Structure of Gemcitabine HCI
CAS No.: 122111-03-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Gemcitabine Hydrochloride (LY 188011 Hydrochloride) is a pyrimidine nucleoside analog antimetabolite and antineoplastic agent that inhibits DNA synthesis and repair, leading to autophagy and apoptosis.
Synonyms: LY 188011 hydrochloride; Gemcitabine(hydrochloride); Gemcitabine HCl
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Nasurullah Mahar ; Amir Al-Ahmed ; Abdulaziz A. Al-Saadi ;
Abstract: The development of rapid and efficient spectroanalytical protocols to detect bioactive drugs in aqueous samples is linked with the evolution of new generations of nanostructured materials. The 2D vanadium carbide (V2CTx) family of MXenes has been proved to be a promising material owing to its excellent plasmonic effects, short-range charge transfer (CT), and covers a wide variety of applications, especially in the fields of sensing and optics. For several years, research is focused on the stability and inter-layers spacing of a few-layered V2CTx in colloidal states. In this work, the synthesis and characterization of vanadium carbide sheets using a soft condition approach were reported. The delamination with the triethylamine (TEA) intercalant resulted in deceased interlayer spacing of 8.13 Å and enhanced the shelf life by up to six weeks. The synthesized highly stable MXene was treated with self-assembled silver nanoparticles (AgNPs) to fabricate a hybrid material as a potential surface-enhanced Raman scattering (SERS) substrate for the detection of ultra-trace quantities of anti-cancer drug gemcitabine (GMC). The developed approach showed an unprecedented limit of detection of 10[-12] M with a wide dynamic range of 10[-4]-10-[12] M. The MXene-based SERS sensor has achieved a Raman signal amplification corresponding to an enhancement factor of 109, with high sensitivity and reproducibility.
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Keywords: Vanadium carbide ; SERS ; Gemcitabine ; Hybrid materials ; Intercalation
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Nasurullah Mahar ; Abdulaziz A. Al-Saadi ;
Abstract: Quantitative detection of trace concentrations of anticancer drug gemcitabine (GMC) was successfully established using the surface-enhanced Raman scattering (SERS) analytical approach. Chemically reduced size-controlled silver nanoparticles (AgNPs) were used as an active SERS substrate which exhibited a significant electrostatic interaction with the target molecules. The developed analytical approach depicted a viable and sensitive means leading to a low limit of detection of 1.5 × 10–10 M and a limit of quantification 3.5 × 10–10 M in aqueous media with an excellent recovery (98%). A consistent linear response featuring a wide dynamic range (10–4–10–9 M) with a coefficient of regression (R2) of 0.9987 could be also achieved. The enhancement in the Raman signal intensities associated with wavenumber shifts was carefully analyzed, and the corresponding vibrational modes were assigned. Density functional theory assessments of the possible drug-substrate interaction scenarios were carried out, and four potential modes of interaction through the primary amine group, the hydroxyl groups, and the pyrimidine nitrogen were proposed.
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Keywords: Surface-enhanced Raman spectroscopy ; Gemcitabine ; Ultralow detection ; Density functional theory ; Silver nanoparticles
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| CAS No. : | 122111-03-9 |
| Formula : | C9H12ClF2N3O4 |
| M.W : | 299.66 |
| SMILES Code : | O=C1N([C@H]2C(F)(F)[C@H](O)[C@@H](CO)O2)C=CC(N)=N1.Cl |
| Synonyms : |
LY 188011 hydrochloride; Gemcitabine(hydrochloride); Gemcitabine HCl
|
| MDL No. : | MFCD01735988 |
| InChI Key : | OKKDEIYWILRZIA-OSZBKLCCSA-N |
| Pubchem ID : | 60749 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302-H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
In Vitro:
|
Cell Line
|
Concentration | Treated Time | Description | References |
| NMFH-1 cells | 20 µM | 24 h | To investigate the effect of gemcitabine on the viability of NMFH-1 cells, the results showed that the IC50 of gemcitabine was 41 µM. | Front Cell Dev Biol. 2021 Nov 25;9:751833. |
| PANC-1 | 1 μM | 72 h | To evaluate the effect of hsa-miR-3178 overexpression on the proliferation and gemcitabine resistance of PANC-1 cells. The results showed that hsa-miR-3178 overexpression significantly increased the proliferation of PANC-1 cells and reduced gemcitabine-induced apoptosis. | Mol Cancer. 2022 May 10;21(1):112. |
| PANC-1-GEM | 150 μM | 72 h | To evaluate the effect of hsa-miR-3178 inhibition on the proliferation and gemcitabine sensitivity of PANC-1-GEM cells. The results showed that hsa-miR-3178 inhibition significantly decreased the proliferation of PANC-1-GEM cells and increased gemcitabine-induced apoptosis. | Mol Cancer. 2022 May 10;21(1):112. |
| H460 cells | 0.5 μM | 48 h | To evaluate gemcitabine-induced apoptosis, results showed that PP242 significantly enhanced gemcitabine-induced apoptosis. | Neoplasia. 2021 Jul;23(7):643-652. |
| H1975 cells | 0.5 μM | 48 h | To evaluate gemcitabine-induced apoptosis, results showed that PP242 significantly enhanced gemcitabine-induced apoptosis. | Neoplasia. 2021 Jul;23(7):643-652. |
| H157 cells | 0.5 μM | 48 h | To evaluate gemcitabine-induced apoptosis, results showed that PP242 significantly enhanced gemcitabine-induced apoptosis. | Neoplasia. 2021 Jul;23(7):643-652. |
| H1299 cells | 10 μM | 12 h | To evaluate gemcitabine-induced DNA damage, results showed that Rictor knockout significantly increased γH2AX levels. | Neoplasia. 2021 Jul;23(7):643-652. |
| T24 cells | 3.8 μM | Gemcitabine treatment significantly increased the ALDHhigh population in T24 cells from 7.9% to 12.6%, and increased the CD44+ subpopulation, as well as the levels of different CSC markers. | Theranostics. 2017 Jul 22;7(12):3053-3067. | |
| 5637 cells | 6.4 μM | Gemcitabine treatment significantly increased the ALDHhigh population in 5637 cells from 9.7% to 19.0%, and increased the CD44+ subpopulation, as well as the levels of different CSC markers. | Theranostics. 2017 Jul 22;7(12):3053-3067. |
In Vivo:
|
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
| Mice | Pancreatic cancer model | Intraperitoneal injection | 100 mg/kg | Single dose | To investigate the effect of Gemcitabine combined with radiotherapy on pancreatic cancer models, results showed that the combined treatment induced M2 reprogramming of TAMs. | Gastroenterology. 2016 Jun;150(7):1659-1672.e5 |
| BALB/c nude mice | Pancreatic cancer xenograft model | Intraperitoneal injection | 5 mg/kg | Every three days for four weeks | To evaluate the effect of hsa-miR-3178 overexpression and inhibition on tumor growth and gemcitabine sensitivity in pancreatic cancer xenograft models. The results showed that hsa-miR-3178 overexpression significantly enhanced tumor growth, while hsa-miR-3178 inhibition significantly slowed tumor growth. | Mol Cancer. 2022 May 10;21(1):112. |
| Nude mice | H460 xenograft model | Intraperitoneal injection | 80 mg/kg | Twice a week, until the end of the experiment | To evaluate the effect of gemcitabine on tumor growth, results showed that Rictor-deficient tumors were more sensitive to gemcitabine treatment. | Neoplasia. 2021 Jul;23(7):643-652. |
| Mice | KrasG12D;p48-Cre; SPARC−/− and KrasG12D;p48-Cre; SPARCWT mouse models | Not specified | 100 mg/kg | Single dose | To investigate whether SPARC-dependent collagen deposition affects intratumoral gemcitabine accumulation and immediate therapeutic response. Results showed that SPARC-dependent collagen deposition did not affect intratumoral gemcitabine accumulation or immediate therapeutic response. | EBioMedicine. 2019 Oct;48:161-168 |
| Nude mice | Bladder cancer xenograft model | Intraperitoneal injection | 50 mg/kg | Administered on days 1, 4, 8, and 11, lasting for 11 days | Gemcitabine treatment significantly inhibited the growth of T24 and 5637 xenografts, but failed to inhibit tumor growth in the second and third rounds of treatment. Gemcitabine treatment increased the CSC population in the tumors, as evidenced by the significant increase in the expression levels of CSC markers CK5, CK14, ALDH1A1, CD44, KLF4, and HMGA2. | Theranostics. 2017 Jul 22;7(12):3053-3067. |
| Bio Calculators | ||||
| Preparing Stock Solutions | ![]() |
1mg | 5mg | 10mg |
|
1 mM 5 mM 10 mM |
3.34mL 0.67mL 0.33mL |
16.69mL 3.34mL 1.67mL |
33.37mL 6.67mL 3.34mL |
|
Tags: Gemcitabine HCl | antimetabolite | chemotherapy | DNA synthesis inhibition | pancreatic cancer | apoptosis | PANC-1 cells | IC50 | cytotoxic | nucleoside analog | 122111-03-9
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