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MedKoo Cat#: 585122 | Name: SJG 136

Description:

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

SJG 136 is a DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumor activity

Chemical Structure

SJG 136
SJG 136
CAS#232931-57-6

Theoretical Analysis

MedKoo Cat#: 585122

Name: SJG 136

CAS#: 232931-57-6

Chemical Formula: C31H32N4O8

Exact Mass: 588.2220

Molecular Weight: 588.62

Elemental Analysis: C, 63.26; H, 5.48; N, 9.52; O, 21.74

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
SJG 136; SJG136; SJG-136
IUPAC/Chemical Name
1,1'-((Propane-1,3-diyl)dioxy)bis(7-methoxy-2-methylidene-1,2,3,10,11,11a-hexahydro-5H-pyrrolo(2,1-c)(1,4)benzodiazepin-5,11-dione)
InChi Key
BJSOOANQHCJYPG-UHFFFAOYSA-N
InChi Code
InChI=1S/C31H32N4O8/c1-16-14-34-24(28(36)32-22-8-6-18(40-3)12-20(22)30(34)38)26(16)42-10-5-11-43-27-17(2)15-35-25(27)29(37)33-23-9-7-19(41-4)13-21(23)31(35)39/h6-9,12-13,24-27H,1-2,5,10-11,14-15H2,3-4H3,(H,32,36)(H,33,37)
SMILES Code
O=C1N2C(C(OCCCOC(C(N3C4)C(NC5=CC=C(OC)C=C5C3=O)=O)C4=C)C(C2)=C)C(NC6=CC=C(OC)C=C16)=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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 588.62 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.

Recalculate based on batch purity %
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: Janjigian YY, Lee W, Kris MG, Miller VA, Krug LM, Azzoli CG, Senturk E, Calcutt MW, Rizvi NA. A phase I trial of SJG-136 (NSC#694501) in advanced solid tumors. Cancer Chemother Pharmacol. 2010 Apr;65(5):833-8. doi: 10.1007/s00280-009-1088-4. Epub 2009 Aug 12. PubMed PMID: 19672598; PubMed Central PMCID: PMC3711187. 2: Arnould S, Spanswick VJ, Macpherson JS, Hartley JA, Thurston DE, Jodrell DI, Guichard SM. Time-dependent cytotoxicity induced by SJG-136 (NSC 694501): influence of the rate of interstrand cross-link formation on DNA damage signaling. Mol Cancer Ther. 2006 Jun;5(6):1602-9. PubMed PMID: 16818520. 3: Reid JM, Buhrow SA, Kuffel MJ, Jia L, Spanswick VJ, Hartley JA, Thurston DE, Tomaszewski JE, Ames MM. Pharmacokinetics, pharmacodynamics and metabolism of the dimeric pyrrolobenzodiazepine SJG-136 in rats. Cancer Chemother Pharmacol. 2011 Sep;68(3):777-86. doi: 10.1007/s00280-010-1517-4. Epub 2010 Dec 28. PubMed PMID: 21188379. 4: Alley MC, Hollingshead MG, Pacula-Cox CM, Waud WR, Hartley JA, Howard PW, Gregson SJ, Thurston DE, Sausville EA. SJG-136 (NSC 694501), a novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumor activity: part 2: efficacy evaluations. Cancer Res. 2004 Sep 15;64(18):6700-6. PubMed PMID: 15374987. 5: Hopton SR, Thompson AS. Nuclear magnetic resonance solution structures of inter- and intrastrand adducts of DNA cross-linker SJG-136. Biochemistry. 2011 May 31;50(21):4720-32. doi: 10.1021/bi102017e. Epub 2011 May 3. PubMed PMID: 21488658. 6: Hartley JA, Spanswick VJ, Brooks N, Clingen PH, McHugh PJ, Hochhauser D, Pedley RB, Kelland LR, Alley MC, Schultz R, Hollingshead MG, Schweikart KM, Tomaszewski JE, Sausville EA, Gregson SJ, Howard PW, Thurston DE. SJG-136 (NSC 694501), a novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumor activity: part 1: cellular pharmacology, in vitro and initial in vivo antitumor activity. Cancer Res. 2004 Sep 15;64(18):6693-9. PubMed PMID: 15374986. 7: Mellinas-Gomez M, Spanswick VJ, Paredes-Moscosso SR, Robson M, Pedley RB, Thurston DE, Baines SJ, Stell A, Hartley JA. Activity of the DNA minor groove cross-linking agent SG2000 (SJG-136) against canine tumours. BMC Vet Res. 2015 Aug 19;11:215. doi: 10.1186/s12917-015-0534-2. PubMed PMID: 26282406; PubMed Central PMCID: PMC4539724. 8: Buhrow SA, Reid JM, Jia L, McGovern RM, Covey JM, Kobs DJ, Grossi IM, Ames MM. LC-MS/MS assay and dog pharmacokinetics of the dimeric pyrrolobenzodiazepine SJG-136 (NSC 694501). J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Aug 7;840(1):56-62. Epub 2006 May 24. PubMed PMID: 16730244. 9: Cheung A, Struble E, He J, Yang C, Wang E, Thurston DE, Liu P. Direct liquid chromatography determination of the reactive imine SJG-136 (NSC 694501). J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):10-20. PubMed PMID: 15994138. 10: Pepper CJ, Hambly RM, Fegan CD, Delavault P, Thurston DE. The novel sequence-specific DNA cross-linking agent SJG-136 (NSC 694501) has potent and selective in vitro cytotoxicity in human B-cell chronic lymphocytic leukemia cells with evidence of a p53-independent mechanism of cell kill. Cancer Res. 2004 Sep 15;64(18):6750-5. PubMed PMID: 15374993. 11: Puzanov I, Lee W, Chen AP, Calcutt MW, Hachey DL, Vermeulen WL, Spanswick VJ, Liao CY, Hartley JA, Berlin JD, Rothenberg ML. Phase I pharmacokinetic and pharmacodynamic study of SJG-136, a novel DNA sequence selective minor groove cross-linking agent, in advanced solid tumors. Clin Cancer Res. 2011 Jun 1;17(11):3794-802. doi: 10.1158/1078-0432.CCR-10-2056. Epub 2011 Feb 23. PubMed PMID: 21346148; PubMed Central PMCID: PMC3107910. 12: Rahman KM, Thompson AS, James CH, Narayanaswamy M, Thurston DE. The pyrrolobenzodiazepine dimer SJG-136 forms sequence-dependent intrastrand DNA cross-links and monoalkylated adducts in addition to interstrand cross-links. J Am Chem Soc. 2009 Sep 30;131(38):13756-66. doi: 10.1021/ja902986x. PubMed PMID: 19725510. 13: Pepper C, Lowe H, Fegan C, Thurieau C, Thurston DE, Hartley JA, Delavault P. Fludarabine-mediated suppression of the excision repair enzyme ERCC1 contributes to the cytotoxic synergy with the DNA minor groove crosslinking agent SJG-136 (NSC 694501) in chronic lymphocytic leukaemia cells. Br J Cancer. 2007 Jul 16;97(2):253-9. Epub 2007 Jun 19. PubMed PMID: 17579621; PubMed Central PMCID: PMC2360304. 14: Guichard SM, Macpherson JS, Thurston DE, Jodrell DI. Influence of P-glycoprotein expression on in vitro cytotoxicity and in vivo antitumour activity of the novel pyrrolobenzodiazepine dimer SJG-136. Eur J Cancer. 2005 Aug;41(12):1811-8. PubMed PMID: 16046116. 15: Hochhauser D, Meyer T, Spanswick VJ, Wu J, Clingen PH, Loadman P, Cobb M, Gumbrell L, Begent RH, Hartley JA, Jodrell D. Phase I study of sequence-selective minor groove DNA binding agent SJG-136 in patients with advanced solid tumors. Clin Cancer Res. 2009 Mar 15;15(6):2140-7. doi: 10.1158/1078-0432.CCR-08-1315. Epub 2009 Mar 10. PubMed PMID: 19276288. 16: Clingen PH, De Silva IU, McHugh PJ, Ghadessy FJ, Tilby MJ, Thurston DE, Hartley JA. The XPF-ERCC1 endonuclease and homologous recombination contribute to the repair of minor groove DNA interstrand crosslinks in mammalian cells produced by the pyrrolo[2,1-c][1,4]benzodiazepine dimer SJG-136. Nucleic Acids Res. 2005 Jun 8;33(10):3283-91. Print 2005. PubMed PMID: 15944449; PubMed Central PMCID: PMC1145189. 17: Varvounis G. An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines. Molecules. 2016 Jan 28;21(2):154. doi: 10.3390/molecules21020154. Review. PubMed PMID: 26828475; PubMed Central PMCID: PMC6273195. 18: Wade Calcutt M, Lee W, Puzanov I, Rothenberg ML, Hachey DL. Determination of chemically reduced pyrrolobenzodiazepine SJG-136 in human plasma by HPLC-MS/MS: application to an anticancer phase I dose escalation study. J Mass Spectrom. 2008 Jan;43(1):42-52. PubMed PMID: 17683023. 19: Martin C, Ellis T, McGurk CJ, Jenkins TC, Hartley JA, Waring MJ, Thurston DE. Sequence-selective interaction of the minor-groove interstrand cross-linking agent SJG-136 with naked and cellular DNA: footprinting and enzyme inhibition studies. Biochemistry. 2005 Mar 22;44(11):4135-47. PubMed PMID: 15766241. 20: Aird RE, Thomson M, Macpherson JS, Thurston DE, Jodrell DI, Guichard SM. ABCB1 genetic polymorphism influences the pharmacology of the new pyrrolobenzodiazepine derivative SJG-136. Pharmacogenomics J. 2008 Aug;8(4):289-96. Epub 2007 Jun 12. PubMed PMID: 17563765.

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