AFMK

Names

[ Name ]:
AFMK

[Synonym ]:
N-[3-(2-Formamido-5-methoxyphenyl)-3-oxopropyl]acetamide
Acetamide, N-[3-[2-(formylamino)-5-methoxyphenyl]-3-oxopropyl]-

Biological Activity

[Description]:

AFMK, antioxidant metabolite of Melatonin, attenuates X-ray-induced oxidative damage to DNA, proteins and lipids in mice. AFMK is a poorer scavenger. The pKa of AFMK at physiological pH is 8.7. Antioxidant capacity[1][2]. AFMK improves the anti-tumor effect of Gemcitabine in PANC-1 cells through the modulation of apoptotic pathway[3].

[Related Catalog]:

Research Areas >> Cancer

[Target]

Human Endogenous Metabolite

[In Vitro]

AFMK is one of the metabolites of melatonin and can be formed by both enzymatic or pseudoenzymatic and nonenzymatic metabolic pathways[1]. AFMK pretreatment significantly inhibits DNA damage. AFMK shows a very high level of in vitro hydroxyl radical scavenging potential which was measured by an electron spin resonance (ESR) study. IC50 values resulting from ESR analysis was 338.08 nM. AFMK, a melatonin metabolite, is a sparingly investigated biogenic amine[2]. AFMK administered to PANC-1 in combination with Gemcitabine inhibits the production of HSP70 and cIAP-2 as compared to the results obtained with Gemcitabine alone[3]. Western Blot Analysis[3] Cell Line: Human pancreatic carcinoma cell line (PANC-1) Concentration: 0.001, 0.1, 10, 1000 nM Incubation Time: Result: Augmented the inhibitory effects on HSP70 expression from 0.47 (Gemcitabine alone) to 0.13 (10 nM AFMK), 0.08 (0.1 nM AFMK) and 0.01 (0.001 nM AFMK).

[In Vivo]

AFMK is a potent antioxidant in vivo. AFMK significantly reverses radiation-induced decline in the total antioxidant capacity of plasma in mice[2]. Animal Model: Male C57BL mice 8 wk of age[2] Dosage: 10 mg/kg body weight Administration: Intraperitoneal injection Result: Radiation-induced decline in the total antioxidant capacity of plasma was significantly reversed in AFMK pretreated mice. AFMK-pretreated irradiated groups showed a significantly lower value of comet tail length and % DNA in tail.

[References]

[1]. Annia Galano, et al. On the free radical scavenging activities of melatonin's metabolites, AFMK and AMK. J Pineal Res. 2013 Apr;54(3):245-57.

[2]. Kailash Manda, et al. AFMK, a melatonin metabolite, attenuates X-ray-induced oxidative damage to DNA, proteins and lipids in mice. J Pineal Res. 2007 Apr;42(4):386-93.

[3]. Anna Leja-Szpak, et al. Melatonin and its metabolite N1-acetyl-N2-formyl-5-methoxykynuramine (afmk) enhance chemosensitivity to gemcitabine in pancreatic carcinoma cells (PANC-1). Pharmacol Rep. 2018 Dec;70(6):1079-1088.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
589.4±50.0 °C at 760 mmHg

[ Melting Point ]:
138-140ºC

[ Molecular Formula ]:
C₁₃H₁₆N₂O₄

[ Molecular Weight ]:
264.277

[ Flash Point ]:
310.3±30.1 °C

[ Exact Mass ]:
264.110992

[ PSA ]:
84.50000

[ LogP ]:
0.82

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.560

[ Storage condition ]:
-20°C

Safety Information

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
45

[ RIDADR ]:
UN 2811 6.1/PG 3

[ HS Code ]:
2924299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%