Benzoadenosine | CAS#60189-62-0 | kinase inhibitor

MedKoo Cat#: 598906 | Name: Benzoadenosine

Description:

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

Benzoadenosine inhibits kinase activity slightly less than does adenosine.

Chemical Structure

Benzoadenosine

CAS#60189-62-0

Theoretical Analysis

MedKoo Cat#: 598906

Name: Benzoadenosine

CAS#: 60189-62-0

Chemical Formula: C14H15N5O4

Exact Mass: 317.1124

Molecular Weight: 317.30

Elemental Analysis: C, 52.99; H, 4.77; N, 22.07; O, 20.17

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Benzoadenosine; NSC 287022; NSC-287022; NSC287022; Lin-benzoadenosine;

IUPAC/Chemical Name

(2R,3R,4S,5R)-2-(8-amino-3H-imidazo[4,5-g]quinazolin-3-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

InChi Key

SPJSEZDBZALDCW-HKUMRIAESA-N

InChi Code

InChI=1S/C14H15N5O4/c15-13-6-1-8-9(2-7(6)16-4-17-13)19(5-18-8)14-12(22)11(21)10(3-20)23-14/h1-2,4-5,10-12,14,20-22H,3H2,(H2,15,16,17)/t10-,11-,12-,14-/m1/s1

SMILES Code

NC1=C2C=C(N=CN3[C@H]4[C@@H]([C@@H]([C@@H](CO)O4)O)O)C3=CC2=NC=N1

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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 317.30 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

1: Lessor RA, Gibson KJ, Leonard NJ. Synthesis and biochemical evaluation of 2'-deoxy-lin-benzoadenosine phosphates. Biochemistry. 1984 Aug 14;23(17):3868-73. PubMed PMID: 6487584. 2: Schmidt MJ, Truex LL, Leonard NJ, Scopes DI, Barrio JR. Effect of lin-benzoadenosine and lin-benzoadenosine 3':5'-monophosphate on cyclic AMP-dependent protein kinase activity in vitro. J Cyclic Nucleotide Res. 1978 Jun;4(3):201-7. PubMed PMID: 214462. 3: Kauffman RF, Lardy HA, Barrio JR, Bario MC, Leonard NJ. Dimensional probes of the enzyme binding sites of adenine nucleotides. Interaction of lin-benzoadenosine 5'-di- and triphosphate with mitochondrial ATP synthetase, purified ATPase, and the adenine nucleotide carrier. Biochemistry. 1978 Sep 5;17(18):3686-92. PubMed PMID: 212101. 4: Leonard NJ, Sprecker MA, Morrice AG. Defined dimensional changes in enzyme substrates and cofactors. Synthesis of lin-benzoadenosine and enzymatic evaluation of derivatives of the benzopurines. J Am Chem Soc. 1976 Jun 23;98(13):3987-94. PubMed PMID: 819479. 5: Bhatnagar D, Hartl FT, Roskoski R Jr, Lessor RA, Leonard NJ. Adenosine cyclic 3',5'-monophosphate dependent protein kinase: nucleotide binding to the chemically modified catalytic subunit. Biochemistry. 1984 Sep 11;23(19):4350-7. PubMed PMID: 6487604. 6: Vanderlijn P, Barrio JR, Leonard NJ. Spectroscopic sensitivity of linear-benzoadenine nucleotides to divalent metal counterions, side chain conformations, micelles, and enzymes. Proc Natl Acad Sci U S A. 1978 Sep;75(9):4204-8. PubMed PMID: 16592561; PubMed Central PMCID: PMC336080. 7: Orozco M, Canela EI, Franco R. A quantum chemical study of the enzymatic deamination of benzoadenine derivatives. A theoretical model of the interactions occurring between nucleosides and the active site of adenosine deaminase. Eur J Biochem. 1990 Feb 22;188(1):155-63. PubMed PMID: 2156693. 8: Scopes DI, Barrio JR, Leonard NJ. Defined dimensional changes in enzyme cofactors: fluorescent "stretched-out" analogs of adenine nucleotides. Science. 1977 Jan 21;195(4275):296-8. PubMed PMID: 188137. 9: Liu H, Lynch SR, Kool ET. Solution structure of xDNA: a paired genetic helix with increased diameter. J Am Chem Soc. 2004 Jun 9;126(22):6900-5. PubMed PMID: 15174859. 10: Leonard NJ, Cruickshank KA, Groziak MP, Clauson GL, Devadas B. Relatives of Watson-Crick DNA, RNA cross sections. Ann N Y Acad Sci. 1986;471:255-65. PubMed PMID: 2425693. 11: VanDerLijn P, Barrio JR, Leonard NJ. Inhibition of adenylate kinase by P1-(lin-benzo-5'-adenosyl)-P4-(5'-adenosyl) tetraphosphate and P1-(lin-benzo-5'-adenosyl)-P5-(5'-adenosyl pentaphosphate. Biochemistry. 1979 Dec 11;18(25):5557-61. PubMed PMID: 229895. 12: Hartl FT, Roskoski R Jr, Rosendahl MS, Leonard NJ. Adenosine cyclic 3',5'-monophosphate dependent protein kinase: interaction of the catalytic subunit and holoenzyme with lin-benzoadenine nucleotides. Biochemistry. 1983 May 10;22(10):2347-52. PubMed PMID: 6305401. 13: Bhatnagar D, Glass DB, Roskoski R Jr, Lessor RA, Leonard NJ. Interaction of guanosine cyclic 3',5'-phosphate dependent protein kinase with lin-benzoadenine nucleotides. Biochemistry. 1985 Feb 26;24(5):1122-9. PubMed PMID: 3006744. 14: Bhatnagar D, Roskoski R Jr, Rosendahl MS, Leonard NJ. Adenosine cyclic 3',5'-monophosphate dependent protein kinase: a new fluorescence displacement titration technique for characterizing the nucleotide binding site on the catalytic subunit. Biochemistry. 1983 Dec 20;22(26):6310-7. PubMed PMID: 6318814.