L 858051 | CAS#110452-75-0 | glucose transport inhibitor

MedKoo Cat#: 596712 | Name: L 858051

Description:

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

L 858051 activates adenylate cyclase and inhibits glucose transport in rat adipocytes.

Chemical Structure

L 858051

CAS#110452-75-0

Theoretical Analysis

MedKoo Cat#: 596712

Name: L 858051

CAS#: 110452-75-0

Chemical Formula: C29H48N2O7

Exact Mass: 536.3462

Molecular Weight: 536.71

Elemental Analysis: C, 64.90; H, 9.01; N, 5.22; O, 20.87

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

L 858051; L-858051; L858051; 7B-Forskolin; Dmpb-forskolin;

IUPAC/Chemical Name

(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-3-vinyldodecahydro-1H-benzo[f]chromen-5-yl 4-(4-methylpiperazin-1-yl)butanoate

InChi Key

PAYHDZDDAHVPDU-ZQVYKFDISA-N

InChi Code

InChI=1S/C29H48N2O7/c1-8-26(4)18-20(33)29(36)27(5)19(32)11-12-25(2,3)23(27)22(35)24(28(29,6)38-26)37-21(34)10-9-13-31-16-14-30(7)15-17-31/h8,19,22-24,32,35-36H,1,9-18H2,2-7H3/t19-,22-,23-,24-,26-,27-,28+,29-/m0/s1

SMILES Code

O=C(O[C@H]1[C@@H](O)[C@@]2([H])C(C)(C)CC[C@H](O)[C@]2(C)[C@]3(O)[C@]1(C)O[C@@](C)(C=C)CC3=O)CCCN4CCN(C)CC4

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

>2 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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 536.71 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: Belacel-Ouari M, Zhang L, Hubert F, Assaly R, Gerbier R, Jockers R, Dauphin F, Lechêne P, Fischmeister R, Manoury B, Leblais V. Influence of cell confluence on the cAMP signalling pathway in vascular smooth muscle cells. Cell Signal. 2017 Jul;35:118-128. doi: 10.1016/j.cellsig.2017.03.025. Epub 2017 Apr 4. PubMed PMID: 28389413. 2: Haj Slimane Z, Bedioune I, Lechêne P, Varin A, Lefebvre F, Mateo P, Domergue-Dupont V, Dewenter M, Richter W, Conti M, El-Armouche A, Zhang J, Fischmeister R, Vandecasteele G. Control of cytoplasmic and nuclear protein kinase A by phosphodiesterases and phosphatases in cardiac myocytes. Cardiovasc Res. 2014 Apr 1;102(1):97-106. doi: 10.1093/cvr/cvu029. Epub 2014 Feb 18. PubMed PMID: 24550350; PubMed Central PMCID: PMC3958623. 3: Funaki C, Hodges RR, Dartt DA. Role of cAMP inhibition of p44/p42 mitogen-activated protein kinase in potentiation of protein secretion in rat lacrimal gland. Am J Physiol Cell Physiol. 2007 Nov;293(5):C1551-60. Epub 2007 Aug 8. PubMed PMID: 17687004. 4: Rochais F, Vandecasteele G, Lefebvre F, Lugnier C, Lum H, Mazet JL, Cooper DM, Fischmeister R. Negative feedback exerted by cAMP-dependent protein kinase and cAMP phosphodiesterase on subsarcolemmal cAMP signals in intact cardiac myocytes: an in vivo study using adenovirus-mediated expression of CNG channels. J Biol Chem. 2004 Dec 10;279(50):52095-105. Epub 2004 Oct 1. PubMed PMID: 15466415. 5: Loir M. Adenosine receptor-adenylate cyclase system in the trout testis: involvement in the regulation of germ cell proliferation. Mol Reprod Dev. 2001 Mar;58(3):307-17. PubMed PMID: 11170272. 6: Yang CM, Chiu CT, Wang CC, Tsao HL, Fan LW. Forskolin inhibits 5-hydroxytryptamine-induced phosphoinositide hydrolysis and Ca+2 Mobilisation in canine cultured aorta smooth muscle cells. Cell Signal. 1999 Sep;11(9):697-704. PubMed PMID: 10530879. 7: Abi-Gerges N, Tavernier B, Mebazaa A, Faivre V, Paqueron X, Payen D, Fischmeister R, Méry PF. Sequential changes in autonomic regulation of cardiac myocytes after in vivo endotoxin injection in rat. Am J Respir Crit Care Med. 1999 Oct;160(4):1196-204. PubMed PMID: 10508807. 8: Yang CM, Pan SL, Chiu CT, Lin CC, Hsu YM. Effect of forskolin on endothelin-induced phosphoinositide hydrolysis and calcium mobilization in cultured canine tracheal smooth muscle cells. J Auton Pharmacol. 1998 Aug;18(4):213-21. PubMed PMID: 9788291. 9: Gillard ER, Khan AM, Mouradi B, Nalamwar O, Stanley BG. Eating induced by perifornical cAMP is behaviorally selective and involves protein kinase activity. Am J Physiol. 1998 Aug;275(2 Pt 2):R647-53. PubMed PMID: 9688705. 10: Gillard ER, Khan AM, Grewal RS, Mouradi B, Wolfsohn SD, Stanley BG. The second messenger cAMP elicits eating by an anatomically specific action in the perifornical hypothalamus. J Neurosci. 1998 Apr 1;18(7):2646-52. PubMed PMID: 9502822. 11: Brundege JM, Diao L, Proctor WR, Dunwiddie TV. The role of cyclic AMP as a precursor of extracellular adenosine in the rat hippocampus. Neuropharmacology. 1997 Sep;36(9):1201-10. PubMed PMID: 9364475. 12: Gillard ER, Khan AM, Ahsan-ul-Haq, Grewal RS, Mouradi B, Stanley BG. Stimulation of eating by the second messenger cAMP in the perifornical and lateral hypothalamus. Am J Physiol. 1997 Jul;273(1 Pt 2):R107-12. PubMed PMID: 9249539. 13: Luo SF, Chiu CT, Tsao HL, Fan LW, Tsai CT, Pan SL, Yang CM. Effect of forskolin on bradykinin-induced calcium mobilization in cultured canine tracheal smooth muscle cells. Cell Signal. 1997 Feb;9(2):159-67. PubMed PMID: 9113415. 14: Yang C, Tsao HL, Chiu CT, Fan LW, Yu SM. Regulation of 5-hydroxytryptamine-induced calcium mobilization by cAMP-elevating agents in cultured canine tracheal smooth muscle cells. Pflugers Arch. 1996 Aug;432(4):708-16. PubMed PMID: 8764973. 15: Green AK, Cobbold PH, Dixon CJ. Cytosolic free Ca2+ oscillations induced by diadenosine 5',5"'-P1,P3-triphosphate and diadenosine 5',5"'-P1,P4-tetraphosphate in single rat hepatocytes are indistinguishable from those induced by ADP and ATP respectively. Biochem J. 1995 Sep 1;310 ( Pt 2):629-35. PubMed PMID: 7654204; PubMed Central PMCID: PMC1135942. 16: Green AK, Cobbold PH, Dixon CJ. Elevated intracellular cyclic AMP exerts different modulatory effects on cytosolic free Ca2+ oscillations induced by ADP and ATP in single rat hepatocytes. Biochem J. 1994 Sep 15;302 ( Pt 3):949-55. PubMed PMID: 7945225; PubMed Central PMCID: PMC1137322. 17: Lorenz JN, Bielefeld DR, Sperelakis N. Regulation of calcium channel current in A7r5 vascular smooth muscle cells by cyclic nucleotides. Am J Physiol. 1994 Jun;266(6 Pt 1):C1656-63. PubMed PMID: 8023895. 18: Klein M. Differential cyclic AMP dependence of facilitation at Aplysia sensorimotor synapses as a function of prior stimulation: augmentation versus restoration of transmitter release. J Neurosci. 1993 Sep;13(9):3793-801. PubMed PMID: 8396169. 19: Alava MA, DeBell KE, Conti A, Hoffman T, Bonvini E. Increased intracellular cyclic AMP inhibits inositol phospholipid hydrolysis induced by perturbation of the T cell receptor/CD3 complex but not by G-protein stimulation. Association with protein kinase A-mediated phosphorylation of phospholipase C-gamma 1. Biochem J. 1992 May 15;284 ( Pt 1):189-99. PubMed PMID: 1318020; PubMed Central PMCID: PMC1132715. 20: Hartzell HC, Budnitz D. Differences in effects of forskolin and an analog on calcium currents in cardiac myocytes suggest intra- and extracellular sites of action. Mol Pharmacol. 1992 May;41(5):880-8. PubMed PMID: 1317001.