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MedKoo Cat#: 581297 | Name: Duocarmycin A

Description:

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

Duocarmycin A is from a Streptomycete. Duocarmycin is a cytotoxic agent, used as the cytotoxic component in antibody-drug conjugates.

Chemical Structure

Duocarmycin A
Duocarmycin A
CAS#118292-34-5

Theoretical Analysis

MedKoo Cat#: 581297

Name: Duocarmycin A

CAS#: 118292-34-5

Chemical Formula: C26H27N3O8

Exact Mass: 509.1798

Molecular Weight: 509.52

Elemental Analysis: C, 61.29; H, 5.34; N, 8.25; O, 25.12

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
Duocarmycin A; DC88-A; Deuocarmycin A;
IUPAC/Chemical Name
Cyclopropa(c)pyrrolo(3,2-e)indole-6-carboxylic acid, 1,2,3,5,6,7,8,8a-octahydro-6-methyl-4,7-dioxo-2-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester, (6R,7bR,8aS)-
InChi Key
FXBDKTDNUNOPMU-PUWSLBIFSA-N
InChi Code
InChI=1S/C26H27N3O8/c1-25(24(33)37-5)22(31)17-19(28-25)14(30)8-16-26(17)9-12(26)10-29(16)23(32)13-6-11-7-15(34-2)20(35-3)21(36-4)18(11)27-13/h6-7,12,16,27-28H,8-10H2,1-5H3/t12-,16?,25-,26+/m1/s1
SMILES Code
O=C([C@@](N1)(C)C(C([C@@]23[C@@](C3)([H])CN(C(C(N4)=CC5=C4C(OC)=C(OC)C(OC)=C5)=O)C2C6)=C1C6=O)=O)OC
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

Preparing Stock Solutions

The following data is based on the product molecular weight 509.52 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: Yu L, Lu Y, Yao Y, Liu Y, Wang Y, Lai Q, Zhang R, Li W, Wang R, Fu Y, Tao Y, Yi S, Gou L, Chen L, Yang J. Promiximab-duocarmycin, a new CD56 antibody-drug conjugates, is highly efficacious in small cell lung cancer xenograft models. Oncotarget. 2017 Dec 26;9(4):5197-5207. doi: 10.18632/oncotarget.23708. eCollection 2018 Jan 12. PubMed PMID: 29435172; PubMed Central PMCID: PMC5797043. 2: Menderes G, Bonazzoli E, Bellone S, Black J, Predolini F, Pettinella F, Masserdotti A, Zammataro L, Altwerger G, Buza N, Hui P, Wong S, Litkouhi B, Ratner E, Silasi DA, Azodi M, Schwartz PE, Santin AD. SYD985, a Novel Duocarmycin-Based HER2-Targeting Antibody-Drug Conjugate, Shows Antitumor Activity in Uterine and Ovarian Carcinosarcoma with HER2/Neu Expression. Clin Cancer Res. 2017 Oct 1;23(19):5836-5845. doi: 10.1158/1078-0432.CCR-16-2862. Epub 2017 Jul 5. PubMed PMID: 28679774; PubMed Central PMCID: PMC5626613. 3: Tercel M, Lee HH, Mehta SY, Youte Tendoung JJ, Bai SY, Liyanage HDS, Pruijn FB. Influence of a Basic Side Chain on the Properties of Hypoxia-Selective Nitro Analogues of the Duocarmycins: Demonstration of Substantial Anticancer Activity in Combination with Irradiation or Chemotherapy. J Med Chem. 2017 Jul 13;60(13):5834-5856. doi: 10.1021/acs.jmedchem.7b00563. Epub 2017 Jun 23. PubMed PMID: 28644035. 4: Menderes G, Bonazzoli E, Bellone S, Black J, Altwerger G, Masserdotti A, Pettinella F, Zammataro L, Buza N, Hui P, Wong S, Litkouhi B, Ratner E, Silasi DA, Huang GS, Azodi M, Schwartz PE, Santin AD. SYD985, a novel duocarmycin-based HER2-targeting antibody-drug conjugate, shows promising antitumor activity in epithelial ovarian carcinoma with HER2/Neu expression. Gynecol Oncol. 2017 Jul;146(1):179-186. doi: 10.1016/j.ygyno.2017.04.023. Epub 2017 May 1. PubMed PMID: 28473206; PubMed Central PMCID: PMC5533304. 5: Lowe DB, Bivens CK, Mobley AS, Herrera CE, McCormick AL, Wichner T, Sabnani MK, Wood LM, Weidanz JA. TCR-like antibody drug conjugates mediate killing of tumor cells with low peptide/HLA targets. MAbs. 2017 May/Jun;9(4):603-614. doi: 10.1080/19420862.2017.1302630. PubMed PMID: 28273004; PubMed Central PMCID: PMC5419083. 6: Jackson PJM, Rahman KM, Thurston DE. The use of molecular dynamics simulations to evaluate the DNA sequence-selectivity of G-A cross-linking PBD-duocarmycin dimers. Bioorg Med Chem Lett. 2017 Jan 1;27(1):102-108. doi: 10.1016/j.bmcl.2016.10.022. Epub 2016 Oct 12. PubMed PMID: 27889454. 7: Giddens AC, Lee HH, Lu GL, Miller CK, Guo J, Lewis Phillips GD, Pillow TH, Tercel M. Analogues of DNA minor groove cross-linking agents incorporating aminoCBI, an amino derivative of the duocarmycins: Synthesis, cytotoxicity, and potential as payloads for antibody-drug conjugates. Bioorg Med Chem. 2016 Nov 15;24(22):6075-6081. doi: 10.1016/j.bmc.2016.09.068. Epub 2016 Sep 30. PubMed PMID: 27745990. 8: Black J, Menderes G, Bellone S, Schwab CL, Bonazzoli E, Ferrari F, Predolini F, De Haydu C, Cocco E, Buza N, Hui P, Wong S, Lopez S, Ratner E, Silasi DA, Azodi M, Litkouhi B, Schwartz PE, Goedings P, Beusker PH, van der Lee MM, Timmers CM, Dokter WH, Santin AD. SYD985, a Novel Duocarmycin-Based HER2-Targeting Antibody-Drug Conjugate, Shows Antitumor Activity in Uterine Serous Carcinoma with HER2/Neu Expression. Mol Cancer Ther. 2016 Aug;15(8):1900-9. doi: 10.1158/1535-7163.MCT-16-0163. Epub 2016 Jun 2. PubMed PMID: 27256376. 9: Koch MF, Harteis S, Blank ID, Pestel G, Tietze LF, Ochsenfeld C, Schneider S, Sieber SA. Structural, Biochemical, and Computational Studies Reveal the Mechanism of Selective Aldehyde Dehydrogenase 1A1 Inhibition by Cytotoxic Duocarmycin Analogues. Angew Chem Int Ed Engl. 2015 Nov 9;54(46):13550-4. doi: 10.1002/anie.201505749. Epub 2015 Sep 16. PubMed PMID: 26373694. 10: Stephenson MJ, Howell LA, O'Connell MA, Fox KR, Adcock C, Kingston J, Sheldrake H, Pors K, Collingwood SP, Searcey M. Solid-Phase Synthesis of Duocarmycin Analogues and the Effect of C-Terminal Substitution on Biological Activity. J Org Chem. 2015 Oct 2;80(19):9454-67. doi: 10.1021/acs.joc.5b01373. Epub 2015 Sep 30. PubMed PMID: 26356089. 11: Elgersma RC, Coumans RG, Huijbregts T, Menge WM, Joosten JA, Spijker HJ, de Groot FM, van der Lee MM, Ubink R, van den Dobbelsteen DJ, Egging DF, Dokter WH, Verheijden GF, Lemmens JM, Timmers CM, Beusker PH. Design, Synthesis, and Evaluation of Linker-Duocarmycin Payloads: Toward Selection of HER2-Targeting Antibody-Drug Conjugate SYD985. Mol Pharm. 2015 Jun 1;12(6):1813-35. doi: 10.1021/mp500781a. Epub 2015 Feb 18. PubMed PMID: 25635711. 12: van der Lee MM, Groothuis PG, Ubink R, van der Vleuten MA, van Achterberg TA, Loosveld EM, Damming D, Jacobs DC, Rouwette M, Egging DF, van den Dobbelsteen D, Beusker PH, Goedings P, Verheijden GF, Lemmens JM, Timmers M, Dokter WH. The Preclinical Profile of the Duocarmycin-Based HER2-Targeting ADC SYD985 Predicts for Clinical Benefit in Low HER2-Expressing Breast Cancers. Mol Cancer Ther. 2015 Mar;14(3):692-703. doi: 10.1158/1535-7163.MCT-14-0881-T. Epub 2015 Jan 14. PubMed PMID: 25589493. 13: Uematsu M, Boger DL. Asymmetric synthesis of a CBI-based cyclic N-acyl O-amino phenol duocarmycin prodrug. J Org Chem. 2014 Oct 17;79(20):9699-703. doi: 10.1021/jo501839x. Epub 2014 Oct 3. PubMed PMID: 25247380; PubMed Central PMCID: PMC4201355. 14: Dokter W, Ubink R, van der Lee M, van der Vleuten M, van Achterberg T, Jacobs D, Loosveld E, van den Dobbelsteen D, Egging D, Mattaar E, Groothuis P, Beusker P, Coumans R, Elgersma R, Menge W, Joosten J, Spijker H, Huijbregts T, de Groot V, Eppink M, de Roo G, Verheijden G, Timmers M. Preclinical profile of the HER2-targeting ADC SYD983/SYD985: introduction of a new duocarmycin-based linker-drug platform. Mol Cancer Ther. 2014 Nov;13(11):2618-29. doi: 10.1158/1535-7163.MCT-14-0040-T. Epub 2014 Sep 4. PubMed PMID: 25189543. 15: Wirth T, Pestel GF, Ganal V, Kirmeier T, Schuberth I, Rein T, Tietze LF, Sieber SA. The two faces of potent antitumor duocarmycin-based drugs: a structural dissection reveals disparate motifs for DNA versus aldehyde dehydrogenase 1 affinity. Angew Chem Int Ed Engl. 2013 Jul 1;52(27):6921-5. doi: 10.1002/anie.201208941. Epub 2013 May 16. PubMed PMID: 23681547. 16: Wolfe AL, Duncan KK, Parelkar NK, Brown D, Vielhauer GA, Boger DL. Efficacious cyclic N-acyl O-amino phenol duocarmycin prodrugs. J Med Chem. 2013 May 23;56(10):4104-15. doi: 10.1021/jm400413r. Epub 2013 May 10. PubMed PMID: 23627265; PubMed Central PMCID: PMC3687800. 17: Tietze LF, Müller M, Duefert SC, Schmuck K, Schuberth I. Photoactivatable prodrugs of highly potent duocarmycin analogues for a selective cancer therapy. Chemistry. 2013 Jan 28;19(5):1726-31. doi: 10.1002/chem.201202773. Epub 2012 Dec 7. PubMed PMID: 23225610. 18: Tang X, Liang X. Metal-mediated targeting in the body. Chem Biol Drug Des. 2013 Mar;81(3):311-22. doi: 10.1111/cbdd.12090. Review. PubMed PMID: 23164152. 19: Tietze LF, Behrendt F, Pestel GF, Schuberth I, Mitkovski M. Synthesis, biological evaluation, and live cell imaging of novel fluorescent duocarmycin analogs. Chem Biodivers. 2012 Nov;9(11):2559-70. doi: 10.1002/cbdv.201200289. PubMed PMID: 23161634. 20: Wolfe AL, Duncan KK, Parelkar NK, Weir SJ, Vielhauer GA, Boger DL. A novel, unusually efficacious duocarmycin carbamate prodrug that releases no residual byproduct. J Med Chem. 2012 Jun 28;55(12):5878-86. doi: 10.1021/jm300330b. Epub 2012 Jun 12. PubMed PMID: 22650244; PubMed Central PMCID: PMC3386426.