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Interaction between ciprofloxacin and melanin: the effect on proliferation and melanization in melanocytes
Artur Beberok1, Ewa Buszman, Dorota Wrześniok
1Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Medical University of Silesia, Jagiellońska 4, PL 41–200 Sosnowiec, Poland.
Abstract:
There have been described serious adverse events caused by ciprofloxacin in pigmented tissues. It is known that some fluoroquinolones bind well to melanin rich tissues, but the relation between their affinity to melanin and the skin or eye toxicity is not well documented. The aim of this study was to examine whether ciprofloxacin binds to melanin, and how this interaction affects the proliferation and melanization in melanocytes. We have demonstrated that complexes which ciprofloxacin forms with melanin possess at least two classes of independent binding sites. Their association constants are K(1)~10(5) M(-1) and K(2)~10(2) M(-1), respectively. Ciprofloxacin has induced evident concentration-dependent loss in melanocytes viability. The value of ED(50) was found to be ~0.5 mM. It has also been shown that ciprofloxacin reduces melanin content, and decreases tyrosinase activity in human skin melanocytes. The ability of ciprofloxacin to interact with melanin and its inhibitory effect on melanization in melanocytes in vitro may explain a potential role of melanin in the mechanisms of ciprofloxacin toxic effects in vivo.
Insights
Ciprofloxacin binds to melanin, impacting melanocyte viability and reducing melanin production. This interaction may explain ciprofloxacin
Area of Science:
- Pharmacology
- Biochemistry
- Toxicology
Background:
- Serious adverse events linked to ciprofloxacin in pigmented tissues.
- Fluoroquinolones' affinity for melanin-rich tissues is known but not fully linked to toxicity.
- The relationship between melanin binding and skin/eye toxicity requires further investigation.
Purpose of the Study:
- To determine if ciprofloxacin binds to melanin.
- To investigate how this interaction affects melanocyte proliferation and melanization.
- To explore the potential role of melanin in ciprofloxacin's toxic effects.
Main Methods:
- Studied the binding of ciprofloxacin to melanin.
- Assessed the effect of ciprofloxacin on melanocyte viability and proliferation.
- Measured melanin content and tyrosinase activity in human skin melanocytes.
Main Results:
- Ciprofloxacin forms complexes with melanin at two distinct binding sites (K(1)~10(5) M(-1), K(2)~10(2) M(-1)).
- Ciprofloxacin induced concentration-dependent loss in melanocyte viability (ED(50)~0.5 mM).
- Ciprofloxacin reduced melanin content and tyrosinase activity in human skin melanocytes.
Conclusions:
- Ciprofloxacin interacts with melanin.
- This interaction inhibits melanization and reduces melanocyte viability.
- Melanin may play a role in the in vivo toxicity mechanisms of ciprofloxacin.
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