9,10-Anthracenediyl-bis(methylene)dimalonic Acid
(Synonyms: 9,10-蒽基-双(亚甲基)二丙二酸,ABMDMA) 目录号 : GC42642
A singlet oxygen acceptor
Cas No.:307554-62-7
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
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- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
9,10-Anthracenediyl-bis(methylene)dimalonic acid (ABMDMA) is a reagent used to detect singlet oxygen generation. This water-soluble derivative of anthracene can be photobleached by singlet oxygen to its corresponding endoperoxide. This reaction can be monitored spectrophotometrically by recording the decrease in optical density at 400 nm (ABMDMA ex/em max. = 380/407 nm in 0.1 M phosphate pH 7.0).[1]
Reference:
[1]. Katayama, Y., and Mori, A. Inhibitory action of (3R)-(−)-4-amino-3-hydroxybutanoic acid on N-amidinobenzamide induced seizure activity in cat brain. IRCS Med. Sci. 5, 437 (1977).
| Cas No. | 307554-62-7 | SDF | |
| 别名 | 9,10-蒽基-双(亚甲基)二丙二酸,ABMDMA | ||
| 化学名 | α9,α10-dicarboxy-9,10-anthracenedipropanoic acid | ||
| Canonical SMILES | OC(C(C(O)=O)CC1=C2C(C=CC=C2)=C(CC(C(O)=O)C(O)=O)C3=C1C=CC=C3)=O | ||
| 分子式 | C22H18O8 | 分子量 | 410.4 |
| 溶解度 | 20mg/mL in DMSO, 30mg/mL in DMF, 0.5 mg/ml in Water | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.4366 mL | 12.1832 mL | 24.3665 mL |
| 5 mM | 0.4873 mL | 2.4366 mL | 4.8733 mL |
| 10 mM | 0.2437 mL | 1.2183 mL | 2.4366 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
ICG-loaded gold nano-bipyramids with NIR activatable dual PTT-PDT therapeutic potential in melanoma cells
Colloids Surf B Biointerfaces 2020 Oct;194:111213.PMID:32622254DOI:10.1016/j.colsurfb.2020.111213.
A great amount of effort is directed towards the progress of cancer treatment approaches aspiring to develop non-invasive, targeted and highly efficient therapies. In this context, Photothermal (PTT) and Photodynamic (PDT) Therapies were proven as promising. This work aims to integrate the therapeutic activities of two near-infrared (NIR) photoactive biomaterials - gold nano-bipyramids (AuBPs) and Indocyanine Green (ICG) - into one single targeted hybrid nanosystem able to operate as dual PTT-PDT agent with higher efficiency compared with each one alone. Firstly, different aspect ratio' AuBPs were systematically investigated in water solution for their intrinsic ability to efficiently generate toxic reactive oxygen species, namely oxygen singlet (1O2), under NIR laser irradiation, as this effect is less investigated in literature. Interestingly, the photodynamic activity of AuBPs measured by monitoring the photooxidation of 9,10-Anthracenediyl-bis(methylene)dimalonic Acid (ABDA) - a well-known 1O2 sensor, is important, counting for 30 % decrease in ABDA optical absorbance for the most active AuBPs, well-correlating with the previously determined photothermal conversion efficiency. Furthermore, ICG was successfully grafted onto the Poly-lactic acid (PLA) coating of plasmonic nanoparticles and, consequently, the as-designed fully integrated hybrid nanosystem shows improved PTT-PDT performance in solution. Specifically, by triggering simultaneous PTT-PDT activities, the 1O2 amount is doubled, while the heating monitoring shows higher and faster increase in temperature compared to AuBPs alone. Finally, the efficiency of the combined PTT-PDT therapeutic activity was validated in vitro against B16-F10 cell line by covalent conjugation of the nanosystem with Folic Acid, which ensures the cellular recognition by overexpression of folate receptor.
Taurine Chloramine and Hydrogen Peroxide as a Potential Source of Singlet Oxygen for Topical Application
Photochem Photobiol 2021 Sep;97(5):963-970.PMID:33657673DOI:10.1111/php.13410.
Singlet oxygen (1 O2 ) is the "active principle" in photodynamic therapy. Taurine chloramine (Tau-NHCl) and hydrogen peroxide (H2 O2 ) are well-tolerated and widely used antiseptics. Due to its mild oxidizing features and stability, Tau-NHCl can be directly used to treat skin diseases. We found that a diluted aqueous mixture of Tau-NHCl and H2 O2 acts as a slow and long-lasting potential source of 1 O2 . The reactions were studied by luminol-enhanced chemiluminescence. Evidence of the formation of 1 O2 was obtained using deuterium oxide, sodium azide and 9,10-Anthracenediyl-bis(methylene)dimalonic Acid, a chemical trap of 1 O2 . The reaction was optimized, and a mechanism was proposed, including theoretical calculations at B3LYP/6-311++G(3df,2p) level of theory, adding D3Bj empirical dispersion and SMD (Water) solvent effects. Chloramines produced by the reactions between HOCl and L-alanine, 3-amino-1-propanesulfonic acid and gamma-aminobutyric acid were also prepared, and their reactivity and stability were compared with Tau-NHCl. We found that Tau-NHCl is more stable and adequate for the production of 1 O2 . In conclusion, we propose applying these drugs combination as a potential source of 1 O2 with applications for skin diseases treatment.
Photodynamic inactivation of Candida albicans using bridged polysilsesquioxane films doped with porphyrin
Bioorg Med Chem 2012 Jul 1;20(13):4032-9.PMID:22672980DOI:10.1016/j.bmc.2012.05.012.
Novel photoactive bridged polysilsesquioxane films were prepared by doped with a porphyrin derivative. The films were formed by acid-catalyzed polycondensation reaction of a precursor of a bridged silsesquioxane, based on the reaction product of (glycidoxypropyl)trimethoxysilane with n-dodecylamine in the presence of 5-(4-carboxyphenyl)-10,15,20-tris(4-methylphenyl)porphyrin, followed by solvent evaporation. This procedure allowed obtaining flexible thin films. Absorption and fluorescence spectroscopic analysis showed the characteristic bands of the porphyrin in the visible region indicating that the photosensitizer is mainly embedded as monomer in the films. Photodynamic properties of the polymeric films were studied in solution containing photooxidizable substrates. Singlet molecular oxygen, O(2)((1)Δ(g)), production was observed by the reaction with 9,10-dimethylanthracene and 9,10-Anthracenediyl-bis(methylene)dimalonic Acid in different media. Also, these films photosensitized the decomposition of l-tryptophan. In vitro investigations showed that these films produce photodynamic inactivation of Candida albicans cells in aqueous suspensions and on their surfaces. These films exhibit a photosensitizing activity causing a ∼2.5 log (99.7%) decrease of cellular survival after 60 min of irradiation with visible light. Also, the photocytotoxicity of the surfaces was tested under condition of microbial growth. Yeast cells exposed to the film and illuminated showed growth delay compared with controls. Studies of photodynamic action mechanism showed that the photoinactivation increased in D(2)O, while cells were protected in the presence of azide ion. In contrast, the addition of mannitol produced a negligible effect on the cellular phototoxicity. These results provide evidence that O(2)((1)Δ(g)) produced by the polymeric film doped with porphyrin can successfully inactivate C. albicans in cell suspensions and deposited on the film surface.
The effect of anionic dicephalic surfactants on fabrication of varied-core nanocarriers for sustained release of porphyrin photosensitizers
J Photochem Photobiol B 2017 Jan;166:169-179.PMID:27915030DOI:10.1016/j.jphotobiol.2016.11.012.
Double-headed anionic surfactants could provide a profound group of efficient stabilizers of new template-mediated nanocarriers for effective encapsulation and sustained release of highly hydrophobic photosensitizers, and therefore their improved therapeutic activity in photodynamic therapy (PDT) protocols. We have thus encapsulated porphyrin-origin dyes, i.e., verteporfin (VP) and meso-tetraphenylporphyrin (TPP) in different types of sodium alkyliminobisacetates, Cn(COONa)2-stabilized nanosystems including biocompatible poly(l-glutamic acid)/poly(l-lysine) - PGA/PLL, multilayer nanocapsules (NCs). The latter were prepared via a layer-by-layer (LbL) approach with either solid (nanoprecipitated), or liquid (nanoemulsion-templated) oil core while zeta potential measurements enabled to evaluate progress of the polyelectrolytes LbL deposition on both cores and the NCs' stability. Backscattering profiles (BS) confirmed the long-lasting stability of the optimized nanosystems, which size (<200nm), polidyspersity and morphology were examined by dynamic light scattering (DLS) and atomic force microscopy (AFM) techniques. Our studies indicated that the encapsulation of VP and TPP in the both type of multilayer NCs increases their solubility in aqueous solution and protects them from the surrounding medium. Mainly, it reduces the photobleaching rate of these porphyrin-type photosensitizers and improves their photochemical properties during irradiation in regards to the free (non-encapsulated) molecules. As far as the core-type is considered, both nanoemulsion-loaded porphyrins, photobleached ca. 15-20% faster than the solid nanoparticle analogs. By using 9,10-Anthracenediyl-bis(methylene)dimalonic Acid (ABMDMA) as a singlet oxygen (1O2) scavenger molecule, the enhanced generation of reactive species was evaluated for the both encapsulated photosensitizers in comparison to their native form. In vitro sustained release under physiological conditions or in the presence of human serum albumin (HSA) was achieved in favor of the solid core NCs for VP and TPP. The designed NCs - offering better chemical and physical stability, high loading capacity for the cargo and ability to release it in a controlled and continuous manner - can be considered as efficacious nanocarriers for PDT.
The detection sensitivity of commonly used singlet oxygen probes in aqueous environments
J Photochem Photobiol B 2020 Mar;204:111787.PMID:31958676DOI:10.1016/j.jphotobiol.2020.111787.
The sensitivity for singlet oxygen (1O2) of two convenient 1O2 probes, 1,3-diphenylisobenzofuran (DPBF) and 9,10-Anthracenediyl-bis(methylene)dimalonic Acid (ABDA), has been investigated in different aqueous environments. Both probes are commercially available at reasonable cost and can be used with standard UV-vis spectrometers. Although DPBF is not soluble in neat water and is not specific to the detection of 1O2, it has very high, essentially diffusion-limited, reactivity towards 1O2; it can trap up to 50% of all 1O2 created in alcohol/water or micellar solution, and even more when replacing H2O by D2O, which makes it highly useful when the process under investigation does not yield much 1O2. On the other hand, ABDA has a much lower reactivity, reacting with only 2% of the singlet oxygen generated in H2O, as well as a smaller extinction coefficient, resulting in a much smaller spectroscopic response, but is soluble in neat water and is specific for 1O2, allowing for discrimination from other reactive oxygen species. The results presented here not only allow a comparative assessment of the usefulness of the two 1O2 probes, but also provide a reference for an accurate absolute quantification of the amount of 1O2 generated in an experiment from the observed absorbance bleach.