CONTACT US
Home > Inhibitors/Agonists> > Septacidin
62362-59-8-Septacidin Septacidin

Septacidin

For research use only. Not for therapeutic Use.

  • CAT Number: I036224
  • CAS Number: 62362-59-8
  • Molecular Formula: C30H51N7O7
  • Molecular Weight: 621.38
  • Purity: 98%
Inquiry Now
Related Small Molecules: LAQ824     (R)-Isomucronulatol     PR-924    

Septacidin (Cat.No:I036224) represents a group of l-heptopyranoses containing nucleoside antibiotics with antitumor, antifungal, and pain-relief activities.


Catalog Number I036224
CAS Number 62362-59-8
Synonyms

Septacidin; NSC-65104; NSC 65104; NSC65104;

Molecular Formula C30H51N7O7
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name N-(2-(((2R,3R,4R,5S,6S)-6-((9H-purin-6-yl)amino)-2-((S)-1,2-dihydroxyethyl)-4,5-dihydroxytetrahydro-2H-pyran-3-yl)amino)-2-oxoethyl)-14-methylpentadecanamide
InChI 1S/C30H51N7O7/c1-19(2)13-11-9-7-5-3-4-6-8-10-12-14-21(40)31-15-22(41)36-23-25(42)26(43)30(44-27(23)20(39)16-38)37-29-24-28(33-17-32-24)34-18-35-29/h17-20,23,25-27,30,38-39,42-43H,3-16H2,1-2H3,(H,31,40)(H,36,41)(H2,32,33,34,35,37)/t20-,23+,25+,26-,27-,30-/m0/s1
InChIKey YBZRLMLGUBIIDN-DKOJYIQKSA-N
SMILES CC(C)CCCCCCCCCCCCC(NCC(N[C@H]1[C@H]([C@@H](O)CO)O[C@H](NC2=C3N=CNC3=NC=N2)[C@@H](O)[C@@H]1O)=O)=O
Reference

1: Tang W, Guo Z, Cao Z, Wang M, Li P, Meng X, Zhao X, Xie Z, Wang W, Zhou A, Lou C, Chen Y. d-Sedoheptulose-7-phosphate is a common precursor for the heptoses of septacidin and hygromycin B. Proc Natl Acad Sci U S A. 2018 Mar 13;115(11):2818-2823. doi: 10.1073/pnas.1711665115. Epub 2018 Feb 26. PubMed PMID: 29483275; PubMed Central PMCID: PMC5856511.
2: Sukkurwala AQ, Adjemian S, Senovilla L, Michaud M, Spaggiari S, Vacchelli E, Baracco EE, Galluzzi L, Zitvogel L, Kepp O, Kroemer G. Screening of novel immunogenic cell death inducers within the NCI Mechanistic Diversity Set. Oncoimmunology. 2014 Apr 16;3:e28473. eCollection 2014. PubMed PMID: 25050214; PubMed Central PMCID: PMC4063139.
3: Price NP, Furukawa T, Cheng F, Qi J, Chen W, Crich D. Biosynthesis of 4-aminoheptose 2-epimers, core structural components of the septacidins and spicamycins. J Antibiot (Tokyo). 2014 May;67(5):405-14. doi: 10.1038/ja.2014.15. Epub 2014 Mar 19. PubMed PMID: 24643053.
4: Mizumura Y. [Spicamycin derivative]. Nihon Rinsho. 2006 Feb;64(2):322-8. Review. Japanese. PubMed PMID: 16454188.
5: Borsook D, Edwards AD. Antineuropathic effects of the antibiotic derivative spicamycin KRN5500. Pain Med. 2004 Mar;5(1):104-8. PubMed PMID: 14996243.
6: Mons S, Fleet GW. An approach to the generation of simple analogues of the antitumour agent spicamycin. Org Biomol Chem. 2003 Nov 7;1(21):3685-91. PubMed PMID: 14649899.
7: DiLorenzo L, Kobierski L, Moore KA, Borsook D. A water-soluble synthetic spicamycin derivative (San-Gly) decreases mechanical allodynia in a rodent model of neuropathic pain. Neurosci Lett. 2002 Sep 13;330(1):37-40. PubMed PMID: 12213629.
8: Suzuki T, Suzuki ST, Yamada I, Koashi Y, Yamada K, Chida N. Total synthesis of spicamycin. J Org Chem. 2002 May 3;67(9):2874-80. PubMed PMID: 11975540.
9: Zhang WJ, Ohnishi K, Yoshida H, Pan L, Maksumova L, Muratkhodjaev F, Luo JM, Shigeno K, Fujisawa S, Naito K, Nakamura S, Shinjo K, Takeshita A, Ohno R. Spicamycin and KRN5500 induce apoptosis in myeloid and lymphoid cell lines with down-regulation of bcl-2 expression and modulation of promyelocytic leukemia protein. Jpn J Cancer Res. 2000 Jun;91(6):604-11. PubMed PMID: 10874212; PubMed Central PMCID: PMC5926402.
10: Suzuki T, Tanaka S, Yamada I, Koashi Y, Yamada K, Chida N. Total synthesis of spicamycin amino nucleoside. Org Lett. 2000 Apr 20;2(8):1137-40. PubMed PMID: 10804573.
11: Sakai T, Kawai H, Kamishohara M, Odagawa A, Suzuki A, Uchida T, Kawasaki T, Tsuruo T, Otake N. Structure-antitumor activity relationship of semi-synthetic Spicamycin derivatives. J Antibiot (Tokyo). 1995 Dec;48(12):1467-80. PubMed PMID: 8557605.
12: Sakai T, Shindo K, Odagawa A, Suzuki A, Kawai H, Kobayashi K, Hayakawa Y, Seto H, Otake N. Absolute configuration of spicamycin, an antitumor antibiotic produced by Streptomyces alanosinicus. J Antibiot (Tokyo). 1995 Aug;48(8):899-900. PubMed PMID: 7592040.
13: Sakai T, Kawai H, Kamishohara M, Odagawa A, Suzuki A, Uchida T, Kawasaki T, Tsuruo T, Otake N. Synthesis and antitumor activities of glycine-exchanged analogs of spicamycin. J Antibiot (Tokyo). 1995 Jun;48(6):504-8. PubMed PMID: 7622437.
14: Kamishohara M, Kawai H, Odagawa A, Isoe T, Mochizuki J, Uchida T, Hayakawa Y, Seto H, Tsuruo T, Otake N. Antitumor activity of SPM VIII, a derivative of the nucleoside antibiotic spicamycin, against human tumor xenografts. J Antibiot (Tokyo). 1994 Nov;47(11):1305-11. PubMed PMID: 8002395.
15: Kamishohara M, Kawai H, Odagawa A, Isoe T, Mochizuki J, Uchida T, Hayakawa Y, Seto H, Tsuruo T, Otake N. Structure-antitumor activity relationship of semi-synthetic spicamycin analogues. J Antibiot (Tokyo). 1993 Sep;46(9):1439-46. PubMed PMID: 8226322.
16: Osda H. [Differentiation inducing compounds]. Tanpakushitsu Kakusan Koso. 1993 Aug;38(11):1791-9. Review. Japanese. PubMed PMID: 8210426.
17: Hayakawa Y, Nakagawa M, Kawai H, Tanabe K, Nakayama H, Shimazu A, Seto H, Otake N. Studies on the differentiation inducers of myeloid leukemic cells. III. Spicamycin, a new inducer of differentiation of HL-60 human promyelocytic leukemia cells. J Antibiot (Tokyo). 1983 Jul;36(7):934-7. PubMed PMID: 6576995.
18: Acton EM, Ryan KJ, Luetzow AE. Antitumor septacidin analogues. J Med Chem. 1977 Nov;20(11):1362-71. PubMed PMID: 915894.
19: Aszalos A, Lemanski P, Berk B, Dutcher JD. Septacidin analogues. Antimicrob Agents Chemother (Bethesda). 1965;5:845-9. PubMed PMID: 5883508.
20: DUTCHER JD, VONSALTZA MH, PANSY FE. SEPTACIDIN, A NEW ANTITUMOR AND ANTIFUNGAL ANTIBIOTIC PRODUCED BY STREPTOMYCES FIBRIATUS. Antimicrob Agents Chemother (Bethesda). 1963;161:83-8. PubMed PMID: 14275007.

Request a Quote