Griseolic acid

MedKoo Cat#: 592689 | Name: Griseolic acid

Description:

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

Griseolic acid is an inhibitor of cyclic adenosine 3',5'-monophosphate phosphodiesterase. II..

Chemical Structure

Griseolic acid

CAS#79030-08-3

Theoretical Analysis

MedKoo Cat#: 592689

Name: Griseolic acid

CAS#: 79030-08-3

Chemical Formula: C14H13N5O8

Exact Mass: 379.0764

Molecular Weight: 379.29

Elemental Analysis: C, 44.33; H, 3.45; N, 18.47; O, 33.75

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Griseolic acid

IUPAC/Chemical Name

(2R,5R,6S,6aS)-5-(6-amino-9H-purin-9-yl)-2-((R)-carboxy(hydroxy)methyl)-6-hydroxy-2,5,6,6a-tetrahydrofuro[3,2-b]furan-2-carboxylic acid

InChi Key

IAPZXUKYTCQQFE-BOPMFSTPSA-N

InChi Code

InChI=1S/C14H13N5O8/c15-9-5-10(17-2-16-9)19(3-18-5)11-6(20)7-4(26-11)1-14(27-7,13(24)25)8(21)12(22)23/h1-3,6-8,11,20-21H,(H,22,23)(H,24,25)(H2,15,16,17)/t6-,7+,8-,11+,14+/m0/s1

SMILES Code

O=C([C@]1([C@H](C(O)=O)O)C=C(O[C@@H](N2C=NC3=C(N)N=CN=C23)[C@H]4O)[C@@]4([H])O1)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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 379.29 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: Takahashi S, Nakagawa F, Kawazoe K, Furukawa Y, Sato S, Tamura C, Naito A. Griseolic acid, an inhibitor of cyclic adenosine 3',5'-monophosphate phosphodiesterase. II. The structure of griseolic acid. J Antibiot (Tokyo). 1985 Jul;38(7):830-4. PubMed PMID: 2993219. 2: Miyakoshi S, Haruyama H, Shioiri T, Takahashi S, Torikata A, Yamazaki M. Biosynthesis of griseolic acids: incorporation of 13C-labeled compounds into griseolic acid A. J Antibiot (Tokyo). 1992 Mar;45(3):394-9. PubMed PMID: 1315729. 3: Murofushi Y, Kimura M, Iijima Y, Yamazaki M, Kaneko M. Studies on griseolic acid derivatives. IV. Synthesis and phosphodiesterase inhibitory activity of acylated derivatives of griseolic acid. Chem Pharm Bull (Tokyo). 1987 Mar;35(3):1036-43. PubMed PMID: 3038344. 4: Murofushi Y, Kimura M, Iijima Y, Yamazaki M, Kaneko M. Studies on griseolic acid derivatives. V. Synthesis and phosphodiesterase inhibitory activity of substituted derivatives of the hydroxy group at the 2'- or 7'-position in griseolic acid. Chem Pharm Bull (Tokyo). 1987 Nov;35(11):4442-53. PubMed PMID: 3442882. 5: Murofushi Y, Kimura M, Kuwano H, Iijima Y, Yamazaki M, Kaneko M. Studies on griseolic acid derivatives. VII. Synthesis and phosphodiesterase inhibitory activity of the C4'-C5' hydrogenated products of griseolic acid and their base-exchanged derivatives. Chem Pharm Bull (Tokyo). 1988 Oct;36(10):3760-9. PubMed PMID: 2854497. 6: Iijima Y, Nakagawa F, Handa S, Oda T, Naito A, Yamazaki M. Biological properties of griseolic acid, a cyclic AMP phosphodiesterase inhibitor with an adenine group. FEBS Lett. 1985 Nov 18;192(2):179-83. PubMed PMID: 2998865. 7: Yasumoto T, Iijima Y, Kaneko M, Yamazaki M. Properties of base-substituted and carboxyl-esterified analogues of griseolic acid, a potent cAMP phosphodiesterase inhibitor. Biochem Pharmacol. 1992 May 28;43(10):2073-81. PubMed PMID: 1318049. 8: Kaneko M, Murofushi Y, Kimura M, Yamazaki M, Iijima Y. Studies on griseolic acid derivatives. I. Synthesis of substituted derivatives of griseolic acid at the N1, C6, C2' or C7' position and their biological activities. Nucleic Acids Symp Ser. 1985;(16):89-92. PubMed PMID: 3003711. 9: Murofushi Y, Kimura M, Iijima Y, Yamazaki M, Kaneko M. Studies on griseolic acid derivatives. VI. Synthesis and phosphodiesterase-inhibitory activity of 6- and N1-substituted derivatives of griseolic acid. Chem Pharm Bull (Tokyo). 1988 Apr;36(4):1309-20. PubMed PMID: 2843300. 10: Mishima HK, Kiuchi Y, Yokoyama T, Yasumoto T, Yamazaki M. A cyclic AMP phosphodiesterase inhibitor, 8'-pivaloyloxymethyl ester (POM-ester) of griseolic acid, lowers rabbit intraocular pressure. Curr Eye Res. 1991 Sep;10(9):817-22. PubMed PMID: 1665121. 11: Mitsui K, Tsuji S, Yamazaki M, Nagai Y. Multiple neurite formation in neuroblastoma cell lines by griseolic acid, a potent inhibitor of cyclic nucleotide phosphodiesterases. J Neurochem. 1991 Aug;57(2):556-61. PubMed PMID: 1649254. 12: Nakagawa F, Okazaki T, Naito A, Iijima Y, Yamazaki M. Griseolic acid, an inhibitor of cyclic adenosine 3',5'-monophosphate phosphodiesterase. I. Taxonomy, isolation and characterization. J Antibiot (Tokyo). 1985 Jul;38(7):824-9. PubMed PMID: 2993218. 13: Hashimoto N, Makino H, Kanatsuka A, Yamazaki M, Yoshida S. Effects of the new phosphodiesterase inhibitor griseolic acid on insulin release in rat pancreatic islets. Arzneimittelforschung. 1990 Oct;40(10):1098-101. PubMed PMID: 1705426. 14: Murofushi Y, Kimura M, Kuwano H, Iijima Y, Yamazaki M, Kaneko M. Studies on griseolic acid derivatives. III. Synthesis and biological activities of the adducts of griseolic acid and their base exchanged derivatives. Nucleic Acids Symp Ser. 1986;(17):45-8. PubMed PMID: 3031627. 15: Knapp S, Madduru MR, Lu Z, Morriello GJ, Emge TJ, Doss GA. Synthesis of griseolic acid B by pi-face-dependent radical cyclization. Org Lett. 2001 Nov 1;3(22):3583-5. PubMed PMID: 11678714. 16: Kiuchi Y. [Changes in ocular hypotensive effect of griseolic acid with isoproterenol, timolol and melanin]. Nippon Ganka Gakkai Zasshi. 1990 Jul;94(7):663-72. Japanese. PubMed PMID: 2171307. 17: Kaneko M, Yamazaki M. [Phosphodiesterase inhibitor: griseolic acid, its' derivatives and their biological activities]. Tanpakushitsu Kakusan Koso. 1995 Jul;40(10):1268-76. Review. Japanese. PubMed PMID: 7568925. 18: Tulshian D, Czarniecki M, Doll RJ, Ahn HS. Synthesis and phosphodiesterase activity of carboxylic acid mimetics of cyclic guanosine 3',5'-monophosphate. J Med Chem. 1993 Apr 30;36(9):1210-20. PubMed PMID: 8387599. 19: Makino H, Suzuki T, Kajinuma H, Yamazaki M, Ito H, Yoshida S. The role of insulin-sensitive phosphodiesterase in insulin action. Adv Second Messenger Phosphoprotein Res. 1992;25:185-99. PubMed PMID: 1372810. 20: Karche NP, Jachak SM, Dhavale DD. Synthesis of griseolic acid analogues: regioselective alpha-facial [1,2]-migration in the rhodium acetate catalyzed reaction of D-glucose derived alpha-diazo-beta-keto ester. J Org Chem. 2003 May 30;68(11):4531-4. PubMed PMID: 12762763.