Nebularine | CAS#550-33-4

MedKoo Cat#: 462792 | Name: Nebularine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nebularine is a purine ribonucleoside and an adenosine analog that has been found in L. nebularis and has diverse biological activities. It reduces herpes simplex virus 1 viral plaque formation in Vero cells and is active against M. phlei, M. avium, M. tuberculosis, and B. abortus. Nebularine is cytotoxic to COS-7 cells and induces pyknosis in mouse sarcoma 180 cells and mouse embryonic skin explants in a concentration-dependent manner. It inhibits root growth of wheat seedlings when used at concentrations ranging from 0.1 to 2 mM.2 Nebularine also inhibits adenosine deaminase.

Chemical Structure

Nebularine

CAS#550-33-4

Theoretical Analysis

MedKoo Cat#: 462792

Name: Nebularine

CAS#: 550-33-4

Chemical Formula: C10H12N4O4

Exact Mass: 252.0859

Molecular Weight: 252.23

Elemental Analysis: C, 47.62; H, 4.80; N, 22.21; O, 25.37

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 550.00	2 Weeks
100mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Desaminoadenosine; Purine riboside; Purinosine; Ribosylpurine; NSC 65423; NSC65423; NSC-65423;

IUPAC/Chemical Name

(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(9H-purin-9-yl)tetrahydrofuran-3,4-diol

InChi Key

MRWXACSTFXYYMV-FDDDBJFASA-N

InChi Code

InChI=1S/C10H12N4O4/c15-2-6-7(16)8(17)10(18-6)14-4-13-5-1-11-3-12-9(5)14/h1,3-4,6-8,10,15-17H,2H2/t6-,7-,8-,10-/m1/s1

SMILES Code

O[C@@H]1[C@@H]([C@H](O[C@]1(N2C=NC3=CN=CN=C32)[H])CO)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Nebularine is a purine ribonucleoside and an adenosine analog.

In vitro activity:

Nebularine showed mild antifungal activity against Magnaphorthe grisea and Trichophyton mentagrophytes, and phenylacetic acid potently inhibited the growth of Pythium ultiumand displayed moderate antifungal activity against Magnaphorthe grisea, Botrytis cinerea, and Trichophyton mentagrophytes. Reference: Mycobiology. 2008 Jun;36(2):110-3. https://pubmed.ncbi.nlm.nih.gov/23990744/

In vivo activity:

When mice bearing leukemia L1010 were treated with a potentially lethal regimen of nebularine administered together with NBMPR-P, a substantial kill of leukemic cells resulted (some mice were long-term survivors). The therapeutic effect was optimal at dosage levels of the protecting agent in excess of those required in nonleukemic mice for protection against the lethal nebularine dosages used, suggesting that the therapeutic effect was due to the joint presence in the leukemic cells of a metabolite of NBMPR-P and nebularine; NBMPR-P protection of the leukemic host against nebularine lethality was necessary for the therapeutic effect to be manifested. Reference: Cancer Res. 1981 Feb;41(2):560-5. https://pubmed.ncbi.nlm.nih.gov/7448803/

	Solvent	mg/mL	mM
Solubility
	DMF	15.0	59.47
	DMSO	30.0	118.94
	PBS (pH 7.2)	1.0	3.96

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 252.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Kim YS, Lee IK, Seok SJ, Yun BS. Chemical Constituents of the Fruiting Bodies of Clitocybe nebularis and Their Antifungal Activity. Mycobiology. 2008 Jun;36(2):110-3. doi: 10.4489/MYCO.2008.36.2.110. Epub 2008 Jun 30. PMID: 23990744; PMCID: PMC3755233. 2. Bohr V. Effects of purine riboside on nucleic acid synthesis in ascites cells. Biochim Biophys Acta. 1978 Jun 22;519(1):125-37. doi: 10.1016/0005-2787(78)90067-9. PMID: 352398. 3. Lynch TP, Paran JH, Paterson AR. Therapy of mouse leukemia L1210 with combinations of nebularine and nitrobenzylthioinosine 5'-monophosphate. Cancer Res. 1981 Feb;41(2):560-5. PMID: 7448803.

In vitro protocol:

In vivo protocol:

1. Lynch TP, Paran JH, Paterson AR. Therapy of mouse leukemia L1210 with combinations of nebularine and nitrobenzylthioinosine 5'-monophosphate. Cancer Res. 1981 Feb;41(2):560-5. PMID: 7448803.

1: Lougiakis N, Marakos P, Pouli N, Fragopoulou E, Tenta R. Synthesis of new nebularine analogues and their inhibitory activity against adenosine deaminase. Chem Pharm Bull (Tokyo). 2015;63(2):134-42. doi: 10.1248/cpb.c14-00731. PMID: 25748785. 2: Paterson AR, Paran JH, Yang S, Lynch TP. Protection of mice against lethal dosages of nebularine by nitrobenzylthioinosine, an inhibitor of nucleoside transport. Cancer Res. 1979 Sep;39(9):3607-11. PMID: 476687. 3: Lynch TP, Paran JH, Paterson AR. Therapy of mouse leukemia L1210 with combinations of nebularine and nitrobenzylthioinosine 5'-monophosphate. Cancer Res. 1981 Feb;41(2):560-5. PMID: 7448803. 4: Swayze EE, Drach JC, Wotring LL, Townsend LB. Synthesis, antiproliferative and antiviral activity of imidazo[4,5-d]isothiazole nucleosides as 5:5 fused analogs of nebularine and 6-methylpurine ribonucleoside. J Med Chem. 1997 Feb 28;40(5):771-84. doi: 10.1021/jm960605z. PMID: 9057864. 5: BROWN GB, WELIKY VS. The synthesis of 9-beta-D-ribofuranosylpurine and the identity of nebularine. J Biol Chem. 1953 Oct;204(2):1019-24. PMID: 13117878. 6: Rahman MS, Humayun MZ. Nebularine (9-2'-deoxy-beta-D-ribofuranosylpurine) has the template characteristics of adenine in vivo and in vitro. Mutat Res. 1997 Jul 3;377(2):263-8. doi: 10.1016/s0027-5107(97)00084-5. PMID: 9247623. 7: Jiricny J, Wood SG, Martin D, Ubasawa A. Oligonucleotide duplexes containing inosine, 7-deazainosine, tubercidin, nebularine and 7-deazanebularine as substrates for restriction endonucleases HindII, SalI and TaqI. Nucleic Acids Res. 1986 Aug 26;14(16):6579-90. doi: 10.1093/nar/14.16.6579. PMID: 3018674; PMCID: PMC311665. 8: Lüdemann HD, Westhof E. Conformations of the nucleoside analogs formycin, 2-azaadenosine, and nebularine in solution. Z Naturforsch C Biosci. 1977 Jul- Aug;32(7-8):528-38. doi: 10.1515/znc-1977-7-809. PMID: 143819. 9: Iwamura H, Hashizume T. Synthesis in nucleoside antibiotics. II. Facile synthesis of nebularine and its analogs by a modified fusion procedure. J Org Chem. 1968 May;33(5):1796-9. doi: 10.1021/jo01269a020. PMID: 5655926. 10: Smith CM, Snyder FF, Fontenelle LJ, Henderson JF. Improved methods for the study of drug effects on purine metabolism and their application to nebularine and 7-deazanebularine. Biochem Pharmacol. 1974 Jul 15;23(14):2023-35. doi: 10.1016/0006-2952(74)90261-5. PMID: 4371446. 11: Suemune H, Miyasaka T. alpha-Oxyalkylation and alpha-amidoalkylation of nebularine tri-O-benzoate via homolytic processes. Nucleic Acids Symp Ser. 1983;(12):1-4. PMID: 6664840. 12: Hashizume T, Iwamura H. A new synthesis of nebularine and 7-D-ribofuranosylpurine (synthesis in nucleoside antibiotics. I. Tetrahedron Lett. 1966 Feb;6:643-8. doi: 10.1016/s0040-4039(01)99678-9. PMID: 5905318. 13: Fu NW. [Protection of cells by nucleoside transport inhibitor combined with nebularine and the therapeutic effect on transplantable mouse tumors]. Zhonghua Zhong Liu Za Zhi. 1985 Mar;7(2):94-8. Chinese. PMID: 3874052. 14: Taniguchi A. [Purine nucleoside phosphorylase (PNP)]. Nihon Rinsho. 2003 Jan;61 Suppl 1:85-90. Japanese. PMID: 12629696. 15: Kozlowska M, Smolenski RT, Makarewicz W, Hoffmann C, Jastorff B, Swierczynski J. ATP depletion, purine riboside triphosphate accumulation and rat thymocyte death induced by purine riboside. Toxicol Lett. 1999 Feb 22;104(3):171-81. doi: 10.1016/s0378-4274(98)00369-5. PMID: 10079051. 16: el Kouni MH, Messier NJ, Cha S. Treatment of schistosomiasis by purine nucleoside analogues in combination with nucleoside transport inhibitors. Biochem Pharmacol. 1987 Nov 15;36(22):3815-21. doi: 10.1016/0006-2952(87)90443-6. PMID: 3689423. 17: Gillerman I, Fischer B. Investigations into the origin of the molecular recognition of several adenosine deaminase inhibitors. J Med Chem. 2011 Jan 13;54(1):107-21. doi: 10.1021/jm101286g. Epub 2010 Dec 7. PMID: 21138280. 18: Kim YS, Lee IK, Seok SJ, Yun BS. Chemical Constituents of the Fruiting Bodies of Clitocybe nebularis and Their Antifungal Activity. Mycobiology. 2008 Jun;36(2):110-3. doi: 10.4489/MYCO.2008.36.2.110. Epub 2008 Jun 30. PMID: 23990744; PMCID: PMC3755233. 19: Sethi S, Ooe M, Sakamoto T, Fujimoto K. Effect of nucleobase change on cytosine deamination through DNA photo-cross-linking reaction via 3-cyanovinylcarbazole nucleoside. Mol Biosyst. 2017 Jun 1;13(6):1152-1156. doi: 10.1039/c7mb00082k. Epub 2017 Apr 28. PMID: 28453010. 20: Haraguchi A, Kinoshita K, Fukai M, Koyama K. A novel nucleoside from the edible mushroom, Tricholoma japonicum. J Nat Med. 2015 Oct;69(4):584-8. doi: 10.1007/s11418-015-0917-5. Epub 2015 May 15. PMID: 25976547.