Design, synthesis, and characterization of a novel hexa-azacyclophane and interactions with d(CGCA3T3GCG)2, ctDNA and T4DNA

Thomas C. Bruice; Yu Chi Yip; Andrei Blaskó; Felice C Lightstone; Kenneth A. Browne; Mark E. Petyak; Jia Luo

doi:10.1016/S0040-4020(97)00501-2

Design, synthesis, and characterization of a novel hexa-azacyclophane and interactions with d(CGCA₃T₃GCG)₂, ctDNA and T4DNA

Thomas C. Bruice, Yu Chi Yip, Andrei Blaskó, Felice C Lightstone, Kenneth A. Browne, Mark E. Petyak, Jia Luo

Biosciences and Biotechnology

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

A novel polyazacyclophane hexa-amine (1) has been designed, synthesized and characterized by X-ray crystallography, ¹H NMR and fluorescence spectroscopy. 1 has the structural shape and disposition of charges complementary to the major groove of B-DNA. Acid dissociation constants for the protonated 1 were pK(a1)(D) = 4.8 and pK(a2)(D) = 8.5. Equilibrium constants for the binding of 1 to ctDNA and T4 DNA were 1.2 x 10⁵ and 1.8 x 10⁶, respectively.

Original language	English (US)
Pages (from-to)	8105-8120
Number of pages	16
Journal	Tetrahedron
Volume	53
Issue number	24
DOIs	https://doi.org/10.1016/S0040-4020(97)00501-2
State	Published - Jun 16 1997

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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Design, synthesis, and characterization of a novel hexa-azacyclophane and interactions with d(CGCA₃T₃GCG)₂, ctDNA and T4DNA. / Bruice, Thomas C.; Yip, Yu Chi; Blaskó, Andrei; Lightstone, Felice C; Browne, Kenneth A.; Petyak, Mark E.; Luo, Jia.

In: Tetrahedron, Vol. 53, No. 24, 16.06.1997, p. 8105-8120.

Research output: Contribution to journal › Article › peer-review

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title = "Design, synthesis, and characterization of a novel hexa-azacyclophane and interactions with d(CGCA3T3GCG)2, ctDNA and T4DNA",

abstract = "A novel polyazacyclophane hexa-amine (1) has been designed, synthesized and characterized by X-ray crystallography, 1H NMR and fluorescence spectroscopy. 1 has the structural shape and disposition of charges complementary to the major groove of B-DNA. Acid dissociation constants for the protonated 1 were pK(a1)(D) = 4.8 and pK(a2)(D) = 8.5. Equilibrium constants for the binding of 1 to ctDNA and T4 DNA were 1.2 x 105 and 1.8 x 106, respectively.",

author = "Bruice, {Thomas C.} and Yip, {Yu Chi} and Andrei Blask{\'o} and Lightstone, {Felice C} and Browne, {Kenneth A.} and Petyak, {Mark E.} and Jia Luo",

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AU - Blaskó, Andrei

AU - Lightstone, Felice C

AU - Browne, Kenneth A.

AU - Petyak, Mark E.

AU - Luo, Jia

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N2 - A novel polyazacyclophane hexa-amine (1) has been designed, synthesized and characterized by X-ray crystallography, 1H NMR and fluorescence spectroscopy. 1 has the structural shape and disposition of charges complementary to the major groove of B-DNA. Acid dissociation constants for the protonated 1 were pK(a1)(D) = 4.8 and pK(a2)(D) = 8.5. Equilibrium constants for the binding of 1 to ctDNA and T4 DNA were 1.2 x 105 and 1.8 x 106, respectively.

AB - A novel polyazacyclophane hexa-amine (1) has been designed, synthesized and characterized by X-ray crystallography, 1H NMR and fluorescence spectroscopy. 1 has the structural shape and disposition of charges complementary to the major groove of B-DNA. Acid dissociation constants for the protonated 1 were pK(a1)(D) = 4.8 and pK(a2)(D) = 8.5. Equilibrium constants for the binding of 1 to ctDNA and T4 DNA were 1.2 x 105 and 1.8 x 106, respectively.

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Design, synthesis, and characterization of a novel hexa-azacyclophane and interactions with d(CGCA₃T₃GCG)₂, ctDNA and T4DNA

Abstract

ASJC Scopus subject areas

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