Talirine-maleimide | Mc-Val-Ala-pbd | CAS#1342820-51-2 | PBD

MedKoo Cat#: 596750 | Name: Talirine-maleimide

Description:

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

Talirine-maleimide, also known as Mc-Val-Ala-pbd, is a pyrrolobenzodiazepine (PBD, a cytotoxic DNA crosslinking) derivative with a maleimide group via a cleavable linker Val-Ala. The maleimide group is reactive to surfuryl group (SH group), and is useful for making antibody drug conjugate (ADC). Talirine-maleimide may be useful for making anticancer drug conjugates.

Chemical Structure

Talirine-maleimide

CAS#1342820-51-2

Theoretical Analysis

MedKoo Cat#: 596750

Name: Talirine-maleimide

CAS#: 1342820-51-2

Chemical Formula: C60H64N8O12

Exact Mass: 1088.4644

Molecular Weight: 1089.21

Elemental Analysis: C, 66.16; H, 5.92; N, 10.29; O, 17.63

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

Mc-Val-Ala-pbd; Talirine, maleimide-;

IUPAC/Chemical Name

6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-((S)-7-methoxy-8-(3-(((S)-7-methoxy-2-(4-methoxyphenyl)-5-oxo-5,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yl)oxy)propoxy)-5-oxo-5,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)phenyl)amino)-1-oxopropan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide

InChi Key

TWQIMWSQDICMSE-DGCIIGOYSA-N

InChi Code

InChI=1S/C60H64N8O12/c1-35(2)56(65-53(69)11-8-7-9-22-66-54(70)20-21-55(66)71)58(73)63-36(3)57(72)64-41-16-12-37(13-17-41)39-25-42-31-61-47-29-51(49(77-5)27-45(47)59(74)67(42)33-39)79-23-10-24-80-52-30-48-46(28-50(52)78-6)60(75)68-34-40(26-43(68)32-62-48)38-14-18-44(76-4)19-15-38/h12-21,27-36,42-43,56H,7-11,22-26H2,1-6H3,(H,63,73)(H,64,72)(H,65,69)/t36-,42-,43-,56-/m0/s1

SMILES Code

O=C(N[C@@H](C(C)C)C(N[C@@H](C)C(NC1=CC=C(C(C2)=CN3[C@]2([H])C=NC4=CC(OCCCOC5=C(OC)C=C6C(N=C[C@@](CC(C7=CC=C(OC)C=C7)=C8)([H])N8C6=O)=C5)=C(OC)C=C4C3=O)C=C1)=O)=O)CCCCCN9C(C=CC9=O)=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

>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 1,089.21 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: Terrill JR, Boyatzis A, Grounds MD, Arthur PG. Treatment with the cysteine precursor l-2-oxothiazolidine-4-carboxylate (OTC) implicates taurine deficiency in severity of dystropathology in mdx mice. Int J Biochem Cell Biol. 2013 Sep;45(9):2097-108. doi: 10.1016/j.biocel.2013.07.009. Epub 2013 Jul 24. PubMed PMID: 23892094. 2: Falktoft B, Lambert IH. Ca2+-mediated potentiation of the swelling-induced taurine efflux from HeLa cells: on the role of calmodulin and novel protein kinase C isoforms. J Membr Biol. 2004 Sep 15;201(2):59-75. PubMed PMID: 15630544. 3: McConkey M, Gillin H, Webster CR, Anwer MS. Cross-talk between protein kinases Czeta and B in cyclic AMP-mediated sodium taurocholate co-transporting polypeptide translocation in hepatocytes. J Biol Chem. 2004 May 14;279(20):20882-8. Epub 2004 Mar 8. PubMed PMID: 15007074. 4: Kubitz R, Saha N, Kühlkamp T, Dutta S, vom Dahl S, Wettstein M, Häussinger D. Ca2+-dependent protein kinase C isoforms induce cholestasis in rat liver. J Biol Chem. 2004 Mar 12;279(11):10323-30. Epub 2003 Dec 16. PubMed PMID: 14679204. 5: Sfakianos MK, Wilson L, Sakalian M, Falany CN, Barnes S. Conserved residues in the putative catalytic triad of human bile acid Coenzyme A:amino acid N-acyltransferase. J Biol Chem. 2002 Dec 6;277(49):47270-5. Epub 2002 Sep 17. PubMed PMID: 12239217. 6: Kiessling K, Ellory JC, Cossins AR. The relationship between hypotonically-induced taurine and K fluxes in trout red blood cells. Pflugers Arch. 2000 Jul;440(3):467-75. PubMed PMID: 10954334. 7: Prasad M, Matthews JB, He XD, Akbarali HI. Monochloramine directly modulates Ca(2+)-activated K(+) channels in rabbit colonic muscularis mucosae. Gastroenterology. 1999 Oct;117(4):906-17. PubMed PMID: 10500074. 8: Zielińska M, Hilgier W, Law RO, Goryński P, Albrecht J. Effects of ammonia in vitro on endogenous taurine efflux and cell volume in rat cerebrocortical minislices: influence of inhibitors of volume-sensitive amino acid transport. Neuroscience. 1999;91(2):631-8. PubMed PMID: 10366020. 9: Schliess F, Kurz AK, vom Dahl S, Häussinger D. Mitogen-activated protein kinases mediate the stimulation of bile acid secretion by tauroursodeoxycholate in rat liver. Gastroenterology. 1997 Oct;113(4):1306-14. PubMed PMID: 9322526. 10: Natarajan R, Ghosh S, Grogan W. Catalytic properties of the purified rat hepatic cytosolic cholesteryl ester hydrolase. Biochem Biophys Res Commun. 1996 Aug 14;225(2):413-9. PubMed PMID: 8753777. 11: Dumaswala R, Brown TL. Sulphydryl modification inhibits taurine transport in human placental brush border membranes. Placenta. 1996 Jul-Aug;17(5-6):329-36. PubMed PMID: 8829216. 12: Upton EL, Law RO. The role of sulphydryl groups in efflux of taurine and GABA from cerebral cortical cells. Adv Exp Med Biol. 1996;403:409-16. PubMed PMID: 8915378. 13: Bursell JD, Kirk K. Swelling-activated K+ transport via two functionally distinct pathways in eel erythrocytes. Am J Physiol. 1996 Jan;270(1 Pt 2):R61-70. PubMed PMID: 8769785. 14: Machida M, Sano K, Arakawa M, Hayashi M, Awazu S. Effects of surfactants and protease inhibitors on nasal absorption of recombinant human granulocyte colony-stimulating factor (rhG-CSF) in rats. Biol Pharm Bull. 1994 Oct;17(10):1375-8. PubMed PMID: 7533020. 15: Martínez A, Muñoz-Clares RA, Guerra G, Morán J, Pasantes-Morales H. Sulfhydryl groups essential for the volume-sensitive release of taurine from astrocytes. Neurosci Lett. 1994 Aug 1;176(2):239-42. PubMed PMID: 7830955. 16: Vissers MC, Stern A, Kuypers F, van den Berg J, Winterbourn CC. Membrane changes associated with lysis of red blood cells by hypochlorous acid. Free Radic Biol Med. 1994 Jun;16(6):703-12. PubMed PMID: 8070673. 17: Gibson JS, Ellory JC, Culliford SJ, Fincham DA. Volume-sensitive KCl co-transport and taurine fluxes in horse red blood cells. Exp Physiol. 1993 Sep;78(5):685-95. PubMed PMID: 8240799. 18: Blumrich M, Petzinger E. Membrane transport of conjugated and unconjugated bile acids into hepatocytes is susceptible to SH-blocking reagents. Biochim Biophys Acta. 1990 Nov 2;1029(1):1-12. PubMed PMID: 2171648. 19: Kleinzeller A, Booz GW, Mills JW, Ziyadeh FN. pCMBS-induced swelling of dogfish (Squalus acanthias) rectal gland cells: role of the Na+,K(+)-ATPase and the cytoskeleton. Biochim Biophys Acta. 1990 Jun 11;1025(1):21-31. PubMed PMID: 2164417. 20: Romano M, Razandi M, Ivey KJ. Effect of cimetidine and ranitidine on drug induced damage to gastric epithelial cell monolayers in vitro. Gut. 1989 Oct;30(10):1313-22. PubMed PMID: 2583559; PubMed Central PMCID: PMC1434397.