ABSTRACT
In 1719, Antonio Menzani di Cuna from the Saint Savior monastery published an alcoholic extract formula made from plant and herb resins under the name Jerusalem Balsam. The Balsam gained high popularity due to its remedial benefits. At the end of the 19 th century, Jerusalem Balsam produced by the hermit Johannes Treutler was found to be particularly popular. We analysed a sample of a valuable find coming from the last decade of the 19 th century, making it probably the oldest surviving Jerusalem Balsam in the world. The purpose of this work was to investigate the composition of the historical sample and to try to determine the origin of its components. This was achieved by comparing the profile of volatile compounds extracted from the balsam using HS-SPME technique with the profile characteristic for plant resins as classic ingredients of the Johannes Treutler formula. The use of two chromatographic columns of different polarity, as well as the transformation of the polar components of the sample into TMS derivatives, allowed to obtain new information on the historical composition of the Balsam. Also, it can be stated with high probability that plant resins were indeed used in the production of the Balsam as referred to in the original recipe of Johannes Treutler. We also discuss challenges in determining the original composition of the Balsam.
Subject(s)
Balsams/history , Resins, Plant/history , Balsams/chemistry , Chemistry, Pharmaceutical , History, 19th Century , Humans , Israel , Resins, Plant/chemistry , Solid Phase MicroextractionABSTRACT
The series of new acetylenic thioquinolines containing propargyl, 2-butynyl, 4-bromo-2-butynyl, and 4-hydroxy-2-butynyl groups has been prepared and tested for antiproliferative activity in vitro against human [SW707 (colorectal adenocarcinoma), CCRF/CEM (leukemia)] and murine [P388 (leukemia), B16 (melanoma)] cancer lines. All the compounds obtained exhibited antiproliferative activity. The most active compounds 7, 16, 17, and 19 have the ID(50) values ranging from 0.2 to 4.6 microg/ml comparable to that of cisplatin used as reference compounds.
Subject(s)
Adenocarcinoma/drug therapy , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Colorectal Neoplasms/drug therapy , Leukemia, Experimental/drug therapy , Melanoma, Experimental/drug therapy , Quinolines/pharmacology , Sulfides/pharmacology , Animals , Antineoplastic Agents/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Humans , Mice , Molecular Structure , Quinolines/chemical synthesis , Quinolines/chemistry , Stereoisomerism , Structure-Activity Relationship , Sulfides/chemical synthesis , Sulfides/chemistryABSTRACT
The structure-activity relationships of new quinoline based compounds were investigated. Quinoline-5,8-dione and styrylquinoline scaffolds were used for the design of potentially active compounds. The novel analogues had comparable antiproliferative activity to cisplatin when evaluated in a bioassay against the P388 leukemia cell line. However, these compounds appeared far less efficient against SK-N-MC neuroepithelioma cells. Analogues without the 5,8-dione structure but containing the 8-carboxylic acid group were also found to induce antiproliferative activity. Hydrophobicity as measured by HPLC did not correlate with antiproliferative activity.
Subject(s)
Antineoplastic Agents/pharmacology , Carboxylic Acids/pharmacology , Cell Proliferation/drug effects , Quinolines/pharmacology , Animals , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Carboxylic Acids/chemical synthesis , Carboxylic Acids/chemistry , Cell Line, Tumor , Drug Screening Assays, Antitumor , Humans , Mice , Molecular Structure , Quinolines/chemical synthesis , Quinolines/chemistry , Structure-Activity RelationshipABSTRACT
A series of new acetylenic thioquinolines containing propargyl, 2-butynyl, or 4-bromo-2-butynyl groups has been prepared and tested for antiproliferative activity in vitro against the cells of human [SW707 (colon cancer), CCRF/CEM (leukemia)] and murine [P388 (leukemia), B16 (melanoma)] cancer lines. All the compounds obtained exhibited antiproliferative activity. The most active compounds 4h and 41-m have ID50 values ranging from 0.2 to 3.6 microg/ml, comparable to that of the reference compound cisplatin.
Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Quinolines/chemical synthesis , Quinolines/pharmacology , Animals , Cell Line, Tumor , Cisplatin/pharmacology , Drug Screening Assays, Antitumor , Humans , Indicators and Reagents , Magnetic Resonance Spectroscopy , Mice , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, Ultraviolet , Tetrazolium Salts , ThiazolesABSTRACT
The series of new 3,4-disubstituted thioquinolines which possess one or two O, S, Se-propargyl groups has been synthesized on the basis of the reaction of thioquinanthrene with alkoxides. All the compounds obtained were tested for their antiproliferative activity in vitro against the cells of three human cancer cell lines: SW707 (colon cancer), T47D (breast cancer), and HCV29T (bladder cancer). Two compounds, 4-(3-hydroxypropoxy)-3'-propargylthio-3,4'-diquinolinyl sulfide (3) and 3-methylthio-4-propargylselenoquinoline (13) exhibited significant cytostatic activity (ID50 < 4 micrograms/ml) against the cells of all the human cancer lines used and are good candidates for further anticancer activity studies in vitro using a broad panel of human and murine cell lines and for in vivo preclinical screening in different mouse transplantable tumor models.
Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Quinolines/chemical synthesis , Quinolines/pharmacology , Animals , Cell Division/drug effects , Cisplatin/pharmacology , Drug Screening Assays, Antitumor , Humans , Indicators and Reagents , Mice , Rhodamines , Tumor Cells, CulturedABSTRACT
The series of the propargyl thioquinolines has been prepared on the basis of the reaction of thioquinanthrene (1) (1,4-dithiino[2,3-c:5,6-c']-diquinoline) with sodium alkoxides. Some of these compounds have revealed good antiproliferative activity in vitro against the cells of human and murine cancer lines. 13C NMR spectra were measured for the studied compounds to examine the electronic properties-activity relationships. A regression study on 10 compounds showed a linear correlation of antiproliferative activity with electronic properties, expressed as the 13C NMR chemical shift for C-4 carbon atom (R2 = 0.97). It was found that compounds with chemical shift for C-4 value falling in the range of 135-140 ppm exhibited significant antiproliferative activity, while compounds which possess moderate or low activity are located in the range 140-165 ppm. This finding leads to the expectation that the antiproliferative activity of propargyl thioquinolines can be predicted using the 13C NMR chemical shift value of their C-4 carbon atom.
Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Quinolines/chemical synthesis , Quinolines/pharmacology , Animals , Cisplatin/pharmacology , Drug Screening Assays, Antitumor , Erythrocytes/drug effects , Humans , Regression Analysis , Sheep/immunology , Structure-Activity Relationship , Tetrazolium Salts , Thiazoles , Tumor Cells, CulturedABSTRACT
The molecular structure of the title compound, C(25)H(18)N(2)O(2)S(2), in the crystal is characterized by almost parallel quinoline and propargyl groups that point in opposite directions out of the quinoline planes. Intermolecular C[triple-bond]C-H...N hydrogen bonding is observed, but the hydrogen-bond geometry is poor.
Subject(s)
Analgesics/chemistry , Anti-Infective Agents/chemistry , Quinolines/chemistry , Crystallography, X-Ray , Hydrogen Bonding , Models, Molecular , Molecular ConformationABSTRACT
In 3-methylthio-4-(propargylthio)quinolinium chloride monohydrate, C(13)H(12)NS(2)(+).Cl(-).H(2)O, and 3-methylthio-4-(propargylthio)quinolinium trichloroacetate, C(13)H(12)NS(2)(+).C(2)Cl(3)O(2)(-), the terminal alkyne group forms C[triple-bond]C-H.O hydrogen bonds of favourable geometry. The conformation of the flexible propargylthio group is different in the two structures.
