1,2,4-Thiadiazolidin-3,5-diones as novel hydrogen sulfide donors

被引：40

作者：

Severino, Beatrice ^{[1
]}

Corvino, Angela ^{[1
]}

Fiorino, Ferdinando ^{[1
]}

Luciano, Paolo ^{[1
]}

Frecentese, Francesco ^{[1
]}

Magli, Elisa ^{[1
]}

Saccone, Irene ^{[1
]}

Di Vaio, Paola ^{[1
]}

Citi, Valentina ^{[2
]}

Calderone, Vincenzo ^{[2
]}

Servillo, Luigi ^{[3
]}

Casale, Rosario ^{[3
]}

Cirino, Giuseppe ^{[1
]}

Vellecco, Valentina ^{[1
]}

Bucci, Mariarosaria ^{[1
]}

Perissutti, Elisa ^{[1
]}

Santagada, Vincenzo ^{[1
]}

Caliendo, Giuseppe ^{[1
]}

机构：

[1] Univ Naples Federico II, Sch Med, Dept Pharm, Via D Montesano 49, I-80131 Naples, Italy

[2] Univ Pisa, Dept Pharm, Via Bonanno 6, I-56126 Pisa, Italy

[3] Univ Campania Luigi Vanvitelli, Dept Biochem Biophys & Gen Pathol, Via L De Crecchio 7, I-80138 Naples, Italy

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2018年 / 143卷

关键词：

Hydrogen sulfide; H2S donors; 1,2,4-Thiadiazolidine-3,5-diones; Release mechanism; H2S DONORS; 1,2,4-THIADIAZOLIDINE-3,5-DIONES; INHIBITORS; CHEMISTRY; MOLECULE; DESIGN;

D O I：

10.1016/j.ejmech.2017.10.068

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Hydrogen sulfide (H2S) is an endogenous modulator that plays significant physio-pathological roles in several biological systems. In this research field there is a large interest in developing selective CBS and CSE inhibitors and H2S releasing moieties, that could be either used as therapeutic agents or linked to known drugs. One of the major problem is the limited availability of chemicals that ensure a controlled release of H2S in vitro as well in vivo. Aiming to obtain novel H2S donors, whose release properties could be appropriately modulated, we have synthesized a series of 1,2,4-thiadiazolidine-3,5-diones (THIA 1-10) as innovative donors that could release H2S in controlled manner. All the synthesized compounds were evaluated for their H2S releasing properties by an amperometric approach and for their vasorelaxant ability on aorta rings. In order to rationalize the obtained results, a detailed study on the release mechanism has been performed using the most efficient H2S donor, THIA 3 (C-max 65.4 mu M and EC50 1.7 mu M). 2017 Elsevier Masson SAS. All rights reserved.

引用

页码：1677 / 1686

页数：10

共 26 条

[1] Selectivity of commonly used pharmacological inhibitors for cystathionine synthase (CBS) and cystathionine lyase (CSE) [J].

Asimakopoulou, Antonia ;

Panopoulos, Panagiotis ;

Chasapis, Christos T. ;

Coletta, Ciro ;

Zhou, Zongmin ;

Cirino, Giuseppe ;

Giannis, Athanassios ;

Szabo, Csaba ;

Spyroulias, Georgios A. ;

Papapetropoulos, Andreas .

BRITISH JOURNAL OF PHARMACOLOGY, 2013, 169 (04) :922-932

[2] Hydrogen sulfide mediates the vasoactivity of garlic [J].

Benavides, Gloria A. ;

Squadrito, Giuseppe L. ;

Mills, Robert W. ;

Patel, Hetal D. ;

Isbell, T. Scott ;

Patel, Rakesh P. ;

Darley-Usmar, Victor M. ;

Doeller, Jeannette E. ;

Kraus, David W. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (46) :17977-17982

[3] Hydrogen sulfide: physiological properties and therapeutic potential in ischaemia [J].

Bos, Eelke M. ;

van Goor, Harry ;

Joles, Jaap A. ;

Whiteman, Matthew ;

Leuvenink, Henri G. D. .

BRITISH JOURNAL OF PHARMACOLOGY, 2015, 172 (06) :1479-1493

[4] Synthesis and Biological Effects of Hydrogen Sulfide (H2S): Development of H2S-Releasing Drugs as Pharmaceuticals [J].

Caliendo, Giuseppe ;

Cirino, Giuseppe ;

Santagada, Vincenzo ;

Wallace, John L. .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (17) :6275-6286

[5] Hydrogen Sulfide Releasing Capacity of Natural Isothiocyanates: Is It a Reliable Explanation for the Multiple Biological Effects of Brassicaceae? [J].

Citi, Valentina ;

Martelli, Alma ;

Testai, Lara ;

Marino, Alice ;

Breschi, Maria C. ;

Calderone, Vincenzo .

PLANTA MEDICA, 2014, 80 (8-9) :610-613

[6] Fragment-based de novo design of a cystathionine γ-lyase selective inhibitor blocking hydrogen sulfide production [J].

Corvino, Angela ;

Severino, Beatrice ;

Fiorino, Ferdinando ;

Frecentese, Francesco ;

Magli, Elisa ;

Perissutti, Elisa ;

Santagada, Vincenzo ;

Bucci, Mariarosaria ;

Cirino, Giuseppe ;

Kelly, Geoff ;

Servillo, Luigi ;

Popowicz, Grzegorz ;

Pastore, Annalisa ;

Caliendo, Giuseppe .

SCIENTIFIC REPORTS, 2016, 6

[7] S-Aroylthiooximes: A Facile Route to Hydrogen Sulfide Releasing Compounds with Structure-Dependent Release Kinetics [J].

Foster, Jeffrey C. ;

Powell, Chadwick R. ;

Radzinski, Scott C. ;

Matson, John B. .

ORGANIC LETTERS, 2014, 16 (06) :1558-1561

[8] Microwave Assisted Organic Synthesis of Heterocycles in Aqueous Media: Recent Advances in Medicinal Chemistry [J].

Frecentese, Francesco ;

Saccone, Irene ;

Caliendo, Giuseppe ;

Corvino, Angela ;

Fiorino, Ferdinando ;

Magli, Elisa ;

Perissutti, Elisa ;

Severino, Beatrice ;

Santagada, Vincenzo .

MEDICINAL CHEMISTRY, 2016, 12 (08) :720-732

[9] Perspective on Recent Developments on Sulfur-Containing Agents and Hydrogen Sulfide Signaling [J].

Jacob, Claus ;

Anwar, Awais ;

Burkholz, Torsten .

PLANTA MEDICA, 2008, 74 (13) :1580-1592

[10] Endogenous production of hydrogen sulfide in mammals [J].

Kamoun, P .

AMINO ACIDS, 2004, 26 (03) :243-254

← 1 2 3 →