title: Design, synthesis and DNA interaction study of new potential DNA bis-intercalators based on glucuronic acid.
abstract: A series of novel potential DNA bis-intercalators were designed and synthesized, in which two glucuronic acids were linked by ethylenediamine, and the glucuronic acid was coupled with various chromophores, including quinoline, acridine, indole and purine, at the C-1 position. The preliminary binding properties of these compounds to calf thymus DNA (CT-DNA) have been investigated by UV-absorption and fluorescence spectroscopy. The results indicated that all the target compounds can interact with CT-DNA, and the acridine derivative, 3b, showed the highest key selection vector (KSV) value, which suggested that compound 3b binds most strongly to CT-DNA.
authors: Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Pharmacy, Ocean University of China, Qingdao 266003, China. flyawayzhao@163.com
authors: Jiuyang
authors: J
authors: Zhao
authors: Wei
authors: W
authors: Li
authors: Rui
authors: R
authors: Ma
authors: Shaopeng
authors: S
authors: Chen
authors: Sumei
authors: S
authors: Ren
authors: Tao
authors: T
authors: Jiang
mesh_terms: D000166:Acridines / Q000737:chemistry / Q000378:metabolism; D004247:DNA / Q000378:metabolism*; D004268:DNA-Binding Proteins / Q000138:chemical synthesis / Q000378:metabolism; D015195:Drug Design; D005965:Glucuronates / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D020723:Glucuronic Acid / Q000737:chemistry* / Q000378:metabolism; D007364:Intercalating Agents / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
chemical_list: D000166:Acridines; D004268:DNA-Binding Proteins; D005965:Glucuronates; D007364:Intercalating Agents; D020723:Glucuronic Acid; D004247:DNA; C427203:calf thymus DNA
references: J Am Chem Soc. 2003 Jul 9;125(27):8070-1
references: 12837054
references: Curr Pharm Des. 2001 Nov;7(17):1745-80
references: 11562309
references: Bioorg Med Chem Lett. 2009 Sep 1;19(17):4974-9
references: 19651510
references: J Inorg Biochem. 2006 Aug;100(8):1344-52
references: 16684567
references: Angew Chem Int Ed Engl. 1998 Oct 2;37(18):2503-2505
references: 29711363
references: J Am Chem Soc. 2011 May 18;133(19):7361-75
references: 21524066
references: Biochemistry. 2011 Oct 25;50(42):9088-113
references: 21863895
references: Science. 1984 Oct 26;226(4673):466-8
references: 6093249
references: Bioorg Med Chem. 2001 Sep;9(9):2215-35
references: 11553460
references: Nat Prod Rep. 2012 Feb;29(2):134-43
references: 22183179
references: J Phys Chem B. 2005 Nov 24;109(46):21997-2002
references: 16853857
references: J Nat Prod. 2000 Jan;63(1):158-68
references: 10650103
references: Bioorg Med Chem. 2004 Aug 15;12(16):4307-12
references: 15332297
references: Curr Opin Pharmacol. 2012 Aug;12(4):398-402
references: 22503290
references: Nat Prod Rep. 2001 Jun;18(3):291-309
references: 11476483
references: Biochemistry. 2010 Jan 26;49(3):452-69
references: 20000367
references: Carbohydr Res. 2000 Oct 6;328(4):445-8
references: 11093699
references: Chem Commun (Camb). 2002 Jan 7;(1):70-1
references: 12120315
references: J Org Chem. 1965 Apr;30:1099-101
references: 14288446
references: J Med Chem. 1997 Jan 31;40(3):261-6
references: 9022792
references: Bioorg Med Chem Lett. 2008 Jul 15;18(14):4142-5
references: 18573660
references: Future Med Chem. 2012 Jun;4(9):1093-111
references: 22709253
references: Carbohydr Res. 2004 Aug 2;339(11):1873-87
references: 15261580
references: Biochemistry. 2010 Jul 6;49(26):5540-52
references: 20499878
references: Biochim Biophys Acta. 1981 Jun 26;654(1):129-34
references: 7272306