- THE PREPARATION OF AMINO BILE ACID DERIVATIVES
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Bile acid derivatives have been prepared by reaction of their mixed anhydrides with diaminoethane.The new compounds have side chains modified by amide bond formation which extends the side chain by two carbon atoms and terminates in a primary amino group.
- Hill, A.,Ross, P. E.,Bouchier, I. A. D.
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- Synthesis of cholic acid-based molecular receptors: Head-to-head cholaphanes
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A novel synthetic strategy for the synthesis of head-to-head cholaphanes (II) using spacers, ethylenediamine or m-xylylenediamine as X and terephthalate as Y, has been reported. The synthesis constitutes the incorporation of different bile acids, viz. cho
- Pandey, Pramod S.,Rai, Roopali,Singh, Rhiddi B.
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- Synthesis of a head to head cholaphane
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A general synthetic route for the construction of head to head cholaphanes, a new type of steroidal macrocycles, has been described.
- Pandey, Pramod S.,Singh, Rhiddi Bir
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- Characterization of novel fluorescent bile salt derivatives for studying human bile salt and organic anion transporters
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Bile salts, such as cholate, glycocholate, taurocholate, and glycochenodeoxycholate, are taken up from the portal blood into hepatocytes via transporters, such as the Na+-taurocholate–cotransporting polypeptide (NTCP) and organic anion–transporting polypeptides (OATPs). These bile salts are later secreted into bile across the canalicular membrane, which is facilitated by the bile salt export pump (BSEP). Apart from bile salt transport, some of these proteins (e.g., OATPs) are also key transporters for drug uptake into hepatocytes. In vivo studies of transporter function in patients by using tracer compounds have emerged as an important diagnostic tool to complement classic liver parameter measurements by determining dynamic liver function both for diagnosis and monitoring progression or improvement of liver diseases. Such approaches include use of radioactively labeled bile salts (e.g., for positron emission tomography) and fluorescent bile salt derivatives or dyes (e.g., indocyanine green). To expand the list of liver function markers, we synthesized fluorescent derivatives of cholic and chenodeoxycholic acid by conjugating small organic dyes to the bile acid side chain. These novel fluorescent probes were able to block substrate transport in a concentration-dependent manner of NTCP, OATP1B1, OATP1B3, OATP2B1, BSEP, and intestinal apical sodium-dependent bile salt transporter (ASBT). Whereas the fluorescent bile acid derivatives themselves were transported across the membrane by OATP1B1, OATP1B3, and OATP2B1, they were not transport substrates for NTCP, ASBT, BSEP, and multidrug resistance-related protein 2. Accordingly, these novel fluorescent bile acid probes can potentially be used as imaging agents to monitor the function of OATPs. SIGNIFICANCE STATEMENT Synthetic modification of common bile acids by attachment of small organic fluorescent dyes to the bile acid side chain resulted in bright, fluorescent probes that interact with hepatic and intestinal organic anion [organic anion–transporting polypeptide (OATP) 1B1, OATP1B3, OATP2B1], bile salt uptake (Na+-taurocholate–cotransporting polypeptide, apical sodium-dependent bile salt transporter), and bile salt efflux (bile salt export pump, multidrug resistance-related protein 2) transporters. Although the fluorescent bile salt derivatives are taken up into cells via the OATPs, the efflux transporters do not transport any of them but one.
- Euler, Adriana,Leuenberger, Michele,Lochner, Martin,Stieger, Bruno,H?usler, Stephanie,H?hn, Vera
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p. 346 - 357
(2021/06/08)
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- Synthesis of new cisplatin derivatives from bile acids
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A series of bile acid derived 1,2- and 1,3-diamines as well as their platinum(II) complexes were designed and synthesized in hope to get a highly cytotoxic compound by the combination of two bioactive moieties. All complexes obtained were subjected to cytotoxicity assays in vitro and some hybrid molecules showed an expected activity.
- ?otowski, Zenon,Hryniewicka, Agnieszka,Morzycki, Jacek W.,Rárová, Lucie,Seroka, Barbara,Sicinski, Rafal R.,Tomkiel, Aneta M.
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- DRUG FORMULATION BASED ON PARTICULATES COMPRISING POLYSACCHARIDE-VITAMIN CONJUGATE
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The present disclosure provides formulations for pharmacologically active reagents, including formulations based on particulates formed from a biodegradable polymer (e.g., a polysaccharide such as dextran) linked to a vitamin or related agent (e.g., folic
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Paragraph 0215-0216
(2017/04/11)
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- Glycogen phosphorylase inhibitor and preparation method and application thereof
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The invention belongs to the technical field of drug synthesis and discloses a glycogen phosphorylase inhibitor and a preparation method and application thereof. The gGlycogen phosphorylase inhibitor has a structural general formula shown as a formula (1)
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Paragraph 0056; 0057; 0058; 0059
(2017/01/02)
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- Synthesis and antimicrobial evaluation of bile acid tridentate conjugates
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Two series of novel bile acid tridentate conjugates with different linkers were synthesized and characterized, and their biological activities in vitro were evaluated. The procedure was straightforward and efficient to be carried out with high overall yield. The antimicrobial activity of the synthesized compounds against Saccharomyces cerevisiae, Aspergillus niger, Escherichia coli and Staphylococcus aureus was investigated in vitro. The best activity of minimal inhibitory concentrations (MICs) for 1c, 1c′, 2c and 2c′ against S. cerevisiae was up to 0.125 μg/mL.
- Huang, Liliang,Sun, Yanhong,Zhu, Hua,Zhang, Yuanqing,Xu, Jia,Shen, Yu-Mei
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body text
p. 701 - 706
(2009/07/19)
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- Synthesis and characterization of organometallic rhenium(I{cyrillic, ukrainian}) and technetium(I{cyrillic, ukrainian}) bile acid complexes
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Eight bile acid derivatives have been synthesized with alkyl chains of various length based tridentate ligand chelating system. These derivatives have been reacted with the precursor [Et4N]2[Re(CO)3Br3] and fac-[M(CO)3(H2O)3]+ (M = 99mTc, Re) in ethanol or ethanol-aqueous media to form water-soluble and stable organometallic complexes in good yields. 1H NMR, 13C NMR, IR and elemental analysis or HRMS spectroscopic analyses confirmed the tridentate complexation of the metal-tricarbonyl fragment exclusively via the tridentate chelates. In addition, the corresponding radioactive technetium-99m complexes were prepared successfully and challenged for stability in physiological phosphate buffer at 37 °C for 24 h. No decomposition of the complexes could be detected under the condition proving the stability of these complexes.
- Huang, Liliang,Zhu, Hua,Xu, Xiaoping,Zhang, Chunchun,Shen, Yu-Mei
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experimental part
p. 3247 - 3253
(2010/01/11)
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- Synthesis and characterization of novel bile-acid - heteroaryl conjugates with N-(2-aminoethyl)amido linker
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Four novel bile acid conjugates N-[2-([2,2′]-bithiophen-5-ylmethyl)aminoethyl]-3α-hydroxy-5β-cholan-24-amide (1), N-[2-([2,2′]-bithiophen-5-ylmethyl)aminoethyl]-3α,7α,12α-trihydroxy-5β-cholan-24-amide (2), N-[2-(1H-pyrrol-2-ylmethyl)aminoethyl]-3α-hydroxy-5β-cholan-24-amide (3), N-[2-(pyridin-2-ylmethyl)aminoethyl]-3α-hydroxy-5β-cholan-24-amide (4) have been synthesized in moderate to good yields, and their structures have been characterized by 1H, 13C, 13C DEPT-135, PFG 1H,13C HMQC, and PFG 1H,13C HMBC NMR spectra. Their molecular weights and elemental compositions have been determined by ESI-TOF mass spectrometry and elemental analyses. Crystal structure of 1 characterized with orthorhombic P212121 space group has also been determined.
- Koivukorpi, Juha,Valkonen, Arto,Lahtinen, Manu,Kolehmainen, Erkki
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scheme or table
p. 53 - 57
(2009/03/12)
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