6123-6129.
• Voronkov, M.G., Adamovich, S.N., and Ushakov, I.A., (2014). Aroxyprotatranes: aroxy derivatives of tris-(2-hydroxyethyl)ammonium. Russian Journal of General Chemistry, 84, 340-342.
• Voronkov, M.G., Albanov, A.I., Aksamentova, T.N., Adamovich, S.N., Chipanina, N.N., Mirskov, R.G., Kochina, T.A., Vrazhnov, D.V., and Litvinov, M.Y., (2009). Tris(2-hydroxyethyl)ammonium salts: 2,8,9-trihydroprotatranes. Russian Journal of General Chemistry, 79, 2339-2346.
• Voronkov, M.G., and Baryshok, V.P., (2010). Atranes as a new generation of biologically active substances. Herald of the Russian Academy of Sciences, 80, 514-521.
• Voronkov, M.G., Kolesnikova, O.P., Rasulov, M.M., and Mirscova, A.N., (2007). Pharmacological activity and clinical effects of trecrezan and other tris-(2-hydroxyethyl)ammonium salts of arylheteroacetic acids (A review). Pharmaceutical Chemistry Journal, 41, 244-248.
• Voronkov, M.G., Mirskova, A.N., and Levkovskaya, G.G., (2002). Carcinostatic, protective, and adaptive activities of tris-(2-hydroxyethyl)ammonium salts of arylheteroacetic acids. Doklady Biological Sciences, 386, 404-406.

In Vitro Antiproliferative, Antibacterial, and Anti-Angiogenic Studies of Triethanolamine-Based Salts

Yıl 2024, Cilt: 14 Sayı: 3, 1192 – 1203, 15.09.2024

Hüseyin Akbaş , Seçil Erden Tayhan , Sema Bilgin

https://doi.org/10.31466/kfbd.1446890

Öz

The triethanolammonium (TEA) cation associated with the anion cyclopropanecarboxylate, mercaptoacetate, trichloroacetate, and 4-dodecylbenzenesulfonate led to the formation of TEA-based salts. The antibacterial activity of the TEA salts was examined against some bacteria and the obtained results were used to calculate minimal inhibitory concentrations (MICs) values. Additionally, the antiproliferative activities of TEA salts were examined in vitro on breast cancer cell line. Furthermore, in vitro scratch assay was performed by HUVECs (human vascular endothelial cell line) to assess the anti-angiogenic effect of these salts. These compounds did not dramatically differentiate the cell viability of cancer cells. On the other hand, it was demonstrated that TEA salts blocked human endothelial cell migration slightly. Therefore, these compounds were determined to have a limited ability to inhibit angiogenesis.

Anahtar Kelimeler

Anti-angiogenic effect, Antiproliferative effect, Antibacterial effect, Triethanolammonium salts

Kaynakça

• Adamovich, S.N., and Mirskova, A.N., (2018). Synthesis of immunoactive tris(2-hydroxyethyl)ammonium 1-R-indol-3-ylsulfanyl(sulfonyl)acetates. Russian Journal of Applied Chemistry, 91, 469-472.
• Adamovich, S.N., Mirskov, R.G., Mirskova, A.N., and Voronkov, M.G., (2012). Biologically active protic (2-hydroxyethyl) ammonium ionic liquids. Liquid aspirin. Russian Chemical Bulletin, 61, 1260-1261.
• Adamovich, S.N., Oborina, E.N., and Mirskova A.N., (2018). Synthesis and pharmacological activity of tris(2-hydroxyethyl)ammonium 4-chlorophenylsulfonylacetate. Russian Journal of Applied Chemistry, 91, 701-705.
• Akbaş, H., Yıldırım, A., Menevşe, Ş., and Gökşen, N., (2020). Antiproliferative and antimicrobial effects of tris(2-hydroxyethyl)ammonium-based protic ionic liquids with some fatty acids. Journal of the Institute of Science and Technology, 10, 2021-2027.
• Akbaş, H., Erden Tayhan S., and Bilgin, S., (2023). A novel approach to determine anti-proliferative, anti-migratory and anti-microbial properties of 2-phenylethylammonium carboxylate molecular salts. Indian Journal of Chemistry, 62, 207-216.
• Akyoshi, O., Takao, K., Shinichi, K., and Yasuhide, Y., (1994). Shampoos and hair rinses containing thioglycolic acid. Espacenet, Patent Number: JPH06116124A.
• Antuganov, D., Timofeev, V., Timofeeva, K., Antuganova, Y., and Kondratenko, Y.A., (2019). Evaluation of protic ionic liquids based on triethanolammonium and tris(hydroxymethyl)methylammonium salts as buffers for 68Ga-radiolabelling of PSMA-HBED-CC. Chemistry Select, 4, 12524-12527.
• Brusina, M.A., Nikolaev, D.N., Fundamenskii, V.S., Gurzhii, V.V., Zolotarev, A.A., Selitrenikov, A.V., Zevatskii, Y.E., Potapkin, A.M., Ramsh, S.M., and Piotrovskii, LB., (2018). Water-soluble form of 1-alkyl(aryl)ımidazole-4,5-dicarboxylic acids. structure and anticonvulsant activity of the triethanolammonium salt of 1-propylimidazole-4,5-dicarboxylic acid. Pharmaceutical Chemistry Journal, 52, 299-303.
• Elmas, G., Okumuş, A., Kılıç, Z., Özbeden, P., Açık, L., Çağdaş Tunalı, B., Türk, M., Çerçi, N.A., and Hökelek, T., (2020). Phosphorus-nitrogen compounds. Part 48. Syntheses of the phosphazenium salts containing 2-pyridyl pendant arm: Structural characterizations, thermal analysis, antimicrobial and cytotoxic activity studies. Indian Journal of Chemistry -Section A, 59, 533-550.
• Environmental Protection Agency, (2014). Amine salts of alkyl (C8-C24) benzenesulfonic acid (olmithylaminopropylamine, isoprodvlamine, mono-, di-, and teiethanolamine); exemption from the requirement of a tolerance. Federal Register, 79, 28444-28447.
• Erden Tayhan, S., Bilgin, S., and Elmastaş, M., (2018). Evaluation of the wound healing potential of teucrioside. International Journal of Chemistry and Technology, 2, 16-19.
• Ferraz, R. , Teixeira, V., Rodrigues, D., Fernandes, R., Prudencio, C., Noronha, J.P., Petrovski, Z., and Branco, L.C., (2014). Antibacterial activity of Ionic Liquids based on ampicillin against resistant bacteria. RSC Advances, 4, 4301-4307.
• Gruzdev, M.S., Shmukler, L.E., Kudryakova, N.O., Kolker, A.M., and Safonova, L.P., (2018). Synthesis and properties of triethanolamine-based salts with mineral and organic acids as protic ionic liquids. Journal of Molecular Liquids, 249, 825-830.
• Ha, A.W., Hong, K.H., Kim, H.S., and Kim, W.K., (2013). Inorganic sulfur reduces cell proliferation by inhibiting of ErbB2 and ErbB3 protein and mRNA expression in MDA-MB-231 human breast cancer cells. Nutrition Research and Practice, 7, 89-95.
• İnan, A., Sünbül, A.B., İkiz, M., Erden Tayhan, S., Bilgin, S., Elmastaş, M., Sayın, K., Ceyhan, G., Köse, M., and İspir, E., (2018). Half-sandwich Ruthenium(II) arene complexes bearing the azo-azomethine ligands: Electrochemical, computational, antiproliferative and antioxidant properties. Journal of Organometallic Chemistry, 870, 76-89.
• İspir, E., İkiz, M., Inan, A., Sünbül, A.B., Erden Tayhan, S., Bilgin, S., Köse, M., Elmastaş, M., (2019). Synthesis, structural characterization, electrochemical, photoluminescence, antiproliferative and antioxidant properties of Co(II), Cu(II) and Zn(II) complexes bearing the azo-azomethine ligands. Journal of Molecular Structure, 1182, 63-71.
• Kondratenko, Y., Kochina, T., Fundamensky, V., Ignatyev, I., Panikorovskii, T., and Nyanikova G., (2016). Triethanolammonium salicylate-protic alkanolammonium ionic liquid. Journal of Molecular Liquids, 221, 1218-1124.
• Kondratenko, Y.A., and Kochina, T.A., (2021). Contribution of the scientific school of academician m.g. Voronkov to the development of the chemistry of biologically active atranes (protatranes and hydrometallatranes) (a review). Russian Journal of General Chemistry, 91, 2331-2351.
• Kondratenko, Y.A., Gurzhii, V.V., Panova, G.G., Anikina, L.M., Udalova, O.R., Krutikov, V.I., Ugolkov, V.L., and Kochina, T.A., (2020). Biological activity of protic ionic liquids based on tris(2-hydroxyethyl)ammonium salts and the crystal structure of tris(2-hydroxyethyl)ammonium malate. Russian Journal of Inorganic Chemistry, 65, 1407-1415.
• Kondratenko, Y.A., Nyanikova, G.G., Molchanova, K.V., and Kochina, TA., (2017). Characteristics of protic ionic liquids based on triethanolammonium salts of biologically active carboxylic acids and their impact on the growth properties of the Rhizopus oryzae fungus. Glass Physics and Chemistry, 43, 445-451.
• Kumer, A., and Khan, M.W., (2021). Synthesis, characterization, antimicrobial activity and computational exploration of ortho toludinium carboxylate ionic liquids. Journal of Molecular Structure, 1245, 131087.
• Lavorgna, M., Iacovino, R., Russo, C., Donato, C.D., Piscitelli, C., and Isidori, M., (2019). A new approach for improving the antibacterial and tumor cytotoxic activities of pipemidic acid by including it in trimethyl-β-cyclodextrin. International Journal of Molecular Sciences, 20, 416.
• Lukyanova, S.V., Gefan, N.G., Adamovich, S.N., Oborina, E.N., Khaptanova, N.V., Kuznetsov, V.I., Ostyak, A.S., Kosilko, V.S., and Balakhonov S.V., (2020). Study of the effect of a biologically active compound tris(2-hydroxyethyl)ammonium 4-chlorophenylsulfanylacetate on the growth of listeria monocytogenes and staphylococcus aureus. Acta Biomedica Scientifica, 5, 47-53.
• Miranda, J.A., Garnero, C., Chattah, A.K., Oliveria, Y.S., Ayala, A.P., and Longhi, M.R., (2019). Furosemide: triethanolamine salt as a strategy to improve the biopharmaceutical properties and photostability of the drug. Crystal Growth & Design, 19, 2060-2068.
• Mirskova, A.N., Adamovich, S.N., Mirskov, R.G., and Voronkov, M.G., (2010). Tris-(2-hydroxyethyl)ammonium 2-methyl- and 2-methyl-4-chlorophenoxyacetate serve as effective inhibitors of thrombocyte aggregation and antioxidants. Doklady Biological Sciences, 433, 244-246.
• Mirskova, A.N., Levkovskaya, G.G., Mirskov, R.G., and Voronkov, M.G., (2008). Hydroxyalkylammonium salts of organylsulfanyl(sulfonyl)acetic acids-New stimulators of biological processes. Russian Journal of Organic Chemistry, 44, 1478-1485.
• Mirskova, A.N., Levkovskaya, G.G., Stupina, A.G., Chkhenkeli, V.A., and Voronkov, M.G., (2003). The effect of tris-(2-hydroxyethyl)ammonium aroxy-, arylthio-, and arylsulfonylacetates on the vital activity of bifidobacteria. Doklady Biological Sciences, 390, 239-241.
• Odinokov, S.E., Glazunov, V.P., and Nabiullin, A.A., (1984). Infrared spectroscopic studies of hydrogen bonding in triethylammonium salts. Part 3.-Strong hydrogen bonding. Journal of the Chemical Society, Faraday Transactions 2: Molecular and Chemical Physics, 80, 899-908.
• Privalova, E.A., Tiguntseva, N.P., Adamovich, S.N., Mirskov, R.G., and Mirskova, A.N., (2017). Tris(2-hydroxyethyl)ammonium arylchalcogenylacetates, growth stimulants of alcohol yeast Saccharomyces cerevisiae, Russian Chemical Bulletin, 66, 1320-1324.
• Toshimitsu, K., (1994). Water-base ink composition for ball-point pen. Espacenet, Patent Number: JPH06100826A.
• Trapp, S., Franco, A., and Mackay, D., (2010). Activity-based concept for transport and partitioning of ıonizing organics. Environmental Science and Technology, 44, 6123-6129.
• Voronkov, M.G., Adamovich, S.N., and Ushakov, I.A., (2014). Aroxyprotatranes: aroxy derivatives of tris-(2-hydroxyethyl)ammonium. Russian Journal of General Chemistry, 84, 340-342.
• Voronkov, M.G., Albanov, A.I., Aksamentova, T.N., Adamovich, S.N., Chipanina, N.N., Mirskov, R.G., Kochina, T.A., Vrazhnov, D.V., and Litvinov, M.Y., (2009). Tris(2-hydroxyethyl)ammonium salts: 2,8,9-trihydroprotatranes. Russian Journal of General Chemistry, 79, 2339-2346.
• Voronkov, M.G., and Baryshok, V.P., (2010). Atranes as a new generation of biologically active substances. Herald of the Russian Academy of Sciences, 80, 514-521.
• Voronkov, M.G., Kolesnikova, O.P., Rasulov, M.M., and Mirscova, A.N., (2007). Pharmacological activity and clinical effects of trecrezan and other tris-(2-hydroxyethyl)ammonium salts of arylheteroacetic acids (A review). Pharmaceutical Chemistry Journal, 41, 244-248.
• Voronkov, M.G., Mirskova, A.N., and Levkovskaya, G.G., (2002). Carcinostatic, protective, and adaptive activities of tris-(2-hydroxyethyl)ammonium salts of arylheteroacetic acids. Doklady Biological Sciences, 386, 404-406.

Toplam 36 adet kaynakça vardır.

Ayrıntılar

Kaynak Göster

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