Structure-based design of nitrosoureas containing tyrosine derivatives as potential antimelanoma agents

Gadjeva, V.

doi:10.1016/s0223-5234(02)01343-0

Cited by 13 publications

(9 citation statements)

References 10 publications

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“…TEMPOL, dissolved in DMSO, produced an identical nitroxide-enhanced MRI signal (as intensity and profile) in anesthetized mice as TEMPOL dissolved in PBS. The final dose of each nitroxide was lower than the LD 50 value calculated for intravenous administration in wild-type mice (38).…”

Section: In Vivo Mri Measurementsmentioning

confidence: 62%

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Tissue Redox Activity as a Hallmark of Carcinogenesis: From Early to Terminal Stages of Cancer

Bakalova

Zhelev

Aoki

et al. 2013

Clinical Cancer Research

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Purpose: The study aimed to clarify the dynamics of tissue redox activity (TRA) in cancer progression and assess the importance of this parameter for therapeutic strategies.Experimental Design: The experiments were carried out on brain tissues of neuroblastoma-bearing, glioma-bearing, and healthy mice. TRA was visualized in vivo by nitroxide-enhanced MRI on anesthetized animals or in vitro by electron paramagnetic resonance spectroscopy on isolated tissue specimens. Two biochemical parameters were analyzed in parallel: tissue total antioxidant capacity (TTAC) and plasma levels of matrix metalloproteinases (MMP).Results: In the early stage of cancer, the brain tissues were characterized by a shorter-lived MRI signal than that from healthy brains (indicating a higher reducing activity for the nitroxide radical), which was accompanied by an enhancement of TTAC and MMP9 plasma levels. In the terminal stage of cancer, tissues in both hemispheres were characterized by a longer-lived MRI signal than in healthy brains (indicating a high-oxidative activity) that was accompanied by a decrease in TTAC and an increase in the MMP2/MMP9 plasma levels. Cancer progression also affected the redox potential of tissues distant from the primary tumor locus (liver and lung). Their oxidative status increased in both stages of cancer.Conclusions: The study shows that tissue redox balance is very sensitive to the progression of cancer and can be used as a diagnostic marker of carcinogenesis. The study also suggests that the noncancerous tissues of a cancer-bearing organism are susceptible to oxidative damage and should be considered a therapeutic target.

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Section: In Vivo Mri Measurementsmentioning

confidence: 62%

“…2,2,6,6-tetramethylpiperidine-1-oxyl-labeled nitrosourea (SLENU) was synthesized according to the procedure described by Gadjeva (38). SLENU is a spin-labeled analog of the conventional anticancer drug 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea (Lomustine).…”

Section: Chemicalsmentioning

confidence: 99%

Tissue Redox Activity as a Hallmark of Carcinogenesis: From Early to Terminal Stages of Cancer

Bakalova

Zhelev

Aoki

et al. 2013

Clinical Cancer Research

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“…In this case, it can be advantageous to introduce the nitroso group by synthesizing the product from an amine and the corresponding nitrosated carbamate as shown in Scheme 125. [338,339] Scheme 125 Formation of an N-Nitrosourea by Reaction of an Amine and a Nitrosated Carbamate [339] Chlorination of urea derivatives can be achieved by standard chlorination procedures such as treatment with sodium hypochlorite or tert-butyl hypochlorite. [340] In addition, trichloroisocyanuric acid is a versatile chlorination agent for urea derivatives including hydantoins.…”

Section: Synthesis Of N-carbamimidoylureasmentioning

confidence: 99%

Acyclic and Cyclic Ureas (Update 2013)

Banert¹,

Dobbs²,

Hall³

et al. 2013

Knowledge Updates 2013/3

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“…Sulphur-containing substrate (tyrosine) analogues show selective cytotoxicity towards melanoma cell lines . Nitrosoureas-containing tyrosine derivatives are evaluated as potential antimelanoma agents (Gadjeva, 2002). Effective melanocyte-toxic therapies must cause vitiligo.…”

Section: Exploiting Melanin Biosynthesis In Melanomamentioning

confidence: 99%

Tissue-selective therapy of cancer

2003

Br J Cancer

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Structure-based design of nitrosoureas containing tyrosine derivatives as potential antimelanoma agents

Cited by 13 publications

References 10 publications

Tissue Redox Activity as a Hallmark of Carcinogenesis: From Early to Terminal Stages of Cancer

Tissue Redox Activity as a Hallmark of Carcinogenesis: From Early to Terminal Stages of Cancer

Acyclic and Cyclic Ureas (Update 2013)

Tissue-selective therapy of cancer

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