MedKoo Cat#: 150183 | Name: Chromomycin A3
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Description:

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

Chromomycin A3 is an anticancer antibiotic, inhibits DNA synthesis by inhibiting DNA gyrase. The antibiotic has potential reactive centers that could interact with GSH, the most abundant non-protein thiol in eukaryotic cells and a putative cofactor involved in the activation of many antibiotics in vivo.

Chemical Structure

Chromomycin A3
Chromomycin A3
CAS#7059-24-7

Theoretical Analysis

MedKoo Cat#: 150183

Name: Chromomycin A3

CAS#: 7059-24-7

Chemical Formula: C57H82O26

Exact Mass: 1182.5090

Molecular Weight: 1183.26

Elemental Analysis: C, 57.86; H, 6.99; O, 35.16

Price and Availability

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5mg USD 450.00 2 Weeks
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Related CAS #
No Data
Synonym
chromomycin a3; Aburamycin B; Toyomycin; Chromomycin A3 [JAN]; CMA3; NSC 58514; NSC58514; NSC-58514;
IUPAC/Chemical Name
[(2R,3S,4R,6S)-6-[[(6S,7S)-6-[(2S,4R,5R,6R)-4-[(2S,4R,5R,6R)-4-[(2S,4S,5S,6S)-5-acetyloxy-4-hydroxy-4,6-dimethyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-7-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-4,10-dihydroxy-3-methyl-5-oxo-7,8-dihydro-6H-anthracen-2-yl]oxy]-4-[(2R,4R,5R,6R)-4-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy-2-methyloxan-3-yl] acetate
InChi Key
ZYVSOIYQKUDENJ-WKSBCEQHSA-N
InChi Code
1S/C57H82O26/c1-21-34(79-40-19-37(53(26(6)75-40)77-28(8)59)82-38-16-33(61)52(70-11)25(5)74-38)15-31-13-30-14-32(54(71-12)51(68)46(63)22(2)58)55(50(67)44(30)49(66)43(31)45(21)62)83-41-18-35(47(64)24(4)73-41)80-39-17-36(48(65)23(3)72-39)81-42-20-57(10,69)56(27(7)76-42)78-29(9)60/h13,15,22-27,32-33,35-42,46-48,52-56,58,61-66,69H,14,16-20H2,1-12H3/t22-,23-,24-,25-,26-,27+,32+,33-,35-,36-,37-,38-,39+,40+,41+,42+,46+,47-,48-,52+,53+,54+,55+,56+,57+/m1/s1
SMILES Code
C[C@@H]1[C@@H](O)[C@H](O[C@H]2C[C@@H](O[C@H]3C[C@](C)(O)[C@@H](OC(C)=O)[C@H](C)O3)[C@H](O)[C@@H](C)O2)C[C@H](O[C@H]4[C@H]([C@H](OC)C([C@@H](O)[C@H](O)C)=O)CC5=C(C(O)=C6C(C=C(O[C@H]7C[C@@H](O[C@@H]8C[C@@H](O)[C@@H](OC)[C@@H](C)O8)[C@@H](OC(C)=O)[C@@H](C)O7)C(C)=C6O)=C5)C4=O)O1
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 1,183.26 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: Slavik M, Carter SK. Chromomycin A3, mithramycin, and olivomycin: antitumor antibiotics of related structure. Adv Pharmacol Chemother. 1975;12(0):1-30. doi: 10.1016/s1054-3589(08)60218-5. PMID: 125531. 2: Saranaruk P, Kariya R, Sittithumcharee G, Boueroy P, Boonmars T, Sawanyawisuth K, Wongkham C, Wongkham S, Okada S, Vaeteewoottacharn K. Chromomycin A3 suppresses cholangiocarcinoma growth by induction of S phase cell cycle arrest and suppression of Sp1‑related anti‑apoptotic proteins. Int J Mol Med. 2020 Apr;45(4):1005-1016. doi: 10.3892/ijmm.2020.4482. Epub 2020 Jan 29. PMID: 32124934; PMCID: PMC7053871. 3: Jensen RH. Chromomycin A3 as a fluorescent probe for flow cytometry of human gynecologic samples. J Histochem Cytochem. 1977 Jul;25(7):573-9. doi: 10.1177/25.7.70448. PMID: 70448. 4: Shafer RH, Roques BP, LePecq JB, Delepierre M. Chromomycin A3 binds to left- handed poly(dG-m5dC). Eur J Biochem. 1988 Apr 15;173(2):377-82. doi: 10.1111/j.1432-1033.1988.tb14009.x. PMID: 3129292. 5: Iranpour FG, Nasr-Esfahani MH, Valojerdi MR, al-Taraihi TM. Chromomycin A3 staining as a useful tool for evaluation of male fertility. J Assist Reprod Genet. 2000 Jan;17(1):60-6. doi: 10.1023/a:1009406231811. PMID: 10754785; PMCID: PMC3455193. 6: Hayasaka T, Inoue Y. Chromomycin A3 studies in aqueous solutions. Spectrophotometric evidence for aggregation and interaction with herring sperm deoxyribonucleic acid. Biochemistry. 1969 Jun;8(6):2342-7. doi: 10.1021/bi00834a014. PMID: 5816376. 7: Nijs M, Creemers E, Cox A, Franssen K, Janssen M, Vanheusden E, De Jonge C, Ombelet W. Chromomycin A3 staining, sperm chromatin structure assay and hyaluronic acid binding assay as predictors for assisted reproductive outcome. Reprod Biomed Online. 2009 Nov;19(5):671-84. doi: 10.1016/j.rbmo.2009.07.002. PMID: 20021715. 8: Guimarães LA, Jimenez PC, Sousa Tda S, Freitas HP, Rocha DD, Wilke DV, Martín J, Reyes F, Deusdênia Loiola Pessoa O, Costa-Lotufo LV. Chromomycin A2 induces autophagy in melanoma cells. Mar Drugs. 2014 Dec 4;12(12):5839-55. doi: 10.3390/md12125839. PMID: 25486109; PMCID: PMC4278204. 9: Aich P, Sen R, Dasgupta D. Role of magnesium ion in the interaction between chromomycin A3 and DNA: binding of chromomycin A3-Mg2+ complexes with DNA. Biochemistry. 1992 Mar 24;31(11):2988-97. doi: 10.1021/bi00126a021. PMID: 1550824. 10: Menéndez N, Nur-e-Alam M, Braña AF, Rohr J, Salas JA, Méndez C. Biosynthesis of the antitumor chromomycin A3 in Streptomyces griseus: analysis of the gene cluster and rational design of novel chromomycin analogs. Chem Biol. 2004 Jan;11(1):21-32. doi: 10.1016/j.chembiol.2003.12.011. PMID: 15112992. 11: Kamiyama M. Mechanism of action of chromomycin A3. 3. On the binding of chromomycin A3 with DNA and physiochemical properties of the complex. J Biochem. 1968 May;63(5):566-72. doi: 10.1093/oxfordjournals.jbchem.a128814. PMID: 4972707. 12: Lolis D, Georgiou I, Syrrou M, Zikopoulos K, Konstantelli M, Messinis I. Chromomycin A3-staining as an indicator of protamine deficiency and fertilization. Int J Androl. 1996 Feb;19(1):23-7. doi: 10.1111/j.1365-2605.1996.tb00429.x. PMID: 8698534. 13: WAKISAKA G, UCHINO H, NAKAMURA T, SOTOVAYASHI H, SHIRAKAWA S, ADACHI A, SAKURAI M. Selective incells by chromomycin A3. Nature. 1963 Apr 27;198:385-6. doi: 10.1038/198385a0. PMID: 13998381. 14: Simões R, Feitosa WB, Mendes CM, Marques MG, Nicacio AC, de Barros FR, Visintin JA, Assumpção ME. Use of chromomycin A3 staining in bovine sperm cells for detection of protamine deficiency. Biotech Histochem. 2009 Jun;84(3):79-83. doi: 10.1080/10520290902843595. PMID: 19306222. 15: Menéndez N, Nur-e-Alam M, Fischer C, Braña AF, Salas JA, Rohr J, Méndez C. Deoxysugar transfer during chromomycin A3 biosynthesis in Streptomyces griseus subsp. griseus: new derivatives with antitumor activity. Appl Environ Microbiol. 2006 Jan;72(1):167-77. doi: 10.1128/AEM.72.1.167-177.2006. PMID: 16391039; PMCID: PMC1352227. 16: Skarbek JD, Brady LR. Isolation of chromomycin A3 from a new subspecies of Streptomyces. Lloydia. 1975 Sep-Oct;38(5):369-77. PMID: 811943. 17: Berman E, Brown SC, James TL, Shafer RH. NMR studies of chromomycin A3 interaction with DNA. Biochemistry. 1985 Nov 19;24(24):6887-93. doi: 10.1021/bi00345a022. PMID: 2416346. 18: Fleischman RW, Schaeppi U, Heyman IA, Phelan RS, Rosenkrantz H, Ilievski V. Preclinical toxicologic evaluation of chromomycin A3 (NSC-58 514) in mice, dogs and monkeys. Toxicol Appl Pharmacol. 1974 Feb;27(2):259-70. doi: 10.1016/0041-008x(74)90197-5. PMID: 4212258. 19: Montanari A, Rosazza JP. Biogenesis of chromomycin A3 by Streptomyces griseus. J Antibiot (Tokyo). 1990 Jul;43(7):883-9. doi: 10.7164/antibiotics.43.883. PMID: 2117602. 20: Toume K, Tsukahara K, Ito H, Arai MA, Ishibashi M. Chromomycins A2 and A3 from marine actinomycetes with TRAIL resistance-overcoming and Wnt signal inhibitory activities. Mar Drugs. 2014 Jun 5;12(6):3466-76. doi: 10.3390/md12063466. PMID: 24905484; PMCID: PMC4071586.