The water-soluble Roussin's red ester acting as a potential photochemical NO-delivery agent: Photolysis reactions, DNA cleavage and anticancer activity

Han Hun Chang, Hung Jen Huang, Yun Lung Ho, Yu-Der Wen, Wei Ning Huang, Show Jen Chiou

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The water-soluble Roussin's red ester [(NO)2Fe(-SCH 2CH2P(O)(CH2OH)2) 2Fe(NO)2] (1), a potential photochemical prodrug of an NO precursor, was synthesized from the reaction of HSCH2CH 2P(O)(CH2OH)2 (F) and [Fe(CO) 2(NO)2]. The IR v(NO) stretching frequencies of complex 1 appear at 1759 (s), 1784 (s) and 1816 (w) cm-1 in buffer (pH = 7.4). NO was released with a stoichiometry ratio Δ[NO]/Δ[1] = 3.6 ± 0.2 when complex 1 was exposed to UV in deaerated aqueous phosphate buffer solution. Here light acts as an On/Off switch for NO release. Incubation of pBR322 supercoiled DNA with complex 1, followed by irradiation, produced DNA strand breakage. In contrast to the addition of carboxy-PTIO (NO radical scavenger), DNA strand breakage was not inhibited when the scavengers of hydroxyl radical and singlet oxygen were added. Complex 1 irradiated under a N2 atmosphere exhibited the same cleavage efficiency as complex 1 irradiated under air. The results show that DNA strand cleavage efficiency depends on the concentration of complex 1, the pH value of the buffer, and the duration of the photolysis of complex 1. The conversion rate from supercoiled (SC form) to nicked circular (NC form) of complex 1 was 2.96 × 10 -2 s-1. The results of a T4 ligase enzymatic assay reveals the nonhydrolytic DNA breakage mechanism. The NO-release ability of complexes 1, 2, and 3 follows the order 1 > 2 > 3. Upon UV-irradiation, complex 1 exhibits cytotoxicity against B16-F10 mouse melanoma cells.

Original languageEnglish
Pages (from-to)6396-6402
Number of pages7
JournalDalton Transactions
Issue number32
DOIs
Publication statusPublished - 2009 Aug 11

Fingerprint

Photolysis
Esters
Buffers
Water
DNA
Irradiation
Superhelical DNA
Singlet Oxygen
Prodrugs
Carbon Monoxide
Cytotoxicity
Ligases
Stoichiometry
Hydroxyl Radical
Stretching
Assays
Phosphates
Switches
Air

All Science Journal Classification (ASJC) codes

  • Inorganic Chemistry

Cite this

Chang, Han Hun ; Huang, Hung Jen ; Ho, Yun Lung ; Wen, Yu-Der ; Huang, Wei Ning ; Chiou, Show Jen. / The water-soluble Roussin's red ester acting as a potential photochemical NO-delivery agent : Photolysis reactions, DNA cleavage and anticancer activity. In: Dalton Transactions. 2009 ; No. 32. pp. 6396-6402.
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abstract = "The water-soluble Roussin's red ester [(NO)2Fe(-SCH 2CH2P(O)(CH2OH)2) 2Fe(NO)2] (1), a potential photochemical prodrug of an NO precursor, was synthesized from the reaction of HSCH2CH 2P(O)(CH2OH)2 (F) and [Fe(CO) 2(NO)2]. The IR v(NO) stretching frequencies of complex 1 appear at 1759 (s), 1784 (s) and 1816 (w) cm-1 in buffer (pH = 7.4). NO was released with a stoichiometry ratio Δ[NO]/Δ[1] = 3.6 ± 0.2 when complex 1 was exposed to UV in deaerated aqueous phosphate buffer solution. Here light acts as an On/Off switch for NO release. Incubation of pBR322 supercoiled DNA with complex 1, followed by irradiation, produced DNA strand breakage. In contrast to the addition of carboxy-PTIO (NO radical scavenger), DNA strand breakage was not inhibited when the scavengers of hydroxyl radical and singlet oxygen were added. Complex 1 irradiated under a N2 atmosphere exhibited the same cleavage efficiency as complex 1 irradiated under air. The results show that DNA strand cleavage efficiency depends on the concentration of complex 1, the pH value of the buffer, and the duration of the photolysis of complex 1. The conversion rate from supercoiled (SC form) to nicked circular (NC form) of complex 1 was 2.96 × 10 -2 s-1. The results of a T4 ligase enzymatic assay reveals the nonhydrolytic DNA breakage mechanism. The NO-release ability of complexes 1, 2, and 3 follows the order 1 > 2 > 3. Upon UV-irradiation, complex 1 exhibits cytotoxicity against B16-F10 mouse melanoma cells.",
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The water-soluble Roussin's red ester acting as a potential photochemical NO-delivery agent : Photolysis reactions, DNA cleavage and anticancer activity. / Chang, Han Hun; Huang, Hung Jen; Ho, Yun Lung; Wen, Yu-Der; Huang, Wei Ning; Chiou, Show Jen.

In: Dalton Transactions, No. 32, 11.08.2009, p. 6396-6402.

Research output: Contribution to journalArticle

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