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Cy5.5 NHS ester (non-sulfonated) Sale

(Synonyms: CY5.5N-羟基琥珀酰亚胺酯) 目录号 : GC11653

Cy5.5-NHS酯是一种近红外胺活性染料,用于标记肽、蛋白质和寡核苷酸的氨基。

Cy5.5 NHS ester (non-sulfonated) Chemical Structure

Cas No.:1469277-96-0

规格 价格 库存 购买数量
10mM (in 1mL DMSO)
¥3,801.00
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5mg
¥1,491.00
现货
25mg
¥2,825.00
现货

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Sample solution is provided at 25 µL, 10mM.

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实验参考方法

Cell experiment [1]:

Cell lines

U87MG

Preparation Method

U87MG cells (1 × 105) were cultured for 24 hours, then the cells were washed with PBS and then incubated at 37 °C in the presence of 100 nM Cy5.5-NHS ester for 10 minutes. After the incubation period, cells were washed three times with ice- cold PBS.

Reaction Conditions

The fluorescence signal of the cells was recorded using an Axiovert 200M fluorescence microscope equipped with a Cy5.5 filter set.

Applications

Cy5.5-NHS ester could be used for fluorescence microscopy imaging study with tumor cell lines such as U87MG, C6, A375M, B16F10 and MDAMB-435, as well as for examining the effect of D-glucose or L-glucose on 2-NBDG accumulation.

Animal experiment [1]:

Animal models

Female athymic nude mice (nu/nu), 4–6 weeks

Preparation Method

Mice were subcutaneously injected with 5 × 106 U87MG glioblastoma cells suspended in 100 μL of PBS. When the tumors reached 0.4–0.6 cm in diameter, the tumor bearing mice were then injected via tail vein with Cy5.5-NHS ester and subjected to optical imaging at various time points postinjection (pi).

Dosage form

0.5 nmol

Applications

Cy5.5-NHS ester could be took advantage of tumor targeting, and the tumor/muscle contrast was clearly visible as early as 30 min postinjection. The highest U87MG tumor/muscle ratio of 3.34 ± 0.23 were achieved 24 hours post-injection for Cy5.5-NHS.

References:

[1]. Zhen C. et al. Near-Infrared Fluorescent Deoxyglucose Analog for Tumor Optical Imaging in Cell Culture and in Living Mice. Bioconjug Chem. 2006 ; 17(3): 662–669.

产品描述

Cy5.5-NHS ester is a near-infrared amine reactive dye for labeling amino groups of peptides, proteins and oligonucleotides. Cy5.5-NHS ester is suitable for fluorescence analysis when the background fluorescence interferes. It can also be used for in vivo imaging experiments. Cy5.5-NHS ester can be dissolved in DMF and DMSO, the maximum excitation light and maximum emission light are around 675 nm and 693 nm, respectively.[1]

In vitro and in vivo experiment indicated that Cy5.5-NHS ester is a nice near-infrared fluorescent dye, which could be used for tumor targeting as well as examining the effect of D-glucose or L-glucose on 2-NBDG accumulation. Moreover, Cy5.5-NHS ester reacts swiftly that the tumor/muscle contrast could be clearly visualized from 30 min up to 24 h pi of 0.5 nmol Cy5.5-NHS. The tumor uptake of Cy5.5-NHS reached a maximum 30 minutes pi. [2]

References:
[1].Ju HR, et al. Non-invasive optical imaging of cathepsin B with activatable fluorogenic nanoprobes in various metastatic models. Biomaterials. 2014. 35: 2302-2311.
[2].Zhen C. et al. Near-Infrared Fluorescent Deoxyglucose Analog for Tumor Optical Imaging in Cell Culture and in Living Mice. Bioconjug Chem. 2006 ; 17(3): 662–669.

Cy5.5-NHS 酯是一种近红外胺活性染料,用于标记肽、蛋白质和寡核苷酸的氨基。 Cy5.5-NHS ester 适用于背景荧光干扰时的荧光分析。它还可用于体内成像实验。 Cy5.5-NHS酯可溶于DMF和DMSO,最大激发光和最大发射光分别在675 nm和693 nm左右。[1]

体外和体内实验表明,Cy5.5-NHS酯是一种很好的近红外荧光染料,可用于肿瘤靶向以及检测D-葡萄糖或L-葡萄糖对2- NBDG积累。此外,Cy5.5-NHS 酯反应迅速,在 0.5 nmol Cy5.5-NHS 的感染后 30 分钟至 24 小时内,肿瘤/肌肉对比清晰可见。 Cy5.5-NHS 的肿瘤摄取在感染后 30 分钟达到最大值。 [2]

Chemical Properties

Cas No. 1469277-96-0 SDF
别名 CY5.5N-羟基琥珀酰亚胺酯
化学名 3-(6-((2,5-dioxopyrrolidin-1-yl)oxy)-6-oxohexyl)-1,1-dimethyl-2-((1E,3E,5E)-5-(1,1,3-trimethyl-1H-benzo[e]indol-2(3H)-ylidene)penta-1,3-dien-1-yl)-1H-benzo[e]indol-3-ium
Canonical SMILES CC1(C)C2=C3C(C=CC=C3)=CC=C2[N+](CCCCCC(ON4C(CCC4=O)=O)=O)=C1/C=C/C=C/C=C5C(C)(C)C6=C(C=CC=C7)C7=CC=C6N\5C
分子式 C44H46ClN3O4 分子量 716.31
溶解度 ≥ 35.8mg/mL in DMSO 储存条件 Store at -20℃, protect from light
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 1.396 mL 6.9802 mL 13.9604 mL
5 mM 0.2792 mL 1.396 mL 2.7921 mL
10 mM 0.1396 mL 0.698 mL 1.396 mL
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Research Update

Optical imaging to trace near infrared fluorescent zinc oxide nanoparticles following oral exposure

Int J Nanomedicine.2012;7:3203-9PMID: 22811605DOI: 10.2147/IJN.S32828

Background: Understanding how nanomaterials are distributed in the body after exposure is important for assessing whether they are safe. In this study, we investigated the behavior and accumulation of nanoscaled and submicron-scaled zinc oxide (ZnO) particles in the body using optical imaging following oral exposure. Methods: To trace these nanoparticles in the body, ZnO nanoparticles were conjugated with a monoreactive hydroxysuccinimide ester of Cy5.5 (Cy5.5-NHS), and the conjugation-stabilizing effect of Cy5.5 on the nanoparticles was evaluated in simulated gastric fluid (pH 1.2) for 7 hours. To compare the distribution of Cy5.5-NHS and Cy5.5-conjugated ZnO nanoparticles, Cy5.5-NHS 0.5 mg/kg and Cy5.5-conjugated ZnO nanoparticles 250 mg/kg were administered orally to healthy rats. We collected blood from the rats at predesignated time points for 7 hours after administration, and optical imaging studies were performed at 1, 2, 3, 5, and 7 hours after dosing. To investigate the extent of nanoparticle accumulation in the organs and tissues, the mice were sacrificed at 23 hours after administration, and the organs were removed and imaged. Results: Cy5.5-conjugated ZnO nanoparticles were stable in simulated gastric fluid for 7 hours. The signal intensity of Cy5.5-NHS in blood was highest 3 hours after oral administration, and Cy5.5-conjugated ZnO nanoparticles showed the highest signal intensity in blood 5-7 hours after administration. In vivo optical images indicated that Cy5.5-NHS showed optical signals in the lung, liver, and gastrointestinal tract after oral administration, whereas Cy5.5-conjugated ZnO nanoparticles were seen only in the gastrointestinal tract. Seven hours following administration, biodistribution studies demonstrated that Cy5.5-NHS accumulated in the lung and liver, and Cy5.5-conjugated ZnO nanoparticles resulted in a strong signal in the kidney and liver. Different-sized ZnO nanoparticles showed dissimilar patterns of biodistribution in ex vivo optical images. Conclusion: ZnO nanoparticles are absorbed into the tissues following oral exposure and their behavior can be monitored and evaluated using optical imaging. Keywords: biodistribution; optical imaging; oral administration; zinc oxide nanoparticles.

Exploring the match between the degradation of the ECM-based composites and tissue remodeling in a full-thickness abdominal wall defect model

Biomater Sci.2021 Nov 23;9(23):7895-7910PMID: 34693955DOI:10.1039/d1bm01096d

The repair of abdominal wall defects is currently a clinical challenge. A naturally derived extracellular matrix (ECM) such as small intestine submucosa (SIS) has received great attention in abdominal wall defect repair because of its remarkable bioactivity, biodegradability and tissue regeneration. The match between material degradation and tissue remodeling is very important for the realization of ideal repair effectiveness. In this study, a near-infrared (NIR) fluorescent dye Cy5.5 NHS ester was used to label ECM-based (ECMB) composites consisting of SIS and chitosan/elastin electrospun nanofibers for monitoring material degradation. The tissue remodeling in the ECMB composites for a full-thickness abdominal wall defect repair was systematically investigated by a series of tests including wall thickness measurement, muscle regeneration analysis and angiogenesis assessment. The main findings were: (1) real-time and noninvasive degradation monitoring of the ECMB composites until complete degradation could be realized by chemical conjugation with a Cy5.5 NHS ester. (2) In a full-thickness abdominal wall defect model, the explant thickness could be used as an intuitional indicator for evaluating the tissue remodeling efficiency in the ECMB composites, and the accuracy of this indicator was verified by various examinations including collagen deposition, angiogenesis, and muscle regeneration. The present study could provide new insight into evaluating tissue repair effectiveness of the ECMB composites.

The internalization mechanisms and trafficking of the pea albumin in Caco-2 cells

Int J Biol Macromol.2022 Jun 25;217:111-119.PMID: 35764167DOI: 10.1016/j.ijbiomac.2022.06.149

Pea albumin (PA) can reach the intestine in the active form because it is highly resistant to gastric acid and proteolytic enzymes after their oral intake, which can supply various bioactivities. However, there is no detailed knowledge of the intestinal cell uptake about PA. The aim of this work was to study the internalization mechanism and intracellular trafficking route of PA. The uptake of PA-cyanine 5.5 NHS ester (Cy5.5) was a time-dependent and concentration-dependent process in Caco-2 cells. Endocytosis inhibitors or small interfering RNA (siRNA) techniques revealed that the internalization of PA-Cy5.5 was energy-dependent and mediated by caveolin-mediated endocytosis. Furthermore, we observed colocalization of PA-Cy5.5 and its subcellular localization in Caco-2 cells by using confocal laser scanning microscopy, which revealed that the intracellular trafficking process of PA-Cy5.5 was related to endoplasmic reticulum, Golgi, and lysosome. Interestingly, PA can alleviate lipopolysaccharide -induced ER stress, which may be the main reason why pea albumin is anti-inflammatory. Overall, our findings suggest caveolin may be critical for PA uptake in enterocytes and could contribute to explore the bioactivities mechanism of pea albumin in body.

Near-infrared fluorescent deoxyglucose analogue for tumor optical imaging in cell culture and living mice

Bioconjug Chem. 2006 May-Jun;17(3):662-9.PMID: 16704203DOI: 10.1021/bc050345c

2-deoxy-2-[18F]fluoro-D-glucose ([18F]FDG) has extensively been used for clinical diagnosis, staging, and therapy monitoring of cancer and other diseases. Nonradioactive glucose analogues enabling the screening of the glucose metabolic rate of tumors are of particular interest for anticancer drug development. A nonradioactive fluorescent deoxyglucose analogue may have many applications for both imaging of tumors and monitoring therapeutic efficacy of drugs in living animals and may eventually translate to clinical applications. We found that a fluorescent 2-deoxyglucose analogue, 2-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-D-glucose (2-NBDG), can be delivered in several tumor cells via the glucose transporters (GLUTs). We therefore conjugated D-glucosamine with a near-infrared (NIR) fluorphor Cy5.5 and tested the feasibility of the Cy5.5-D-glucosamine (Cy5.5-2DG) conjugate for NIR fluorescence imaging of tumors in a preclinical xenograft animal model. Cy5.5-2DG was prepared by conjugating Cy5.5 monofunctional N-hydroxysuccinimide ester (Cy5.5-NHS) and D-glucosamine followed by high-performance liquid chromatography purification. The accumulation of Cy5.5-2DG and Cy5.5-NHS in different tumor cell lines at 37 and 4 degrees C were imaged using a fluorescence microscope. Tumor targeting and retention of Cy5.5-2DG and Cy5.5-NHS in a subcutaneous U87MG glioma and A375M melanoma tumor model were evaluated and quantified by a Xenogen IVIS 200 optical cooled charged-coupled device system. Fluorescence microscopy imaging shows that Cy5.5-2DG and Cy5.5-NHS are taken up and trapped by a variety of tumor cell lines at 37 degrees C incubation, while they exhibit marginal uptake at 4 degrees C. The tumor cell uptake of Cy5.5-2DG cannot be blocked by the 50 mM D-glucose, suggesting that Cy5.5-2DG may not be delivered in tumor cells by GLUTs. U87MG and A375M tumor localization was clearly visualized in living mice with both NIR fluorescent probes. Tumor/muscle contrast was clearly visible as early as 30 min postinjection (pi), and the highest U87MG tumor/muscle ratios of 2.81 +/- 0.10 and 3.34 +/- 0.23 were achieved 24 h pi for Cy5.5-2DG and Cy5.5-NHS, respectively. While as a comparison, the micropositron emission tomography imaging study shows that [18F]FDG preferentially localizes to the U87MG tumor, with resulting tumor/muscle ratios ranging from 3.89 to 4.08 after 30 min to 2 h postadministration of the probe. In conclusion, the NIR fluorescent glucose analogues, Cy5.5-2DG and Cy5.5-NHS, both demonstrate tumor-targeting abilities in cell culture and living mice. More studies are warranted to further explore their application for optical tumor imaging. To develop NIR glucose analogues with the ability to target GLUTs/hexokinase, it is highly important to select NIR dyes with a reasonable molecular size.

A fluorescent photoprobe for the imaging of endothelin receptors

Bioconjug Chem.2007 May-Jun;18(3):685-94.PMID: 17417816DOI: 10.1021/bc060264w

A novel fluorescent photoprobe for the imaging of endothelin A receptors (ET(A)R) was developed. Based on the nonpeptidyl, high-affinity, and selective ET(A)R antagonist 3-benzo[1,3]dioxol-5-yl-5-hydroxy-5-(4-methoxyphenyl)-4-(3,4,5-trimethoxybenzyl)-5H-furan-2-one (PD 156707), a modification of the lead structure with a PEG-spacer containing an amino moiety was performed. Labeling of this precursor with the fluorescent marker Cy 5.5 NHS-ester was accomplished by adaption of common peptide labeling procedures. The affinity of the Cy 5.5-labeled receptor antagonist was evaluated using human carcinoma cell lines with different degrees of ET(A)R expression. Fluorescence microscopy revealed that ET(A)R-positive MCF-7 human breast adenocarcinoma and HT-1080 human fibrosarcoma cells effectively bind the photoprobe at very low doses (nM), while ET(A)R-negative MDA-MB-435 human breast cancer cells showed no fluorescence signal. Binding specificity of the probe could be demonstrated by predosing with a specific ET(A)R antibody or the parent antagonist PD 156707 as a competing inhibitor. The results suggest that the modified photoprobe tightly binds to ET(A) receptors and thus may be a possible candidate for the imaging of ET(A)R-overexpressing tissues in vivo.