Magnetoliposomes as carriers for promising antitumor thieno[3,2-<em>b</em>]pyridin-7-arylamines: photophysical and biological studies

Ana Rita O. Rodrigues; B. G. Almeida; Juliana M. Rodrigues; Maria Jo?o R. P. Queiroz; R. C. Calhelha; Isabel C. F. R. Ferreira; A. Pires; A. M. Pereira; J. P. Araújo; Paulo J. G. Coutinho; Elisabete M. S. Castanheira

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Magnetoliposomes as carriers for promising antitumor thieno[3,2-b]pyridin-7-arylamines: photophysical and biological studies

机译：磁脂质体作为有前途的抗肿瘤噻吩并[3,2- b ]吡啶-7-芳基胺的载体：光物理和生物学研究

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Magnetoliposomes containing superparamagnetic manganese ferrite nanoparticles were tested as nanocarriers for two new promising antitumor drugs, a N-(3-methoxyphenyl)thieno[3,2-b]pyridin-7-amine (1) and a N-(2-methoxy-phenyl)thieno[3,2-b]pyridin-7-amine (2). The fluorescence emission of both compounds was studied in different polar and non-polar media, evidencing a strong intramolecular charge transfer character of the excited state of both compounds. These in vitro potent antitumor thienopyridine derivatives were successfully incorporated in both aqueous and solid magnetoliposomes, with encapsulation efficiencies higher than 75%. The magnetic properties of magnetoliposomes containing manganese ferrite nanoparticles were measured for the first time, proving a superparamagnetic behaviour. Growth inhibition assays on several human tumor cell lines showed very low GI₅₀ values for drug-loaded aqueous magnetoliposomes, comparing in most cell lines with the ones previously obtained using the neat compounds. These results are important for future drug delivery applications using magnetoliposomes in oncology, through a dual therapeutic approach (simultaneous chemotherapy and magnetic hyperthermia). 展开▼

机译：测试了含有超顺磁性锰铁氧体纳米颗粒的磁脂质体作为纳米载体的两种新的有前景的抗肿瘤药物，即 N -（3-甲氧基苯基）噻吩并[3,2- b ] pyridin-7 -胺（1）和 N -（2-甲氧基-苯基）噻吩并[3,2- b ]吡啶7-胺（2）。在不同的极性和非极性介质中研究了这两种化合物的荧光发射，证明了这两种化合物的激发态都具有很强的分子内电荷转移特性。这些体外有效的抗肿瘤噻吩并吡啶衍生物已成功地掺入含水和固体磁脂质体中，包封率均高于75％。首次测量了含锰铁氧体纳米颗粒的磁脂质体的磁性能，证明了其超顺磁性行为。在几种人类肿瘤细胞系上的生长抑制试验表明，载药的水性脂质体的GI _{50 值非常低，与大多数使用纯化合物获得的细胞系相比。这些结果对于通过磁脂质体在肿瘤学中通过双重治疗方法（同时化疗和磁热疗）的未来药物递送应用而言非常重要。} 展开▼

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《RSC Advances》 |2017年第25期|共10页

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Ana Rita O. Rodrigues; B. G. Almeida; Juliana M. Rodrigues; Maria Jo?o R. P. Queiroz; R. C. Calhelha; Isabel C. F. R. Ferreira; A. Pires; A. M. Pereira; J. P. Araújo; Paulo J. G. Coutinho; Elisabete M. S. Castanheira;
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1. Magnetoliposomes as carriers for promising antitumor thieno[3,2-b] pyridin-7-arylamines: photophysical and biological studies [J] . Rodrigues Ana Rita O., Almeida B. G., Rodrigues Juliana M., RSC Advances . 2017,第25期

机译：磁罗脂作为承诺抗肿瘤Thieno的载体[3,2-B]吡啶-7-芳基胺：光药和生物学研究

2. Novel cyano- and amidino-substituted derivatives of thieno[2,3-b]- and thieno[3,2-b]thiophene-2-carboxanilides and thieno]3',2':4,5]thieno- and thieno[2',3':4,5]thieno [2,3-c]quinolones: Synthesis, photochemical synthesis, DNA binding, and antitumor [J] . Ivana Jarak, Marijeta Kralj, Ivo Piantanida, Bioorganic and medicinal chemistry . 2006,第8期

机译：硫代[2,3-b]-和硫代[3,2-b]噻吩-2-甲酰苯胺和硫代] 3'，2'：4,5]硫代-和硫代[[]的氰基和a基取代的衍生物2'，3'：4,5] thieno [2,3-c]喹诺酮类化合物：合成，光化学合成，DNA结合和抗肿瘤

3. Novel cyano- and amidino-substituted derivatives of thieno[2,3-b]- and thieno[3,2-b]thiophene-2-carboxanilides and thieno]3',2':4,5]thieno- and thieno[2',3':4,5]thieno [2,3-c]quinolones: Synthesis, photochemical synthesis, DNA binding, and antitumor [J] . Ivana Jarak, Marijeta Kralj, Ivo Piantanida, Bioorganic and Medicinal Chemistry . 2006,第8期

机译：硫代[2,3-b]-和硫代[3,2-b]噻吩-2-甲酰苯胺和硫代] 3'，2'：4,5]硫代-和硫代[[]的氰基和a基取代的衍生物2'，3'：4,5]噻吩并[2,3-c]喹诺酮类化合物：合成，光化学合成，DNA结合和抗肿瘤

4. Synthesis of 3,7-Dialkylthieno2',3':4,5thieno3,2-bthieno2,3-dthiophenes (DCnFT4) and their Application in Semi-conducting Polymers [C] . Jieyu Hu, James R. Matthews, Mingqian He Materials Research Society Meeting . 2011

机译：合成3,7-二烷基噻吩2'，3'：4,5噻吩3,2-b噻吩（DCNFT4）及其在半导体聚合物中的应用

5. Thieno[3,2-d]- and pyrrolo[3,2-d]pyrimidines and their C-nucleosides: Synthesis and biological evaluation [D] . Temburnikar, Kartik Waman 2012

机译：噻吩并[3,2-d]-和吡咯并[3,2-d]嘧啶及其C-核苷的合成及生物学评价

6. 1-Aryl-3-[4-(thieno[3,2-d]pyrimidin-4-yloxy)phenyl]ureas as VEGFR-2 Tyrosine Kinase Inhibitors: Synthesis, Biological Evaluation, and Molecular Modelling Studies [O] . Pedro Soares, Raquel Costa, Hugo J. C. Froufe, 2006

机译：1-芳基-3- [4-（硫代[3,2-d]嘧啶-4-基氧基）苯基]脲作为VEGFR-2酪氨酸激酶抑制剂：合成，生物学评估和分子模型研究

7. Magnetoliposomes as carriers for promising antitumor thieno3,2-bpyridin-7-arylamines: photophysical and biological studies [O] . Rodrigues Ana Rita O., Almeida B. G., Rodrigues Juliana M., 2017

机译：磁脂质体作为有前途的抗肿瘤噻吩并3,2-b吡啶-7-芳基胺的载体：光物理和生物学研究

8. Promising Research Areas-I. A Study of the Biological Effects of Chemical Substances Employing the Concepts and Techniques of Physical Chemistry [R] . McManus, J. F. A. 1968

机译：有希望的研究领域 - 我。用物理化学概念和技术研究化学物质的生物学效应

1. Aminoacyl derivatives of 4,9-dihydro-10H-pyrido3,2-b-thieno-3,2-e1,4diazepinone and of 4,9-dihydro-10H-pyrido3,2-b-thieno3,4-e1,4diazepinone, their preparation and pharmaceutical compositions containing them [P] . 外国专利： EP0213450B1 . 1992-01-08

机译：4,9-二氢-10H-吡啶并[3,2-b]-噻吩并-[3,2-e] [1,4]二氮杂酮和4,9-二氢-10H-吡啶并[3,2]的氨酰基衍生物-b]-噻吩并[3,4-e] [1,4]二氮杂pin酮，其制剂和含有它们的药物组合物

2. Aminoacyl derivatives of 4,9-dihydro-10H-pyrido3,2-b-thieno-3,2-e1,4diazepinone and of 4,9-dihydro-10H-pyrido3,2-b-thieno3,4-e1,4diazepinone, their preparation and pharmaceutical compositions containing them [P] . 外国专利： EP0213450A3 . 1988-03-30

机译：4,9-二氢-10H-吡啶并[3,2-b]-噻吩并-[3,2-e] [1,4]二氮杂酮和4,9-二氢-10H-吡啶并[3,2]的氨酰基衍生物-b]-噻吩并[3,4-e] [1,4]二氮杂pin酮，其制剂和含有它们的药物组合物

3. Aminoacyl derivatives of 4,9-dihydro-10H-pyrido3,2-b-thieno-3,2-e1,4diazepinone and of 4,9-dihydro-10H-pyrido3,2-b-thieno3,4-e1,4diazepinone, their preparation and pharmaceutical compositions containing them [P] . 外国专利： EP0213450A2 . 1987-03-11

机译：4,9-二氢-10H-吡啶并[3,2-b]-噻吩并-[3,2-e] [1,4]二氮杂酮和4,9-二氢-10H-吡啶并[3,2]的氨酰基衍生物-b]-噻吩并[3,4-e] [1,4]二氮杂pin酮，其制剂和含有它们的药物组合物

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Magnetoliposomes as carriers for promising antitumor thieno[3,2-b]pyridin-7-arylamines: photophysical and biological studies

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