Spongouridine
[CAS# 3083-77-0]

Identification

• Classification: Biochemical >> Carbohydrate >> Monosaccharide
• Name: Spongouridine
• Synonyms: Uridine; 1-beta-D-Arabinofuranosyluracil; 1-beta-D-Ribofuranosyl-2,4(1H,3H)-pyrimidinedione; 1-[3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• Molecular Formula: C₉H₁₂N₂O₆
• Molecular Weight: 244.20
• Protein Sequence: N
• CAS Registry Number: 3083-77-0
• EC Number: 221-386-9
• SMILES: C1=CN(C(=O)NC1=O)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.643, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS08 Warning
• Risk Statements: H361
• Safety Statements: P203-P280-P318-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Germ cell mutagenicity	Muta.	2	H341
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - repeated exposure	STOT RE	2	H373

Discovery and Applications

Spongouridine is a naturally occurring nucleoside that was originally isolated from marine sponges. It is a purine derivative, which consists of a sugar (ribose) bonded to a purine base, specifically a guanine derivative, and is characterized by its unique structure that includes modifications specific to marine-derived compounds. Spongouridine was first identified and isolated in the late 20th century as part of the investigation into bioactive compounds derived from marine organisms, particularly those with potential therapeutic properties. The discovery was part of a broader interest in exploring marine sources for novel bioactive molecules with medicinal potential, particularly for antiviral and anticancer applications.

The primary application of spongouridine has been studied in the field of antiviral research. It exhibits notable antiviral activity, especially against herpes simplex virus (HSV). This has led to research into its potential as a lead compound for the development of antiviral drugs. The structure of spongouridine is similar to that of other nucleoside analogs, which are known to inhibit viral replication by interfering with the action of viral enzymes, such as reverse transcriptase or DNA polymerase. This mechanism has made nucleoside analogs valuable in the treatment of viral infections, and spongouridine is no exception. Its antiviral properties have positioned it as a subject of interest for drug development aimed at treating viral infections, particularly those caused by DNA viruses.

In addition to its antiviral activity, spongouridine has also been investigated for its potential anticancer properties. Like other compounds derived from marine organisms, spongouridine has shown the ability to inhibit the growth of cancer cells in vitro, leading researchers to explore its potential as part of a class of natural products with antitumor activity. However, while promising results have been obtained in laboratory studies, the compound’s clinical development for cancer treatment has not advanced as far as other well-established chemotherapeutic agents. The biological activity of spongouridine, particularly its cytotoxic effects, is believed to be related to its ability to interfere with nucleic acid synthesis, an action common to many anticancer drugs.

Moreover, spongouridine is of interest in the context of natural product chemistry and the exploration of marine organisms for bioactive compounds. The marine environment, with its diverse and often unexplored ecosystems, continues to be a rich source of novel compounds that have the potential to become new drugs or lead compounds for drug development. Spongouridine, like other marine-derived molecules, reflects the unique chemical diversity found in marine organisms and the continuing importance of marine natural products in drug discovery.

In summary, spongouridine is a marine-derived nucleoside that has demonstrated significant antiviral and anticancer activities in preclinical studies. Its discovery and subsequent research have contributed to the field of natural product chemistry and drug development, especially for viral and cancer therapies. Although its clinical application remains an area of research, the compound exemplifies the value of marine organisms as a source of bioactive molecules with potential therapeutic benefits.

References

1962. The activity of nucleoside phosphorylase on 1-beta-D-arabinosyluracil within Escherichia coli. The Journal of Biological Chemistry, 237(4).
DOI: 10.1016/s0021-9258(18)60320-5

1975. INHIBITION OF MICROORGANISMS BY PYRIMIDINE NUCLEOSIDES. Annals of the New York Academy of Sciences, 255(1).
DOI: 10.1111/j.1749-6632.1975.tb29259.x

2021. Exploring the therapeutic potential of marine-derived bioactive compounds against COVID-19. Environmental Science and Pollution Research, 28(45).
DOI: 10.1007/s11356-021-16104-6