Synthesis and Cytotoxic Activity of Methyl Glycyrrhetinate Esterified with Amino Acids

2012 ◽  
Vol 67 (7) ◽  
pp. 731-746 ◽  
Author(s):  
René Csuk ◽  
Stefan Schwarz ◽  
Bianka Siewert ◽  
Ralph Kluge ◽  
Dieter Ströhl

Methyl glycyrrhetinate was esterified at position C3 of ring A using different amino acids. A short, unbranched chain of four carbon atoms with two amino groups in positions 2 and 4 was shown to be the most active compound of this series (IC50 = 0:8 M on liposarcoma Lipo cells). These compounds trigger apoptosis as shown by an acridine orange/ethidium bromide assay, trypan blue tests and DNA laddering experiments.

Consideration of the implications of the zwitterion hypothesis of Bjerrum (1923) makes it desirable to state afresh the principles underlying the methods commonly employed in the titration of amino-acids. Deductions of considerable theoretical importance, cf., e. g ., Calvery (1933) are still being made on the supposition that the alkalimetric formaldehyde titration method of Sørensen (1907) and the corresponding alcohol method of Foreman (1920) and of Willstätter and Waldschmidt-Leitz (1921) estimate the carboxyl groups of amino-acids whilst the acidimetric acetone titration of Linderstrøm-Lang (1928) estimates the amino-groups. Yet the zwitterion hypothesis indicates that this assumption is the reverse of the truth. Discussion is greatly facilitated by collective consideration of recent physico-chemical evidence clarifying the principles upon which these common bio-chemical methods rest. In a recent discussion of two of the titrimetric methods (Van Slyke and Kirk, 1933) the existence of this evidence is ignored, so that it becomes necessary to systematize and elaborate the empirical argument of these authors in the light of the relevant investigations of Grünhut (1919), Cray and Westrip (1925), Michaelis and Mizutani (1925), Birch and Harris (1930, b ), and Levy (1933). At the same time new and useful developments are indicated.


2015 ◽  
Vol 1 (1) ◽  
pp. 28
Author(s):  
Suryani Hutomo ◽  
Chandra Kurniawan

Kunyit (Curcuma Zonga) merupakan tanaman yang dapat tumbuh di daerah tropis dan sub tropis. Di Indonesia, kunyit menyebar secara merata di seluruh daerah. Kurkumin yang merupakan unsur utama kunyit, merupakan antioksidan yang kuat. Penelitian terdahulu melaporkan bahwa ekstrak etanolik Curcuma Zonga menyebabkan kematian sel sejumlah separuhnya pada sel HeLa setelah dipapar selama 24 jam dengan konsentrasi 184,5 lg/ml, tetapi tipe kematian sel dan mekanismenya belum jelas. Tujuan penelitian ini adalah untuk mengkaji pengaruh ekstrak Curcuma Zonga pada tipe kematian sel HeLa. Sel HeLa (5 x104 sel/well) dikultur dalam RPMI 1640 semalam sebelum stimulasi. Ekstrak etanol kunyit (150 lg/ml) ditambahkan pada kultur HeLa dan diinkubasi selama 24 jam dalam medium tanpa antibiotik. Analisis tipe kematian sel HeLa dilakukan dengan menggunakan mikroskop fuoresence setelah doubZe staining acridine orange/ethidium bromide (AO/EB). Doksorubisin (0,5625 Ig/ml) digunakan sebagai kontrol positif induksi apoptosis. Hasil penelitian menunjukkan bahwa ekstrak Curcuma Zongamenyebabkan kematian sel berupa apoptosis pada sebagian besar sel HeLa yang ditandai dengan perubahan warna sel menjadi orange. Analisa statistik menunjukkan perbedaan yang bermakna antara kelompok kontrol negatif dengan kelompok stimulasi dalam jumlah sel yang mengalami apoptosis. Disimpulkan bahwa ekstrak Curcuma Zonga mampu menginduksi apoptosis pada sebagian besar sel HeLa. Kata kunci: ekstrak Curcuma Zonga, sel HeLa, apopt


2019 ◽  
Vol 1 (2) ◽  
pp. 79-87
Author(s):  
Masriani

Cancer has been considered as problematic medical issues both in developed and developing countries. Pycnarrhena cauliflora or Sengkubak (Pycnarrhena cauliflora) has a potential value as alternatives for anticancer medication. This study aims to evaluate the cytotoxic activities of Sengkubak (Pycnarrhena cauliflora), and investigate the induction for apoptosis mechanisms from the extracts n-hexane, dichloromethane, and methanol from roots, branches the leaves to HeLa cancer cells. The cytotoxic activities were analyzed by performing MTT methods, while induction analysis of apoptosis was conducted by utilizing the Acridine Orange/Ethidium Bromide (AO/EB) as visual nuclear methodologies. The extracts of roots dichloromethane showed the highest cytotoxic activities accounted for IC50 70µg/mL and these extracts were able to induce the apoptosis mechanisms. This study concludes that the Sengkubak (Pycnarrhena cauliflora) has the ability as a potential alternative for anticancer medications.


1969 ◽  
Vol 15 (9) ◽  
pp. 891-901 ◽  
Author(s):  
D W Palmer ◽  
T Peters

Abstract A simple automated method is described for determining the level of total free amino acids in the blood. The method utilizes the AutoAnalyzer, and is based on the formation of colored complexes by uniting free amino groups with 2,4,6-trinitrobenzene sulfonate (TNBS). Proteins do not interfere because the free amino acids are first separated by dialysis. Characteristics of the reaction and potential clinical applications of the procedure are discussed.


2000 ◽  
Vol 658 ◽  
Author(s):  
Slavi C. Sevov

ABSTRACTHybrid inorganic/organic materials with open-framework or layered structures are known for many transition metals linked by functionalized organic molecules such as organic diphosphonates, polycarboxylates, polynitriles, etc., species with more than one equivalent functional groups. We have studied the effect of pH on such a system of cobaltmethylenediphosphonate and report three new compounds, Na3Co[(O3PCH2PO3)(OH)],Na2Co(O3PCH2PO3)•H2O, and Co2[(O3PCH2PO3)(H2O)], that form at very basic, moderately basic, and acidic conditions, respectively. More interestingstructural chemistry should be expected from linkers with two or more different functionalities. Both the carboxylic and phosphonic groups in carboxyethylphosphonic acid are used to coordinate to cobalt or calcium atoms in the new compounds Co3(O3PCH2CH2COO)2•6H2O and Ca(O3PCH2CH2COOH)•H2O. Taking one more step further in complexity we have also studied linkers with three different functional groups, phosphonated amino acids. The structures of two new compounds, Zn(O3PCH2CH(NH3)COO) and Zn(O3PCH2CH2CH(NH3)COO), are threedimensional frameworks made of zinccoordinated by both the carboxylic and phosphonic ends of the organic molecules. The amino groups are protonated and terminal in the voids of the frameworks.


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