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Chemical Structure| 35013-72-0 Chemical Structure| 35013-72-0

Structure of Biotin-NHS
CAS No.: 35013-72-0

Chemical Structure| 35013-72-0

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CAS No.: 35013-72-0

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Biotin NHS is a membrane-permeable compound for labeling intracellular proteins by forming irreversible amide bonds.

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Wrobel, Konrad ; Deregowska, Anna ; Betlej, Gabriela ; Walczak, Malgorzata ; Wnuk, Maciej ; Lewinska, Anna , et al.

Abstract: Polyamidoamine (PAMAM) dendrimers are widely used as a part of drug delivery systems (DDS) to improve anticancer drug bioavailability. In the present study, monophosphates of nucleosides, anti-nucleosides (cytarabine, C and fludarabine, F) and synthetic glucocorticoid dexamethasone (D) were attached to the third generation (G3) PAMAM dendrimer via phosphamide pH-sensitive linker. Conjugates were found to be stable at neutral pH, whereas acid-triggered hydrolysis of phosphamide bond was observed at pH 5. The anticancer action of selected biotinylated mono- and di-conjugates, namely CP-, FP-, DP-CP- and DP-FP-PAMAM dendrimers was then compared to cytotoxic activity of free drugs using four cellular models of leukemia in vitro, i.e., K-562, LAMA-84, THP-1 and HL-60 cells. Ten nM DP-CP-conjugate lowered metabolic activity, caused G0/G1 cell cycle arrest and induced apoptotic cell death in HL-60 cells compared to non-cytotoxic and non-cytostatic action of free drugs when used at the same concentration 10 nM CP-, DP-FP- and FP-conjugates also promoted a decrease in metabolic activity in K-562, LAMA-84, and THP-1 and HL-60 cells, resp., however, without a sign of cytotoxicit. In conclusion, we show that the anticancer potential of CP and FP in leukemia cells may be enhanced by the conjugation with PAMAM dendrimers, especially in the presence of DP in selected exptl. settings.

Keywords: PAMAM G3 dendrimer conjugates ; Cytarabine ; Fludarabine ; Dexamethasone ; pH-cleavable linker ; Leukemia cell apoptosis

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Wrobel, Konrad ; Wolowiec, Stanislaw ; Markowicz, Joanna ; Walajtys-Rode, Elzbieta ; Uram, Lukasz ;

Abstract: Recent achievement in anticancer therapy considers the application of repurposed drugs in optimal combinations with the use of specific carriers for their targeted delivery. As a result, new optimized medications with reduced side effects can be obtained. In this study, two known anticancer drugs, celecoxib and/or simvastatin, were conjugated covalently with PAMAM G3 dendrimer and tested in vitro against human squamous carcinoma (SCC-15-15) and glioblastoma (U-118 MG) cells, as well as normal human fibroblasts (BJ). The obtained conjugates were also substituted with biotin and R-glycidol to increase their affinity for cancer cells and were characterized with NMR spectroscopy and dynamic light scattering technique. Conjugates furnished with two celecoxib and four simvastatin residues revealed the very high effectiveness and dramatically decreased the SCC-15 and U-118 MG cell viability at very low concentrations with IC50 equal to about 3 μM. Its action was 20–50-fold stronger than that of either drug alone or as a mixture. Combined conjugate revealed also additive action since it was 2–8-fold more effective than conjugates with either single drug. The combined conjugate revealed rather low specificity since it was also highly cytotoxic for BJ cells. Despite this, it may be concluded that biotinylated and R-glycidylated PAMAM G3 dendrimers substituted with both celecoxib and simvastatin can be considered as a new perspective anticancer agent, effective in therapy of malignant, incurable glioblastomas.

Keywords: drug delivery system ; biotinylated ; R-glycidylated PAMAM G3 dendrimers ; celecoxib ; simvastatin ; molecular size ; cytotoxicity ; human squamous carcinoma (SCC-15-15) ; human glioblastoma (U-118 MG) ; normal human fibroblasts (BJ)

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Alternative Products

Product Details of Biotin-NHS

CAS No. :35013-72-0
Formula : C14H19N3O5S
M.W : 341.38
SMILES Code : O=C(CC1)N(OC(CCCC[C@@H]2SC[C@]([C@]2([H])N3)([H])NC3=O)=O)C1=O
MDL No. :MFCD00078531
InChI Key :YMXHPSHLTSZXKH-RVBZMBCESA-N
Pubchem ID :6710714

Safety of Biotin-NHS

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H315-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Isoform Comparison

Biological Activity

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT02936037 Multiple Sclerosis Phase 3 Active, not recruiting September 2019 -
NCT01572506 Anemia Not Applicable Completed - United States, District of Col... More >>umbia VA Medical Center, Washington D.C. Washington, District of Columbia, United States, 20422 United States, Maryland National Institute of Aging, Clinical Research Unit Baltimore, Maryland, United States, 21224 Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.93mL

0.59mL

0.29mL

14.65mL

2.93mL

1.46mL

29.29mL

5.86mL

2.93mL
Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2
 

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