Red-emitting rhodamines with hydroxylated, sulfonated, and phosphorylated dye residues and their use in fluorescence nanoscopy
Fluorescent dyes emitting red light are frequently used in conventional and super-resolution microscopy of biological samples, although the variety of the useful dyes is limited. We describe the synthesis of rhodamine-based fluorescent dyes with absorption and emission maxima in the range of 621-637...
Gespeichert in:
| Hauptverfasser: | , |
|---|---|
| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
11 September 2012
|
| In: |
Chemistry - a European journal
Year: 2012, Jahrgang: 18, Heft: 41, Pages: 12986-12998 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201201168 |
| Online-Zugang: | Verlag, Volltext: http://dx.doi.org/10.1002/chem.201201168 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201201168 
|
| Verfasserangaben: | Kirill Kolmakov, Christian A. Wurm, René Hennig, Erdmann Rapp, Stefan Jakobs, Vladimir N. Belov, and Stefan W. Hell |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 1582463476 | ||
| 003 | DE-627 | ||
| 005 | 20230427193228.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 181031s2012 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1002/chem.201201168 |2 doi | |
| 035 | |a (DE-627)1582463476 | ||
| 035 | |a (DE-576)512463476 | ||
| 035 | |a (DE-599)BSZ512463476 | ||
| 035 | |a (OCoLC)1341021880 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 30 |2 sdnb | ||
| 100 | 1 | |a Kolmakov, Kirill |e VerfasserIn |0 (DE-588)1170126251 |0 (DE-627)1037509749 |0 (DE-576)512396213 |4 aut | |
| 245 | 1 | 0 | |a Red-emitting rhodamines with hydroxylated, sulfonated, and phosphorylated dye residues and their use in fluorescence nanoscopy |c Kirill Kolmakov, Christian A. Wurm, René Hennig, Erdmann Rapp, Stefan Jakobs, Vladimir N. Belov, and Stefan W. Hell |
| 264 | 1 | |c 11 September 2012 | |
| 300 | |a 13 | ||
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Gesehen am 31.10.2018 | ||
| 520 | |a Fluorescent dyes emitting red light are frequently used in conventional and super-resolution microscopy of biological samples, although the variety of the useful dyes is limited. We describe the synthesis of rhodamine-based fluorescent dyes with absorption and emission maxima in the range of 621-637 and 644-660 nm, respectively and demonstrate their high performance in confocal and stimulated emission depletion (STED) microscopy. New dyes were prepared by means of reliable chemical transformations applied to a rhodamine scaffold with three variable positions. They feature polarity, water solubility, variable net charges, improved stabilities of N-hydroxysuccinimidyl (NHS) esters, as well as large fluorescence quantum yields in dye solutions and antibody conjugates. The photophysical and imaging properties of dyes containing three different polar groups, namely primary phosphate, sulfonic acid (in two different positions), and hydroxyl were compared. A dye with two primary phosphate groups was explored as a valuable alternative to dyes with “classical” sulfonic acid groups. Due to the increased net charge of the phosphorylated dye (q=−4 at pH 8), it demonstrated a far better electrophoretic mobility compared with analogues with two sulfonic acid groups (q=−2). As an example, one fluorescent dye was designed to be especially convenient for practical use. It is characterized by sufficiently high chemical stability of the NHS ester, its simple isolation, handling, and solubility in aqueous buffers, as well as in organic solvents. All these features, accompanied by a zero net charge in conjugates, were accomplished by the introduction of hydrophilic groups of two types: two hydroxyl groups and one sulfonic acid residue. | ||
| 650 | 4 | |a fluorescence | |
| 650 | 4 | |a rhodamines | |
| 650 | 4 | |a chromophores | |
| 650 | 4 | |a conjugation | |
| 650 | 4 | |a electrophoresis | |
| 650 | 4 | |a microscopy | |
| 700 | 1 | |a Hell, Stefan |d 1962- |e VerfasserIn |0 (DE-588)139815716 |0 (DE-627)613785681 |0 (DE-576)313195889 |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Chemistry - a European journal |d Weinheim : Wiley-VCH, 1995 |g 18(2012), 41, Seite 12986-12998 |h Online-Ressource |w (DE-627)270935193 |w (DE-600)1478547-X |w (DE-576)078707404 |x 1521-3765 |7 nnas |a Red-emitting rhodamines with hydroxylated, sulfonated, and phosphorylated dye residues and their use in fluorescence nanoscopy |
| 773 | 1 | 8 | |g volume:18 |g year:2012 |g number:41 |g pages:12986-12998 |g extent:13 |a Red-emitting rhodamines with hydroxylated, sulfonated, and phosphorylated dye residues and their use in fluorescence nanoscopy |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1002/chem.201201168 |x Verlag |x Resolving-System |3 Volltext |
| 856 | 4 | 0 | |u https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201201168 |x Verlag |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20181031 | ||
| 993 | |a Article | ||
| 994 | |a 2012 | ||
| 998 | |g 139815716 |a Hell, Stefan |m 139815716:Hell, Stefan |d 130000 |d 130001 |d 700000 |d 718000 |e 130000PH139815716 |e 130001PH139815716 |e 700000PH139815716 |e 718000PH139815716 |k 0/130000/ |k 1/130000/130001/ |k 0/700000/ |k 1/700000/718000/ |p 7 |y j | ||
| 999 | |a KXP-PPN1582463476 |e 3030145239 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"recId":"1582463476","language":["eng"],"type":{"media":"Online-Ressource","bibl":"article-journal"},"note":["Gesehen am 31.10.2018"],"person":[{"family":"Kolmakov","given":"Kirill","roleDisplay":"VerfasserIn","display":"Kolmakov, Kirill","role":"aut"},{"given":"Stefan","family":"Hell","role":"aut","roleDisplay":"VerfasserIn","display":"Hell, Stefan"}],"title":[{"title":"Red-emitting rhodamines with hydroxylated, sulfonated, and phosphorylated dye residues and their use in fluorescence nanoscopy","title_sort":"Red-emitting rhodamines with hydroxylated, sulfonated, and phosphorylated dye residues and their use in fluorescence nanoscopy"}],"relHost":[{"physDesc":[{"extent":"Online-Ressource"}],"id":{"issn":["1521-3765"],"zdb":["1478547-X"],"eki":["270935193"],"doi":["10.1002/(ISSN)1521-3765"]},"origin":[{"publisherPlace":"Weinheim","dateIssuedKey":"1995","publisher":"Wiley-VCH","dateIssuedDisp":"1995-"}],"part":{"year":"2012","pages":"12986-12998","issue":"41","text":"18(2012), 41, Seite 12986-12998","volume":"18","extent":"13"},"pubHistory":["1.1995 -"],"recId":"270935193","language":["eng"],"type":{"media":"Online-Ressource","bibl":"periodical"},"note":["Fortsetzung der Druck-Ausgabe","Gesehen am 27. Februar 2017"],"disp":"Red-emitting rhodamines with hydroxylated, sulfonated, and phosphorylated dye residues and their use in fluorescence nanoscopyChemistry - a European journal","title":[{"title":"Chemistry - a European journal","title_sort":"Chemistry - a European journal"}]}],"physDesc":[{"extent":"13 S."}],"name":{"displayForm":["Kirill Kolmakov, Christian A. Wurm, René Hennig, Erdmann Rapp, Stefan Jakobs, Vladimir N. Belov, and Stefan W. Hell"]},"id":{"doi":["10.1002/chem.201201168"],"eki":["1582463476"]},"origin":[{"dateIssuedKey":"2012","dateIssuedDisp":"11 September 2012"}]} | ||
| SRT | |a KOLMAKOVKIREDEMITTIN1120 | ||