MedKoo Cat#: 146393 | Name: Anthramycin

Description:

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

Anthramycin is a pyrrolobenzodiazepine (PBD) antibiotic derived from Streptomyces refuineus, known for its potent antitumor activity. It exerts its effects by binding covalently to the minor groove of DNA, leading to the inhibition of DNA replication and RNA synthesis. Due to its cytotoxic properties, anthramycin has been investigated for use in cancer chemotherapy, particularly in targeting rapidly dividing tumor cells. However, its clinical application is limited by high toxicity and poor stability.

Chemical Structure

Anthramycin
Anthramycin
CAS#4803-27-4

Theoretical Analysis

MedKoo Cat#: 146393

Name: Anthramycin

CAS#: 4803-27-4

Chemical Formula: C16H17N3O4

Exact Mass: 315.1219

Molecular Weight: 315.33

Elemental Analysis: C, 60.94; H, 5.43; N, 13.33; O, 20.29

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
Anthramycin;
IUPAC/Chemical Name
(E)-3-((11R,11aS)-9,11-dihydroxy-8-methyl-5-oxo-5,10,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)acrylamide
InChi Key
VGQOVCHZGQWAOI-YQRHFANHSA-N
InChi Code
1S/C16H17N3O4/c1-8-2-4-10-13(14(8)21)18-15(22)11-6-9(3-5-12(17)20)7-19(11)16(10)23/h2-5,7,11,15,18,21-22H,6H2,1H3,(H2,17,20)/b5-3+/t11-,15+/m0/s1
SMILES Code
CC1=CC=C2C(N[C@H](O)[C@@H]3CC(\C=C\C(N)=O)=CN3C2=O)=C1O
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 315.33 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: Mantaj J, Jackson PJ, Rahman KM, Thurston DE. From Anthramycin to Pyrrolobenzodiazepine (PBD)-Containing Antibody-Drug Conjugates (ADCs). Angew Chem Int Ed Engl. 2017 Jan 9;56(2):462-488. doi: 10.1002/anie.201510610. Epub 2016 Nov 15. PMID: 27862776; PMCID: PMC5215561. 2: Hurley LH. Pyrrolo(1,4)benzodiazepine antitumor antibiotics. Comparative aspects of anthramycin, tomaymycin and sibiromycin. J Antibiot (Tokyo). 1977 May;30(5):349-70. doi: 10.7164/antibiotics.30.349. PMID: 328469. 3: Leimgruber W, Batcho AD, Schenker F. The structure of anthramycin. J Am Chem Soc. 1965 Dec 20;87(24):5793-5. doi: 10.1021/ja00952a051. PMID: 5845428. 4: Haque T, Rahman KM, Thurston DE, Hadgraft J, Lane ME. Topical delivery of anthramycin I. Influence of neat solvents. Eur J Pharm Sci. 2017 Jun 15;104:188-195. doi: 10.1016/j.ejps.2017.03.043. Epub 2017 Mar 31. PMID: 28373034. 5: Reynolds VL, Hurley LH. Comparison of properties of the in vitro and cellular anthramycin-DNA adducts and characterization of the reaction of anthramycin with chromatin. Chem Biol Interact. 1982 Nov;42(2):141-51. doi: 10.1016/0009-2797(82)90128-4. PMID: 7151226. 6: Vargiu AV, Ruggerone P, Magistrato A, Carloni P. Anthramycin-DNA binding explored by molecular simulations. J Phys Chem B. 2006 Dec 7;110(48):24687-95. doi: 10.1021/jp063155n. PMID: 17134232. 7: Hurley LH. The minor groove covalent reactive drugs anthramycin and (+)-CC-1065 and their interstrand cross-linking derivatives. IARC Sci Publ. 1994;(125):295-312. PMID: 7806319. 8: Kaneko T, Wong H, Doyle TW, Rose WC, Bradner WT. Bicyclic and tricyclic analogues of anthramycin. J Med Chem. 1985 Mar;28(3):388-92. doi: 10.1021/jm00381a020. PMID: 3973905. 9: Kaplan DJ, Hurley LH. Anthramycin binding to deoxyribonucleic acid-mitomycin C complexes. Evidence for drug-induced deoxyribonucleic acid conformational change and cooperativity in mitomycin C binding. Biochemistry. 1981 Dec 22;20(26):7572-80. doi: 10.1021/bi00529a036. PMID: 6798992. 10: Graves DE, Stone MP, Krugh TR. Structure of the anthramycin-d(ATGCAT)2 adduct from one- and two-dimensional proton NMR experiments in solution. Biochemistry. 1985 Dec 17;24(26):7573-81. doi: 10.1021/bi00347a011. PMID: 4092025.