Sonodynamic and sonocatalytic damage of BSA molecules by Cresol Red, Cresol Red-DA and Cresol Red-DA-Fe under ultrasonic irradiation
Highlights
► Cresol Red derivatives were used to study interaction and damage to BSA. ► Sonodynamic and sonocatalytic activities of Cresol Red derivatives were studied at first. ► Some quenchers were used to determine the kind of the generated ROS.
Introduction
For nearly 20 years, a lot of scientific researches have been made on the photodynamic diagnosis and therapy because of a great application prospect in tumor effective treatment and early diagnosis [1], [2], [3]. However, the photodynamic method also has some fatal and unconquerable defects. For instance, the tissue penetration ability of the excitation light is very poor, which limits the widely use in treating various tumors [4]. Ultrasound is a kind of mechanical vibration wave which can make energy noninvasively focusing on deep tissue and maintains the focus energy in a small volume because of its strong penetration capacity and focusing ability [5], [6], [7]. Therefore, some researchers have paid great attention to the use of ultrasonic irradiation instead of light to activate photosensitisers [8], [9]. Sonodynamic therapy (SDT) is a new modality for treating cancer and it is based on a local activation of a systematically administered sonosensitiser (that is, most of photosensitive drugs) by ultrasound [10]. This method of treating diseases induced by ultrasound has been widely applied in clinic [11].
An ideal sonosensitiser should display obvious selectivity to the target tissue, and not cause the mutagenic, carcinogenic or allergic effects, and also demonstrate safety or non-toxicity in therapy and not damage normal healthy cells. Cresol Red (o-Cresolsulfonphthalein) is a kind of common medication for renal diagnosis and an acid phenolsulfonphthaleins dyes [12]. It should reveal sonodynamic activity according to the photosensitiveness [13]. Xylenol Orange (Cresol Red-DA: 3,3′-Bis [N,N-di (carboxymethyl) aminomethyl]-o-cresolsulfonphthalein) is a hexahydroxy organic acid using as an indicator in complexometric analysis. Also, it is usually used in medicine, analytical chemistry and biochemistry fields. Because of the presence of three benzene rings and the possibility forming a big potential plane [14], Cresol Red and Xylenol Orange (Cresol Red-DA) should have special effect on various biomolecules. As sonosensitive compounds, they can enter into the intracellular part and kill the cancer cells under ultrasonic irradiation [15], [16], [17]. In addition, Xylenol Orange (Cresol Red-DA) can also form stable colored complexes with a variety of metal ions [18]. Metal ions are important on the biological membranes for maintaining normal structures and physiological functions of the lipids and membrane proteins [19], [20], [21]. Particularly, according to the high charge number, small ion radius and strong electrostatic effect, iron ion is easier to form complex with those nitrogen–oxygen mixed ligands. As a Fenton-like reagent, iron-Xylenol Orange (Cresol Red-DA) complex (Cresol Red-DA-Fe(III): 3,3′-Bis [N,N-di (carboxymethyl) aminomethyl]-o-cresolsulfonphthalein-Ferrous(III)) can generate the hydroxyl radicals () through the splitting of the coordinated water (H2O) under ultrasonic irradiation. That is, under ultrasonic irradiation the Cresol Red-DA-Fe(III) will show the sonocatalytic and sonodynamic antitumour activities at the same time. Thus, the Cresol Red-DA-Fe(III) can be thought of as a multifunctional antitumor drug.
Serum albumin can function as the storage depot for endogenous and exogenous compounds. In general, it plays an important role in transport of many small molecular compounds in blood plasma [22]. The intrinsic fluorescence of protein mainly comes from the tryptophan residue. The composition analysis shows that Human serum albumin (HSA) contains a single tryptophan residue (Trp-214) [23], while bovine serum albumin (BSA) has two tryptophan residues (Trp-212 and Trp-234). Definitely, Trp-212 is located within a hydrophobic binding pocket of the protein and Trp-134 is located on the surface of the molecule [24]. In addition, as homologous protein, BSA and HSA have the same sequence and configuration [25]. So, as a convention the BSA was selected as a model protein in this experiment.
In this paper, the interaction of the BSA with Cresol Red derivatives (Cresol Red, Cresol Red-DA, Cresol Red-DA-Fe(III)) and the damage of BSA under ultrasonic irradiation in the presence of Cresol Red derivatives were studied by means of UV–vis and fluorescence spectra. CD spectras of BSA + Cresol Red derivatives (Cresol Red, Cresol Red-DA or Cresol Red-DA-Fe(III)) solutions with or without ultrasonic irradiation were also mentioned by the circular dichroism spectrometer. Besides, the influences of ultrasonic irradiation time, Cresol Red derivatives concentration and ionic strength on the damage of BSA were reviewed. At last, the generation of ROS under ultrasonic irradiation in the presence of Cresol Red derivatives is estimated and the kind of ROS is also determined. Maybe, this report can offer some meaningful and valuable references to expand the application of sonocatalytic therapy (SDT) and sonodynamic therapy (SCT) methods in future tumor treatment.
Section snippets
Reagents and apparatus
Bovine serum albumin (BSA, biochemical reagent, Aoboxing Biotechnological Company, China) was acted as a model protein to study the interaction and sonodynamic and sonocatalytic damage. Cresol Red (o-Cresolsulfonphthalein, analytical purity, Sinopharm Chemical Reagent Co. Ltd, China) and Cresol Red-DA (Xylenol Orange) (3,3′-Bis [N,N-di (carboxymethyl) aminomethyl]-o-cresolsulfonphthalein, analytical purity, Sinopharm Chemical Reagent Co. Ltd, China) were used as the sonosensitizers. Ferric
Infrared spectra of Cresol Red, Cresol Red-DA and Cresol Red-DA-Fe(III)
From Fig. 3, it can be seen that the peaks of Cresol Red, Cresol Red-DA and Cresol Red-DA-Fe(III) at 1339, 1411 and 1384 cm−1 shows the characteristic peaks of sulphonic acid ester of Cresol Red derivatives. After the Cresol Red-DA-Fe(III) formed by mixing Fe(III) and Cresol Red-DA, the ν(C–N) of Cresol Red-DA changed from 1043 to 1047 cm−1, but the peaks of sulphonic acid ester still exist. It demonstrates that the formation of Cresol Red-DA-Fe(III) complex does not destroy the ring of sulphonic
Conclusion
In this paper, the interaction of BSA with Cresol Red derivatives (Cresol Red, Cresol Red-DA and Cresol Red-DA-Fe(III)) were studied by fluorescence spectroscopy. The fluorescence spectral monitoring results, Stern–Volmer dynamic quenching constant (Ksv), quenching rate constant of biomolecule (Kq), static fluorescence quenching association constant (KLB) and equilibrium constants (KA), indicate that these Cresol Red derivatives could bind with the BSA molecule and the fluorescence quenching
Acknowledgments
The authors greatly acknowledge the Liaoning Provincial Department of Education Innovation Team Projects (LT2012001), Shenyang Science and Technology Plan Projects (F12-277-1-15) and Liaoning University “211” Engineering Construction Project for financial support. The authors also thank our colleagues and other students for their participating in this work.
References (42)
- et al.
Med. Laser Appl.
(2009) - et al.
FEBS Lett.
(2002) - et al.
Cancer Lett.
(1993) Ultrasound Med. Biol.
(1993)Ultrasound Med. Biol.
(2000)- et al.
Bioorg. Med. Chem. Lett.
(2011) - et al.
J. Photochem. Photobiol. B
(1996) Talanta
(1990)- et al.
Biochim. Biophys. Acta
(1997) - et al.
Ultrasonics
(2011)
Ultrasonics
Ultrasonics
Biochim. Biophys. Acta
Groot
J. Hepatol.
J. Photochem. Photobiol. B
Anal. Biochem.
J. Mol. Struct.
J. Photochem. Photobiol. A
Anal. Biochem.
Ultrasonics
Spectrochim. Acta Mol. Biomol. Spectrosc.
Cited by (11)
Synthesis and Sonodynamic Antibacterial Activity Evaluation of Three Novel Fluoroquinolone Compounds
2023, Ultrasound in Medicine and BiologyDevelopment of a calcium hydroxide–dye kimchi ripening indicator and its application in kimchi packaging
2023, Food ChemistryCitation Excerpt :CR, BB, and BP are sulfonphthalein dyes that contain sulfonic acid in their molecular structures. The sulfonic acid peaks of CR, BB, and BP were observed at 1339 cm−1 (Zou et al., 2013). MR is a type of azo dye with an azo group in its molecular structure.
Basic electrolyzed water coupled with ultrasonic treatment improves the functional properties and digestibility of Antarctic krill proteins
2022, Food Research InternationalCitation Excerpt :Previous studies showed that the changes in fluorescence intensity could be used to reflect the damage of ultrasound to protein molecules (He et al., 2015b,a). In Fig. 2B, the fluorescence intensity of all AKP samples decreased with increasing ultrasonic treatment time, which was mainly due to the oxidation of Trp, Phe and Tyr residues by ultrasonic treatment (Zou et al., 2013). However, the fluorescence intensity of the USBEW-treated samples was clearly higher than that of the USDW-treated samples, indicating that the USBEW treatment caused less damage to AKPs.
Spectroscopic investigation on the sonodynamic damage to protein in the presence of eosine B
2015, Ultrasonics SonochemistryCitation Excerpt :Therefore, continued research to find better, smarter, more effective treatments is urgently needed. In recent years, the photodynamic therapy has attracted much attention of scholars because of a great application prospect in cancer treatments [1,2]. But this method has a prominent shortcoming, the poor tissue penetration ability of the excitation light [3], which limits its use in treating tumors.
Spectroscopic investigation of the interaction of water-soluble azocalix[4]arenes with bovine serum albumin
2015, Bioorganic ChemistryCitation Excerpt :However, the negative peaks of BSA (curves b, c and d) slightly increase when m-MAC-Calix and p-MAC-Calix added to BSA at 222 nm. It may be due to the presence of potential chirality of m-MAC-Calix and p-MAC-Calix, which maintains or increases α-helix content of BSA molecules [48]. In this paper, three water-soluble azocalix[4]arene derivatives (o-MAC-Calix, m-MAC-Calix and p-MAC-Calix) were synthesized.
Spectroscopic investigation on sonodynamic and sonocatalytic damage of BSA molecules by Thymol Blue (TB) derivants under ultrasonic irradiation
2014, Spectrochimica Acta - Part A: Molecular and Biomolecular SpectroscopyCitation Excerpt :Also, the amino acid groups can form stable complexes with many metal ions [10–14]. According to the high charge number, small ion radius and strong electrostatic effect, iron ion is easier to form complex with some sonosensitizers with amino acid groups (for example: Thymol Blue-DA) [15]. As a Fenton-like reagent, the iron ion complex part can generate hydroxyl radicals (OH) and superoxide anion (O2−) under ultrasonic irradiation.