L-755507 | CAS#159182-43-1 | β3-adrenergic receptor Agonist |MedKoo

L-755507
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 532084

CAS#: 159182-43-1

Description: L-755507 is a potent β3-adrenergic receptor partial agonist > 1000-fold selective over β1- and β2-adrenoceptors (EC50 values are 0.43, 580 and > 10000 nM for activation of cloned human β3-, β1- and β2-adrenoceptors respectively). L-755507 stimulates lipolysis in rhesus adipocytes in vitro (EC50 = 3.9 nM).

Chemical Structure

L-755507

CAS# 159182-43-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 532084
Name: L-755507
CAS#: 159182-43-1
Chemical Formula: C30H40N4O6S
Exact Mass: 584.27
Molecular Weight: 584.732
Elemental Analysis: C, 61.62; H, 6.90; N, 9.58; O, 16.42; S, 5.48

Price and Availability

Size	Price	Availability
10mg	USD 350	2 Weeks
25mg	USD 700	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: L-755507; L 755507; L755507.

IUPAC/Chemical Name: 1-hexyl-3-[4-[[4-[2-[[(2S)-2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]phenyl]sulfamoyl]phenyl]urea

InChi Key: NYYJKMXNVNFOFQ-MHZLTWQESA-N

InChi Code: InChI=1S/C30H40N4O6S/c1-2-3-4-5-19-32-30(37)33-24-10-16-29(17-11-24)41(38,39)34-25-8-6-23(7-9-25)18-20-31-21-27(36)22-40-28-14-12-26(35)13-15-28/h6-17,27,31,34-36H,2-5,18-22H2,1H3,(H2,32,33,37)/t27-/m0/s1

SMILES Code: O=C(NC1=CC=C(S(=O)(NC2=CC=C(CCNC[C@H](O)COC3=CC=C(O)C=C3)C=C2)=O)C=C1)NCCCCCC

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:

Product Data:

Product Data

Instruction:

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Biological target:	L755507 is a potent, selective agonist of β3-AR with an IC50 of 35 nM.
In vitro activity:	L755507 successfully disrupts the c-Myc-MAX heterodimer, resulting in decreased expression of c-Myc target genes. Spectroscopic and computational experiments demonstrated that L755507 binds to the c-Myc peptide and thereby stabilizes the helix-loop-helix conformation of the c-Myc transcription factor. Taken together, this study suggests that L755507 effectively inhibits the c-Myc-MAX heterodimerization and may be used for further optimization to develop a c-Myc-targeted antineoplastic drug. Reference: J Biol Chem. 2021 Jul;297(1):100903. https://pubmed.ncbi.nlm.nih.gov/34157284/
In vivo activity:	Similarly, stimulation with the selective human beta(3)AR agonist L-755,507 significantly increased contractility in the TGbeta(3) mice (160%), with no effect in wild-type mice, as determined by hemodynamic measurements and by end-systolic pressure-volume relations. Reference: Circulation. 2001 Nov 13;104(20):2485-91. https://pubmed.ncbi.nlm.nih.gov/11705829/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	30.0	51.31
	DMSO	70.9	121.20
	Ethanol	44.2	75.65
	Ethanol:PBS (pH 7.2) (1:3)	0.3	0.43

Preparing Stock Solutions

The following data is based on the product molecular weight 584.73 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. Singh A, Kumar A, Kumar P, Nayak N, Bhardwaj T, Giri R, Garg N. A novel inhibitor L755507 efficiently blocks c-Myc-MAX heterodimerization and induces apoptosis in cancer cells. J Biol Chem. 2021 Jul;297(1):100903. doi: 10.1016/j.jbc.2021.100903. Epub 2021 Jun 23. PMID: 34157284; PMCID: PMC8294579. 2. Kimura K, Sasaki N, Asano A, Mizukami J, Kayahashi S, Kawada T, Fushiki T, Morimatsu M, Yoshida T, Saito M. Mutated human beta3-adrenergic receptor (Trp64Arg) lowers the response to beta3-adrenergic agonists in transfected 3T3-L1 preadipocytes. Horm Metab Res. 2000 Mar;32(3):91-6. doi: 10.1055/s-2007-978597. PMID: 10786926. 3. Kohout TA, Takaoka H, McDonald PH, Perry SJ, Mao L, Lefkowitz RJ, Rockman HA. Augmentation of cardiac contractility mediated by the human beta(3)-adrenergic receptor overexpressed in the hearts of transgenic mice. Circulation. 2001 Nov 13;104(20):2485-91. doi: 10.1161/hc4501.098933. PMID: 11705829.
In vitro protocol:	1. Singh A, Kumar A, Kumar P, Nayak N, Bhardwaj T, Giri R, Garg N. A novel inhibitor L755507 efficiently blocks c-Myc-MAX heterodimerization and induces apoptosis in cancer cells. J Biol Chem. 2021 Jul;297(1):100903. doi: 10.1016/j.jbc.2021.100903. Epub 2021 Jun 23. PMID: 34157284; PMCID: PMC8294579. 2. Kimura K, Sasaki N, Asano A, Mizukami J, Kayahashi S, Kawada T, Fushiki T, Morimatsu M, Yoshida T, Saito M. Mutated human beta3-adrenergic receptor (Trp64Arg) lowers the response to beta3-adrenergic agonists in transfected 3T3-L1 preadipocytes. Horm Metab Res. 2000 Mar;32(3):91-6. doi: 10.1055/s-2007-978597. PMID: 10786926.
In vivo protocol:	1. Kohout TA, Takaoka H, McDonald PH, Perry SJ, Mao L, Lefkowitz RJ, Rockman HA. Augmentation of cardiac contractility mediated by the human beta(3)-adrenergic receptor overexpressed in the hearts of transgenic mice. Circulation. 2001 Nov 13;104(20):2485-91. doi: 10.1161/hc4501.098933. PMID: 11705829.

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1: Afeli SA, Hristov KL, Petkov GV. Do β3-adrenergic receptors play a role in guinea pig detrusor smooth muscle excitability and contractility? Am J Physiol Renal Physiol. 2012 Jan 15;302(2):F251-63. doi: 10.1152/ajprenal.00378.2011. PubMed PMID: 21993887; PubMed Central PMCID: PMC3340921.

2: Sato M, Hutchinson DS, Evans BA, Summers RJ. The beta3-adrenoceptor agonist 4-[[(Hexylamino)carbonyl]amino]-N-[4-[2-[[(2S)-2-hydroxy-3-(4-hydroxyphenoxy)prop yl]amino]ethyl]-phenyl]-benzenesulfonamide (L755507) and antagonist (S)-N-[4-[2-[[3-[3-(acetamidomethyl)phenoxy]-2-hydroxypropyl]amino]-ethyl]phenyl] benzenesulfonamide (L748337) activate different signaling pathways in Chinese hamster ovary-K1 cells stably expressing the human beta3-adrenoceptor. Mol Pharmacol. 2008 Nov;74(5):1417-28. doi: 10.1124/mol.108.046979. PubMed PMID: 18684840.

3: Kohout TA, Takaoka H, McDonald PH, Perry SJ, Mao L, Lefkowitz RJ, Rockman HA. Augmentation of cardiac contractility mediated by the human beta(3)-adrenergic receptor overexpressed in the hearts of transgenic mice. Circulation. 2001 Nov 13;104(20):2485-91. PubMed PMID: 11705829.

4: Kimura K, Sasaki N, Asano A, Mizukami J, Kayahashi S, Kawada T, Fushiki T, Morimatsu M, Yoshida T, Saito M. Mutated human beta3-adrenergic receptor (Trp64Arg) lowers the response to beta3-adrenergic agonists in transfected 3T3-L1 preadipocytes. Horm Metab Res. 2000 Mar;32(3):91-6. PubMed PMID: 10786926.

5: Parmee ER, Naylor EM, Perkins L, Colandrea VJ, Ok HO, Candelore MR, Cascieri MA, Deng L, Feeney WP, Forrest MJ, Hom GJ, MacIntyre DE, Miller RR, Stearns RA, Strader CD, Tota L, Wyvratt MJ, Fisher MH, Weber AE. Human beta3 adrenergic receptor agonists containing cyclic ureidobenzenesulfonamides. Bioorg Med Chem Lett. 1999 Mar 8;9(5):749-54. PubMed PMID: 10201841.

6: Umekawa T, Yoshida T, Sakane N, Kogure A, Kondo M, Honjyo H. Trp64Arg mutation of beta3-adrenoceptor gene deteriorates lipolysis induced by beta3-adrenoceptor agonist in human omental adipocytes. Diabetes. 1999 Jan;48(1):117-20. PubMed PMID: 9892231.

7: Naylor EM, Colandrea VJ, Candelore MR, Cascieri MA, Colwell LF Jr, Deng L, Feeney WP, Forrest MJ, Hom GJ, MacIntyre DE, Strader CD, Tota L, Wang PR, Wyvratt MJ, Fisher MH, Weber AE. 3-Pyridylethanolamines: potent and selective human beta 3 adrenergic receptor agonists. Bioorg Med Chem Lett. 1998 Nov 3;8(21):3087-92. PubMed PMID: 9873681.

8: Parmee ER, Ok HO, Candelore MR, Tota L, Deng L, Strader CD, Wyvratt MJ, Fisher MH, Weber AE. Discovery of L-755,507: a subnanomolar human beta 3 adrenergic receptor agonist. Bioorg Med Chem Lett. 1998 May 5;8(9):1107-12. PubMed PMID: 9871717.

9: Fisher MH, Amend AM, Bach TJ, Barker JM, Brady EJ, Candelore MR, Carroll D, Cascieri MA, Chiu SH, Deng L, Forrest MJ, Hegarty-Friscino B, Guan XM, Hom GJ, Hutchins JE, Kelly LJ, Mathvink RJ, Metzger JM, Miller RR, Ok HO, Parmee ER, Saperstein R, Strader CD, Stearns RA, MacIntyre DE, et al. A selective human beta3 adrenergic receptor agonist increases metabolic rate in rhesus monkeys. J Clin Invest. 1998 Jun 1;101(11):2387-93. PubMed PMID: 9616210; PubMed Central PMCID: PMC508828.

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