9-Hydroxycrisamicin A

9-Hydroxycrisamicin A

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Category Antibiotics
Catalog number BBF-00995
CAS
Molecular Weight 614.51
Molecular Formula C32H22O13

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Description

9-Hydroxycrisamicin A is a climycin homolog produced by Micromonospora sp. SA246. It has weak anti-Gram-positive bacteria activity, MIC is 6.25-25/mL. It has a strong growth inhibitory effect on human tumor cell lines.

Specification

IUPAC Name 17-methyl-5-(2,7,9-trihydroxy-17-methyl-13-oxo-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1,3(8),4,6,9-pentaen-5-yl)-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),5-triene-2,4,7,9,13-pentone
Canonical SMILES CC1C2=C(C3C(O1)CC(=O)O3)C(=O)C4=C(C2=O)C(=O)C(=CC4=O)C5=CC6=C(C(=C5)O)C(=C7C8C(CC(=O)O8)OC(C7=C6O)C)O
InChI InChI=1S/C32H22O13/c1-8-19-24(31-15(42-8)6-17(35)44-31)29(40)21-12(27(19)38)3-10(4-13(21)33)11-5-14(34)22-23(26(11)37)28(39)20-9(2)43-16-7-18(36)45-32(16)25(20)30(22)41/h3-5,8-9,15-16,31-33,38,40H,6-7H2,1-2H3
InChI Key RGSLIARMZRMUIB-UHFFFAOYSA-N

Properties

Appearance Red Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Neoplastics (Tumor)
Melting Point 260°C(dec.)

Reference Reading

1. 9-Hydroxycrisamicin A, a new cytotoxic isochromanquinone antibiotic produced by Micromonospora sp. SA246
W H Yeo, B S Yun, N I Back, Y H Kim, S S Kim, E K Park, K S Whang, S H Yu J Antibiot (Tokyo). 1997 Jul;50(7):546-50. doi: 10.7164/antibiotics.50.546.
9-Hydroxycrisamicin A, a new cytotoxic isochromanquinone antibiotic, was isolated from a soil microorganism SA246 which was identified as Micromonospora sp. The molecular formula of 9-hydroxycrisamicin A was determined as C32H22O13 based on the HRFAB-MS analysis, and the structure was determined by various NMR experiments. 9-Hydroxycrisamicin A showed weak antimicrobial activity against Gram-positive bacteria and strong cytotoxic activity against some human cancer cell lines such as SK-OV-3 (ovarian), HCT15 (colon), SK-MEL-2 (melanoma), A549 (lung), XF498 (central nervous system) with ED50 of 0.47-0.65 microgram/ml.
2. A new compound from Micromonospora sp. SA246, 9-hydroxycrisamicin-A, activates hepatitis B virus replication
Seok Won Yoon, In Young Park, Bo Hwa Sohn, Jaehyouk Lee, Woon Hyung Yeo, Young Ik Lee Biochem Biophys Res Commun. 2004 Jul 2;319(3):859-65. doi: 10.1016/j.bbrc.2004.05.061.
A new compound from Micromonospora sp. SA246, 9-hydroxycrisamicin-A (9-HCA-A), showed potential for activating hepatitis B virus (HBV) replication. To define the mechanism of 9-HCA-A, we used HepG2 2.2.15 cells which support HBV replication. 9-HCA-A activated HBV replication, increased episomal and integrated HBV DNA content, and increased secretions of HBV antigens (HBsAg and HBeAg) into culture medium. 9-HCA-A also activated HBV transcription in Hep2 2.2.15 cell line. To examine transcriptional control mechanisms, we analyzed the effect of 9-HCA-A on four different HBV promoters (Core, PreS1, PreS2, and X) in hepatoma cell line. 9-HCA-A responsive element was located at HBx promoter. By EMSA, we showed that 9-HCA-A activated the HBx promoter by detaching the 9-HCA-A responsive element binding protein (9H-REBP). Protein phosphatase (PP2A1) treatment detaches the 9H-REBP from the HBx promoter, similar to 9-HCA-A, while protein kinase A treatment does not detach the 9H-REBP from the HBx promoter. Our results showed that 9H- REBP functions as a repressor of HBV replication while 9-HCA-A activated protein phosphatase released the BP on the HBx promoter, thus activating HBV replication.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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