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抗肿瘤药物4'-(9-吖啶基氨基)-间甲氧基甲磺酰苯胺盐酸盐(m-AMSA)与核酸的相互作用。

Interaction of the antitumour drug 4'-(9-acridinylamino)-methanesulfon-m-anisidine.HCl (m-AMSA) with nucleic acids.

作者信息

Hudecz F, Kajtár J, Szekerke M

出版信息

Nucleic Acids Res. 1981 Dec 21;9(24):6959-73. doi: 10.1093/nar/9.24.6959.

DOI:10.1093/nar/9.24.6959
PMID:6174949
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC327654/
Abstract

The interaction of AMSA with nucleic acids was studied by several techniques. Melting temperature and CD studies equally suggest that AMSA-binding is interfering with the secondary structure of DNA. An overlap by two mechanism of binding seems to exist. Based on the CD measurements at low drug concentration intercalation is the most likely way of binding. At higher drug concentration stacking interaction predominates leading to cooperativity and formation of oriented sheets of aromatic ring-systems as reflected in the optical activity induced in the metachromatic band of the achiral drug. No base-pair specificity could be confirmed; however, a high affinity of AMSA to poly(A) chains was demonstrated. The CD measurements did not indicate any significant interaction with RNA. The selectivity of the AMSA-DNA interaction can be regarded as an important argument in favour of the role of this interaction in the anti-tumour effect of the drug.

摘要

通过多种技术研究了AMSA与核酸的相互作用。解链温度和圆二色性研究均表明,AMSA结合会干扰DNA的二级结构。似乎存在两种结合机制的重叠。根据低药物浓度下的圆二色性测量结果,插入是最可能的结合方式。在较高药物浓度下,堆积相互作用占主导,导致协同作用并形成芳香环系统的定向片层,这在手性药物的异染带中诱导的光学活性中得到体现。未证实有碱基对特异性;然而,已证明AMSA对聚(A)链具有高亲和力。圆二色性测量未表明与RNA有任何显著相互作用。AMSA与DNA相互作用的选择性可被视为支持这种相互作用在该药物抗肿瘤作用中发挥作用的重要论据。

相似文献

1
Interaction of the antitumour drug 4'-(9-acridinylamino)-methanesulfon-m-anisidine.HCl (m-AMSA) with nucleic acids.抗肿瘤药物4'-(9-吖啶基氨基)-间甲氧基甲磺酰苯胺盐酸盐(m-AMSA)与核酸的相互作用。
Nucleic Acids Res. 1981 Dec 21;9(24):6959-73. doi: 10.1093/nar/9.24.6959.
2
Protein-associated deoxyribonucleic acid strand breaks in L1210 cells treated with the deoxyribonucleic acid intercalating agents 4'-(9-acridinylamino) methanesulfon-m-anisidide and adriamycin.用脱氧核糖核酸嵌入剂4'-(9-吖啶基氨基)甲磺酰基间茴香胺和阿霉素处理的L1210细胞中与蛋白质相关的脱氧核糖核酸链断裂
Biochemistry. 1981 Nov 10;20(23):6553-63. doi: 10.1021/bi00526a006.
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Interaction of 4'-(9-acridinylamino)methanesulfon-m-anisidide with DNA and inhibition of oncornavirus reverse transcriptase and cellular nucleic acid polymerases.4'-(9-吖啶基氨基)甲磺基间茴香胺与DNA的相互作用以及对致癌RNA病毒逆转录酶和细胞核酸聚合酶的抑制作用。
Cancer Res. 1978 May;38(5):1300-6.
4
Interaction of the antitumor drug 4'-(9-acridinylamino)methanesulfon-m-anisidide and related acridines with nucleic acids.抗肿瘤药物4'-(9-吖啶基氨基)甲磺酰间茴香胺及相关吖啶与核酸的相互作用。
Mol Pharmacol. 1981 Sep;20(2):404-14.
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Cooperative sequestration of m-AMSA in L1210 cells.m-AMSA在L1210细胞中的协同隔离
Biochem Pharmacol. 1982 Oct 15;31(20):3269-77. doi: 10.1016/0006-2952(82)90561-5.
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DNA intercalating properties of tetrahydro-9-aminoacridines. Synthesis and 23Na NMR spin-lattice relaxation time measurements.四氢-9-氨基吖啶的DNA嵌入特性。合成及23Na核磁共振自旋晶格弛豫时间测量。
J Med Chem. 1990 Jan;33(1):93-7. doi: 10.1021/jm00163a015.
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Lethal activity and kinetic response of cultured human cells to 4'-(9-acridinylamino)methanesulfon-m-anisidine.培养的人类细胞对4'-(9-吖啶基氨基)甲磺酰基间茴香胺的致死活性和动力学反应。
Cancer Res. 1982 Jan;42(1):107-11.
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Molecular interaction between bleomycin and amsacrine in the presence of cupric ions.博来霉素与安吖啶在铜离子存在下的分子相互作用。
J Inorg Biochem. 1986 Aug;27(4):271-85. doi: 10.1016/0162-0134(86)80067-8.
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Enhancement of viral growth by the antitumor drug 4'-(9-acridinylamino) methanesulfon-m-anisidide (m-AMSA).抗肿瘤药物4'-(9-吖啶基氨基)甲磺基间茴香胺(m-AMSA)对病毒生长的促进作用。
Biochem Pharmacol. 1983 Sep 1;32(17):2615-8. doi: 10.1016/0006-2952(83)90032-1.

引用本文的文献

1
Design of a new DNA-polyintercalating drug, a bisacridinyl peptidic analogue of Triostin A.一种新型DNA多插入药物的设计,即曲菌素A的双吖啶基肽类似物。
Biochem J. 1985 Feb 1;225(3):829-32. doi: 10.1042/bj2250829.

本文引用的文献

1
On the complex formation of acridine dyes with DNA. VII. Dependence of the binding on the dye structure.关于吖啶染料与DNA的络合物形成。 VII. 结合对染料结构的依赖性。
Biopolymers. 1969;8(5):595-608. doi: 10.1002/bip.1969.360080504.
2
Interaction of 9-peptidylaminoacridines with proteins and nucleic acids.9-肽基氨基吖啶与蛋白质和核酸的相互作用。
J Biol Chem. 1974 Jan 25;249(2):420-7.
3
Potential antitumor agents. 14. Acridylmethanesulfonanilides.潜在的抗肿瘤药物。14. 吖啶基甲磺酰苯胺类化合物。
J Med Chem. 1974 Sep;17(9):922-30. doi: 10.1021/jm00255a003.
4
Potential antitumor agents. 16.4'-(Acridin-9-ylamino)methanesulfonanilides.潜在的抗肿瘤药物。16. 4'-(吖啶-9-基氨基)甲磺酰苯胺类
J Med Chem. 1975 Nov;18(11):1110-7. doi: 10.1021/jm00245a013.
5
DNA-binding characteristics of acridinylmethanesulphonanilide drugs: comparison with antitumour properties.吖啶基甲磺酰苯胺类药物的DNA结合特性:与抗肿瘤特性的比较。
Eur J Cancer (1965). 1976 Dec;12(12):995-1001. doi: 10.1016/0014-2964(76)90066-9.
6
Interaction of acridines and tetrahydroacridines with DNA at low DNA/dye ratios.吖啶和四氢吖啶在低DNA/染料比例下与DNA的相互作用。
Biochim Biophys Acta. 1977 May 17;476(2):122-30. doi: 10.1016/0005-2787(77)90089-2.
7
Cell-cycle-specific chromosome damage following treatment of cultured Chinese hamster cells with 4'-[(9-acridinyl)-amino]methanesulphon-m-anisidide-HCl.用4'-[(9-吖啶基)-氨基]甲磺基-间-茴香胺盐酸盐处理培养的中国仓鼠细胞后细胞周期特异性染色体损伤。
J Natl Cancer Inst. 1978 May;60(5):1155-61.
8
Kinetic response of cultured Chinese hamster cells to treatment with 4'-[(9-acridinyl)-amino]methanesulphon-m-anisidide-HCl.培养的中国仓鼠细胞对4'-[(9-吖啶基)-氨基]甲磺基间茴香胺盐酸盐处理的动力学反应。
J Natl Cancer Inst. 1978 May;60(5):1147-53. doi: 10.1093/jnci/60.5.1147.
9
Phase I clinical and pharmacological study of 4'-(9-acridinylamino)-methanesulfon-m-anisidide using an intermittent biweekly schedule.使用每两周一次的间歇给药方案对4'-(9-吖啶基氨基)-甲磺基间茴香胺进行的I期临床和药理学研究。
Cancer Res. 1979 Oct;39(10):3881-4.
10
Interaction of antitumor drugs with human erythrocyte ghost membranes and mastocytoma P815: a spin label study.抗肿瘤药物与人类红细胞血影膜及肥大细胞瘤P815的相互作用:一项自旋标记研究。
Biochem Biophys Res Commun. 1979 Feb 28;86(4):1051-7. doi: 10.1016/0006-291x(79)90223-7.