来自加勒比被囊动物的其他抗肿瘤海鞘素：晶体结构及体内活性
Additional antitumor ecteinascidins from a Caribbean tunicate: crystal structures and activities in vivo.
作者信息
Sakai R, Rinehart K L, Guan Y, Wang A H
机构信息
School of Chemical Sciences, University of Illinois, Urbana 61801.
出版信息
Proc Natl Acad Sci U S A. 1992 Dec 1;89(23):11456-60. doi: 10.1073/pnas.89.23.11456.
Abstract
Ecteinascidins (Ets), isolated from the Caribbean tunicate Ecteinascidia turbinata, protect mice in vivo against P388 lymphoma, B16 melanoma, M5076 ovarian sarcoma, Lewis lung carcinoma, and the LX-1 human lung and MX-1 human mammary carcinoma xenografts. Crystal structures of two tris(tetrahydroisoquinoline) Ets were investigated with single crystals of the 21-O-methyl-N12-formyl derivative of Et 729 and the natural N12-oxide of Et 743. Representatives of an additional class of Ets, Et 722 and Et 736, isolated from the same organism, were assigned tetrahydro-beta-carboline-substituted bis(tetrahydroisoquinoline) structures by NMR and fast atom bombardment MS spectra.
摘要
从加勒比被囊动物Ecteinascidia turbinata中分离出的海鞘素（Ets），可在体内保护小鼠免受P388淋巴瘤、B16黑色素瘤、M5076卵巢肉瘤、Lewis肺癌以及LX - 1人肺癌和MX - 1人乳腺癌异种移植瘤的侵害。利用Et 729的21 - O - 甲基 - N12 - 甲酰基衍生物和Et 743的天然N12 - 氧化物的单晶研究了两种三（四氢异喹啉）Ets的晶体结构。从同一生物体中分离出的另一类Ets的代表，即Et 722和Et 736，通过核磁共振（NMR）和快原子轰击质谱（MS）光谱被确定为四氢 - β - 咔啉取代的双（四氢异喹啉）结构。
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本文引用的文献
1
Molecular mechanisms of binding and single-strand scission of deoxyribonucleic acid by the antitumor antibiotics saframycins A and C.抗肿瘤抗生素沙弗霉素A和C与脱氧核糖核酸结合及单链断裂的分子机制
Biochemistry. 1982 Feb 2;21(3):419-28. doi: 10.1021/bi00532a001.
2
The in vitro interaction of naphthyridinomycin with deoxyribonucleic acids.萘啶霉素与脱氧核糖核酸的体外相互作用。
Chem Biol Interact. 1985 Jan;52(3):361-75. doi: 10.1016/0009-2797(85)90030-4.
3
[Improvement of working conditions, one of the essential tasks of the occupational physician].[改善工作条件是职业医生的基本任务之一]
Rev Med Suisse Romande. 1987 Feb;107(2):105-9.
4
Molecular structure, conformation and interactions of antitumor antibiotic cyanonaphthridinomycin, a covalent binder of DNA.
J Biomol Struct Dyn. 1988 Dec;6(3):489-502. doi: 10.1080/07391102.1988.10506502.
5
DNA sequence specificity of the pyrrolo[1,4]benzodiazepine antitumor antibiotics. Methidiumpropyl-EDTA-iron(II) footprinting analysis of DNA binding sites for anthramycin and related drugs.吡咯并[1,4]苯并二氮杂䓬类抗肿瘤抗生素的DNA序列特异性。安丝菌素及相关药物DNA结合位点的甲炔丙基-EDTA-铁（II）足迹分析。
Biochemistry. 1986 Mar 25;25(6):1249-58. doi: 10.1021/bi00354a009.
6
Mode of action of saframycin antitumor antibiotics: sequence selectivities in the covalent binding of saframycins A and S to deoxyribonucleic acid.沙夫拉霉素抗肿瘤抗生素的作用模式：沙夫拉霉素A和S与脱氧核糖核酸共价结合中的序列选择性
Chem Res Toxicol. 1990 May-Jun;3(3):262-7. doi: 10.1021/tx00015a012.
7
Bioactive compounds from aquatic and terrestrial sources.
J Nat Prod. 1990 Jul-Aug;53(4):771-92. doi: 10.1021/np50070a001.
8
Facile formation of a crosslinked adduct between DNA and the daunorubicin derivative MAR70 mediated by formaldehyde: molecular structure of the MAR70-d(CGTnACG) covalent adduct.甲醛介导下DNA与柔红霉素衍生物MAR70之间易形成交联加合物：MAR70-d(CGTnACG)共价加合物的分子结构
Proc Natl Acad Sci U S A. 1991 Jun 1;88(11):4845-9. doi: 10.1073/pnas.88.11.4845.
9
Formaldehyde cross-links daunorubicin and DNA efficiently: HPLC and X-ray diffraction studies.甲醛能有效地使柔红霉素与DNA交联：高效液相色谱法和X射线衍射研究。
Biochemistry. 1991 Apr 23;30(16):3812-5. doi: 10.1021/bi00230a002.
10
Naphthyridinomycin-DNA adducts: a molecular modeling study.萘啶霉素-DNA加合物：一项分子模拟研究。
J Antibiot (Tokyo). 1991 Aug;44(8):885-94. doi: 10.7164/antibiotics.44.885.
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