Literature DB >> 27774133

NO Photoreleaser-Deoxyadenosine and -Bile Acid Derivative Bioconjugates as Novel Potential Photochemotherapeutics.

Maria Luisa Navacchia1, Aurore Fraix2, Nicola Chinaglia3, Eleonora Gallerani4, Daniela Perrone3, Venera Cardile5, Adriana C E Graziano5, Massimo L Capobianco1, Salvatore Sortino2.   

Abstract

This contribution reports the synthesis of some novel bioconjugates with anticancer activity and able to release nitric oxide (NO) under visible light excitation. The 4-nitro-2-(trifluoromethyl)aniline derivative, a suitable NO photodonor, was conjugated with 2'-deoxyadenosine and urso- and cheno-deoxycholic acid derivatives, through a thioalkylic chain or the 4-alkyl-1,2,3-triazole moiety. Photochemical experiments demonstrated the effective release of NO from 2'-deoxyadenosine and ursodeoxycholic acid conjugates under the exclusive control of visible light inputs. Studies for the in vitro antiproliferative activity against leukemic K562 and colon carcinoma HCT116 cell lines are reported for all the compounds as well as a case study of photocytotoxicity against HCT116.

Entities:  

Keywords:  2′-deoxyadenosine conjugates; NO photorelease; bile acid conjugates; photochemotherapeutics

Year:  2016        PMID: 27774133      PMCID: PMC5066146          DOI: 10.1021/acsmedchemlett.6b00257

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN: 1948-5875            Impact factor:   4.345


  28 in total

1.  Amplified nitric oxide photorelease in DNA proximity.

Authors:  Fiorella L Callari; Salvatore Sortino
Journal:  Chem Commun (Camb)       Date:  2008-03-20       Impact factor: 6.222

Review 2.  Nitric oxide release: part II. Therapeutic applications.

Authors:  Alexis W Carpenter; Mark H Schoenfisch
Journal:  Chem Soc Rev       Date:  2012-02-24       Impact factor: 54.564

Review 3.  Photochemical delivery of nitric oxide.

Authors:  Peter C Ford
Journal:  Nitric Oxide       Date:  2013-02-13       Impact factor: 4.427

4.  Labeling deoxyadenosine for the preparation of functional conjugated oligonucleotides.

Authors:  Massimo L Capobianco; Elena Marchesi; Daniela Perrone; Maria Luisa Navacchia
Journal:  Bioconjug Chem       Date:  2013-08-21       Impact factor: 4.774

5.  Metal complexes as photochemical nitric oxide precursors: potential applications in the treatment of tumors.

Authors:  Alexis D Ostrowski; Peter C Ford
Journal:  Dalton Trans       Date:  2009-08-27       Impact factor: 4.390

Review 6.  Nitric oxide: new evidence for novel therapeutic indications.

Authors:  Sunil J Wimalawansa
Journal:  Expert Opin Pharmacother       Date:  2008-08       Impact factor: 3.889

7.  Synthetic bile acid derivatives inhibit cell proliferation and induce apoptosis in HT-29 human colon cancer cells.

Authors:  Sang Eun Park; Hye Joung Choi; Su Bog Yee; Hae Young Chung; Hongsuk Suh; Yung Hyun Choi; Young Hyun Yoo; Nam Deuk Kim
Journal:  Int J Oncol       Date:  2004-07       Impact factor: 5.650

Review 8.  Solid tumor physiology and hypoxia-induced chemo/radio-resistance: novel strategy for cancer therapy: nitric oxide donor as a therapeutic enhancer.

Authors:  Hiroyasu Yasuda
Journal:  Nitric Oxide       Date:  2008-05-06       Impact factor: 4.427

9.  Polychromophoric metal complexes for generating the bioregulatory agent nitric oxide by single- and two-photon excitation.

Authors:  Peter C Ford
Journal:  Acc Chem Res       Date:  2008-01-09       Impact factor: 22.384

10.  Gold-nanoparticle extraction and reversed-electrode-polarity stacking mode combined to enhance capillary electrophoresis sensitivity for conjugated nucleosides and oligonucleotides containing thioether linkers.

Authors:  Valentina Bosi; Elena Sarti; Maria Luisa Navacchia; Daniela Perrone; Luisa Pasti; Alberto Cavazzini; Massimo L Capobianco
Journal:  Anal Bioanal Chem       Date:  2015-05-10       Impact factor: 4.142

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  7 in total

1.  Evaluation of the Anticancer Activity of a Bile Acid-Dihydroartemisinin Hybrid Ursodeoxycholic-Dihydroartemisinin in Hepatocellular Carcinoma Cells.

Authors:  Tzu-En Huang; Yi-Ning Deng; Jui-Ling Hsu; Wohn-Jenn Leu; Elena Marchesi; Massimo L Capobianco; Paolo Marchetti; Maria Luisa Navacchia; Jih-Hwa Guh; Daniela Perrone; Lih-Ching Hsu
Journal:  Front Pharmacol       Date:  2020-11-10       Impact factor: 5.810

Review 2.  Physiology and Physical Chemistry of Bile Acids.

Authors:  Maria Chiara di Gregorio; Jacopo Cautela; Luciano Galantini
Journal:  Int J Mol Sci       Date:  2021-02-10       Impact factor: 5.923

Review 3.  Bile Acid Conjugates with Anticancer Activity: Most Recent Research.

Authors:  Maria Luisa Navacchia; Elena Marchesi; Daniela Perrone
Journal:  Molecules       Date:  2020-12-23       Impact factor: 4.411

4.  Nanoscale lipid vesicles functionalized with a nitro-aniline derivative for photoinduced nitric oxide (NO) delivery.

Authors:  Nancy Sharma; Ajay Kumar Dhyani; Srujan Marepally; D Amilan Jose
Journal:  Nanoscale Adv       Date:  2019-11-20

Review 5.  Modified Nucleosides, Nucleotides and Nucleic Acids via Click Azide-Alkyne Cycloaddition for Pharmacological Applications.

Authors:  Daniela Perrone; Elena Marchesi; Lorenzo Preti; Maria Luisa Navacchia
Journal:  Molecules       Date:  2021-05-22       Impact factor: 4.411

6.  Rational Design of Nucleoside-Bile Acid Conjugates Incorporating a Triazole Moiety for Anticancer Evaluation and SAR Exploration.

Authors:  Maria Luisa Navacchia; Elena Marchesi; Lara Mari; Nicola Chinaglia; Eleonora Gallerani; Riccardo Gavioli; Massimo Luigi Capobianco; Daniela Perrone
Journal:  Molecules       Date:  2017-10-12       Impact factor: 4.411

7.  Synthesis and Biological Investigation of Bile Acid-Paclitaxel Hybrids.

Authors:  Elisabetta Melloni; Elena Marchesi; Lorenzo Preti; Fabio Casciano; Erika Rimondi; Arianna Romani; Paola Secchiero; Maria Luisa Navacchia; Daniela Perrone
Journal:  Molecules       Date:  2022-01-12       Impact factor: 4.411

  7 in total

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