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Synthesis of organoarsenic, organoantimony, and organobismuth poly(ether esters) from reaction with glycyrrhetinic acid and their preliminary activity against pancreatic cancer cell lines

Published on Jun 1, 2013in Journal of the Chinese Advanced Materials Society
· DOI :10.1080/22243682.2013.812281
Charles E. Carraher24
Estimated H-index: 24
(FAU: Florida Atlantic University),
Ngoc Trang Caroline Truong2
Estimated H-index: 2
(FAU: Florida Atlantic University)
+ 2 AuthorsNancy T. Trang5
Estimated H-index: 5
(UTA: University of Texas at Arlington)
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Abstract
Polyether esters were rapidly formed employing the interfacial condensation of Group VA triphenylmetal dihalides with glycyrrhetinic acid in moderate yield and chain length. Infrared spectroscopy shows the formation of metal–oxygen bonds. The products are a mixture of bridging and non-bridging structures about the metal atom. Proton NMR and MALDI MS results are consistent with the formation of the polyether esters. Some of the polymers exhibit inhibition of the growth of pancreatic cancer cell lines.
  • References (66)
  • Citations (8)
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References66
Newest
Published on Jun 1, 2013in Immunopharmacology and Immunotoxicology 2.09
Mi Eun Kim10
Estimated H-index: 10
(UPR-RP: UPRRP College of Natural Sciences),
Hyung Keun Kim14
Estimated H-index: 14
(Chonnam National University)
+ 2 AuthorsJun Sik Lee11
Estimated H-index: 11
(UPR-RP: UPRRP College of Natural Sciences)
Abstract18β-Glycyrrhetinic acid (β-GA) is a natural triterpenoid compound derived from licorice root. β-GA has been demonstrated to exert antiviral and antitumor effects. However, the effects of the maturation and immunostimulatory functions of dendritic cells (DCs) remain to be clearly elucidated. In this study, we attempted to determine whether β-GA could influence DCs surface molecule expression, antigen uptake capacity, cytokine production and capacity to induce T-cell differentiation. The D...
14 Citations Source Cite
Charles E. Carraher24
Estimated H-index: 24
(FAU: Florida Atlantic University),
Amitabh Battin6
Estimated H-index: 6
(FAU: Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(UTA: University of Texas at Arlington)
The conductivity of the polyamine derived from titanocene dichloride and 2-nitro-1,4-phenylenediamine increases to 101 to 103 fold when doped with iodine. Larger increases are found for the analogous polyamines except derived from zirconocene dichloride (increased 103–104 fold) and hafnocene dichloride (105–106 fold) and for certain other diamines. The conductivity of the product of titanocene dichloride and N-methyl-1,4-phenylenediamine increased 105 fold when doped. By comparison, conductivity...
12 Citations Source Cite
Published on Jan 1, 2013in Antimicrobial Agents and Chemotherapy 4.71
Danyelle R. Long1
Estimated H-index: 1
(MSU: Montana State University),
Julia Mead1
Estimated H-index: 1
(MSU: Montana State University)
+ 2 AuthorsJovanka M. Voyich33
Estimated H-index: 33
(MSU: Montana State University)
Methicillin-resistant Staphylococcus aureus (MRSA) has become a major source of infection in hospitals and in the community. Increasing antibiotic resistance in S. aureus strains has created a need for alternative therapies to treat disease. A component of the licorice root Glycyrrhiza spp., 18β-glycyrrhetinic acid (GRA), has been shown to have antiviral, antitumor, and antibacterial activity. This investigation explores the in vitro and in vivo effects of GRA on MRSA pulsed-field gel electropho...
30 Citations Source Cite
Published on Dec 1, 2012in Virology Journal 2.46
Michele E. Hardy20
Estimated H-index: 20
(MSU: Montana State University),
Jay M. Hendricks3
Estimated H-index: 3
(MSU: Montana State University)
+ 1 AuthorsNicholas R Faunce2
Estimated H-index: 2
(MSU: Montana State University)
Background Glycyrrhizin (GA) and primary metabolite 18β-glycyrrhetinic acid (GRA) are pharmacologically active components of the medicinal licorice root, and both have been shown to have antiviral and immunomodulatory properties. Although these properties are well established, the mechanisms of action are not completely understood. In this study, GA and GRA were tested for the ability to inhibit rotavirus replication in cell culture, toward a long term goal of discovering natural compounds that ...
23 Citations Source Cite
Published on Nov 13, 2012in PLOS ONE 2.78
Jay M. Hendricks3
Estimated H-index: 3
(MSU: Montana State University),
Carol Hoffman1
Estimated H-index: 1
(MSU: Montana State University)
+ 1 AuthorsMichele E. Hardy20
Estimated H-index: 20
(MSU: Montana State University)
Glycyrrhizin, an abundant bioactive component of the medicinal licorice root is rapidly metabolized by gut commensal bacteria into 18β-glycyrrhetinic acid (GRA). Either or both of these compounds have been shown to have antiviral, anti-hepatotoxic, anti-ulcerative, anti-tumor, anti-allergenic and anti-inflammatory activity in vitro or in vivo. In this study, the ability of GRA to modulate immune responses at the small intestinal mucosa when delivered orally was investigated. Analysis of cytokine...
11 Citations Source Cite
Published on May 1, 2012in Bioorganic & Medicinal Chemistry Letters 2.45
Lijun Wang17
Estimated H-index: 17
(CAS: Chinese Academy of Sciences),
Chang-An Geng15
Estimated H-index: 15
(CAS: Chinese Academy of Sciences)
+ 5 AuthorsJi-Jun Chen24
Estimated H-index: 24
(CAS: Chinese Academy of Sciences)
Fifty-seven derivatives of glycyrrhetinic acid (GA) were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated in HepG 2.2.15 cells. Among them, sixteen compounds showed greater anti-HBV activity than GA, especially, compounds 29, 32, 35, 41 exhibited significantly inhibitory activities against HBV DNA replication with IC50 values of 5.71, 5.36, 8.90 and 9.08 mu M, respectively. The structure-activity relationships (SARs) of GA derivatives were discussed for exploring novel ...
18 Citations Source Cite
Published on Jan 1, 2012in DNA and Cell Biology 2.92
Shohreh Nafisi18
Estimated H-index: 18
,
Mahyar Bonsaii5
Estimated H-index: 5
+ 1 AuthorsKhosrou Abdi8
Estimated H-index: 8
Glycyrrhizin (GL), a molecule of glycyrrhetinic acid (GA), is an aqueous extract from licorice root. These compounds are well known for their anti-inflammatory, hepatocarcinogenesis, antiviral, and interferon-inducing activities. This study is the first attempt to investigate the binding of GL and GA with DNA. The effect of ligand complexation on DNA aggregation and condensation was investigated in aqueous solution at physiological conditions, using constant DNA concentration (6.25 mM) and vario...
12 Citations Source Cite
Published on Oct 1, 2011in Inorganic Chemistry Communications 1.79
Min Hong1
Estimated H-index: 1
(Liaocheng University),
Handong Yin14
Estimated H-index: 14
(Liaocheng University)
+ 1 AuthorsXi-Ying You1
Estimated H-index: 1
(Liaocheng University)
Abstract Two novel organoantimony(V) complexes [Ph 3 SbL a ] 2 ( 1 ) and [Ph 3 SbL b ] 2 ( 2 ) (H 2 L a = 5-{[(2-carboxyphenyl)methylene]amino}-4-chlorobenzoic acid, and H 2 L b = 5-{[(2-carboxyphenyl)methylene]amino}-2-chlorobenzoic acid) have been synthesized by the reaction of triphenylantimony dichloride and Schiff base ligands with the ratio of 1:1, and characterized by elemental analysis, IR, 1 H and 13 C NMR spectroscopy. X-ray single-crystal diffraction analyses reveal that two highly sy...
5 Citations Source Cite
Published on Jul 1, 2011in Journal of Polymer Materials 0.41
Charles E. Carraher24
Estimated H-index: 24
,
Yoshinobu Naoshima12
Estimated H-index: 12
(Okayama University of Science)
+ 4 AuthorsAmitabh Battin6
Estimated H-index: 6
6 Citations
Published on May 27, 2011in Materials 2.97
Michael R. Roner19
Estimated H-index: 19
,
Charles E. Carraher24
Estimated H-index: 24
(FAU: Florida Atlantic University)
+ 1 AuthorsGirish Barot11
Estimated H-index: 11
(BU: Boston University)
Polymers containing platinum and to a lesser extent tin, have repeatedly demonstrated antitumor activity in vitro and in vivo against a variety of cell and tumor types. The mechanisms responsible for the antitumor activity include inducing a delay in cell proliferation and sister chromatid exchanges blocking tumor growth. As most DNA and some RNA viruses require, and even induce, infected cells to initiate DNA replication and subsequent cell division, compounds with antitumor activity will very ...
17 Citations Source Cite
Cited By8
Newest
Published on Oct 1, 2018in Macromolecular Rapid Communications 4.08
Joji Tanaka5
Estimated H-index: 5
(Warw.: University of Warwick),
Thomas P. Davis82
Estimated H-index: 82
(Warw.: University of Warwick),
Paul Wilson34
Estimated H-index: 34
(Warw.: University of Warwick)
2 Citations Source Cite
Charles E. Carraher24
Estimated H-index: 24
(FAU: Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(UTA: University of Texas at Arlington)
+ 5 AuthorsPaul Slawek2
Estimated H-index: 2
(FAU: Florida Atlantic University)
Polyesters were rapidly synthesized employing interfacial polymerization from reaction of the salt of camphoric acid with Group VA (Group 15) triphenylmetallic dihalides. Yields range from 25 to 46 percent with chain lengths about 250. Infrared spectroscopy shows the formation of two new bands one assigned to the symmetrical M–O stretching and the second assigned to the asymmetrical M–O stretching. The bridging structure about the metal atom increases as the metal atom size increases. MALDI MS a...
2 Citations Source Cite
Saira Jabeen5
Estimated H-index: 5
(QAU: Quaid-i-Azam University),
Ayesha Kausar20
Estimated H-index: 20
(QAU: Quaid-i-Azam University)
+ 2 AuthorsSagheer Gul5
Estimated H-index: 5
(QAU: Quaid-i-Azam University)
In this investigation, blends of poly(vinyl alcohol) and chitosan cross-linked with bis phenol-F-diglycidyl ether were prepared by solution casting method. Epoxy acted as a cross-linker and content was varied from 3.80 × 10−3 to 3.80 × 10−2 mol. Morphology of the blend was examined using scanning electron microscopy which showed homogenous morphology suggesting good miscibility between blend components. FTIR showed significant shifting of peak at 1063 cm−1 to higher frequency implying that inter...
4 Citations Source Cite
Published on Jul 2, 2016in Journal of Macromolecular Science, Part A 1.16
Charles E. Carraher7
Estimated H-index: 7
(FAU: Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(UTA: University of Texas at Arlington)
+ 6 AuthorsLindsey Miller4
Estimated H-index: 4
(UTA: University of Texas at Arlington)
ABSTRACTWe describe the initial synthesis of DMSO and water-soluble titanocene polyethers through reaction of the titanocene dichloride and various poly(ethylene glycols) employing commercially available reactants. Infrared, proton NMR, and MALDI MS results are consistent with the titanocene-containing polyether structure. The materials are polymeric with chain lengths ranging from 1500 to 4. They exhibit good inhibition of a variety of cancer cell lines including two pancreatic cancer cell line...
4 Citations Source Cite
Charles E. Carraher7
Estimated H-index: 7
(FAU: Florida Atlantic University),
Alicia Morrison2
Estimated H-index: 2
(FAU: Florida Atlantic University)
+ 3 AuthorsLindsey Miller4
Estimated H-index: 4
(UTA: University of Texas at Arlington)
4 Citations Source Cite
Published on Nov 1, 2014in Inorganica Chimica Acta 2.43
Charles E. Carraher7
Estimated H-index: 7
(FAU: Florida Atlantic University),
Ngoc Trang Caroline Truong2
Estimated H-index: 2
(FAU: Florida Atlantic University)
+ 3 AuthorsNancy T. Trang5
Estimated H-index: 5
(UTA: University of Texas at Arlington)
Abstract Polyether esters are rapidly formed employing the interfacial condensation of organotin dihalides with glycyrrhetinic acid in high yield and oligomeric to polymeric chain length. Infrared spectroscopy shows the formation of tin–oxygen bonds. The products are a mixture of bridging and non-bridging structures about the tin atom. Proton NMR and MALDI MS results are consistent with the formation of the poly(ether esters). The dimethyltin, dibutyltin, and diphenyltin polymers exhibit good in...
7 Citations Source Cite
Published on Sep 23, 2014in Molecules 3.06
Donal M. Keogan3
Estimated H-index: 3
,
Darren M. Griffith13
Estimated H-index: 13
(RCSI: Royal College of Surgeons in Ireland)
: Bismuth compounds have been used extensively as medicines and in particular for the treatment of gastrointestinal ailments. In addition to bismuth’s well known gastroprotective effects and efficacy in treating H. pylori infection it also has broad anti-microbial, anti-leishmanial and anti-cancer properties. Aspects of the biological chemistry of bismuth are discussed and biomolecular targets associated with bismuth treatment are highlighted. This review strives to provide the reader with an up...
40 Citations Source Cite