ArticleMolecular cancer therapeutics2011
Enigmol: a novel sphingolipid analogue with anticancer activity against cancer cell lines and in vivo models for intestinal and prostate cancer.
Article in Molecular cancer therapeutics, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
29 citing papers in PubMed, 61 citations in OpenAlex.
- Article
- Article
- Don't Be Surprised When These Surprise You: Some Infrequently Studied Sphingoid Bases, Metabolites, and Factors That Should Be Kept in Mind During Sphingolipidomic Studies.International journal of molecular sciences · 2025Review
- Glycerol Extraction of Bioactive Compounds from Thanaka (ACS omega · 2024Article
- Effects ofActa medica Philippina · 2024Article
- Dietary choline and sphingomyelin choline moiety intake and risk of colorectal cancer: a case-control study.European journal of clinical nutrition · 2023Article
- Targeting Sphingosine 1-Phosphate Metabolism as a Therapeutic Avenue for Prostate Cancer.Cancers · 2023Review
- 1-Deoxysphinganine initiates adaptive responses to serine and glycine starvation in cancer cells via proteolysis of sphingosine kinase.Journal of lipid research · 2022Article
- Dietary Sphingolipids Contribute to Health via Intestinal Maintenance.International journal of molecular sciences · 2021Review
- Metabolites from halophilic bacterial isolates3 Biotech · 2021Article
- Gut bacteria of Varanus salvator possess potential antitumour molecules.International microbiology : the official journal of the Spanish Society for Microbiology · 2021Article
- Sphingolipid biosynthesis in man and microbes.Natural product reports · 2018Review
- AKT as a key target for growth promoting functions of neutral ceramidase in colon cancer cells.Oncogene · 2018Article
- Facile Chemoselective Strategy toward Capturing Sphingoid Bases by a Unique Glutaraldehyde-Functionalized Resin.ACS omega · 2018Article
- Ethanolic extract ofRSC advances · 2018Article
- Digestion of Ceramide 2-Aminoethylphosphonate, a Sphingolipid from the Jumbo Flying Squid Dosidicus gigas, in Mice.Lipids · 2017Article
- Role of neutral ceramidase in colon cancer.FASEB journal : official publication of the Federation of American Societies for Experimental Biology · 2016Article
- Biological Effects of Naturally Occurring Sphingolipids, Uncommon Variants, and Their Analogs.Neuromolecular medicine · 2016Review
- Discovery of a Fluorinated Enigmol Analog with Enhanced in Vivo Pharmacokinetic and Anti-Tumor Properties.ACS medicinal chemistry letters · 2016Article
- 1-Deoxysphingolipids Encountered Exogenously and Made de Novo: Dangerous Mysteries inside an Enigma.The Journal of biological chemistry · 2015Review
Corrections and comments
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Authors and funding
11 authors at 2 institutions in 1 country.
Funding
Abstract
Sphingoid bases are cytotoxic for many cancer cell lines and are thought to contribute to suppression of intestinal tumorigenesis in vivo by ingested sphingolipids. This study explored the behavior of a sphingoid base analogue, (2S,3S,5S)-2-amino-3,5-dihydroxyoctadecane (Enigmol), that cannot be phosphorylated by sphingosine kinases and is slowly N-acylated and therefore is more persistent than natural sphingoid bases. Enigmol had potential anticancer activity in a National Cancer Institute (NCI-60) cell line screen and was confirmed to be more cytotoxic and persistent than naturally occurring sphingoid bases using HT29 cells, a colon cancer cell line. Although the molecular targets of sphingoid bases are not well delineated, Enigmol shared one of the mechanisms that has been found for naturally occurring sphingoid bases: normalization of the aberrant accumulation of β-catenin in the nucleus and cytoplasm of colon cancer cells due to defect(s) in the adenomatous polyposis coli (APC)/β-catenin regulatory system. Enigmol also had antitumor efficacy when administered orally to Min mice, a mouse model with a truncated APC gene product (C57Bl/6J(Min/+) mice), decreasing the number of intestinal tumors by half at 0.025% of the diet (w/w), with no evidence of host toxicity until higher dosages. Enigmol was also tested against the prostate cancer cell lines DU145 and PC-3 in nude mouse xenografts and suppressed tumor growth in both. Thus, Enigmol represents a novel category of sphingoid base analogue that is orally bioavailable and has the potential to be effective against multiple types of cancer.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.