Synthesis, chemical hydrolysis and biological evaluation of doxorubicin carbamate derivatives for targeting cancer cell

被引：0

作者：

Naji, Hasanain Amer ^{[1
]}

Mohammed, Mohammed H. ^{[1
]}

Jawad, Hassan Ali M. ^{[1
]}

机构：

[1] Mustansiriyah Univ, Dept Pharmaceut Chem, Coll Pharm, Baghdad, Iraq

来源：

REVISTA LATINOAMERICANA DE HIPERTENSION | 2021年 / 16卷 / 04期

关键词：

Doxorubicin; prodrugs; Carbamate; chemical hydrolysis; CARBONIC-ANHYDRASE-IX; INHIBITORS; LINKAGES; PRODRUGS; RELEASE; DESIGN;

D O I：

10.5281/zenodo.5812114

中图分类号：

R6 [外科学];

学科分类号：

1002 ; 100210 ;

摘要：

Doxorubicin structure has been attached to (urea or thiourea) of 4-amino benzene sulfonamide via carbamate bond for minimizing doxorubicin side effects and reducing tumor resistance. The structures of compounds were characterized by melting point, H-1-NMR spectra, C-13-NMR spectra and UV spectra. Chemical hydrolysis study of compound (IV) in different phosphate buffer (pH 5, 6.5 & 7.4) shows high stability at pH (7.4), and require more acidic condition to hydrolyze. In vitro cytotoxicity assay on MCF-7 has been studied, for compounds II & IV (IC50= 9.57 mu g/ml & IC50= 10.28 mu g/ml respectively) show significant cytotoxicity compared to free doxorubicin (IC50= 11.14 mu g/ml) this be attributed to the action of conjugated molecule.

引用

页码：287 / 293

页数：7

共 23 条

[1] Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX [J].

Abbate, F ;

Casini, A ;

Owa, T ;

Scozzafava, A ;

Supuran, CT .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (01) :217-223

[2] Human monoclonal antibodies targeting carbonic anhydrase IX for the molecular imaging of hypoxic regions in solid tumours [J].

Ahlskog, J. K. J. ;

Schliemann, C. ;

Marlind, J. ;

Qureshi, U. ;

Ammar, A. ;

Pedley, R. B. ;

Neri, D. .

BRITISH JOURNAL OF CANCER, 2009, 101 (04) :645-657

[3] Synthesis and in vitro anticancer screening of some novel 4-[2-amino-3-cyano-4-substituted-5,6,7,8-tetrahydroquinolin-1-(4H)-yl]benzenesulfonamides [J].

Al-Said, Mansour S. ;

Ghorab, Mostafa M. ;

Al-qasoumi, Saleh I. ;

El-Hossary, Ebaa M. ;

Noaman, Eman .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (07) :3011-3018

[4]

Al-Ziaydi A. G., 2020, VIRUS DIS, P1

[5] Carbonic anhydrase inhibitors: Synthesis and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with 4-substituted 3-pyridinesulfonamides [J].

Brzozowski, Zdzislaw ;

Slawinski, Jaroslaw ;

Saczewski, Franciszek ;

Innocenti, Alessio ;

Supuran, Claudiu T. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (06) :2396-2404

[6] Carbonic anhydrase inhibitors.: Design of fluorescent sulfonamides as probes of tumor-associated carbonic anhydrase IX that inhibit isozyme IX-mediated acidification of hypoxic tumors [J].

Cecchi, A ;

Hulikova, A ;

Pastorek, J ;

Pastoreková, S ;

Scozzafava, A ;

Winum, JY ;

Montero, JL ;

Supuran, CT .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (15) :4834-4841

[7] Release from polymeric prodrugs: Linkages and their degradation [J].

D'Souza, AJM ;

Topp, EM .

JOURNAL OF PHARMACEUTICAL SCIENCES, 2004, 93 (08) :1962-1979

[8]

Gaylord Norman G., 1960, ORG CHEM

[9] Biodegradable Block Copolymer-Doxorubicin Conjugates via Different Linkages: Preparation, Characterization, and In Vitro Evaluation [J].

Hu, Xiuli ;

Liu, Shi ;

Huang, Yubin ;

Chen, Xuesi ;

Jing, Xiabin .

BIOMACROMOLECULES, 2010, 11 (08) :2094-2102

[10] Polyvinylpyrrolidone Loaded-MnZnFe2O4Magnetic Nanocomposites Induce Apoptosis in Cancer Cells Through Mitochondrial Damage and P53Pathway [J].

Kareem, Sahira Hassan ;

Naji, Amel Muhson ;

Taqi, Zainab J. ;

Jabir, Majid S. .

JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS, 2020, 30 (12) :5009-5023

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