13556-29-1

Basic information

• Product Name: HC RED NO. 8
• Synonyms: HC RED NO. 8
• CAS NO: 13556-29-1
• Molecular Formula: C₁₇H₁₆N₂O₂
• Molecular Weight: 280.32
• Mol File: 13556-29-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: HC RED NO. 8(CAS DataBase Reference)
• NIST Chemistry Reference: HC RED NO. 8(13556-29-1)
• EPA Substance Registry System: HC RED NO. 8(13556-29-1)

Safety Data

• Hazardous Substances Data: 13556-29-1(Hazardous Substances Data)

Usage

Uses

Used in Hair Dye Industry:
HC Red No. 8 is used as a colorant in hair dyes for providing long-lasting vibrant red shades. It is often combined with other dyes to create a range of tones and shades.
Used in Cosmetic Products:
HC Red No. 8 is used as a colorant in cosmetic products to impart a rich red color. Its low skin sensitization potential makes it suitable for use in various cosmetic formulations.
It is important to perform a patch test before applying products containing HC Red No. 8 to the skin or hair to avoid any potential allergic reactions.

Upstream product

• 82-44-0 1-chloroanthracene-9,10-dione 
• 109-76-2 Trimethylenediamine 

Downstream Products

• 200942-38-7 2-(4-{3-[3-(9,10-Dioxo-9,10-dihydro-anthracen-1-ylamino)-propylcarbamoyl]-propionylamino}-benzyl)-malonic acid di-tert-butyl ester 

Relevant articles and documents

Novel anthraquinone derivatives with redox-active functional groups capable of producing free radicals by metabolism: Are free radicals essential for cytotoxicity?

The mode of action of antitumour anthraquinone derivatives (i.e. mitoxantrone) is not clearly established yet. It includes, among others, intercalation and binding to DNA, bioreduction and aerobic redox cycling. A series of anthraquinone derivatives, with potentially bioreducible groups sited in the side chain, have been synthesized and biologically evaluated. Their redox and cytotoxic activities were screened. Derivatives which bear a 2-(dimethylamino)ethylamino substituent, known to confer high DNA affinity, demonstrated cytotoxicity but not redox activity (beside the anthraquinone reduction). Conversely, derivatives which showed redox activity were not cytotoxic toward the P388 cell line. The results suggest that bioreduction is not the main mode of action in the cytotoxicity of anthraquinones.

Cytotoxic efficacy of an anthraquinone linked platinum anticancer drug

Platinum complexes are widely used in cancer chemotherapy; however, they are associated with toxicity, high "non-specific" reactivity and relatively poor pharmacokinetic profiles. In particular, their low cellular uptake and rapid metabolic inactivation means that the amount of "active" drug reaching the nuclear compartment is low. Our strategy to facilitate nuclear accumulation was to introduce a hydrophobic anthraquinone (1C3) moiety to the Pt-complex. Anthraquinones are known to readily intercalate into DNA strands and hence, the Pt-1C3 complex may represent an effective system for the delivery of the platinum moiety to nuclear DNA. Efficacy of the complex was determined by measuring the extent and potency of cytotoxicity in comparison to cisplatin and an anthraquinone based anticancer drug, doxorubicin. The Pt-1C3 complex generated higher levels of cytotoxicity than cisplatin, with a potency of 19 ± 4 μM in the DLD-1 cancer cell line. However, this potency was not significantly different to that of the 1C3 moiety alone. To examine the reason for the apparent lack of platinum related cytotoxicity, the cellular distribution was characterised. Confocal fluorescence microscopy indicated that the Pt-1C3 complex was rapidly sequestered into lysosomes, in contrast to the nuclear localisation of doxorubicin. In addition, there was negligible DNA associated Pt following administration of the novel complex. Thus, the addition of a 1C3 moiety generated sequestration of the complex to lysosomes, thereby preventing localisation to the nucleus.

Tumour targeting prodrugs activated by metallo matrixproteinases

A-(B)n—X ??(I) A-(B)n-Q ??(II) Numbers in Parentheses denote examples in the specification A compound is of general formula (I) wherein (A) is a moiety comprising one of more of a heterocylcic ring, a carbocyclic ring and a fused ring system, the ring or ring system being essential for a biological activity of the compound by action at a nucleic acid or protein target (B) is a bivalent spacer molecule attached directly to the ring system n is an integer 0 or 1 and (X) is a monovalent moiety containing a amide bond that is cleavable by the action of a matrix metalloproteinase enzyme such as to produce a compound of formula (II) wherein the efficacy of the biological activity of the compound of formula (II) is increased over that of the compound of formula (I).

Anthraquinone intercalators as carrier molecules for second-generation platinum anticancer drugs

A series of complexes PtAm2L [where Am2 = (NH3)2, ethylenediamine(en), 1,2-diaminocyclohexane (DACH) or (NH3)(c-C6H11NH2) and where L is a bidentate 1,1-dicarboxylate ligand tethered to 1- aminoanthraquinone by various spacers] was prepared and screened in vitro against P388 leukemia cells. The free ligands displayed moderate activity and the corresponding platinum complexes were tenfold more active. The nature of the linker chain does not seem to affect the potency of the complexes. The potency depends on the nature of the inert amine ligand [NH3 > DACH > en]. The low aqueous solubility of these complexes prevented any in vivo studies and the preparation of water soluble analogs is currently under way.