Non‐selective Action of 4‐Hydroxyanisole on Melanoma Cells In Vivo

Schwabe, K.; Fichtner, Iduna; Tschiersch, B.

doi:10.1111/j.1600-0749.1990.tb00255.x

Cited by 5 publications

(4 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The toxicity for these compounds was the same in the normal non-tumorigenic parental cell line and the two tumorigenic transformed lines R19 and CIRAS I. These data agree with earlier published results that 4HA has nonspecific toxicity effects (Schwiabe et al, 1990;Wallevik et al, 1984). In addition, we have shown that transfection by J L ' O 0 2 6 6 8 10 12…”

Section: Discussionsupporting

confidence: 91%

“…Recent studies have shown that 4-hydroxyanisole (4HA) and other phenolic compounds are known to have cytotoxic activity against pigmented cells such as melanocytes, as well as pigmented melanoma (Kanclerz and Chapman, 1986;Kanclerz and Zbytniewski, 1981;Meyskens, 1984;Riley, 1984;Riley et al, 1975). However, further studies did not all agree and some showed specific activity of 4HA against pigmented cells (Bleehen, 1976;Dewey et al, 1977;Kulkarne and Nathanson, 1989;Meyskens, 1984), while others showed non-specific activity against a wide range of different cells (Schwiabe et al, 1990;Thody et al, 1988;Wallevik et al, 1984). In fact, one study indicated activity toward non-pigmented cells but increased activity against pigmented cells, and it was proposed that there were possibly two mechanisms of action, a specifically directed mechanism through tyrosinase conversion of 4HA into toxic radicals and a non-specific mode of action of 4HA on the inhibition of DNA and RNA synthesis (Kulkarne and Nathanson, 1989).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Response of Transformed and Normal Mouse Cell Lines to Anti‐Melanin Compounds, Hyperthermia, and Radiation

Raaphorst

Azzam

1992

Pigment Cell Research

View full text Add to dashboard Cite

Five cell lines (one parental, two transformed melanin producing, and two transformed non-melanin producing) were evaluated for the responses to 2- and 4-hydroxyanisole (2HA, 4HA) alone or combined with hyperthermia or radiation. All cells exhibited a non-specific toxic response to the two compounds and the effect was exposure time and concentration dependent and was greater for 4HA compared to 2HA. In addition, the two melanin-producing cell lines were more sensitive, demonstrating specific toxicity to such cell lines. The treatment with either 2HA or 4HA combined with heat and radiation resulted mostly in additive or antagonistic effects, except for one combination of 2HA plus radiation in the melanin-producing R25 cells. Thus, while these compounds may be useful in therapy for pigmented melanomas, combined treatment with radiation is not recommended.

show abstract

Section: Discussionsupporting

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Response of Transformed and Normal Mouse Cell Lines to Anti‐Melanin Compounds, Hyperthermia, and Radiation

Raaphorst

Azzam

1992

Pigment Cell Research

View full text Add to dashboard Cite

show abstract

“…This is made evident from the study of 4HA. Many studies on this substrate, which is used in melanoma therapy, have been published (10)(11)(12)(13). However, the behavior of 4HA as tyrosinase substrate has never been properly detailed.…”

Section: Introductionmentioning

confidence: 99%

Kinetic study of the oxidation of 4‐hydroxyanisole catalyzed by tyrosinase

Espina¹,

Varón

Tudela³

et al. 1997

IUBMB Life

View full text Add to dashboard Cite

Despite the importance of the substrate 4‐hydroxyanisole in melanoma therapy, the kinetics of its oxidation catalyzed by tyrosinase has never been properly characterized. This approach is reported here for the first time. The applicability to 4‐hydroxyanisole of the reaction mechanism of tyrosinase previously proposed for other monophenols has been corroborated. The Michaelis constant for the oxidation of 4‐hydroxyanisole catalyzed by mushroom tyrosinase was (62±1.5jt]μM at pH 7 and increased when the pH decreased, reaching a value of (195±5jt]μM at pH 5.5. However the maximum steady‐state rate, whose value was (0.54±0.01jt]μM/min, did not change with the pH. The apparent catalytic constant was (184±5jt]s‐1, around twenty three times higher than that previously described for L‐tyrosine (8 s‐l).

show abstract

“…Riley and his associates [21] indicated that 4-hydroxyanisole is a potent depigmenting agent and has some in vivo and in vitro antimelanoma effect in animals and humans. A number of recent studies, however, indicated that 4-hydroxyanisole does not have any selective cytotoxicity to pigment cells [22].…”

Section: Phenolsmentioning

confidence: 98%

Exploitation of Pigment Biosynthesis Pathway as a Selective Chemotherapeutic Approach for Malignant Melanoma.

Jimbow¹,

Iwashina²,

Alena³

et al. 1993

J Invest Dermatol

View full text Add to dashboard Cite

Human malignant melanoma represents a difficult therapeutic challenge to both medical scientists and practicing physicians. However, the biologic uniqueness of the tumor may provide opportunities for exploitation in therapeutics. This study proposed to undertake a systemic approach to the chemotherapy of malignant melanoma based upon the uniqueness of pigment-cell metabolic pathway pertaining to conversion of tyrosine and dopa with subsequent formation of melanin by tyrosinase and its related enzymes. The sulphur homologue of tyrosine, cysteinylphenol (CP), its amine derivative, cysteaminylphenol (CAP), and their N-acetyl and alpha-methyl derivatives have been synthesized and tested in in vivo and in vitro melanocytotoxicity and antimelanoma effects. These phenolic thioethers (PTEs) and phenolic thioether amine (amides) (PTEAs), which are substrates of tyrosinase, showed significant cytotoxicity that is selective to melanocytes and melanoma cells. Most previous attempts to impair the melanin pathway as a therapeutic strategy have been of limited success because they have been directed to catecholic compounds that are unstable and insufficient in lethality at physiologically tolerable doses. By contrast, our approach relies on phenolic compounds, PTEs and PTEAs, which are more stable than catechols and become toxic only after oxidation by tyrosinase. We found PTEA as the most promising agent for the future development of chemotherapeutic agents. The possible biologic, chemical, and pharmacologic reactions of these synthetic compounds within the melanoma cells are studied and discussed.

show abstract

Non‐selective Action of 4‐Hydroxyanisole on Melanoma Cells In Vivo

Cited by 5 publications

References 9 publications

Response of Transformed and Normal Mouse Cell Lines to Anti‐Melanin Compounds, Hyperthermia, and Radiation

Response of Transformed and Normal Mouse Cell Lines to Anti‐Melanin Compounds, Hyperthermia, and Radiation

Kinetic study of the oxidation of 4‐hydroxyanisole catalyzed by tyrosinase

Exploitation of Pigment Biosynthesis Pathway as a Selective Chemotherapeutic Approach for Malignant Melanoma.

Contact Info

Product

Resources

About