- Haemolytic activity of formyl- and acetyl-derivatives of bile acids and their gramine salts
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Bile acids (lithocholic: LCA, deoxycholic: DCA and cholic: CA) and their formyl- and acetyl-derivatives can be used as starting material in chemical synthesis of compounds with different biological activity strongly depended on their chemical structures. Our previous studies showed that biological activity of bile acids salts with gramine toward human erythrocytes was significantly different from the activity of bile acids alone. Moreover, gramine effectively modified the membrane perturbing activity of other steroids. As a continuation of our work, the haemolytic activity of formyl- and acetyl-substituet bile acids as well as their gramine salts was studied in vitro. The structures of new compounds were confirmed by spectral (NMR, FT-IR) analysis, mass spectrometry (ESI-MS) as well as PM5 semiempirical methods. The results shown that the haemolytic activity of formyl- and acetyl-LCA and DCA was significantly higher in comparison with their native forms at the whole concentration range. At high concentration, formyl derivative of CA was as effective as LCA and DCA derivatives whereas at lower concentration its haemolytic activity was at the level of original acid. The acetyl-CA was not active as membrane perturbing agents. Furthermore, gramine significantly decreased the membrane-perturbing activity of hydrophobic bile acids derivatives. The results obtained with the cellular system are in line with physicochemical calculation.
- Kozanecka-Okupnik, Weronika,Jasiewicz, Beata,Pospieszny, Tomasz,Matuszak, Monika,Mrówczyńska, Lucyna
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- Structure and dynamics of a molecular hydrogel derived from a tripodal cholamide
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Tripodal cholamide 1 is a supergelator of aqueous fluids. A variety of physical techniques, including cryo-transmission electron microscopy (TEM), circular dichroism (CD), steady-state fluorescence, time-resolved fluorescence, and dynamic light-scattering, were employed to understand the structure and dynamics of the gel. Fluorescent probes [ANS (8-anilinonaphthalene-1-sulfonic acid) and pyrene] reported two critical aggregation concentrations (CAC 1 and CAC2) of 1 in predominantly aqueous media, with the minimum gel concentration (MGC) being close to CAC2. Fluorescence lifetime measurements with pyrene revealed ineffective quenching of pyrene fluorescence by oxygen, possibly caused by slower Brownian diffusion due to the enhanced viscosity in the gel phase. The study of the gelation kinetics by monitoring the ultrafast dynamics of ANS revealed a progressive increase in the aggregate size and the microviscosity of the aqueous pool encompassed by the self-assembled fibrillar network (SAFIN) during the gelation. The striking difference between microviscosity and bulk (macroscopic) viscosity of the gel is also discussed.
- Mukhopadhyay, Samrat,Maitra, Uday,Ira,Krishnamoorthy, Guruswamy,Schmidt, Judith,Talmon, Yeshayahu
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- Synthesis and spectroscopic studies of new bile acid derivatives linked by a 1,2,3-triazole ring
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A novel method for the synthesis of cholic acid derivatives has been developed using 'click chemistry'. Intermolecular 1,3-dipolar cycloaddition of the propargyl ester and azide groups of 3α-azidoacetoxy-7α, 12α-diformyloxy-5β-cholan-24-oate gave a new dimer and oligomer linked by a 1,2,3-triazole ring. The structures of the products were confirmed by spectral (1H NMR, 13C NMR, and FT-IR) analysis, mass spectrometry and PM5 semiempirical methods. Estimation of the pharmacotherapeutic potential has been accomplished for the synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASSs).
- Pospieszny, Tomasz,Ma?ecka, Izabela,Paryzek, Zdzis?aw
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- Synthesis and in vitro cholesterol dissolution by 23- and 24-phosphonobile acids
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A new class of 23- and 24-phosphonobile acids have been synthesized from bile acid and their in vitro cholesterol-dissolving efficiency have been estimated. 24-Phosphonobile salts (PBSs) are slightly more efficient in solubilizing cholesterol than 23-PBSs and natural bile salts. The cholesterol solubilizing power is influenced by the structure of PBSs, and is considerably reduced with an increase in the bulk pH.
- Babu, Ponnusamy,Maitra, Uday
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- The preparation of bile acid amines and oxazolines. II. The synthesis of the amides and oxazolines of ursodeoxycholic acid, deoxycholic acid, hyodeoxycholic acid and cholic acid
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Bile acid amides and oxazolines were synthesized by a sequence of steps involving the reaction of the free bile acid with formic acid to yield the formyloxy derivative, preparation of the formyloxy acid chloride, condensation of the acid chloride with 2-amino-2-methyl-1-propanol to give the amide and, finally, cyclization of the amide with thionyl chloride to give the oxazoline. The oxazolines were characterized by physical constants, thin layer and gas-liquid chromatography and identified by elemental analysis and gas-liquid chromatography-mass spectrometry. Some of the bile acid oxazoline derivatives alter the activity of bacterial 7-dehydroxylases in vitro, and inhibit the growth of certain anaerobic bacteria in pure culture.
- Cohen,May,McSherry,Mosbach
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- Recognition of a flavin analogue by novel bile acid-based receptors: Effects of hydrogen bonding and aromatic π-stacking interactions
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Molecular recognition properties are reported for novel bile acid-based receptors that incorporate 2,6-diaminopyridine as a recognition unit. Apart from hydrogen-bonding interactions, the bile acid receptors exhibit significant aromatic π-stacking interactions with the aromatic fused ring of the flavin derivative. These studies provide rationalisation for the differences in binding behaviour of bile acid receptors having differing aromatic arm lengths towards a flavin analogue.
- Muwal, Pradeep Kumar,Chhatra, Rajesh Kumar,Das, Shubhajit,Pandey, Pramod S.
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- Perfluoroalkyl bile esters: A new class of efficient gelators of organic and aqueous-organic media
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A new class of fluorinated gelators derived from bile acids is reported. Perfluoroalkyl chains were attached to the bile acids through two different ester linkages and were synthesized following simple transformations. The gelation property of these deriv
- Banerjee, Supratim,Vidya,Savyasachi,Maitra, Uday
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- A Scalable stereoselective synthesis of scymnol
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A high-yielding, stereoselective synthesis of scymnol 1 has been carried out in five steps starting from commercially available cholic acid 2. The synthesis was designed with the aim of eventual large-scale processing. Triformyloxycholic acid chloride 4 was treated with the magnesium enolate of diethyl malonate to afford the β-keto diester, diethyl 3α,7α, 12α-triformyloxy-24-oxo-5β-cholestane-26,27-dioate 5. The key step in the synthesis was the stereoselective hydroganation of β-keto diester 5 to give the corresponding β-hydroxy diester 6 using a BINAP nithenium(n) catalyst. Subsequent reduction of the diester moiety and deprotection of the hydroxyl groups afforded scymnol 1.
- Adhikari, Raju,Cundy, Darren J.,Francis, Craig L.,Gebara-Coghlan, Mariana,Krywult, Beata,Lubin, Carolyn,Simpson, Gregory W.,Yang, Qi
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- Azobenzene-bridged bile acid dimers: An interesting class of conjugates with conformation-controlled bioactivity
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The synergetic combination of the distinct properties of azobenzene and bile acid could afford stable tweezer-like conformation with tunable hydrophilic and hydrophobic channels, thus increasing their antimicrobial activity toward both Gram-positive and Gram-negative bacteria, which can be conveniently switched off when the conformation turn back to the extended state.
- Li, Weina,Li, Yan,Yin, Xianpeng,Liang, Yun,Li, Jian,Wang, Chen,Lan, Yue,Wang, Hui,Ju, Yong,Li, Guangtao
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supporting information
p. 2539 - 2543
(2016/05/24)
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- Synthesis, characterization and biological activity of hydroxyl- bisphosphonic analogs of bile acids
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Bisphosphonates (BPs) are now the most widely used drugs for diseases associated with increased bone resorption, such as osteoporosis, and tumor bone diseases. A significant drawback of the BPs is their poor oral absorption that is enhanced by the presence of bile acid substituents in the bisphosphonate framework, with no toxic effects. A straightforward synthesis of bile acid-containing hydroxy-bisphosphonates and a full characterization of these pharmaceutically important molecules, including an evaluation of affinity and the mechanism of binding to hydroxyapatite, is presented. The biological activity of bile acid-containing bisphosphonate salts was determined using the neutral-red assay on the L929 cell line and primary cultures of osteoclasts. The bioactivity of the new compounds was found superior than bisphosphonates of established activity.
- Bortolini, Olga,Fantin, Giancarlo,Fogagnolo, Marco,Rossetti, Stefano,Maiuolo, Loredana,Di Pompo, Gemma,Avnet, Sofia,Granchi, Donatella
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scheme or table
p. 221 - 229
(2012/07/28)
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- Metal-free efficient, general and facile iododecarboxylation method with biodegradable co-products
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The development of a novel, efficient and robust method for the general conversion of aliphatic and aromatic carboxylic acids to organic iodides without the use of heavy metals or strong oxidizing agents is reported. Commercially available N-iodoamides were used for both initiation and halogen donation under irradiative conditions. Isolation of the product is extremely simple and the major co-product is removed as a water-soluble biodegradable material. Copyright
- Kulbitski, Kseniya,Nisnevich, Gennady,Gandelman, Mark
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supporting information; experimental part
p. 1438 - 1442
(2011/07/30)
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- Synthesis and olfactory activity of unnatural, sulfated 5β-bile acid derivatives in the sea lamprey (Petromyzon marinus)
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A variety of unnatural bile acid derivatives (9a-9f) was synthesized and used to examine the specificity with which the sea lamprey (Petromyzon marinus) olfactory system detects these compounds. These compounds are analogs of petromyzonol sulfate (PS, 1), a component of the sea lamprey migratory pheromone. Both the stereochemical configuration at C5 (i.e., 5α vs. 5β) and the extent and sites of oxygenation (hydroxylation or ketonization) of the bile acid derived steroid skeleton were evaluated by screening the compounds for olfactory activity using electro-olfactogram recording. 5β-Petromyzonol sulfate (9a) elicited a considerable olfactory response at sub-nanomolar concentration. In addition, less oxygenated systems (i.e., 9b-9e) elicited olfactory responses, albeit with less potency. The sea lamprey sex pheromone mimic 9f (5β-3-ketopetromyzonol sulfate) was also examined and found to produce a much lower olfactory response. Mixture studies conducted with 9a and PS (1) suggest that stimulation is occurring via similar modes of activation, demonstrating a relative lack of specificity for recognition of the allo-configuration (i.e., 5α) in sea lamprey olfaction. This attribute could facilitate design of pheromone analogs to control this invasive species.
- Burns, Aaron C.,Sorensen, Peter W.,Hoye, Thomas R.
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experimental part
p. 291 - 300
(2011/03/21)
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- Movel photoacid generators, resist compositons, and patterning processes
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Photoacid generators generate sulfonic acids of formula (1a) or (1c) upon exposure to high-energy radiation. ????????R1-COOCH(CF3)CF2SO3-H+?????(1a) ????????R1-O-COOCH(CF3)CF2SO3-H+?????(1c) R1 is a C20-C50 hydrocarbon group having a steroid structure. The photoacid generators are compatible with resins and can control acid diffusion and are thus suited for use in chemically amplified resist compositions.
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Page/Page column 69
(2009/04/23)
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- Recognition properties of flavin analogues with bile acid-based receptors: Role of steric effects in hydrogen bond based molecular recognition
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The recognition properties of 7,8-dimethyl flavin analogues by bile acid-based receptors that contain 2,6-diaminopyridine and the dioctylamide of 2,6-diaminopyridine in CHCl3 were determined. The results show that the bile acid-based receptors bind 7,8-dimethyl flavin analogues less effectively as compared to 7,8-unsubstituted flavins reported earlier, which is contrary to the known fact that the association constants increase with increasing electron-donating capacity of the substituents at the 7 and 8 positions of the flavin analogues. CSIRO 2008.
- Chattopadhyay, Prosenjit,Nagpal, Rekha,Pandey, Pramod S.
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p. 216 - 222
(2008/09/18)
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- Synthesis of cholaphanes by ring closing metathesis
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The synthesis of cholaphanes by ring closing metathesis (RCM) of 3α,7α,12α,24-tetraol allyl derivatives, obtained from cholic acid, was attempted. The reactions of tetraol 3,24-diallyl ether or 3,24-diacrylate were not satisfactory. However, diallyl derivatives of disteroidal 3,3′- or 24,24′-ortho-phthalates reacted smoothly affording cyclic dimers in good yields. In all the reactions studied, the E isomers of the macrocycles were obtained in excess.
- Czajkowska, Dorota,Morzycki, Jacek W.
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p. 2851 - 2855
(2007/10/03)
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- The "triamino-analogue" of methyl allocholate; a rigid, functionalised scaffold for supramolecular chemistry
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Cholic acid 1 has been converted into triamine 5 with the all-trans polycyclic allocholanoyl skeleton and co-directed, axial amino groups; the potential of this system as a scaffold is illustrated by conversion to a preorganised anion receptor. The Royal
- Bhattarai, Khadga M.,Del Amo, Vicente,Magro, Germinal,Sisson, Adam L.,Joos, Jean-Baptiste,Charmant, Jonathan P. H.,Kantacha, Anob,Davis, Anthony P.
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p. 2335 - 2337
(2008/03/28)
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- A New Generation of "Cholaphanes": Steroid-Derived Macrocyclic Hosts with Enhanced Solubility and Controlled Flexibility
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The macrocyclic "cholaphanes" 3a - c were synthesized from the inexpensive steroid cholic acid. Like earlier relatives they feature substantial cavities with inward-directed hydroxyl groups, suitable for binding polar molecules such as carbohydrates in nonpolar media. New features are the externally directed alkyl chains, promoting solubility in organic solvents, and (in the case of 3b/c) reduced conformational freedom resulting from truncation of the steroidal side-chain. In particular, modeling shows that the smallest macrocycle 3c possesses very little flexibility, preferring an open conformation which is also revealed in the X-ray crystal structure of its pentahydrate. NMR studies indicated that all three cholaphanes form 1:1 complexes with octyl β-D-glucoside in CDCl3, with Ka = 600-1560 M-1. Cholaphanes 3b/c proved able to extract methyl β-D-glucoside from aqueous solutions into CHCl3. The transport of methyl β-D-glucoside across a chloroform barrier was also demonstrated for 3c.
- Bhattarai, Khadga M.,Davis, Anthony P.,Perry, Justin J.,Walter, Christopher J.,Menzer, Stephan,Williams, David J.
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p. 8463 - 8473
(2007/10/03)
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- 7β-Hydroxy bile alcohols: Facile synthesis and 2D 1H NMR studies of 5β-cholestane-3α,7β,12α,25-tetrol
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A rapid and easily performed procedure for the synthesis of 5β- cholestane-3α,7β,12α,25-tetrol by means of an efficient homologation sequence of the intermediate, 3α,7β,12α-triformyloxy-24-oxo-25-diazo-25- homo-5β-cholane is described. The reaction sequence involved treating the intermediate, α-diazoketone in methanol with 3% AgNO3 or Ag2O, anhydrous Na2CO3, Na2S2O3/H2O resulting in the formation of homoursocholic acid in high yield. Esterification of the homoursocholic acid in methanol containing a catalytic amount of methanesulfonic acid under microwave irradiation conditions gave methyl homoursocholate. The subsequent treatment of methyl homoursocholate with methyl magnesium iodide provided 5β- cholestane-3α,7β,12α,25-tetrol in 88% yield. The products and synthetic intermediates prepared in these studies were fully characterized by the results of 1D and 2D NMR, and high-resolution mass spectral studies. These studies will help in further investigation of the defect of cholic acid biosynthesis in patients with cerebrotendinous xanthomatosis (CTX) as well as other inborn errors of bile acid metabolism.
- Dayal, Bishambar,Ertel,Padia,Rapole,Salen
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p. 409 - 414
(2007/10/03)
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- Anti-fungal compounds
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Compounds of the general formula (7): STR1 wherein X is a hydrogen atom or a hydroxyl group, Y is a hydrogen atom or a hydroxyl group and at least one of X and Y is a hydroxyl group and Z is a hydroxyl group or a methylol (--CH2 OH) group, have anti-fungal activity, especially against organisms selected from Candida spp. and the athlete's foot/ringworm organisms Trichophyton mentagrophytes and Microsporum audonii. Compounds in which Z is a methylol (--CH2 OH) group are claimed per se.
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- Antimicrobial activity of cholane compounds. Cholic and deoxycholic acids derivatives (Part 1)
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A series of compounds of (3 α, 5 β, 7 α, 12 α) 3, 7, 12-trihydroxy and (3 α, 5 β, 12 α) 3, 12-dihydroxy-cholanic acids was synthesized and their in vitro antibacterial activity was determined against a variety of Gram-negative and Gram-positive strains. Some of the compounds show an interesting antimicrobial activity against Gram-positive strains.
- Bellini,Quaglio,Guarneri,Cavazzini
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p. 185 - 190
(2007/10/02)
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- Labelled bile acids
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The present invention provides compounds having the general formula STR1 wherein R is STR2 and A is 0 or 1, B is 0 to 4, C is 0 to 4, Z is Se or Te, R6 is --OH or an amino acid residue, R7 is hydrogen or saturated C1 to C
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