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Chemical Structure| 95058-81-4 Chemical Structure| 95058-81-4
Chemical Structure| 95058-81-4

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CAS No.: 95058-81-4

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Gemcitabine (LY 188011) is a pyrimidine nucleoside analog antimetabolite and an antineoplastic agent that hinders DNA synthesis and repair, leading to both autophagy and apoptosis.

Synonyms: LY 188011; DDFC; NSC 613327

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Federica Carnamucio ; Victoria A. Garcia ; Fatemah S. Sunbul ; Ottavia Giuffrè ; Sandro R. P. da Rocha ;

Abstract: Osteosarcoma (OS) is the most prevalent primary bone malignancy and ranks as the third most common cancer in children, almost exclusively metastasizing to the lungs. Upon initial OS diagnosis, approximately 20% of patients are also diagnosed with clinically detectable lung metastases (OSLM). Systemic gemcitabine (GMT) is the second line therapy for OSLM, but it has limited efficacy due to poor lung distribution. Orally inhaled GMT is in clinical studies and has been shown to upregulate the apoptotic Fas receptor (FasR) expression in OS cells in the lungs, but fails to eradicate lung mets due to its poor lung disposition. Traditional liposomal GMT formulations may offer improved lung safety and retention, but struggle with storage stability and drug loading. We have developed a new GMT unilmellar liposomal formulation that has enhanced GMT loading, high storage stability (<5% GMT leakage in six months storage at 2-8 °C), and is also suitable for oral inhalation. Importantly, we have subsequently developed a strategy for reproducible preparation of the formulation using as single step, GMP-ready, continuous microfluid platform. We also evaluated the efficacy of the formulation in promoting cell death and to rescuing FasR expression in OSLM tumor cells, and we demonstrated that GMT activity is preserved. We also demonstrated that our formulation is well tolerated at repeated doses upon local delivery to the lungs in healthy mice, since no change in body weight or health status have been observed.

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Davi ; Kajal ;

Abstract: Genetic mutations can significantly impact the cell’s susceptibility to environmental stress. The fission yeast Schizosaccharomyces pombe is an established eukaryotic model for studying the cellular responses to various environmental stresses. This work investigated a missense mutation (S239F) identified in Suc22, the small subunit of the ribonucleotide reductase (RNR). RNR is an essential enzyme for the biosynthesis of dNTPs required for DNA replication and repair. We found that the suc22-S239F mutation increases the susceptibility to the replication stress induced by hydroxyurea (HU), not the DNA-damaging agents such as UV, methyl methanesulfate, and CPT. HU is a drug commonly used in laboratories to instigate DNA replication stress as it is an inhibitor of RNR. The intricate mechanisms governing the cellular responses to HU have been extensively studied in the past decades, and the involvement of suc22-S239F mutation presents a new dimension to our understanding of cellular responses to replication stress. The Suc22 is indispensable for DNA synthesis and cell survival. The suc22-S239F mutation involves substituting serine at position 239 with phenylalanine within the small subunit of RNR. Here we show that fission yeast bearing the suc22-S239F mutation exhibits significantly increased sensitivity to chronic replication stress, not acute replication stress induced by HU as compared to wild-type cells. Previous studies have demonstrated that the increased sensitivity to chronic treatment with HU can be caused by several interconnected pathways such as replication stress, oxidative stress, and cytokines arrest. Our results showed that while the replication checkpoint remains functional, the HU sensitivity of the suc22-S239F mutant is likely due to replication stress, not oxidative stress. Therefore, the suc22-S239F mutation acts as an intriguing entry point to studying the intricate mechanisms through which genetic variations amplify the cell susceptibility to replication stress. These findings not only enhance our understanding of stress-induced cytotoxicity but also hold potential implications for the development of innovative therapeutics for the treatment of cancer or other diseases.

Keywords: DNA replication checkpoint ; Hydroxyurea ; Ribonucleotide Reductase ; Schizosaccharomyces pombe

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Mashael Y. Alyahya ; Saman Khan ; Sankhadip Bhadra ; Rittu E. Samuel ; Yong-jie Xu ;

Abstract: Schizosaccharomyces pombe is an established yeast model for studying the cellular mechanisms conserved in humans, such as the DNA replication checkpoint. The replication checkpoint deals with replication stress caused by numerous endogenous and exogenous factors that perturb fork movement. If undealt with, perturbed forks collapse, causing chromosomal DNA damage or cell death. Hydroxyurea (HU) is an inhibitor of ribonucleotide reductase (RNR) commonly used in checkpoint studies. It produces replication stress by depleting dNTPs, which slows the movement of ongoing forks and thus activates the replication checkpoint. However, HU also causes side effects such as oxidative stress, particularly under chronic exposure conditions, which complicates the studies. To find a drug that generates replication stress more specifically, we tested three other RNR inhibitors gemcitabine, guanazole and triapine in S. pombe under various experimental conditions. Our results show that guanazole and triapine can produce replication stress more specifically than HU under chronic, not acute drug treatment conditions. Therefore, using the two drugs in spot assay, the method commonly used for testing drug sensitivity in yeasts, should benefit the checkpoint studies in S. pombe and likely the research in other model systems.

Keywords: S. pombe ; ribonucleotide reductase ; hydroxyurea ; guanazole ; gemcitabine ; triapine ; the DNA replication checkpoint ; oxidative stress ; Rad3 ; Cds1 ; Chk1 ; genome stability

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Alternative Products

Product Details of Gemcitabine

CAS No. :95058-81-4
Formula : C9H11F2N3O4
M.W : 263.20
SMILES Code : [C@H]2(N1C(N=C(N)C=C1)=O)C([C@H](O)[C@H](O2)CO)(F)F
Synonyms :
LY 188011; DDFC; NSC 613327
MDL No. :MFCD00869720
InChI Key :SDUQYLNIPVEERB-QPPQHZFASA-N
Pubchem ID :60750

Safety of Gemcitabine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H361
Precautionary Statements:P501-P202-P201-P264-P280-P302+P352-P308+P313-P337+P313-P305+P351+P338-P362+P364-P332+P313-P405

Application In Synthesis of Gemcitabine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 95058-81-4 ]

[ 95058-81-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 14316-61-1 ]
  • [ 95058-81-4 ]
  • N-phenoxyacetyl-gemcitabine [ No CAS ]
YieldReaction ConditionsOperation in experiment
6.54 g In N,N-dimethyl-formamide; at 20℃; for 5h; A solution of gemcitabine (5.0g, 19mmol) and <strong>[14316-61-1]phenoxyacetic anhydride</strong> (6.0g, 20.9mmol) in anhydrous Nu,Nu-dimethylformamide (200ml) was stirred at room temperature. After 5 hours, the mixture was concentrated in vacuo and triturated with ethyl acetate. The solids were isolated by filtration and dried in a vacuum oven for 30 minutes furnishing N-phenoxyacetyl-gemcitabine (6.54g) as a white solid. 1 H NMR (400 MHz, DMSO-d6): 1 1.15 (1 H, s), 8.29 (1 H, d), 7.31 (2H, t), 7.20 (1 H, d), 7.06-6.88 (3H, m), 6.32 (1 H, d), 6.19 (1 H, t), 5.36-5.25 (1 H, m), 4.85 (2H, s), 4.28-4.12 (1 H, m), 3.97-3.87 (1 H, m), 3.81 (1 H, d), 3.74-3.60 (1 H, m)
  • 2
  • [ 95058-81-4 ]
  • [ 114248-23-6 ]
 

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